Woodstock Homes under $500,000

Woodstock Homes under $500,000

Welcome to Woodstock, a charming town nestled in the heart of the picturesque Catskills region of New York. Renowned for its vibrant arts scene, rich history, and breathtaking natural beauty, Woodstock offers a unique blend of small-town charm and modern convenience. With its lush landscapes, stunning mountain views, and a plethora of recreational activities, it’s no wonder that this idyllic town has become a sought-after destination for families, artists, and nature enthusiasts alike.

One of the most appealing aspects of Woodstock is the accessibility of homes under $500,000. Whether you’re a first-time homebuyer, looking to downsize, or seeking a cozy getaway, the real estate market here offers a diverse selection of properties that cater to various needs and tastes. From quaint cottages with rustic charm to contemporary homes that embrace the surrounding nature, there’s something for everyone.

Imagine waking up to the serene sounds of nature, with hiking trails, art galleries, and local markets just a stone's throw away. Woodstock is not just a place to live; it’s a lifestyle. The community is vibrant and welcoming, with year-round events that celebrate local culture, music, and art.

With homes available at an affordable price point, now is the perfect time to explore the possibilities of calling Woodstock your home. Embrace the opportunity to live in a place where creativity flourishes and nature thrives. Discover your dream home in Woodstock today, and begin your new chapter in this enchanting town!

Newest Woodstock Homes under $500,000

816 Burgess, Woodstock
$424,999
3 Beds ⋅ 3 Baths

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
$380,000
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. 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:

242 N Main St, Woodstock
$379,950
The detached Colonial-style structure boasts a total finished area of 2,182 square feet, offering ample space with two rental units. With a solid wood siding exterior and a well-maintained condition, this property comes with immediate rental income and long-term appreciation. The basement provides additional storage or potential for further development, enhancing the overall value proposition.

242 N Main St, Woodstock

Listing courtesy of Beltway Realty, LLC.. 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:

605 Cedar Ct, Woodstock
$399,900
3 Beds ⋅ 3 Baths
Beautifully maintained split foyer home nestled in the desirable Orchard View community. It features 3 spacious bedrooms, 3 full bathrooms, and a 2-car garage. Step inside to find stunning hardwood floors throughout the main living areas, plus crown molding and recessed lighting that create an inviting atmosphere. The heart of the home is the country-style kitchen, featuring modern appliances including a built-in microwave, dishwasher, and electric range, making meal prep a delight. Enjoy casual dining in the eat-in area or host gatherings in the family room that seamlessly connects to the kitchen. The primary suite features a spacious bath and a large walk-in closet. The fully finished basement is ideal for entertaining or relaxing, with convenient access to the garage. Outside, you enjoy the new deck overlooking serene wooded views, perfect for morning coffee or evening gatherings. In a vibrant community, residents enjoy nearby parks and community amenities. With a spacious 0.53-acre lot, this home offers both tranquility and convenience, making it a perfect place to create lasting memories.

605 Cedar Ct, Woodstock

Listing courtesy of Samson Properties. Contact:

358 W Spring St, Woodstock
$329,900
4 Beds ⋅ 2 Baths
Welcome home to this beautifully RENOVATED Cape Cod offering modern comfort, classic charm, and ideal location in the heart of Woodstock, Virginia. Featuring an inviting open floor plan, this spacious home offers four bedrooms and two full baths, providing plenty of room for family, guest, or a home office. The thoughtfully updated interior creates a bright, welcoming atmosphere with an easy flow between the living, dining, and kitchen areas- perfect for everyday living and entertaining. A large full unfinished basement provides abundant storage and tremendous potential for future living space, a workshop recreation area, or whatever best suits your needs. Step outside and enjoy the large covered deck, an ideal spot for morning coffee, outdoor dining, or entertaining family and friends while taking in the beautiful mountain views. The expansive backyard offers plenty of room for gardening, recreation, pets or simply relaxing and enjoying the outdoors. Located in town and close to the town park and all of Woodstock's amenities, this home combines the convenience of being near shopping, dining, recreation and community activities with the peaceful beauty of the Shenandoah Valley.

358 W Spring St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

268 Parkside Ct, Woodstock
$349,900
3 Beds ⋅ 3 Baths
Welcome to this beautifully upgraded townhouse offering 1,872 square feet of living space! Beautiful Northwood LVP flooring throughout the main level. The kitchen features quartz countertops, $500 upgraded backsplash, white cabinetry, and a gas range. Upstairs, you'll find three generously sized bedrooms, including a primary suite complete with a walk-in closet and private ensuite bathroom. A spacious linen closet in the upstairs hallway adds even more convenient storage, along with new shelving throughout all closets. The home has had significant upgrades, including a stunning $20,000 handicap-accessible walk-in shower with stone walls, and $7,000 Stainmaster upgraded carpet. Dual A/C and heating system. Additional features include a single-car attached garage, a laundry station, and a shed in the backyard for extra storage. Move-in ready. Schedule your tour today!

268 Parkside Ct, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

769 S Water St, Woodstock
$479,000
4 Beds ⋅ 2 Baths
One of a kind, hidden gem in the heart of the Town of Woodstock. This 4 BR, 2 Bath split level home with garage is perfectly sited on a private, 3.2-acre wooded homesite. A truly scenic vista located so close to the the Town of Woodstock. There is always something fun to do and enjoy in Woodstock--where vineyards, hiking,, fine restaurants, and quaint cafes are located very nearby. The Valley Health Shenandoah Hospital is located across the street. You love to explore your own nature trails and also visit the Indian Spring Wetland park directly across the street. Grocery, banks, quaint dining, and recreational opportunities are within minutes. This home features an upgraded kitchen and baths, a newer roof in 2019, HVAC- furnace replaced in 2022. This multi-level split home has a sunny primary bedroom with French doors leading to a private deck. You'll love morning coffee or evening cocktails on the deck while enjoying the sounds of nature. Three additional bedrooms, including the attic space, which will easily serve as a home office. The living and dining room open with French doors to a patio--ideal for entertaining. The living room has a wood-burning fireplace with built-in bookcases on either side. Gleaming hardwood flooring is found in this area, as well as in the 3 bedrooms. The upgraded kitchen is a chef's delight with custom cabinetry, upgraded countertops, ceramic flooring, and stainless steel appliances. Now is the time to discover this private oasis located in the heart of the Town of Woodstock within the beautiful Shenandoah Valley. The property is a mix of ferns, mature hardwood trees, a meandering stream and a cleared lush lawn. Wildlife abounds with new fawns frolicking through the yard. A natural stream originates on the property and runs to the Indian Spring Wetland Park area. Huge rock and boulders dot the landscape throughout the woods. You can expand the house--consider all the opportunities to design and build out this property to your absolute heart's content. Schedule a Tour today!

769 S Water St, Woodstock

Listing courtesy of Samson Properties. Contact:

170 Clubhouse Ct, Woodstock
$345,000
3 Beds ⋅ 2 Baths
You can have it all with this 3-bedroom home located in the Leisure Point community! The open living room, dining room, and kitchen make a great space for gatherings. The living room features hardwood floors and vaulted ceilings. Down the hallway you'll find the primary bedroom with an ensuite bath and walk-in closet, two additional bedrooms, a full bath, as well as a laundry station and linen closet. Recent updates include new carpet, fresh paint, and shingles replaced in 2019, making this one move-in ready. Step outside to a spacious backyard with an outbuilding, and take in the beautiful mountain views from your front porch over a morning coffee or evening tea. Living in Leisure Point means private community access to the Shenandoah River — picture riverside picnics, fishing, or a relaxing stroll through nature.

170 Clubhouse Ct, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

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