Woodstock Real Estate

**Discover the Charm of Woodstock, New York**

Nestled in the picturesque Catskill Mountains, Woodstock, New York, is a haven for artists, nature lovers, and anyone seeking a vibrant community steeped in history and creativity. Known for its rich cultural heritage, Woodstock gained fame as the site of the legendary 1969 music festival, which, although held in Bethel, forever linked the town to the spirit of peace and music.

Today, Woodstock is a delightful blend of bohemian charm and modern amenities. Stroll through the quaint streets lined with unique boutiques, art galleries, and cozy cafes. The local art scene thrives, with numerous festivals and events celebrating everything from music to visual arts, making it a perfect place for artists and art enthusiasts alike.

Nature is at the heart of Woodstock, offering countless opportunities for outdoor adventures. Hike the scenic trails of the nearby Catskill Park, or take a leisurely stroll along the stunning Ashokan Reservoir. In winter, the area transforms into a snowy wonderland, perfect for skiing and snowboarding enthusiasts.

The community is warm and welcoming, with a strong emphasis on sustainability and local living. Residents enjoy a blend of small-town charm and a vibrant social scene, with farmers' markets, live music, and community events that foster connections among neighbors.

Whether you’re looking for a weekend retreat or a permanent residence, Woodstock offers a unique lifestyle that celebrates art, nature, and community. Come and experience the enchanting allure of Woodstock—where every day feels like a new adventure waiting to unfold!

Newest Listings in Woodstock

$1,750,000

5 Beds ⋅ 3 Baths ⋅ 5113873 MLS

EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set on a beautifully landscaped .55-acre lot bordering the lovely Kedron Brook, the property offers a rare combination of historic character, modern comfort, and effortless Village living. The interiors are bright and charming, seamlessly blending architectural details with thoughtful updates. The main level is designed for both everyday living and entertaining, with a well-appointed kitchen and dining area complemented by a gracious formal dining room featuring built-in china cabinets and French doors. Adjacent the dining room at the front of the house is a formal sitting room, while across the foyer, a spacious living room with built-in bookshelves centers around a cozy fireplace. Upstairs, five bedrooms and two baths provide generous accommodations for family and friends. Outside, a private deck off the kitchen offers a peaceful setting for outdoor dining and hosting social gatherings. An attached two-car garage and upgraded mechanical systems, including mini-splits for heating and cooling, add modern convenience. Just a short stroll from Woodstock Village’s acclaimed shops, restaurants, galleries, cultural, and recreational offerings, this exceptional property captures the timeless appeal of Village living while offering the comfort and functionality of today. Enjoy the annual Wassail Parade from your own front porch, and view of the Mount Tom Star from the ell of the house. Note: some photos virtually adjusted.

18 Pleasant St, Woodstock

$575,000

5113870 MLS

64 Acres in the Heart of the White Mountains! Discover an incredible opportunity to own 63.64 acres of wooded land in desirable Woodstock, NH, just minutes from Lincoln, Loon Mountain Resort, and the area’s most popular attractions! With approximately 1,830 feet of road frontage along scenic Lost River Road (Route 112), this expansive parcel offers privacy, rolling terrain, seasonal streams, beautiful mountain surroundings, and endless possibilities. Located in a town without traditional zoning, the property offers exciting potential for a private mountain retreat, family compound, or future development, subject to applicable town and state approvals. Enjoy year-round adventures with skiing at Loon Mountain, hiking throughout Franconia Notch and the White Mountain National Forest, exploring Lost River Gorge, visiting the magical Ice Castles, and taking scenic drives along the Kancamagus Highway. Experience breathtaking fall foliage, nearby rivers and lakes, snowmobiling, and endless outdoor recreation. Just minutes from downtown Lincoln and North Woodstock’s restaurants, shops, and family attractions. A rare opportunity to own a substantial piece of the White Mountains in one of New Hampshire’s most sought-after four-season destinations!

Lot 206-044 Lost River, Woodstock

$545,000

2 Beds ⋅ 3 Baths ⋅ 5113819 MLS

**Classic Woodstock character, generous living spaces, and the ease of low-maintenance living.** Just minutes from Woodstock Village, this beautifully maintained Federal-style brick townhouse offers privacy, comfort, and convenience in an established residential community. With approximately 2,268 square feet of finished living space across three levels, the home offers the comfort and flexibility of a single-family residence without the demands of extensive property maintenance. Freshly painted and updated with new hardwood floors, the inviting interior features a fireplace, comfortable gathering spaces, and a versatile first-floor bonus room with pocket doors, ideal for an office, den, or studio. The eat-in kitchen opens to an oversized deck overlooking lawns, perennial gardens, mature trees, and surrounding woodland. A finished walkout lower level adds valuable living space, with natural light, a full bathroom, laundry, and direct backyard access. Association services include lawn care, snow removal, trash collection, and common grounds maintenance, leaving more time to enjoy Woodstock. The location is exceptional. Woodstock Farmers' Market is just down the street, while nearby trailheads connect to Marsh-Billings-Rockefeller National Historical Park. Woodstock Village, the Woodstock Inn & Resort, Billings Farm & Museum, and outstanding dining and shopping are minutes away. **Offered at $495,000, with a $50,000 seller credit at closing for a full-price cash offer OR a 5% seller credit for a full-price financed offer**, subject to applicable terms and lender limitations. Property is subject to the Woodstock Community Trust Local Deeds covenant requiring qualified local employment and primary residency, with certain exceptions. See attached covenant for details.

121 Townhouse Way Unit 20, Woodstock

$1,749,000

5 Beds ⋅ 5 Baths ⋅ 5113766 MLS

Located right in the Village of Woodstock, 81 Central Street has both excellent visibility, road and sign frontage on Central Street (Rt 4) and an easy walk to everything. It is currently divided up as three connected units and is zoned "Office/Residential". The charming brick cape house in the front (c. 1821) is currently configured as an office but was formerly a residence, and rented for $5,000 per month. The downstairs office area has an open floorplan plus a full bath, but could easily be reconfigured differently with the addition of interior walls. Upstairs are two rooms (formerly bedrooms) and a shell-bathroom which is plumbed and ready for appliances and finishing. The middle building is now a 3 bedroom 2 bath apartment with full kitchen, laundry, living room, office and central A/C and is currently rented for $5,000/month. The rear studio is a 1 bedroom 1 1/2 bath apartment with open living room / kitchen area, currently rented for $2,200 per month. The property also features a two-car detached, heated garage plus parking for 5-6 other cars, plus a lovely shaded lawn.

81 Central St, Woodstock

$459,900

2 Beds ⋅ 2 Baths ⋅ 5113760 MLS

Deer Park Resort is just over an hour from Manchester and two hours north of Boston in the heart of the White Mountains. Set on 65 manicured acres, including a private five-acre lake, Deer Park offers year-round enjoyment. Deer Park is located in Grafton County 30 miles N of Plymouth along Highway 112 off exit 32 on I93 near Loon Mountain Ski Area. Lincoln/ Woodstock area is the gateway to one of the state's most popular scenic drives, the Kancamagus Highway. North Woodstock is a quaint little walking town just five minute walk from Deer Park local restaurants and shopping just around the corner. Whatever your pleasure, Franconia Notch State Park in the White Mountains of NH consists of 6,693 acres for swimming, camping, scenic driving, picnicking, biking, and hiking. Use our distinctive resort community as home base to enjoy fabulous scenic drives, some of the county's finest hiking, marvelous fishing, challenging golf, glider rides, horsebackriding in franconia are just a short drive up 93 thrilling moose-watching adventures and much more.... This property has a fantastic location just a short stroll to the Rec center or the beach area for summer fun and winter shuttle service to Loon ski area for winter enjoyment . Vaulted ceilings in main living area opens up to a beautiful porch overlooking the river and multiple options for mtn biking or skiing at Cannon, Bretton Woods , or Loon . Consider this your basecamp in the White mountains . .

75 Riverfront Dr Unit 208, Woodstock

$12,000

1 Beds ⋅ 1 Baths ⋅ 5113684 MLS

Charming 1-Bedroom Condo at Deer Park Resort – Quarter Share Ownership Discover your own getaway in the heart of the White Mountains! This charming garden-style condo at Deer Park Resort features 1 bedroom, 1 full bath, and 886 square feet of comfortable living space, making it an ideal retreat for a small family or a relaxing mountain escape. This quarter-share property offers 13 weeks of ownership per year, with use of the property one week out of every four, providing a wonderful opportunity to enjoy all four seasons in the White Mountains. Conveniently located just off I-93, the condo is a short distance from local shops, restaurants, and area attractions. Loon Mountain is approximately 3 miles away, offering easy access to a fun-filled day on the slopes during the winter months. In the summer, enjoy Deer Park’s beautiful spring-fed pond and beach area. The on-site health club features an indoor swimming pool, racquetball courts, and a spacious great room overlooking the pond, complete with a pool table, foosball, and air hockey.

156 Deer Park Dr Unit 128TD, Woodstock

$350,000

1 Beds ⋅ 1 Baths ⋅ 5113625 MLS

A rare opportunity to own 11.58 private acres in S. Woodstock, ideally situated in one of Vermont’s most sought-after rural settings. With an existing driveway, well, electric service, septic system, and a modest mobile home already in place, this property offers the infrastructure and flexibility to enjoy the land now while considering its future potential. The land is the true centerpiece. Wooded acreage, natural clearings, gentle slopes, and a peaceful country setting create an ideal backdrop for a Vermont getaway, recreational property, hunting retreat, equestrian use, or future building site. The existing 536-square-foot, 1-bed, 1-bath mobile home provides a simple place to stay while enjoying everything the property and surrounding area have to offer. For equestrian enthusiasts, the location is especially compelling. The property is within approximately two miles of the Green Mountain Horse Association (GMHA) and sits directly along the GMHA Paul Kendall Trail, providing an exceptional connection to one of Vermont’s premier equestrian communities and trail networks. The surrounding area is renowned for its horse farms, riding trails, open countryside, and beautiful back roads. The property is also well positioned for the quintessential Vermont second-home lifestyle, with Killington Resort, Saskadena Six, Billings Farm & Museum, Woodstock, and South Woodstock all within easy reach. Enjoy skiing, hiking, horseback riding, cycling, farm visits, fine dining, and the timeless character of the Woodstock area, then return to your own private acreage. From 1985 through 2020, a family of four occupied a three-bedroom home and used the existing septic system without reported issues. The seller has also completed a soil evaluation and septic inspection, with both reports available in the attached documents. Lastly, the seller would be willing to discuss removal of the mobile home if it is not needed by the new buyer. Schedule a private tour today!

1190 Long Hill Rd, Woodstock

$350,000

5113624 MLS

A rare opportunity to own 11.58 private acres in S. Woodstock, ideally situated in one of Vermont’s most sought-after rural settings. With an existing driveway, well, electric service, septic system, and a modest mobile home already in place, this property offers the infrastructure and flexibility to enjoy the land now while considering its future potential. The land is the true centerpiece. Wooded acreage, natural clearings, gentle slopes, and a peaceful country setting create an ideal backdrop for a Vermont getaway, recreational property, hunting retreat, equestrian use, or future building site. The existing 536-square-foot, 1-bed, 1-bath mobile home provides a simple place to stay while enjoying everything the property and surrounding area have to offer. For equestrian enthusiasts, the location is especially compelling. The property is within approximately two miles of the Green Mountain Horse Association (GMHA) and sits directly along the GMHA Paul Kendall Trail, providing an exceptional connection to one of Vermont’s premier equestrian communities and trail networks. The surrounding area is renowned for its horse farms, riding trails, open countryside, and beautiful back roads. The property is also well positioned for the quintessential Vermont second-home lifestyle, with Killington Resort, Saskadena Six, Billings Farm & Museum, Woodstock, and South Woodstock all within easy reach. Enjoy skiing, hiking, horseback riding, cycling, farm visits, fine dining, and the timeless character of the Woodstock area all while returning to your own private acreage. From 1985 through 2020, a three-bedroom home occupied by a family of four utilized the existing septic system without reported issues. The seller has also completed a soil evaluation and septic inspection, with both reports available in the attached documents. Lastly, the seller would be willing to discuss removal of the mobile home if it is not needed by the new buyer. Schedule a private tour today!

1190 Long Hill Rd, Woodstock

$549,000

3 Beds ⋅ 2 Baths ⋅ 5113572 MLS

Welcome to this newly updated sun-filled craftsman home, ideally located just 4 miles from the heart of Woodstock Village and 11 miles from Killington Ski Resort. Set on 5 acres with a lovely pond, this property offers the perfect blend of privacy, convenience, and Vermont charm. The home features a bright and inviting interior with one bedroom on the main level and two additional bedrooms and a full bath on the lower level. A spacious wraparound porch extends the living space outdoors, providing the perfect spot to relax, entertain, and enjoy the peaceful surroundings. Whether you’re looking for a primary residence, Vermont getaway, or a home base for year-round recreation, this beautifully updated chalet offers easy access to skiing, dining, shopping, hiking, and everything the Woodstock and Killington areas have to offer.

139 Doe Hill Way, Woodstock

$549,000

3 Beds ⋅ 2 Baths ⋅ 5113119 MLS

Nestled in the heart of historic Woodstock. This 1875 colonial abuts Mt. Peg with direct access to the trail system. A large shed in the backyard could be used as a workshop and/or storage, ample space for gardening and very private backyard for entertaining. The house had some upgrades to the kitchen and bathrooms and still boasts some of the original features including hardwood floors in the bedrooms upstairs. First floor has a mudroom, large oversized kitchen with cherry cabinets, stainless steel appliances and stone countertops anchored with an island and opens to the dining area. There is a handsome set of French doors that walk out onto a stone patio. The living room is spacious with a wood burning fireplace and a small room that could be used as an office. The second floor has 3 bedrooms and a full bath. The primary bedroom has ample space to add a separate bathroom. This home has a newer heating system. It's a great project for a buyer wanting to put in some sweat equity and refurbish this lovely old home. Walk to town with easy access to all amenities including restaurants and stores. Easy access to mountain biking, hiking and cross country skiing. There is an inspection report available. Come take a look- this house is located in a wonderful neighborhood and waiting for the perfect buyer to embrace a fun project.

8 Golf Ave, Woodstock

$749,000

3 Beds ⋅ 3 Baths ⋅ 5113057 MLS

Enjoy expansive views from every level of this beautifully updated, 3-bedroom, 3-full-bath Blake Hill condominium. As a highly desirable end unit, this property welcomes you with a classic bluestone entryway and a large wrap-around porch perfect for outdoor relaxing. Inside, the multi-level floor plan offers exceptional privacy, with an open-concept main level showcasing soaring vaulted ceilings, a dining area, and a living room centered around a cozy wood-burning fireplace with custom built-ins. The large chef's kitchen features stylish appointments, upscale appliances, and a premium Sub-Zero refrigerator. Adjacent the kitchen is a large bedroom with an attached bath, perfect accommodations for friends or family, while a functional mudroom rounds out the main floor. An en suite primary bedroom and sitting area/office serves as a secluded retreat on the entire second level. The fully finished ground level adds significant living space with a sizable third bedroom, full bath, secondary family room with its own fireplace, and massive extra bonus room with dedicated storage. Residents also enjoy access to the community swimming pool, which was completely updated in the summer of 2026. With its proximity to Woodstock Village and the Upper Valley’s many cultural and recreational offerings, this turnkey property is a must-see. Note: Some photos are virtually staged. Public Open House: Sunday, October 11 from 11am-1pm.

264 Blake Hill Rd Unit Z, Woodstock

$130,000

2 Beds ⋅ 1 Baths ⋅ 5113028 MLS

Low Maintenance Mountain Living, Minutes from Loon Tucked into a quiet corner of the park with more privacy than you'd expect, this clean, well-kept home has a warm, rustic feel. It can come fully furnished, so it's ready to enjoy from day one. Loon Mountain Resort and downtown Lincoln are less than 15 minutes away, putting ski days, the Kancamagus, and the town's restaurants and shops all within easy reach. You enter through a mudroom addition, the perfect drop zone for boots, skis, and gear after a day outside. The oversized kitchen and living area gives you plenty of room to cook, gather, and spread out, and two bedrooms complete the layout. A second exit opens directly to the private backyard and its outdoor fireplace, made for cool White Mountain evenings. The property directly borders White Mountain Motorsports Park, so racing fans can have Saturday nights at the track right next door. If you're looking for a convenient, low-maintenance place in the mountains without the constraints of condominium living, this one deserves a look. With the option to purchase fully furnished, you could be settled in for ski season without hauling a single piece of furniture up north. Reach out for more details or to schedule a showing.

21 Scenic Dr, Woodstock

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