Woodstock Homes under $500,000

Woodstock Homes under $500,000

Welcome to Woodstock, a charming town nestled in the heart of the beautiful Catskills in New York. Known for its rich artistic heritage and vibrant community, Woodstock offers a unique blend of small-town charm and natural beauty, making it an ideal place to call home. With its picturesque landscapes, eclectic shops, and thriving arts scene, this town has something for everyone.

One of the most appealing aspects of Woodstock is its affordability in the housing market. For those looking to settle down in this serene environment, there are a variety of homes available for under $500,000. Whether you’re seeking a quaint cottage surrounded by nature, a cozy bungalow with modern amenities, or a spacious family home, Woodstock has options that cater to diverse preferences and budgets.

Living in Woodstock means you’ll enjoy access to stunning hiking trails, serene lakes, and vibrant local events, such as the renowned Woodstock Film Festival and various art exhibitions. The community is tight-knit, with friendly neighbors who take pride in their town’s rich history and culture.

Moreover, Woodstock is conveniently located within a short drive to larger cities like Kingston and Poughkeepsie, providing residents with easy access to urban amenities while still enjoying the tranquility of rural life.

With its affordable housing options and enchanting atmosphere, Woodstock is not just a place to live; it’s a place to thrive. Discover your dream home in this artistic haven and experience the best of what this remarkable town has to offer!

Newest Woodstock Homes under $500,000

344 Lora Dr, Woodstock
$345,000
3 Beds ⋅ 2 Baths
Located in Woodstock , this home offers a perfect blend of traditional style and modern comfort. Built in 2006, this property features a classic brick exterior that exudes warmth and low maintenance Step inside to discover an inviting open floor plan that seamlessly connects the living spaces, creating an atmosphere of spaciousness and light. The flooring is a mix of warmth carpeting and rich wood floors providing both comfort and style. The skylight fills the space with natural light enhancing the ambiance. This conveniently located home features three bedrooms and two full bathrooms including a soaking tub ensuring a retreat for relaxation. The heart of the home is the well-equipped kitchen, appliances including a built-in range, refrigerator, and microwave. Whether you're preparing a gourmet meal or enjoying a casual breakfast this kitchen is laid out for holiday cooking.. Energy-efficient windows to provide comfortable temps year round. The laundry area adds to the convenience of daily living, Outside, the property features a private concrete driveway leading to an attached garage with easy access. The 0.16-acre lot offers a manageable outdoor space, perfect for enjoying quiet moments or entertaining friends. This home is more than just a residence; it embodies a lifestyle of comfort and ease. Convenient location near the hospital, restaurants, shopping, vineyards, parks and more. This delightful, easy to maintain duplex is available for showing. Celebrate the holidays at Home.

344 Lora Dr, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

140 Donna Dr, Woodstock
$350,000
2 Beds ⋅ 2 Baths
Experience the perfect blend of main-level luxury and beautiful mountain views in this well-maintained 2-bedroom, 2-bath brick duplex, perfectly positioned on an oversized 0.27-acre corner lot in the desirable Camelot Estates community. Offering 1,629 square feet of thoughtfully designed space, this home features an attached 2-car garage, an oversized concrete driveway, and professionally landscaped grounds with attractive native plantings. Inside, you will find hardwood flooring throughout most of the home, 9'+ ceilings with crown molding, and a spacious living room centered around a cozy propane fireplace with a handsome mantel. The oversized primary suite offers a true sanctuary with a large walk-in closet and a private bath complete with a separate shower and a jet whirlpool tub. The generous second bedroom features a unique bump-out design and captures beautiful mountain views. Additional highlights include abundant closet and storage space, a permanent propane hookup for your grill, and a quiet backyard perfect for relaxing or entertaining. Conveniently located just minutes from downtown Woodstock, shopping, restaurants, medical offices, the hospital, and the Shenandoah County Fairgrounds. With no HOA, all-brick construction, and pristine move-in ready condition, this non-smoking home offers low-maintenance living in a peaceful, scenic setting.

140 Donna Dr, Woodstock

Listing courtesy of Samson Properties. Contact:

2930 Hernwood Rd, Woodstock
$499,000
3 Beds ⋅ 2 Baths
NEW ACTIVE and priced below appraised value, celebrate the holidays in your new home - On market November 6, Open houses Nov 7 and Nov 8 from Noon to 3pm. This beautiful custom tudor cottage is dripping with custom charm inside and out. Location! It sits directly on Patapsco State Park in beautiful Woodstock - hike and bike the popular McKeldin area right from your front door. Enjoy nature while just minutes to major commuter routes via I70. High speed internet, PRIVACY on an over 1ac lot with mature trees. The adorable barn currently houses horses and a goat, with rental of pasture space from the neighbor to the back. Inside you're going to find more charm, wood and stone accents, beautiful hardwoods on the first floor, mostly new appliances. Roof was done in 2025. The 2 first floor bedrooms share a full bath featuring retro tile work. The 2nd floor primary bedroom is HUGE with a large primary bathroom and two walk-in closets. The carpet in the 1st and 2nd floor bedrooms is brand new and many of the living spaces feature new paint. There's nothing cookie-cutter about this home, featuring custom solid wood cabinets in the kitchen, detailed molding in the family room, the arched front door and entry, stone and wood accent walls and incredible fireplace. Enjoy listing to the hoot of an owl, the call of an eagle and all that nature living in Patapsco State Park as you sit on your covered front porch. Or watch the horses from the back deck overlooking your large back yard. Plenty of room for gardening while the mature trees in the front yard provide shade. There are two paved driveways, so plenty of parking for you and your guests. Convert the barn for other uses, or the neighbor is willing to talk with the new owner about similar arrangements to lease the pasture behind the house for livestock, there's lots of horses in the neighborhood. Don't need that barn and don't want to deal with the maintenance? but love looking at the horses, the current tenant that leases the barn and paddocks would love to stay, but is ready to move if the new owner prefers their privacy. The large basement is a blank slate for you to set up as you'd like. The oversized garage will fit the longest vehicle you can think of and still have room to spare. Move in and put your own touches on this home while you enjoy all of the things this home has to offer.

2930 Hernwood Rd, Woodstock

Listing courtesy of Hagan Realty. Contact:

10500 Old Court Rd, Woodstock
$150,000
3 Beds ⋅ 1 Baths
REAL ESTATE AUCTION featuring ON SITE and SIMULCAST ONLINE BIDDING!! Online Bidding Opens - Tuesday, December 8, 2026. Live On Site Auction - Thursday, December 10, 2026 at 1:00 PM. List price is opening bid only. Circa 1905 two story Victorian style home on 1± acre in the historic village of Granite, in western Baltimore County. The property fronts on Old Court Road, the main street of one of the county’s best-preserved 19th century quarrying communities, a village whose granite helped build landmarks in Baltimore and Washington, D.C. Surrounded by wooded hills, the Patapsco River valley and quiet country roads, yet within easy reach of Randallstown, Ellicott City and the Baltimore Beltway, the location pairs rural character and genuine history with practical access to the region. The auction affords homebuyers, renovators and investors an opportunity to acquire a charming Victorian style home with deep local roots on a generous lot.

10500 Old Court Rd, Woodstock

Listing courtesy of A.J. Billig & Company. Contact:

1229 Ox Rd, Woodstock
$370,000
3 Beds ⋅ 2 Baths
Enjoy easy one-level living in this well-maintained ranch home at 1229 Ox Road! Featuring 3 bedrooms, 2 full baths, an oversized attached 2-car garage, and a full unfinished walk-up basement, this home offers plenty of space and convenience close to town. The spacious living room flows into a large eat-in kitchen with a generous dining area, providing a great space for entertaining family and friends. Just off the kitchen, the screened-in porch is the perfect spot to enjoy your morning coffee or unwind at the end of the day. The backyard firepit offers another inviting space to gather and enjoy the outdoors. The primary bedroom features a ceiling fan, laminate flooring, a large closet, and a private bath with a shower. Two additional generously sized bedrooms offer ceiling fans and window blinds, while the full hall bath features a tub/shower combination with grab bars. Main-level laundry includes a washer and gas dryer for added convenience. The full walk-up basement has painted walls and flooring and offers excellent potential for storage, hobbies, or future living space. Additional highlights include an oversized concrete driveway with ample parking, a garage with extra workshop space and a refrigerator, and a roof approximately 5 years old. Conveniently located near shopping, restaurants, the hospital, and I-81, this home is ready for its next owner to make it their own!

1229 Ox Rd, Woodstock

Listing courtesy of Re/Max Roots. Contact:

610 Cedar Ct, Woodstock
$415,000
4 Beds ⋅ 3 Baths
BEAUTIFULLY UPDATED HOME WITH AN OPEN FLOOR PLAN AND DESIRABLE CUL-DE-SAC LOCATION! This inviting 4-bedroom, 3-bath home offers the perfect combination of comfort, functionality, and thoughtful updates! Step inside to discover a bright and airy open floor plan featuring vaulted ceilings, abundant natural light, and updated flooring throughout the main living area. The gorgeous gourmet kitchen is sure to impress with new countertops and appliances (2023) and flows seamlessly into the dining and living areas, making it ideal for everyday living and entertaining. A standout feature of this home is its TWO primary suites, each complete with a private full bathroom, offering flexibility for guests or multigenerational living. Two additional bedrooms, a third full bathroom, and a convenient laundry room complete the interior. Step outside onto the spacious deck, freshly stained in 2026, overlooking a backyard that backs to trees for added privacy. Additional highlights include a 10x12 storage shed with electricity. Major improvements offer added peace of mind, including a NEWER ROOF and HVAC system (2022), updated main living area flooring, kitchen countertops and appliances (2023), and a new sidewalk and fence (2023). Tucked away on a cul-de-sac and conveniently located near the town park and swimming pool, this well-maintained home offers an exceptional combination of space, updates, and location. MOVE-IN READY AND WAITING FOR YOU TO CALL IT HOME!

610 Cedar Ct, Woodstock

Listing courtesy of Funkhouser Real Estate Group. Contact:

816 Burgess, Woodstock
$399,900
3 Beds ⋅ 3 Baths
YOUR OWN LITTLE FARM RIGHT IN THE HEART OF WOODSTOCK! 816 Burgess Court | Woodstock, VA Who says you can’t have country living with the convenience of town? Welcome to your very own mini homestead, tucked away on a quiet cul-de-sac in Woodstock, Virginia! Imagine enjoying your morning coffee surrounded by peace and quiet, tending to your gardens, growing your own vegetables, and creating your own little farm—all without sacrificing convenience! Located just minutes from I-81, shopping, restaurants, and everything Woodstock has to offer, this beautiful home gives you the best of both worlds. No neighbors directly behind you, no through traffic, and plenty of room to enjoy the outdoors! Inside, you’ll find a spacious, lovingly maintained home with room for everyone. One of the most exciting features is the versatile lower level, currently being used as a workout area. NEED MORE LIVING SPACE OR DREAMING OF ADDITIONAL INCOME? Imagine transforming the lower level into a private in-law suite, guest quarters, multigenerational living space, or even a potential rental unit for additional income, subject to local zoning, permits, and approvals. The possibilities are incredible! Whether you’re dreaming of a garden-filled backyard, a peaceful retreat, space for extended family, or a property that can grow with your needs, this home offers so much potential. A LITTLE BIT OF COUNTRY, A WHOLE LOT OF CHARM, AND THE CONVENIENCE OF TOWN! Come experience the possibilities for yourself. Schedule your private showing today!

816 Burgess, Woodstock

Listing courtesy of Kathy Jean Campbell. Contact:

10809 Davis Ave, Woodstock
$150,000
4 Beds ⋅ 2 Baths
This property will be sold at ONLINE AUCTION. LIST PRICE REPRESENTS OPENING BID. Bring your vision and unlock the potential of this classic Cape Cod in Woodbine! This home is in need of renovation and offers an excellent opportunity for investors, renovators, or buyers looking to create a home tailored to their own style. The traditional Cape Cod layout provides a solid starting point, with plenty of possibilities for reimagining the existing spaces and making the most of the property. Conveniently located in Woodbine with easy access to surrounding communities, this property is ready for its next chapter. Bring your ideas, your contractor, your handy family members and your vision—this one is full of potential! Bidding will open at 12:00 Noon on Friday, October 23, 2026 and close at 1:00 pm on Monday, October 26, 2026. Additional Auction Terms: 10% buyer's premium will be added to the winning bid. Buyer's Agent must be registered as an agent on the auction website prior to the time buyer places 1st bid. Property is sold AS-IS, no inspection contingency. No financing contingency. Buyer pays all transfer & recordation taxes. 10% Earnest Money Deposit due at contract execution.

10809 Davis Ave, Woodstock

Listing courtesy of Keller Williams Legacy. Contact:

564 W Spring St, Woodstock
$360,000
5 Beds ⋅ 4 Baths
Spacious 5-bedroom, 3.5-bath traditional home on .39 acres in the heart of Woodstock, offering three levels of living space and a convenient location near the town’s amenities including a town park just a block away with tennis courts, swimming pool, soccer field, etc.. The main level features a living room with gas fireplace, dining room, wood-floored kitchen, family room with Jotul cast-iron wood stove, laundry room, and full bath. Upstairs, the primary bedroom offers generous space and a private bath with separate shower and soaking tub, along with three additional bedrooms and another full bath. The third level provides a fifth bedroom and half bath, offering additional flexibility for living or work space. Hardwood and wood flooring is featured throughout much of the home. Outside, the property includes a "Williamsburg Roll" brick patio, garage/shop, and large storage shed.

564 W Spring St, Woodstock

Listing courtesy of Preslee Real Estate. Contact:

335 S Commerce St, Woodstock
$339,000
3 Beds ⋅ 2 Baths
Discover a beautifully maintained three-bedroom, two-bathroom home in charming downtown Woodstock. Designed for convenient single-level living, the property is equally well suited as a primary residence or an investment opportunity, including short-term rental or traditional lease use. The open-concept living and dining areas create a bright, welcoming flow throughout the home. At the rear, the private primary suite includes a walk-in closet and direct access to the back deck and yard. Framed by mature landscaping and scenic views, the deck provides a peaceful setting for quiet mornings or relaxing evenings. A convenient location with easy access to all of the following: • Woodstock Town Park, downtown cafés and shops, banking, and health care facilities are all nearby. • Seven Bends State Park provides convenient access to outdoor recreation. • Interstate 81 is less than two miles away, and Route 11 is approximately half a mile from the home. Call today to discuss how this amazing property can be yours.

335 S Commerce St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

238 Indian Spring Rd, Woodstock
$330,000
3 Beds ⋅ 2 Baths
Welcome to 238 Indian Spring Road! Solid split-foyer home on nearly half an acre parcel. Built in 1976, this home offers an easy layout and outdoor space to enjoy. The kitchen features light wood cabinetry with a peninsula that makes entertaining easy. The combined kitchen and dining area leads through a sliding glass door onto the covered back deck with a ceiling fan — a great spot for morning coffee or evening dinners. Beneath the deck, the walkout basement offers easy access through its own sliding glass doors. Cozy up in the living room by the brick fireplace on chilly evenings. The basement offers a second brick fireplace, making it easy to add a rec room or extra living space. Baseboard heating keeps things simple and efficient, with air conditioning window units. Outside, you'll find an above-ground pool for summer days and a storage shed for extra space — all set on a spacious 0.46-acre lot with room to spread out. This home is very close to Woodstock's Indian Springs Wetland Park - a peaceful 1-acre nature reserve with a walking trail and observation deck. Located just minutes from downtown Woodstock - with lots of restaurants, shops, a movie theater, and more! Schedule your showing today!

238 Indian Spring Rd, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

1023 Sun Poppy Ct, Woodstock
$399,000
3 Beds ⋅ 2 Baths
This is your opportunity to own a Beautiful home in Hisey Park. A place to simplify your lifestyle without giving up comfort, space, or convenience. This home features three bedrooms with two baths, granite countertops, all on one-easy level. If you're ready to downsize, planning for retirement, or simply tired of dealing with maintenance or stairs, then this is the one for you. New Appliances were installed in 2024 & come with a transferrable warranty until 2029, The Water Heater was installed in 2025, Mowing & Snow Removal are paid until 12/31/2026. Come view this low-maintenance property, relax on the Patio, take in the wildlife, the mature landscaping and imagine it as Home!

1023 Sun Poppy Ct, Woodstock

Listing courtesy of ERA Valley Realty. Contact:

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