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Price improvement!!! Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.

146 Duke Of Gloucester St, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

$1,950,000

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat. schedule your showing today.

6 Beds ⋅ 4 Baths

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat. schedule your showing today.

192 Duke Of Gloucester, Annapolis

Listing courtesy of Samson Properties. Contact:

$1,925,000

Enjoy waterfront living in the sought-after Loch Haven community. This feature rich four-level home with generous living spaces and high ceilings is positioned on 63 feet of waterfront along the protected deep waters of Pocahontas Creek providing quick unobstructed boating access to the South River, Chesapeake Bay and beyond. Recent improvements include a new roof (2026) and two new HVAC systems (2024 and 2026). The open-concept main level features water views, hardwood floors, abundant natural light, and a gourmet kitchen with a large island, stainless steel appliances, double ovens, a gas cooktop with grill, a custom tile backsplash and solid hickory cabinets. The kitchen opens to the family room with a stone-surround gas fireplace and direct access to the full home width screened porch overlooking the water for seamless indoor/outdoor living and entertainment. A formal dining room, bedroom, full bath, and laundry room complete this level. The second level also featuring hardwood floors contains the spacious primary suite with a full home width private waterfront deck, unobstructed creek views, a walk-in closet, an ensuite bath with oversized shower, separate soaking tub, and double vanity. Two additional bedrooms, each with full ensuite baths, complete the second level. The third floor offers a fifth bedroom, flex space, and a full bath. The lower level includes a recreation room, gym, full bath, storage, and utility space. The landscaped waterfront lot with irrigation system gently slopes to the private pier, 20,000-pound boat lift (with new cradle 2026), 30 amp of power and fresh water at the pier, kayak storage and fire pit. The oversized three-car garage provides substantial storage space for vehicles and more. Loch Haven amenities include a private sandy beach, community marina and boat ramp, playground, tennis, pickleball and basketball courts, walking trails, and year-round social activities. This is a well-appointed waterfront home offering flexible living spaces, recent major improvements, and outstanding boating access.

5 Beds ⋅ 6 Baths

Enjoy waterfront living in the sought-after Loch Haven community. This feature rich four-level home with generous living spaces and high ceilings is positioned on 63 feet of waterfront along the protected deep waters of Pocahontas Creek providing quick unobstructed boating access to the South River, Chesapeake Bay and beyond. Recent improvements include a new roof (2026) and two new HVAC systems (2024 and 2026). The open-concept main level features water views, hardwood floors, abundant natural light, and a gourmet kitchen with a large island, stainless steel appliances, double ovens, a gas cooktop with grill, a custom tile backsplash and solid hickory cabinets. The kitchen opens to the family room with a stone-surround gas fireplace and direct access to the full home width screened porch overlooking the water for seamless indoor/outdoor living and entertainment. A formal dining room, bedroom, full bath, and laundry room complete this level. The second level also featuring hardwood floors contains the spacious primary suite with a full home width private waterfront deck, unobstructed creek views, a walk-in closet, an ensuite bath with oversized shower, separate soaking tub, and double vanity. Two additional bedrooms, each with full ensuite baths, complete the second level. The third floor offers a fifth bedroom, flex space, and a full bath. The lower level includes a recreation room, gym, full bath, storage, and utility space. The landscaped waterfront lot with irrigation system gently slopes to the private pier, 20,000-pound boat lift (with new cradle 2026), 30 amp of power and fresh water at the pier, kayak storage and fire pit. The oversized three-car garage provides substantial storage space for vehicles and more. Loch Haven amenities include a private sandy beach, community marina and boat ramp, playground, tennis, pickleball and basketball courts, walking trails, and year-round social activities. This is a well-appointed waterfront home offering flexible living spaces, recent major improvements, and outstanding boating access.

3596 S River Ter, Edgewater

Listing courtesy of EXP Realty, LLC. Contact:

$1,900,000

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

1820 Baltimore Annapolis Blvd, Annapolis

$1,895,000

Welcome to an exceptional private estate in St. Margaret's, where sophisticated living meets effortless indoor-outdoor entertaining. Tucked behind a gated entrance and set on beautifully landscaped grounds, this expansive residence offers an impressive blend of luxury, versatility, and thoughtful design. The main level welcomes you with a grand foyer, solid red oak hardwood floors, and a stunning two-story living room featuring a gas fireplace and custom built-ins. The gourmet kitchen is truly the heart of the home, showcasing Wolf and Sub-Zero appliances, quartz countertops, marble backsplash, Miele dishwasher, beverage refrigerator, walk-in pantry, and abundant custom storage. The adjacent all-seasons room, complete with a wood-burning stove, provides a warm and inviting space to relax year-round. The main-level primary suite is a private retreat with its own gas fireplace, dual custom walk-in closets, built-in safe, and spa-inspired bath featuring a jetted soaking tub, oversized glass shower with dual shower heads and body sprayers, and dual marble vanities. A flexible additional room on the main level offers endless possibilities as an office, guest room, or additional bedroom. Above the oversized two-car garage, a separate bonus suite with full bath and closet provides exceptional flexibility for guests, an au pair, home gym, private office or additional bedroom Upstairs, a spacious loft-style lounge provides additional entertaining space, while three generously sized bedrooms offer walk-in closets and access to private or Jack-and-Jill baths. The lower level is designed for fun and entertaining, featuring a large open recreation area with polished concrete floors, indoor rock-climbing wall, built-in dartboard, beverage refrigerator, and a wood-paneled office/media room with custom built-ins and wet bar. Extensive unfinished storage, multiple utility-floored storage rooms, and a secure storage room with built-in safe and passcode entry provide an abundance of space. Outside, enjoy a custom paver patio with built-in gas grill, dedicated entertaining area, separate stone fire pit, private garden with raised planting beds, expansive side yard, and built-in basketball hoop. The property offers three garage bays, a circular driveway with auto court and five additional parking spaces, plus an attached storage shed. Recent updates include HVAC system improvements to both first and second-floor HVAC systems. A natural gas generator provides backup power for the tankless water heater, primary living spaces, and network/Wi-Fi infrastructure. With its gated privacy, remarkable entertaining spaces, luxury finishes, flexible living arrangements, extensive storage, and exceptional mechanical updates, 1820 Baltimore Annapolis Boulevard offers a truly distinctive lifestyle in sought-after Annapolis.

Welcome to an exceptional private estate in St. Margaret's, where sophisticated living meets effortless indoor-outdoor entertaining. Tucked behind a gated entrance and set on beautifully landscaped grounds, this expansive residence offers an impressive blend of luxury, versatility, and thoughtful design. The main level welcomes you with a grand foyer, solid red oak hardwood floors, and a stunning two-story living room featuring a gas fireplace and custom built-ins. The gourmet kitchen is truly the heart of the home, showcasing Wolf and Sub-Zero appliances, quartz countertops, marble backsplash, Miele dishwasher, beverage refrigerator, walk-in pantry, and abundant custom storage. The adjacent all-seasons room, complete with a wood-burning stove, provides a warm and inviting space to relax year-round. The main-level primary suite is a private retreat with its own gas fireplace, dual custom walk-in closets, built-in safe, and spa-inspired bath featuring a jetted soaking tub, oversized glass shower with dual shower heads and body sprayers, and dual marble vanities. A flexible additional room on the main level offers endless possibilities as an office, guest room, or additional bedroom. Above the oversized two-car garage, a separate bonus suite with full bath and closet provides exceptional flexibility for guests, an au pair, home gym, private office or additional bedroom Upstairs, a spacious loft-style lounge provides additional entertaining space, while three generously sized bedrooms offer walk-in closets and access to private or Jack-and-Jill baths. The lower level is designed for fun and entertaining, featuring a large open recreation area with polished concrete floors, indoor rock-climbing wall, built-in dartboard, beverage refrigerator, and a wood-paneled office/media room with custom built-ins and wet bar. Extensive unfinished storage, multiple utility-floored storage rooms, and a secure storage room with built-in safe and passcode entry provide an abundance of space. Outside, enjoy a custom paver patio with built-in gas grill, dedicated entertaining area, separate stone fire pit, private garden with raised planting beds, expansive side yard, and built-in basketball hoop. The property offers three garage bays, a circular driveway with auto court and five additional parking spaces, plus an attached storage shed. Recent updates include HVAC system improvements to both first and second-floor HVAC systems. A natural gas generator provides backup power for the tankless water heater, primary living spaces, and network/Wi-Fi infrastructure. With its gated privacy, remarkable entertaining spaces, luxury finishes, flexible living arrangements, extensive storage, and exceptional mechanical updates, 1820 Baltimore Annapolis Boulevard offers a truly distinctive lifestyle in sought-after Annapolis.

1820 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,895,000

** Private first-look appointments are available. Contact the listing agent to schedule for a first-look. ** A rare find in Eastport: an oversized attached two-car garage, plus a driveway and additional off-street parking, in a walkable waterfront neighborhood where garages are hard to come by. Beyond the striking exterior is a brand-new, ground-up home spanning three expansive levels, featuring 6 bedrooms, 4.5 baths, a chef-inspired kitchen with an oversized island and walk-in pantry, a main-level bedroom, an impressive primary suite, upper-level laundry, and a third-floor loft ideal for an office, guest space, or studio. Outside, enjoy a fully fenced yard, patio, and covered front porch — all just a short walk from Eastport’s marinas, restaurants, waterfront lifestyle, and downtown Annapolis.

** Private first-look appointments are available. Contact the listing agent to schedule for a first-look. ** A rare find in Eastport: an oversized attached two-car garage, plus a driveway and additional off-street parking, in a walkable waterfront neighborhood where garages are hard to come by. Beyond the striking exterior is a brand-new, ground-up home spanning three expansive levels, featuring 6 bedrooms, 4.5 baths, a chef-inspired kitchen with an oversized island and walk-in pantry, a main-level bedroom, an impressive primary suite, upper-level laundry, and a third-floor loft ideal for an office, guest space, or studio. Outside, enjoy a fully fenced yard, patio, and covered front porch — all just a short walk from Eastport’s marinas, restaurants, waterfront lifestyle, and downtown Annapolis.

914 Van Buren St, Annapolis

Listing courtesy of Realty ONE Group Capital. Contact:

$1,895,000

Experience the rare opportunity to build a custom luxury residence on a prime homesite in the heart of sought-after Severna Park. Perfectly positioned in one of Anne Arundel County’s most desirable communities, 624A Old County Road offers the ideal blend of timeless design, modern functionality, and exceptional convenience — all within the renowned Severna Park Blue Ribbon school district and just moments from shopping, dining, marinas, parks, and major commuter routes to Annapolis, Baltimore, Washington D.C., and Fort Meade. This thoughtfully designed to-be-built home showcases quality craftsmanship and elevated finishes throughout, featuring over-the-top standard inclusions rarely found in new construction today. Designed with both everyday living and entertaining in mind, the home offers spacious open-concept living areas, 10-foot ceilings on the main level, a 4-stop elevator, and a versatile loft entertaining space complete with wet bar and beverage refrigerator. The exterior architecture blends classic and modern influences with stone accents, standing seam metal roofing, covered front porch, rooftop terrace, Trex decking, and a striking French Country-inspired aesthetic. Inside, the gourmet kitchen is appointed with semi-custom soft-close cabinetry, oversized island, quartz or granite countertops, Kohler farmhouse sink, and a premium GE Café appliance package including cooktop, wall oven, Advantium microwave, counter-depth refrigerator, and dishwasher. The luxurious primary suite serves as a private retreat with a spa-inspired bath featuring a freestanding heated jetted tub, expansive walk-in shower, dual vanities, designer tilework, and elevated finishes throughout. Built with efficiency, durability, and comfort at the forefront, the home includes 2x6 construction, engineered floor systems, spray foam insulation, Low-E windows, high-efficiency dual-zone Carrier HVAC systems, natural gas service, public water and sewer, fire suppression system, and a spacious 3-car garage. Additional highlights include LVP flooring throughout the main living spaces, recessed lighting, natural gas fireplace, ceiling fans in all bedrooms, elevated trim package, and abundant storage opportunities. A rare chance to personalize and create your dream home in one of Severna Park’s most convenient and desirable locations — where luxury new construction, exceptional schools, and an unmatched lifestyle come together.

Experience the rare opportunity to build a custom luxury residence on a prime homesite in the heart of sought-after Severna Park. Perfectly positioned in one of Anne Arundel County’s most desirable communities, 624A Old County Road offers the ideal blend of timeless design, modern functionality, and exceptional convenience — all within the renowned Severna Park Blue Ribbon school district and just moments from shopping, dining, marinas, parks, and major commuter routes to Annapolis, Baltimore, Washington D.C., and Fort Meade. This thoughtfully designed to-be-built home showcases quality craftsmanship and elevated finishes throughout, featuring over-the-top standard inclusions rarely found in new construction today. Designed with both everyday living and entertaining in mind, the home offers spacious open-concept living areas, 10-foot ceilings on the main level, a 4-stop elevator, and a versatile loft entertaining space complete with wet bar and beverage refrigerator. The exterior architecture blends classic and modern influences with stone accents, standing seam metal roofing, covered front porch, rooftop terrace, Trex decking, and a striking French Country-inspired aesthetic. Inside, the gourmet kitchen is appointed with semi-custom soft-close cabinetry, oversized island, quartz or granite countertops, Kohler farmhouse sink, and a premium GE Café appliance package including cooktop, wall oven, Advantium microwave, counter-depth refrigerator, and dishwasher. The luxurious primary suite serves as a private retreat with a spa-inspired bath featuring a freestanding heated jetted tub, expansive walk-in shower, dual vanities, designer tilework, and elevated finishes throughout. Built with efficiency, durability, and comfort at the forefront, the home includes 2x6 construction, engineered floor systems, spray foam insulation, Low-E windows, high-efficiency dual-zone Carrier HVAC systems, natural gas service, public water and sewer, fire suppression system, and a spacious 3-car garage. Additional highlights include LVP flooring throughout the main living spaces, recessed lighting, natural gas fireplace, ceiling fans in all bedrooms, elevated trim package, and abundant storage opportunities. A rare chance to personalize and create your dream home in one of Severna Park’s most convenient and desirable locations — where luxury new construction, exceptional schools, and an unmatched lifestyle come together.

624-A Old County Rd, Severna Park

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,874,000

Welcome to “The Staycation Home”—an extraordinary private retreat tucked away on nearly 4 secluded acres in sought-after Cross Creek at Compass Pointe. Hidden from the cul-de-sac behind mature trees, a long private driveway opens to this impressive brick-front Colonial with a spacious parking area, designer-paver entrance and welcoming covered front porch. Offering more than 8,300 sq. ft. of finished living space, this home delivers an incredible combination of space, privacy and resort-style living. Enter the dramatic 2-story foyer with designer hardwood staircase, formal living and dining rooms, and a light-filled conservatory. Beyond the foyer, the home opens to a spacious family room with gas fireplace, kitchen and sunroom. The kitchen features granite countertops, stainless steel appliances, center island and custom pantry. A second staircase, tucked-away desk area, mudroom/laundry and access to the 3-car garage add everyday convenience. The family room and sunroom feature remote-controlled blinds. A main-level bedroom with private full bath offers the perfect space for guests or multigenerational living. Double doors open directly to the incredible wraparound 3-season deck. The sunroom also opens through French doors, allowing the indoor and outdoor spaces to flow together. Designed for entertaining, the deck features peaked wood ceilings, skylights, 4 remote-controlled ceiling fans, rope lighting, speakers and a custom grill with hood—all overlooking the backyard oasis. Upstairs are 5 bedrooms, including an impressive primary suite with tray ceiling, spacious bath with dual vanity, jetted soaking tub and separate shower, plus an exceptional custom walk-in closet featuring built-in organizers, felt-lined locking jewelry drawers, pull-out clothing-prep bars, full-length pull-out mirror and dedicated tie and belt storage. One additional bedroom has a private full bath, two share a Jack-and-Jill bath, and another features its own full bath. All bedrooms include custom closet systems, ceiling fans and blinds. The expansive lower level is an entertainer's dream! Multiple bonus rooms offer flexibility for a gym, office, guest space or hobbies. Enjoy an open recreation area, dedicated theater room, family room with gas fireplace, custom-designed bar with sink, additional lounge area, office, pantry and abundant storage. The pool table currently in the recreation area conveys with the home. Walk out to a covered paver patio with rope lighting, remote-controlled ceiling fans and speakers, then step into your own private resort. The heated saltwater pool and spa feature a large sun-shelf entry, waterfalls, extensive landscaping and an oversized paver patio perfect for lounging, dining and entertaining. A designated playground area adds even more outdoor enjoyment, while the surrounding mature tree line creates an incredible sense of privacy. Front and backyard irrigation helps maintain the beautifully landscaped grounds. The owners have also invested in the updates that matter most, including a new roof, 3 updated furnace/A/C systems and hot water heater installed in 2021. The interior has been recently painted throughout in a fresh neutral palette, cabinetry has been refreshed, bathroom vanities updated, and original recessed lighting replaced with modern flat-panel LED lighting. Open the doors, fire up the grill, swim beneath the waterfalls, soak in the spa, watch a movie in your theater or gather around the custom bar. With 6 bedrooms, 3 finished levels, a 3-car garage and nearly 4 private acres surrounded by nature, this isn't simply a home—it's a lifestyle. Welcome to your year-round Staycation!

6 Beds ⋅ 7 Baths

Welcome to “The Staycation Home”—an extraordinary private retreat tucked away on nearly 4 secluded acres in sought-after Cross Creek at Compass Pointe. Hidden from the cul-de-sac behind mature trees, a long private driveway opens to this impressive brick-front Colonial with a spacious parking area, designer-paver entrance and welcoming covered front porch. Offering more than 8,300 sq. ft. of finished living space, this home delivers an incredible combination of space, privacy and resort-style living. Enter the dramatic 2-story foyer with designer hardwood staircase, formal living and dining rooms, and a light-filled conservatory. Beyond the foyer, the home opens to a spacious family room with gas fireplace, kitchen and sunroom. The kitchen features granite countertops, stainless steel appliances, center island and custom pantry. A second staircase, tucked-away desk area, mudroom/laundry and access to the 3-car garage add everyday convenience. The family room and sunroom feature remote-controlled blinds. A main-level bedroom with private full bath offers the perfect space for guests or multigenerational living. Double doors open directly to the incredible wraparound 3-season deck. The sunroom also opens through French doors, allowing the indoor and outdoor spaces to flow together. Designed for entertaining, the deck features peaked wood ceilings, skylights, 4 remote-controlled ceiling fans, rope lighting, speakers and a custom grill with hood—all overlooking the backyard oasis. Upstairs are 5 bedrooms, including an impressive primary suite with tray ceiling, spacious bath with dual vanity, jetted soaking tub and separate shower, plus an exceptional custom walk-in closet featuring built-in organizers, felt-lined locking jewelry drawers, pull-out clothing-prep bars, full-length pull-out mirror and dedicated tie and belt storage. One additional bedroom has a private full bath, two share a Jack-and-Jill bath, and another features its own full bath. All bedrooms include custom closet systems, ceiling fans and blinds. The expansive lower level is an entertainer's dream! Multiple bonus rooms offer flexibility for a gym, office, guest space or hobbies. Enjoy an open recreation area, dedicated theater room, family room with gas fireplace, custom-designed bar with sink, additional lounge area, office, pantry and abundant storage. The pool table currently in the recreation area conveys with the home. Walk out to a covered paver patio with rope lighting, remote-controlled ceiling fans and speakers, then step into your own private resort. The heated saltwater pool and spa feature a large sun-shelf entry, waterfalls, extensive landscaping and an oversized paver patio perfect for lounging, dining and entertaining. A designated playground area adds even more outdoor enjoyment, while the surrounding mature tree line creates an incredible sense of privacy. Front and backyard irrigation helps maintain the beautifully landscaped grounds. The owners have also invested in the updates that matter most, including a new roof, 3 updated furnace/A/C systems and hot water heater installed in 2021. The interior has been recently painted throughout in a fresh neutral palette, cabinetry has been refreshed, bathroom vanities updated, and original recessed lighting replaced with modern flat-panel LED lighting. Open the doors, fire up the grill, swim beneath the waterfalls, soak in the spa, watch a movie in your theater or gather around the custom bar. With 6 bedrooms, 3 finished levels, a 3-car garage and nearly 4 private acres surrounded by nature, this isn't simply a home—it's a lifestyle. Welcome to your year-round Staycation!

1654 Braid Hills Dr, Pasadena

Listing courtesy of Douglas Realty LLC. Contact:

$1,850,000

Welcome to 11 Ridge Road, a beautifully renovated and expanded Cape Cod situated on a fabulous lot in the sought-after community of Linstead on the Severn. Filled with natural light, this 4-bedroom, 2.5-bath home blends timeless charm with modern updates and exceptional indoor and outdoor living spaces. The inviting living room features a cozy fireplace, while the beautifully renovated kitchen boasts a full suite of Thermador appliances. The flexible floor plan offers two main-level bedrooms (one could be a great home office), including a spacious primary suite with a beautifully updated bath, and two additional bedrooms upstairs. Convenient main-level laundry and plenty of storage space in the basement. The outdoor spaces are just as impressive! A charming screened porch, spacious paver patio, and gas-heated pool with automatic cover create the perfect setting for entertaining, relaxing, and enjoying days at home. The fabulous, fully fenced yard completes this wonderful backyard retreat. Extensively renovated and thoughtfully maintained, the home features numerous recent improvements, including a beautifully updated kitchen and bathrooms, new James Hardie siding and gutters, an upgraded 400-amp electrical panel, a Bosch hybrid HVAC system, and updated laundry appliances. These significant investments offer both style and peace of mind. But life at 11 Ridge Road is about more than just the home - it's about enjoying everyday moments and making memories.. Nestled along the Severn River, Linstead on the Severn is one of Severna Park's most treasured waterfront neighborhoods, known for its natural beauty, established charm, and strong sense of community. Imagine mornings by the river, neighborhood gatherings with friends, and evenings relaxing on your screened porch or around the pool. Situated on a peninsula surrounded by Sullivan Cove, Yantz Creek, and the Severn River, this water-privileged community offers multiple private community beaches, a playground, pavilion, and community pier and boat ramp. The voluntary citizens association hosts social events throughout the year and it’s just a few minutes from the B&A Trail, local coffee shops, shopping, dining, parks, and everything that makes Severna Park such a special place to call home. Beautifully updated, designed for entertaining, and perfectly positioned to enjoy the Linstead lifestyle - welcome home to 11 Ridge Road!

4 Beds ⋅ 3 Baths

Welcome to 11 Ridge Road, a beautifully renovated and expanded Cape Cod situated on a fabulous lot in the sought-after community of Linstead on the Severn. Filled with natural light, this 4-bedroom, 2.5-bath home blends timeless charm with modern updates and exceptional indoor and outdoor living spaces. The inviting living room features a cozy fireplace, while the beautifully renovated kitchen boasts a full suite of Thermador appliances. The flexible floor plan offers two main-level bedrooms (one could be a great home office), including a spacious primary suite with a beautifully updated bath, and two additional bedrooms upstairs. Convenient main-level laundry and plenty of storage space in the basement. The outdoor spaces are just as impressive! A charming screened porch, spacious paver patio, and gas-heated pool with automatic cover create the perfect setting for entertaining, relaxing, and enjoying days at home. The fabulous, fully fenced yard completes this wonderful backyard retreat. Extensively renovated and thoughtfully maintained, the home features numerous recent improvements, including a beautifully updated kitchen and bathrooms, new James Hardie siding and gutters, an upgraded 400-amp electrical panel, a Bosch hybrid HVAC system, and updated laundry appliances. These significant investments offer both style and peace of mind. But life at 11 Ridge Road is about more than just the home - it's about enjoying everyday moments and making memories.. Nestled along the Severn River, Linstead on the Severn is one of Severna Park's most treasured waterfront neighborhoods, known for its natural beauty, established charm, and strong sense of community. Imagine mornings by the river, neighborhood gatherings with friends, and evenings relaxing on your screened porch or around the pool. Situated on a peninsula surrounded by Sullivan Cove, Yantz Creek, and the Severn River, this water-privileged community offers multiple private community beaches, a playground, pavilion, and community pier and boat ramp. The voluntary citizens association hosts social events throughout the year and it’s just a few minutes from the B&A Trail, local coffee shops, shopping, dining, parks, and everything that makes Severna Park such a special place to call home. Beautifully updated, designed for entertaining, and perfectly positioned to enjoy the Linstead lifestyle - welcome home to 11 Ridge Road!

11 Ridge Rd, Severna Park

Listing courtesy of Compass. Contact:

$1,850,000

Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just minutes from Exit 22, approximately 10 minutes to Route 50, and only 15 minutes to historic downtown Annapolis. For boating enthusiasts, this property is truly second to none. The private pier features a 10,000-pound boat lift, water and electric service, including two 220-volt outlets, three boat slips, floating dock and approximately 5+ feet of water at mean low water, making it ideal for larger vessels. A nearby marina and gas dock provide exceptional convenience for fueling, maintenance, and everyday boating adventures. The owners have meticulously maintained and updated the home with major improvements, including a new roof (2021) and upper-level HVAC system (2025). The exterior is equally impressive, featuring an attached two-car garage and driveway parking for up to six additional vehicles. Whether you're hosting family gatherings or waterfront celebrations, there's room for everyone. Step inside and you'll immediately be captivated by breathtaking water views. The welcoming living room features the first of two fireplaces and overlooks the creek, creating the perfect setting to relax year-round. As you continue into the heart of the home, you'll discover an expansive dining area surrounded by panoramic water views that will have you lingering over every meal. Sliding doors lead to a covered brick patio and an incredible backyard designed for entertaining on any scale—from everyday cookouts to milestone celebrations, weddings, corporate events, and unforgettable waterfront parties. Pet owners will appreciate the professionally installed invisible fence, allowing your four-legged family members to safely enjoy the expansive yard. The main level also offers a spacious kitchen, large family room, private office with a convenient half bath, a generously sized bedroom, and a full laundry room. Upstairs, the luxurious owner's suite offers stunning sunrise views over the creek and features an incredible layout with his-and-her bathrooms, a walk-in closet, and a true owner's retreat experience. Two additional bedrooms share a spacious full bath, while the loft provides the perfect second gathering space for movie nights, gaming, reading, or studying. A second laundry room on the upper level adds everyday convenience, and the walk-up attic with pull-down stairs provides abundant storage. Need even more flexibility? A detached waterfront office equipped with its own mini-split heating and cooling system creates the ideal work-from-home environment, art studio, or private retreat—all while enjoying incredible views of Gingerville Creek. Properties offering this combination of panoramic waterfront views, exceptional boating amenities, generous living space, thoughtful updates, and an unbeatable Annapolis-area location are extraordinarily rare. Complete photos, floor plans, and additional details will be available soon. Don't miss your opportunity to own one of the area's premier waterfront homes

4 Beds ⋅ 5 Baths

Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just minutes from Exit 22, approximately 10 minutes to Route 50, and only 15 minutes to historic downtown Annapolis. For boating enthusiasts, this property is truly second to none. The private pier features a 10,000-pound boat lift, water and electric service, including two 220-volt outlets, three boat slips, floating dock and approximately 5+ feet of water at mean low water, making it ideal for larger vessels. A nearby marina and gas dock provide exceptional convenience for fueling, maintenance, and everyday boating adventures. The owners have meticulously maintained and updated the home with major improvements, including a new roof (2021) and upper-level HVAC system (2025). The exterior is equally impressive, featuring an attached two-car garage and driveway parking for up to six additional vehicles. Whether you're hosting family gatherings or waterfront celebrations, there's room for everyone. Step inside and you'll immediately be captivated by breathtaking water views. The welcoming living room features the first of two fireplaces and overlooks the creek, creating the perfect setting to relax year-round. As you continue into the heart of the home, you'll discover an expansive dining area surrounded by panoramic water views that will have you lingering over every meal. Sliding doors lead to a covered brick patio and an incredible backyard designed for entertaining on any scale—from everyday cookouts to milestone celebrations, weddings, corporate events, and unforgettable waterfront parties. Pet owners will appreciate the professionally installed invisible fence, allowing your four-legged family members to safely enjoy the expansive yard. The main level also offers a spacious kitchen, large family room, private office with a convenient half bath, a generously sized bedroom, and a full laundry room. Upstairs, the luxurious owner's suite offers stunning sunrise views over the creek and features an incredible layout with his-and-her bathrooms, a walk-in closet, and a true owner's retreat experience. Two additional bedrooms share a spacious full bath, while the loft provides the perfect second gathering space for movie nights, gaming, reading, or studying. A second laundry room on the upper level adds everyday convenience, and the walk-up attic with pull-down stairs provides abundant storage. Need even more flexibility? A detached waterfront office equipped with its own mini-split heating and cooling system creates the ideal work-from-home environment, art studio, or private retreat—all while enjoying incredible views of Gingerville Creek. Properties offering this combination of panoramic waterfront views, exceptional boating amenities, generous living space, thoughtful updates, and an unbeatable Annapolis-area location are extraordinarily rare. Complete photos, floor plans, and additional details will be available soon. Don't miss your opportunity to own one of the area's premier waterfront homes

120 Island View Dr, Annapolis

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$1,850,000

Rare mixed-use opportunity on Annapolis' premier commercial corridor. Positioned directly on West Street (MD Route 450), this versatile, income-producing building pairs a roughly 2,000 SF ground-floor showroom with two legal second-floor apartments and a substantial detached garage with workshop — all on a 12,428 SF lot with private parking for about six vehicles, a genuine premium on this corridor. The ground level is an open, high-visibility showroom with direct West Street frontage, well suited to retail, a gallery or design studio, professional offices, or a service business. Upstairs, two legal apartments (2BR/1BA each, per owner) deliver real live/work flexibility — one is currently configured as offices with a full kitchen. Run your business below and lease or occupy above, lease every component separately, or use the upper level as executive offices. The three-bay detached garage is a true standout: two overhead doors plus a rear man-door, its own heating system, and a wood stove for year-round use — conditioned workshop and storage that's nearly impossible to replicate in this location. Major systems are already addressed, with two newer HVAC units and a newer roof reducing near-term capital needs. Public water and sewer, 200+ amp electric service, and a Flood Zone X location (outside the Special Flood Hazard Area) round out a favorable operating profile. BCE (Business Corridor Enhancement) zoning supports a broad mix of commercial and residential uses, giving owner-operators, investors, and developers exceptional flexibility on one of Annapolis' busiest, highest-visibility corridors. Schedule your private tour today. Information deemed reliable but not guaranteed. Square footage, apartment legality, zoning uses, and systems to be independently verified by buyer.

1977 West St, Annapolis

Listing courtesy of Real Broker, LLC - Chester. Contact:

$1,800,000

This is the one you've been waiting for! Welcome to 3675 1st Avenue, a stunning new construction (2024) home located in the desirable Selby-on-the-Bay community of Edgewater with waterfront access and shared pier! Experience the peace and intense relaxation associated with living on the water in this beautiful new build which features a wrap around deck and five 12 foot sliding doors that open six feet wide, allowing true inside/outside living. Fall asleep to the sound of the waves crashing against the shore. The open-concept main level has a large living room (with electric fireplace), dining room, and gourmet kitchen. Kitchen features a ten burner double gas stove/oven and an oversized center island. Laundry and powder room are conveniently located on the main level as well as a full secondary owner's suite! The upper level owner suite features a walk-in closet and spa-style en-suite bathroom with a 72 inch standalone tub. The generously sized secondary bedrooms get plenty of natural light and have ample closet space. The lower level is a two car garage with an enormous amount of storage space. Space under stairs has been fitted and plumbed for a bathroom. The large level yard, is ideal for entertaining or gardening. Property has not one but two driveways that will easily accommodate four cars. Other Highlights: Bamboo flooring throughout Smart hub light switches Hot water heater is tankless propane (continuous water 24/7!) Well and septic are Mayo City This is a rare opportunity to purchase new construction in one of Edgewater’s most sought-after waterfront communities. Just minutes to Annapolis, major commuter routes, and local marinas. Schedule your showing today!

5 Beds ⋅ 4 Baths

This is the one you've been waiting for! Welcome to 3675 1st Avenue, a stunning new construction (2024) home located in the desirable Selby-on-the-Bay community of Edgewater with waterfront access and shared pier! Experience the peace and intense relaxation associated with living on the water in this beautiful new build which features a wrap around deck and five 12 foot sliding doors that open six feet wide, allowing true inside/outside living. Fall asleep to the sound of the waves crashing against the shore. The open-concept main level has a large living room (with electric fireplace), dining room, and gourmet kitchen. Kitchen features a ten burner double gas stove/oven and an oversized center island. Laundry and powder room are conveniently located on the main level as well as a full secondary owner's suite! The upper level owner suite features a walk-in closet and spa-style en-suite bathroom with a 72 inch standalone tub. The generously sized secondary bedrooms get plenty of natural light and have ample closet space. The lower level is a two car garage with an enormous amount of storage space. Space under stairs has been fitted and plumbed for a bathroom. The large level yard, is ideal for entertaining or gardening. Property has not one but two driveways that will easily accommodate four cars. Other Highlights: Bamboo flooring throughout Smart hub light switches Hot water heater is tankless propane (continuous water 24/7!) Well and septic are Mayo City This is a rare opportunity to purchase new construction in one of Edgewater’s most sought-after waterfront communities. Just minutes to Annapolis, major commuter routes, and local marinas. Schedule your showing today!

3675 1st Ave, Edgewater

Listing courtesy of Corner House Realty. Contact:

Historic charm, expansive grounds, and an extraordinary collection of outbuildings come together at 1554 Millersville Road. Known as the Dr. Harry Baldwin Gantt House, this distinctive property dates back to the 1860s and is recognized in the Maryland Inventory of Historic Properties and Anne Arundel County's Inventory of Historic Resources. Situated on approximately 16 acres, the estate features sweeping lawns, open fields, mature trees, and a winding paved driveway. Offering approximately 6,300 square feet, the residence includes six bedrooms, three full baths, and two half baths. Rich in architectural character, the home showcases beautiful wood floors, detailed moldings, built-in cabinetry, multiple fireplaces, exposed brick accents, and a graceful staircase. Tall windows overlook the grounds, while French doors lead to a covered porch. A spacious kitchen with a center island and a third-floor loft bedroom area with a kitchenette add to the home's versatility. The property's extensive outbuildings are truly exceptional! A massive detached workshop with heated floors and additional storage is ideal for woodworking, automotive projects, or the serious hobbyist. A three-car garage near the residence, a separate four-bay garage perfect for farming equipment or recreational vehicles, and a picturesque barn with twin cupolas provide incredible flexibility and storage. Adding to its appeal, the property borders approximately 33 acres of Anne Arundel County parkland currently under construction. Whether envisioned as a private country estate, hobby farm, or simply a peaceful retreat, this remarkable property offers endless possibilities. Conveniently located near Crofton and Annapolis, it combines the tranquility of country living with easy access to everyday amenities. A rare opportunity to own a piece of Maryland history with the space, character, and versatility to make it your own!

Historic charm, expansive grounds, and an extraordinary collection of outbuildings come together at 1554 Millersville Road. Known as the Dr. Harry Baldwin Gantt House, this distinctive property dates back to the 1860s and is recognized in the Maryland Inventory of Historic Properties and Anne Arundel County's Inventory of Historic Resources. Situated on approximately 16 acres, the estate features sweeping lawns, open fields, mature trees, and a winding paved driveway. Offering approximately 6,300 square feet, the residence includes six bedrooms, three full baths, and two half baths. Rich in architectural character, the home showcases beautiful wood floors, detailed moldings, built-in cabinetry, multiple fireplaces, exposed brick accents, and a graceful staircase. Tall windows overlook the grounds, while French doors lead to a covered porch. A spacious kitchen with a center island and a third-floor loft bedroom area with a kitchenette add to the home's versatility. The property's extensive outbuildings are truly exceptional! A massive detached workshop with heated floors and additional storage is ideal for woodworking, automotive projects, or the serious hobbyist. A three-car garage near the residence, a separate four-bay garage perfect for farming equipment or recreational vehicles, and a picturesque barn with twin cupolas provide incredible flexibility and storage. Adding to its appeal, the property borders approximately 33 acres of Anne Arundel County parkland currently under construction. Whether envisioned as a private country estate, hobby farm, or simply a peaceful retreat, this remarkable property offers endless possibilities. Conveniently located near Crofton and Annapolis, it combines the tranquility of country living with easy access to everyday amenities. A rare opportunity to own a piece of Maryland history with the space, character, and versatility to make it your own!

1554 Millersville Rd, Millersville

Listing courtesy of Samson Properties. Contact:

Well-Established and Profitable Daycare Business for Sale Excellent opportunity to acquire a well-established and profitable daycare business with a strong reputation and an attractive, low monthly rent. Licensed for 80+ children, this established operation offers an excellent foundation for continued success and future growth. The facility features: 7 classrooms designed for childcare and learning 2 separate children’s bathrooms, designated for boys and girls 1 separate staff bathroom Large kitchen area Convenient open parking for staff and families Attractive, low rental rate to help manage operating expenses This is an ideal opportunity for an experienced childcare operator looking to expand or an entrepreneur seeking to enter the childcare industry with an established business and existing reputation. CONFIDENTIAL SALE – PLEASE DO NOT DISTURB To protect the business and its daily operations, buyers, agents, and other interested parties must not visit the property, approach employees, contact staff, or make inquiries directly at the facility. All inquiries, requests for additional information, and property appointments must be coordinated exclusively through the listing agent. Unauthorized visits or contact with employees are strictly prohibited. Location information will be provided only after a confidentiality agreement has been signed.

Cut Roadway, Severna Park

Listing courtesy of CENTURY 21 New Millennium. Contact:

Welcome to 1378 Kinloch Circle — Glen Oban's Finest Nestled in the highly sought-after Glen Oban community, this address offers a rare combination of top-tier amenities: 10/10 school ratings, a marina with deep MLW, a brand-new playground, basketball and tennis courts, a community pool, and an active association hosting year-round events. Finding a few of these features in one neighborhood is uncommon — finding all of them is what makes Glen Oban truly exceptional. This beautifully updated mid-century modern home elevates that already-desirable setting into a genuine buyer's dream. As you approach, the sheer scale of the nearly 2-acre lot comes into view — plenty of room for kids to play, pets to roam, or even a future pool. The U-shaped driveway and two-car garage provide generous parking for family and guests alike. You can enter through the formal front door into a striking entryway, or through the newly renovated patio directly into the beautifully remodeled kitchen. Inside, the main level showcases the home's mid-century modern character with walls of windows, soaring ceilings, and natural light throughout the day. Thoughtful, high-end upgrades are evident everywhere — white oak flooring throughout the main level, premium kitchen appliances, natural stone countertops, and a newly renovated pantry, mudroom, bathrooms, patio, and decking. The seamless flow between the kitchen, dining room, sunken electric fireplace, and spacious living room creates a truly stunning gathering space. Upstairs, the bedroom level features four bedrooms, including an en-suite primary and a full guest bath. Each bedroom is generously sized, and the primary suite offers his-and-hers closets plus a private walk-out balcony. The top level opens to a loft overlooking the living space below, complete with its own full bathroom — ideal as a home office, playroom, art studio, or easily enclosed to create a fifth bedroom. Downstairs, the nearly 6,000-square-foot home continues to impress with a soundproof movie room, temperature-controlled wine cellar, an au-pair/in-law suite with its own living area and kitchenette, a pellet stove, and a spacious game room. Outside, mature landscaping and a fig tree line create a peaceful, private retreat — all just 10 minutes from Annapolis and 35 minutes from Baltimore/DC. This is a rare opportunity in an exceptional community. Don't wait — this one won't last.

5 Beds ⋅ 6 Baths

Welcome to 1378 Kinloch Circle — Glen Oban's Finest Nestled in the highly sought-after Glen Oban community, this address offers a rare combination of top-tier amenities: 10/10 school ratings, a marina with deep MLW, a brand-new playground, basketball and tennis courts, a community pool, and an active association hosting year-round events. Finding a few of these features in one neighborhood is uncommon — finding all of them is what makes Glen Oban truly exceptional. This beautifully updated mid-century modern home elevates that already-desirable setting into a genuine buyer's dream. As you approach, the sheer scale of the nearly 2-acre lot comes into view — plenty of room for kids to play, pets to roam, or even a future pool. The U-shaped driveway and two-car garage provide generous parking for family and guests alike. You can enter through the formal front door into a striking entryway, or through the newly renovated patio directly into the beautifully remodeled kitchen. Inside, the main level showcases the home's mid-century modern character with walls of windows, soaring ceilings, and natural light throughout the day. Thoughtful, high-end upgrades are evident everywhere — white oak flooring throughout the main level, premium kitchen appliances, natural stone countertops, and a newly renovated pantry, mudroom, bathrooms, patio, and decking. The seamless flow between the kitchen, dining room, sunken electric fireplace, and spacious living room creates a truly stunning gathering space. Upstairs, the bedroom level features four bedrooms, including an en-suite primary and a full guest bath. Each bedroom is generously sized, and the primary suite offers his-and-hers closets plus a private walk-out balcony. The top level opens to a loft overlooking the living space below, complete with its own full bathroom — ideal as a home office, playroom, art studio, or easily enclosed to create a fifth bedroom. Downstairs, the nearly 6,000-square-foot home continues to impress with a soundproof movie room, temperature-controlled wine cellar, an au-pair/in-law suite with its own living area and kitchenette, a pellet stove, and a spacious game room. Outside, mature landscaping and a fig tree line create a peaceful, private retreat — all just 10 minutes from Annapolis and 35 minutes from Baltimore/DC. This is a rare opportunity in an exceptional community. Don't wait — this one won't last.

1378 Kinloch Cir, Arnold

Listing courtesy of RE/MAX Distinctive Real Estate, Inc.. Contact:

Ooh la la, Eastport. There is something unmistakably special about life here—and 820 Bay Ridge Avenue captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence delivers the rare combination of space, sophistication, outdoor living, and walkability, all just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and a gracious brick front porch create a picture-perfect welcome. Step inside to more than 4,000 square feet of beautifully finished living across FOUR levels, where rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters create a home that feels polished without ever feeling fussy. Thoughtfully customized during construction, the residence includes numerous builder upgrades, enhanced electrical features, and details designed to make everyday living as effortless as the home is beautiful. At its heart is a fabulous kitchen with honed granite countertops, premium appliances, abundant cabinetry, and a generous center island opening seamlessly to the family room and upgraded gas fireplace. The formal dining room is ready for holidays, celebrations, and memorable dinners, while the adjoining sitting room or study is perfect for working from home, curling up with a favorite book, or ending the evening with a bourbon. And then there is the outdoor living. Morning coffee on the front porch overlooking the flower garden. Dinner in your private English courtyard. Cocktails under the stars on the second-floor terrace. Professionally enhanced landscaping creates an intimate retreat, while ceiling fans, a dedicated natural gas line for grilling, and the opportunity for a future fire feature make these spaces as functional as they are beautiful. Upstairs, the primary suite feels like a private escape, with a custom walk-in closet, spa-inspired bath, and expansive sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft brings even more possibilities—a home office, fitness studio, media room, guest retreat, or whatever life calls for next. The finished lower level adds a spacious family room and full bath, providing even more flexibility for entertaining, extended stays, or multigenerational living. And in a feature rarely found, the home was designed with the future in mind with a framed elevator shaft, allowing an elevator to be added without compromising the architecture or thoughtful floor plan. But perhaps the greatest luxury of 820 Bay Ridge Avenue is everything waiting just outside your front door. Walk to St. Mary’s. Walk to dinner. Walk to neighborhood cafés and marinas. Walk to the Annapolis Yacht Club and Eastport Yacht Club. Cross the Spa Creek Drawbridge into Historic Downtown Annapolis and City Dock. Spend the afternoon on the Chesapeake, meet friends for dinner on the water, browse the shops and galleries downtown, or take the water taxi home after an evening out. Morning coffee around the corner. An afternoon on the water. Dinner in Eastport. Ice cream at City Dock. School, sailing, restaurants, shopping, marinas, yacht clubs, and downtown Annapolis—all without having to get in the car. And somehow, you still come home to more than 4,000 square feet, four finished levels, beautiful outdoor spaces, exceptional privacy, extensive custom upgrades, and future elevator capability. No need to choose between space, sophistication, and walkability. Here, you get all three. Polished. Coastal. Effortlessly Annapolis. Ooh la la, indeed.

4 Beds ⋅ 5 Baths

Ooh la la, Eastport. There is something unmistakably special about life here—and 820 Bay Ridge Avenue captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence delivers the rare combination of space, sophistication, outdoor living, and walkability, all just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and a gracious brick front porch create a picture-perfect welcome. Step inside to more than 4,000 square feet of beautifully finished living across FOUR levels, where rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters create a home that feels polished without ever feeling fussy. Thoughtfully customized during construction, the residence includes numerous builder upgrades, enhanced electrical features, and details designed to make everyday living as effortless as the home is beautiful. At its heart is a fabulous kitchen with honed granite countertops, premium appliances, abundant cabinetry, and a generous center island opening seamlessly to the family room and upgraded gas fireplace. The formal dining room is ready for holidays, celebrations, and memorable dinners, while the adjoining sitting room or study is perfect for working from home, curling up with a favorite book, or ending the evening with a bourbon. And then there is the outdoor living. Morning coffee on the front porch overlooking the flower garden. Dinner in your private English courtyard. Cocktails under the stars on the second-floor terrace. Professionally enhanced landscaping creates an intimate retreat, while ceiling fans, a dedicated natural gas line for grilling, and the opportunity for a future fire feature make these spaces as functional as they are beautiful. Upstairs, the primary suite feels like a private escape, with a custom walk-in closet, spa-inspired bath, and expansive sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft brings even more possibilities—a home office, fitness studio, media room, guest retreat, or whatever life calls for next. The finished lower level adds a spacious family room and full bath, providing even more flexibility for entertaining, extended stays, or multigenerational living. And in a feature rarely found, the home was designed with the future in mind with a framed elevator shaft, allowing an elevator to be added without compromising the architecture or thoughtful floor plan. But perhaps the greatest luxury of 820 Bay Ridge Avenue is everything waiting just outside your front door. Walk to St. Mary’s. Walk to dinner. Walk to neighborhood cafés and marinas. Walk to the Annapolis Yacht Club and Eastport Yacht Club. Cross the Spa Creek Drawbridge into Historic Downtown Annapolis and City Dock. Spend the afternoon on the Chesapeake, meet friends for dinner on the water, browse the shops and galleries downtown, or take the water taxi home after an evening out. Morning coffee around the corner. An afternoon on the water. Dinner in Eastport. Ice cream at City Dock. School, sailing, restaurants, shopping, marinas, yacht clubs, and downtown Annapolis—all without having to get in the car. And somehow, you still come home to more than 4,000 square feet, four finished levels, beautiful outdoor spaces, exceptional privacy, extensive custom upgrades, and future elevator capability. No need to choose between space, sophistication, and walkability. Here, you get all three. Polished. Coastal. Effortlessly Annapolis. Ooh la la, indeed.

820 Bay Ridge Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,795,000

Nestled in the serene community of Galesville, this exquisite Waterfront ranch-style residence with an additional 3 bedroom rental home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Set on a sprawling 0.98-acre lot with 119 feet of waterfront along the picturesque Lerch Creek, this home is a true sanctuary. Step inside to discover a thoughtfully designed interior that exudes warmth and sophistication. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating an inviting space for both relaxation and entertaining. The Dinning area, adorned with a cozy gas fireplace and elegant mantel, serves as the heart of the home, while large windows bathe the space in natural light and provide stunning views of the tranquil water. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, an island for casual dining, and ample cabinetry. Enjoy the convenience of an eat-in kitchen, perfect for intimate meals or gatherings. The primary suite offers a private retreat with a luxurious en-suite bathroom, complete with a walk-in shower. With two spacious bedrooms and two full bathrooms, this residence accommodates both comfort and privacy. Additional interior highlights include beautiful wood floors, ceiling fans, and modern window treatments that enhance the home's aesthetic. Outside, the property boasts a beautifully landscaped yard with level areas for outdoor activities, complemented by a porch on the waterside for al fresco dining or morning coffee. The community amenities are unparalleled, featuring a swimming pool, tennis courts, and direct access to the river for kayaking, fishing, and boating-ideal for those who appreciate an active lifestyle. Major renovations completed in 2025 on 4852 Church Lane to ensure that this home is in excellent condition, combining modern conveniences with timeless charm. The exterior is crafted from durable brick, providing both elegance and longevity, while the ample parking space accommodates guests with ease. Experience the tranquility of riverfront living, where every day feels like a vacation. This property is not just a home; it's a lifestyle, offering the perfect blend of luxury, comfort, and natural beauty. Embrace the opportunity to make this stunning residence your own and enjoy the exclusive lifestyle it offers and only a short walk to two Waterfront restaurants within the Galesville Village. Also included is 4850 Church Lane a 3 Bedroom home on the property that is currently a rental but could be a guest home

2 Beds ⋅ 2 Baths

Nestled in the serene community of Galesville, this exquisite Waterfront ranch-style residence with an additional 3 bedroom rental home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Set on a sprawling 0.98-acre lot with 119 feet of waterfront along the picturesque Lerch Creek, this home is a true sanctuary. Step inside to discover a thoughtfully designed interior that exudes warmth and sophistication. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating an inviting space for both relaxation and entertaining. The Dinning area, adorned with a cozy gas fireplace and elegant mantel, serves as the heart of the home, while large windows bathe the space in natural light and provide stunning views of the tranquil water. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, an island for casual dining, and ample cabinetry. Enjoy the convenience of an eat-in kitchen, perfect for intimate meals or gatherings. The primary suite offers a private retreat with a luxurious en-suite bathroom, complete with a walk-in shower. With two spacious bedrooms and two full bathrooms, this residence accommodates both comfort and privacy. Additional interior highlights include beautiful wood floors, ceiling fans, and modern window treatments that enhance the home's aesthetic. Outside, the property boasts a beautifully landscaped yard with level areas for outdoor activities, complemented by a porch on the waterside for al fresco dining or morning coffee. The community amenities are unparalleled, featuring a swimming pool, tennis courts, and direct access to the river for kayaking, fishing, and boating-ideal for those who appreciate an active lifestyle. Major renovations completed in 2025 on 4852 Church Lane to ensure that this home is in excellent condition, combining modern conveniences with timeless charm. The exterior is crafted from durable brick, providing both elegance and longevity, while the ample parking space accommodates guests with ease. Experience the tranquility of riverfront living, where every day feels like a vacation. This property is not just a home; it's a lifestyle, offering the perfect blend of luxury, comfort, and natural beauty. Embrace the opportunity to make this stunning residence your own and enjoy the exclusive lifestyle it offers and only a short walk to two Waterfront restaurants within the Galesville Village. Also included is 4850 Church Lane a 3 Bedroom home on the property that is currently a rental but could be a guest home

4852 & 4850 Church Ln, Galesville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,795,000

***BRAND NEW & MOVE-IN READY*** Welcome to this breathtaking modern farmhouse, a seamless blend of contemporary style, rustic charm and high-end, contemporary luxury. Located down a stately private driveway and nestled on a premium 5-acre homesite, this setting balances peaceful seclusion with refined functionality. The exterior welcomes you with a sophisticated mix of crisp white Hardie plank and woodgrain siding, warm cedar accents, stone water table and columns and premium black Pella wood windows. Inside, this meticulously crafted home offers nearly 6,000 finished square feet of exceptional living space including 5 bedrooms, 4.5 beautifully appointed bathrooms, and a finished basement designed for effortless entertainment. At the heart of the home is a stunning gourmet kitchen featuring stylish timber and dove slim shaker cabinetry, large center island, calacatta quartz countertops and slab backsplash, a professional-grade 48” dual fuel 6 burner range, artisan range hood, and refined brass and rose gold fixtures. Additional main level amenities include 7.5” couture engineered hardwood floors, 10’ ceilings, a spacious family room with modern gas fireplace and large picture windows, formal dining room, private office, morning room, built-ins and custom trim work throughout. The second level consists of 4 bedrooms, 3 full baths and a multi-purpose loft – perfect for an entertainment lounge, playroom or second office. The luxurious owner's suite offers an expansive and thoughtfully designed layout featuring a modern gas fireplace, wet bar, a 220+ sqft walk-in closet with custom organization system, and a spa-like bath with walk-in shower clad with floor to ceiling tile, standalone soaking tub and high-end cabinetry. The finished lower level includes an expansive recreational room, 5th bedroom, a full bath and ample storage space. Additional amenities include over 500 sqft of covered outdoor living space including a screened-in porch, 3 car garage, 400A electric service, high efficiency dual zone hvac, EV charging prewire and so much more. Enjoy all these amenities on a breathtaking homesite with NO HOA or restrictive covenants. This stunning one-of-a-kind property will not last long, schedule your private tour today!

5 Beds ⋅ 5 Baths

***BRAND NEW & MOVE-IN READY*** Welcome to this breathtaking modern farmhouse, a seamless blend of contemporary style, rustic charm and high-end, contemporary luxury. Located down a stately private driveway and nestled on a premium 5-acre homesite, this setting balances peaceful seclusion with refined functionality. The exterior welcomes you with a sophisticated mix of crisp white Hardie plank and woodgrain siding, warm cedar accents, stone water table and columns and premium black Pella wood windows. Inside, this meticulously crafted home offers nearly 6,000 finished square feet of exceptional living space including 5 bedrooms, 4.5 beautifully appointed bathrooms, and a finished basement designed for effortless entertainment. At the heart of the home is a stunning gourmet kitchen featuring stylish timber and dove slim shaker cabinetry, large center island, calacatta quartz countertops and slab backsplash, a professional-grade 48” dual fuel 6 burner range, artisan range hood, and refined brass and rose gold fixtures. Additional main level amenities include 7.5” couture engineered hardwood floors, 10’ ceilings, a spacious family room with modern gas fireplace and large picture windows, formal dining room, private office, morning room, built-ins and custom trim work throughout. The second level consists of 4 bedrooms, 3 full baths and a multi-purpose loft – perfect for an entertainment lounge, playroom or second office. The luxurious owner's suite offers an expansive and thoughtfully designed layout featuring a modern gas fireplace, wet bar, a 220+ sqft walk-in closet with custom organization system, and a spa-like bath with walk-in shower clad with floor to ceiling tile, standalone soaking tub and high-end cabinetry. The finished lower level includes an expansive recreational room, 5th bedroom, a full bath and ample storage space. Additional amenities include over 500 sqft of covered outdoor living space including a screened-in porch, 3 car garage, 400A electric service, high efficiency dual zone hvac, EV charging prewire and so much more. Enjoy all these amenities on a breathtaking homesite with NO HOA or restrictive covenants. This stunning one-of-a-kind property will not last long, schedule your private tour today!

1230 Indian Landing Rd, Millersville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,795,000

SOME HOMES ARE IMPRESSIVE. OTHERS ARE UNFORGETTABLE. Welcome to 1621 Millersville Road, a remarkable private estate where 3.37 acres of breathtaking surroundings, more than 6,200 square feet of beautifully appointed living space, and an extraordinary resort-inspired lifestyle come together in one exceptional offering. From the moment you arrive, there's a sense that you've discovered something special. Beyond the doors, gracious interiors unfold with dramatic architectural details, elegant arched hallways, beautiful millwork, two fireplaces, and expansive gathering spaces designed for everything from intimate evenings to unforgettable celebrations. But the real magic begins outdoors. Imagine long summer afternoons beside your heated swimming pool, cocktails beneath the stunning entertaining pavilion, candlelit dinners on the expansive slate patio, and evenings spent enjoying the privacy of your own magnificent grounds. This is the kind of setting that turns an ordinary weekend into an extraordinary escape—without ever leaving home. Inside, the beautifully designed residence offers four spacious ensuite bedrooms, inviting living and entertaining areas, a wonderful kitchen, and rooftop balconies that provide peaceful places to retreat above it all. Every season brings another reason to fall in love, from spectacular summer entertaining to cozy winter evenings beside the fire. Significant recent investments further enhance this exceptional property, including HVAC improvements, substantial septic upgrades with a new drain field and pump pit, renovations to the home's wing, roof improvements, updated fixtures, and extensive landscaping. Ideally positioned with convenient access to Annapolis, Baltimore, Washington, D.C., and BWI Airport, this extraordinary estate offers a rare combination of privacy, acreage, elegance, and accessibility. At $1,795,000, the opportunity is as compelling as the lifestyle. This isn't simply a place to live. It's a place to entertain beautifully, escape effortlessly, and make every day feel like something worth celebrating. Some properties must be experienced to be fully appreciated. This is one of them.

4 Beds ⋅ 6 Baths

SOME HOMES ARE IMPRESSIVE. OTHERS ARE UNFORGETTABLE. Welcome to 1621 Millersville Road, a remarkable private estate where 3.37 acres of breathtaking surroundings, more than 6,200 square feet of beautifully appointed living space, and an extraordinary resort-inspired lifestyle come together in one exceptional offering. From the moment you arrive, there's a sense that you've discovered something special. Beyond the doors, gracious interiors unfold with dramatic architectural details, elegant arched hallways, beautiful millwork, two fireplaces, and expansive gathering spaces designed for everything from intimate evenings to unforgettable celebrations. But the real magic begins outdoors. Imagine long summer afternoons beside your heated swimming pool, cocktails beneath the stunning entertaining pavilion, candlelit dinners on the expansive slate patio, and evenings spent enjoying the privacy of your own magnificent grounds. This is the kind of setting that turns an ordinary weekend into an extraordinary escape—without ever leaving home. Inside, the beautifully designed residence offers four spacious ensuite bedrooms, inviting living and entertaining areas, a wonderful kitchen, and rooftop balconies that provide peaceful places to retreat above it all. Every season brings another reason to fall in love, from spectacular summer entertaining to cozy winter evenings beside the fire. Significant recent investments further enhance this exceptional property, including HVAC improvements, substantial septic upgrades with a new drain field and pump pit, renovations to the home's wing, roof improvements, updated fixtures, and extensive landscaping. Ideally positioned with convenient access to Annapolis, Baltimore, Washington, D.C., and BWI Airport, this extraordinary estate offers a rare combination of privacy, acreage, elegance, and accessibility. At $1,795,000, the opportunity is as compelling as the lifestyle. This isn't simply a place to live. It's a place to entertain beautifully, escape effortlessly, and make every day feel like something worth celebrating. Some properties must be experienced to be fully appreciated. This is one of them.

1621 Millersville Rd, Millersville

Listing courtesy of Coldwell Banker Realty. Contact:

$1,790,000

OPEN HOUSE Saturday 10/24 from 1-3PM. Historic Portland Manor – Allendale is privately set on 4.5 acres off sought-after Brooks Woods Road, surrounded by mature trees, neighboring acreage, and pastoral surroundings. A heritage tree-lined drive leads to the residence, framed by established landscaping, gorgeous brick walkways surrounding the home, landscape lighting, covered porches, and a renovated in-ground pool. Dating back to the late 1700s, with additions completed in the early 1800s, the home has been thoughtfully restored and updated while preserving its historic integrity and original craftsmanship. Offering an estimated 5,060 square feet, the property includes six bedrooms and four and a half baths across the main residence and separate in-law suite. Interior features include original heart pine flooring, restored historic windows, six fireplaces, a traditional central hall layout, three staircases, multiple gathering spaces, and extensive custom built-ins and storage throughout. The main level includes a formal dining room with marble fireplace and adjoining butler’s pantry, family room with restored marble fireplace, living room with fireplace and custom built-ins, greenhouse room, powder room, and multiple access points to the home’s covered porches and outdoor living spaces. The custom kitchen features extensive handmade cabinetry and tile work, custom shelving and pantry storage, soapstone and butcher block countertops, commercial-grade gas cooking with a double gas range, vent hood, griddle, separate service sink, and generous preparation space designed for entertaining and everyday functionality. A storage closet beneath the main staircase and extensive built-in cabinetry throughout the connecting gallery to the in-law suite provide exceptional functional storage rarely found in historic homes. The second level includes the primary suite with a large walk-in closet, private kitchenette, fireplace, and ensuite bath. Two additional bedrooms are located on this level, each featuring fireplaces, with one offering an ensuite bathroom. The third floor offers two additional bedrooms, a full bathroom, a large finished storage closet, and expansive attic storage space. The separate in-law suite, originally constructed in 1785, includes a living and dining area, kitchenette, full bathroom with private laundry, and an upper-level bedroom with vaulted A-frame ceiling. The residence includes eight exterior doors leading to approximately 1,000 square feet of covered brick porches, landscaped walkways, pool areas, and outdoor gathering spaces, creating a seamless connection between the home and grounds. Additional upgrades include fresh exterior paint on the entire home (2026), high-efficiency foam insulation in the attic, roof space, and crawlspace, and a comprehensive exterior restoration. The siding was removed and rebuilt with new Rockwool sidewall insulation, plywood sheathing, and infiltration fabric. Outdoor features include a fully renovated 20’ x 40’ pool (2025), pool house, custom fire pit patio with built-in seating, large deck with new decking (2025), fenced areas, extensive landscape lighting, and a custom Williamsburg-style chicken coop. Major system updates include two high-efficiency HVAC systems, plumbing system replaced in 2013, electrical systems and new 400-amp electric service was redone (2025). The exterior was fully repainted in 2026. A rare offering combining historic character, extensive restoration, privacy, acreage, and modern livability, conveniently located near The Cannon Club, local farmers markets, waterfront dining, and commuter routes. Two Tax IDs convey.

OPEN HOUSE Saturday 10/24 from 1-3PM. Historic Portland Manor – Allendale is privately set on 4.5 acres off sought-after Brooks Woods Road, surrounded by mature trees, neighboring acreage, and pastoral surroundings. A heritage tree-lined drive leads to the residence, framed by established landscaping, gorgeous brick walkways surrounding the home, landscape lighting, covered porches, and a renovated in-ground pool. Dating back to the late 1700s, with additions completed in the early 1800s, the home has been thoughtfully restored and updated while preserving its historic integrity and original craftsmanship. Offering an estimated 5,060 square feet, the property includes six bedrooms and four and a half baths across the main residence and separate in-law suite. Interior features include original heart pine flooring, restored historic windows, six fireplaces, a traditional central hall layout, three staircases, multiple gathering spaces, and extensive custom built-ins and storage throughout. The main level includes a formal dining room with marble fireplace and adjoining butler’s pantry, family room with restored marble fireplace, living room with fireplace and custom built-ins, greenhouse room, powder room, and multiple access points to the home’s covered porches and outdoor living spaces. The custom kitchen features extensive handmade cabinetry and tile work, custom shelving and pantry storage, soapstone and butcher block countertops, commercial-grade gas cooking with a double gas range, vent hood, griddle, separate service sink, and generous preparation space designed for entertaining and everyday functionality. A storage closet beneath the main staircase and extensive built-in cabinetry throughout the connecting gallery to the in-law suite provide exceptional functional storage rarely found in historic homes. The second level includes the primary suite with a large walk-in closet, private kitchenette, fireplace, and ensuite bath. Two additional bedrooms are located on this level, each featuring fireplaces, with one offering an ensuite bathroom. The third floor offers two additional bedrooms, a full bathroom, a large finished storage closet, and expansive attic storage space. The separate in-law suite, originally constructed in 1785, includes a living and dining area, kitchenette, full bathroom with private laundry, and an upper-level bedroom with vaulted A-frame ceiling. The residence includes eight exterior doors leading to approximately 1,000 square feet of covered brick porches, landscaped walkways, pool areas, and outdoor gathering spaces, creating a seamless connection between the home and grounds. Additional upgrades include fresh exterior paint on the entire home (2026), high-efficiency foam insulation in the attic, roof space, and crawlspace, and a comprehensive exterior restoration. The siding was removed and rebuilt with new Rockwool sidewall insulation, plywood sheathing, and infiltration fabric. Outdoor features include a fully renovated 20’ x 40’ pool (2025), pool house, custom fire pit patio with built-in seating, large deck with new decking (2025), fenced areas, extensive landscape lighting, and a custom Williamsburg-style chicken coop. Major system updates include two high-efficiency HVAC systems, plumbing system replaced in 2013, electrical systems and new 400-amp electric service was redone (2025). The exterior was fully repainted in 2026. A rare offering combining historic character, extensive restoration, privacy, acreage, and modern livability, conveniently located near The Cannon Club, local farmers markets, waterfront dining, and commuter routes. Two Tax IDs convey.

5503 Brooks Woods Rd, Lothian

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,775,000

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

5 Beds ⋅ 4 Baths

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

3124 Starboard Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,775,000

Waterfront on the Chesapeake Bay! Welcome to 7017 Bay Front Drive, a charming two-story summer cottage in Annapolis with unobstructed views of the Bay and Bay Bridge. Watch the Blue Angels fly overhead, catch Fourth of July fireworks, or simply enjoy the boats passing by — all from home. Swim, kayak, fish, crab, paddle board, or boat right from your front yard. The main level offers an open-concept kitchen, dining area, and family room designed to maximize waterfront views, plus a sleeping area with half bath and closet, a full bath, and laundry. Upstairs, the entire level serves as a private primary suite with sweeping Bay views and its own full bath. Outside features riprap shoreline protection, a storage shed for waterfront gear, and an existing pier and boat slip ready to be restored. More than a cottage — it’s your front-row seat to life on the Chesapeake Bay.

2 Beds ⋅ 3 Baths

Waterfront on the Chesapeake Bay! Welcome to 7017 Bay Front Drive, a charming two-story summer cottage in Annapolis with unobstructed views of the Bay and Bay Bridge. Watch the Blue Angels fly overhead, catch Fourth of July fireworks, or simply enjoy the boats passing by — all from home. Swim, kayak, fish, crab, paddle board, or boat right from your front yard. The main level offers an open-concept kitchen, dining area, and family room designed to maximize waterfront views, plus a sleeping area with half bath and closet, a full bath, and laundry. Upstairs, the entire level serves as a private primary suite with sweeping Bay views and its own full bath. Outside features riprap shoreline protection, a storage shed for waterfront gear, and an existing pier and boat slip ready to be restored. More than a cottage — it’s your front-row seat to life on the Chesapeake Bay.

7017 Bay Front Dr, Annapolis

Listing courtesy of Home Towne Real Estate. Contact:

$1,775,000

Located on the South River in Riva, within the Greater Annapolis area, this custom-built waterfront home is tucked away on a private lane shared by just three homes, offering the perfect blend of privacy, tranquility, and unforgettable panoramic open-water views. Completed in 2022, it combines timeless design, luxury finishes, and the peace of mind that comes with newer construction, allowing you to spend more time enjoying the waterfront and less time maintaining your home. Designed to make the most of its exceptional setting, every detail reflects thoughtful planning, quality craftsmanship, and timeless style. The main living areas were designed to capture the river views, with expansive windows that fill the home with natural light and create an easy connection to the outdoors. At the heart of the home, the gourmet kitchen features 42-inch cabinetry, stainless steel appliances, a generous center island, abundant pantry storage, and opens effortlessly to the dining and living areas, where the South River becomes the backdrop to everyday living. A dedicated office on the main level provides the perfect work-from-home space and can easily serve as a guest bedroom, adding flexibility to fit your lifestyle. Step outside to the waterside deck and take in the panoramic South River views, where boats, wildlife, and spectacular sunsets create a backdrop that changes every day. The primary suite is a private retreat featuring its own waterfront balcony, a spacious sitting area, oversized walk-in closet, and a spa-inspired bath complete with a luxurious steam shower. The walk-out lower level expands the home's living space with radiant heated floors, a full wet bar, and direct access to the waterfront, providing exceptional flexibility for entertaining, recreation, overnight guests, or multigenerational living. The waterfront lifestyle extends well beyond the home with exceptional community amenities, including a waterfront clubhouse, boat ramp, kayak launch, fishing pier, and community piers, making it easy to enjoy everything the South River has to offer. Here, you'll enjoy the rare combination of waterfront privacy and everyday convenience, just minutes from historic Annapolis, Edgewater, local coffee shops, waterfront dining at Mike's Crab House, and convenient access to Routes 50 and 97. Whether you're searching for a full-time waterfront residence or the perfect weekend retreat, this home offers the very best of South River living. Come experience it for yourself.

Located on the South River in Riva, within the Greater Annapolis area, this custom-built waterfront home is tucked away on a private lane shared by just three homes, offering the perfect blend of privacy, tranquility, and unforgettable panoramic open-water views. Completed in 2022, it combines timeless design, luxury finishes, and the peace of mind that comes with newer construction, allowing you to spend more time enjoying the waterfront and less time maintaining your home. Designed to make the most of its exceptional setting, every detail reflects thoughtful planning, quality craftsmanship, and timeless style. The main living areas were designed to capture the river views, with expansive windows that fill the home with natural light and create an easy connection to the outdoors. At the heart of the home, the gourmet kitchen features 42-inch cabinetry, stainless steel appliances, a generous center island, abundant pantry storage, and opens effortlessly to the dining and living areas, where the South River becomes the backdrop to everyday living. A dedicated office on the main level provides the perfect work-from-home space and can easily serve as a guest bedroom, adding flexibility to fit your lifestyle. Step outside to the waterside deck and take in the panoramic South River views, where boats, wildlife, and spectacular sunsets create a backdrop that changes every day. The primary suite is a private retreat featuring its own waterfront balcony, a spacious sitting area, oversized walk-in closet, and a spa-inspired bath complete with a luxurious steam shower. The walk-out lower level expands the home's living space with radiant heated floors, a full wet bar, and direct access to the waterfront, providing exceptional flexibility for entertaining, recreation, overnight guests, or multigenerational living. The waterfront lifestyle extends well beyond the home with exceptional community amenities, including a waterfront clubhouse, boat ramp, kayak launch, fishing pier, and community piers, making it easy to enjoy everything the South River has to offer. Here, you'll enjoy the rare combination of waterfront privacy and everyday convenience, just minutes from historic Annapolis, Edgewater, local coffee shops, waterfront dining at Mike's Crab House, and convenient access to Routes 50 and 97. Whether you're searching for a full-time waterfront residence or the perfect weekend retreat, this home offers the very best of South River living. Come experience it for yourself.

20 Shore Walk Rd, Riva

Listing courtesy of Engel & Volkers Annapolis. Contact:

$1,750,000

Enjoy this large scenic lot w/ fully finished rancher & oversized 2 car garage just outside of downtown Annapolis. Open floor plan, cathedral ceilings, hardwood floors, skylights & more. Bulkheaded waterfront w/ 4 deep water slips. Main floor living, plus a walk out lower level. You will not want to miss this property!! It is truly one of a kind! Call agent for details. Interior photos, floor plan & additional information to follow. Do not enter property without an appointment.

3 Beds ⋅ 3 Baths

Enjoy this large scenic lot w/ fully finished rancher & oversized 2 car garage just outside of downtown Annapolis. Open floor plan, cathedral ceilings, hardwood floors, skylights & more. Bulkheaded waterfront w/ 4 deep water slips. Main floor living, plus a walk out lower level. You will not want to miss this property!! It is truly one of a kind! Call agent for details. Interior photos, floor plan & additional information to follow. Do not enter property without an appointment.

314 Kingsberry Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

$1,750,000

If you love a home that breathes history, you’ll fall in love with this one. Ideally situated at 102 Duke of Gloucester Street, the property rests along one of the area’s most historic streets—named in the late 1600s in honor of Prince William, The Duke of Gloucester. Some of the images in this listing have been lightly visually enhanced. Set on one of the most desirable stretches of the street, this classic Annapolis home is one where history, character, and everyday livability come together beautifully. Directly across from St. Mary’s Church, this four-bedroom, 3.5-bath residence offers just under 3,000 square feet perched on a generous lot with ample private parking. Its location places you within effortless walking distance of Spa Creek, Main Street, Ego Alley, the Annapolis Yacht Club, and Eastport—an extraordinary position that puts the very best of Annapolis at your doorstep. From the moment you cross the threshold, the charm is unmistakable. This home is filled with warm natural light and the energy of a true Annapolis residence that has been has been lived in, loved, and appreciated in its time. Rich wood, original details, and an authentic sense of place create an atmosphere that simply cannot be replicated in a new build. Among its most beautiful details are the original panes of glass showcased at the front of the home, along with rare, old-growth Georgia hard-pine edge-grain floors, and an original letter box—craftsmanship and materials that are increasingly difficult, if not impossible, to find today. The second floor showcases an especially inviting primary suite with a huge bath filled with warm morning light— a peaceful place to begin each day surrounded by the character of historic Annapolis. An additional full bath and bedrooms right down the hall. A bright and spacious grand room crowns the 3rd floor to be used as you like for an additional bedroom, exercise, and artist haven, office - you decide! The lower level is fitted with the original brick floors and offers a private full suite—an exceptional space for guests, extended family, or separate living arrangement. Additionally it includes its own secluded workshop, a rare and charming feature for someone who enjoys working with their hands, tackling projects, or simply having a dedicated place to create. Easily accessed from the kitchen breakfast area, the rear yard is one of the property’s most unexpected treasures. This generous outdoor space, not often found in downtown, offers privacy, a place to garden, entertain or simply letting the dog run and play. You will have your own highly desired and remarkably convenient parking for downtown living with room for two full-size vehicles or up to three compact cars, complemented by additional ample street parking. A fire-suppression system adds an additional layer of peace of mind to this historic residence. The sewer line was updated within the last 8 years and the roof was replaced in 2016 with 50 year rated shingles. But perhaps what makes this home most special is what cannot be measured in square footage. It has soul. The wood is rich. The light is warm. The architecture carries the imprint of another era. And the location is nearly impossible to duplicate. For those who appreciate the romance of an old home—the imperfections, the craftsmanship, the history, and the stories embedded within its walls—102 Duke of Gloucester Street offers something increasingly rare: a genuine piece of Annapolis that still still feels like a home.