Woodstock Real Estate

Woodstock Real Estate

Welcome to Woodstock, a charming city nestled in the heart of New York's Hudson Valley region. Known for its picturesque landscapes, vibrant arts scene, and historic architecture, Woodstock offers a unique blend of small-town charm and cultural richness.

In Woodstock, you'll find a thriving community of artists, musicians, and creatives who have been drawn to the area for its inspiring natural beauty and creative energy. The city is home to numerous art galleries, music venues, and cultural events that showcase the talents of local and visiting artists alike.

Nature lovers will appreciate Woodstock's proximity to the Catskill Mountains, where they can explore hiking trails, go skiing in the winter, or simply enjoy the stunning views of the surrounding wilderness. The city also boasts a variety of parks and outdoor spaces, perfect for picnics, leisurely strolls, or simply unwinding amidst nature.

For those interested in history, Woodstock offers a glimpse into its past through its well-preserved historic buildings and landmarks. Visitors can explore the Woodstock Artists Association & Museum, which showcases the work of local artists and celebrates the city's rich artistic heritage.

Whether you're looking to immerse yourself in the arts, connect with nature, or simply enjoy the laid-back atmosphere of a small town, Woodstock has something to offer everyone. Come discover the magic of this vibrant city in the Hudson Valley!

Newest Listings in Woodstock

39 Snow King Rd, Woodstock
$699,000
3 Beds ⋅ 2 Baths ⋅ 5115650 MLS
Welcome to Lost Valley! Tucked into a quiet North Woodstock neighborhood, 39 Snow King Road offers a welcoming White Mountains getaway with 3 bedrooms, 2 baths, and thoughtful updates throughout. The kitchen features custom hickory cabinetry and quartz countertops, bringing natural warmth and style to the heart of the home. New windows and doors, a new septic system, and a whole-house water filtration system and softener add everyday comfort and convenience. Whether you’re seeking a year-round residence or a mountain retreat, this home offers a peaceful place to recharge and enjoy the outdoor adventures of the White Mountain National Forest. Come discover your North Country escape!

39 Snow King Rd, Woodstock
156 Deer Park Dr Unit 137D, Woodstock
$12,000
1 Beds ⋅ 1 Baths ⋅ 5115503 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 upper level garden-style condo at Deer Park Resort features 1 bedroom, 1 full bath, propane fireplace 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 137D, Woodstock
19 Jack O Lantern Dr Unit Unit 16, Woodstock
$405,000
3 Beds ⋅ 3 Baths ⋅ 5115334 MLS
Welcome to Jack O’Lantern Resort! Situated along the first hole of the The Jack golf course, this 3-bedroom, 2.5-bathroom condo offers some of the best golf views in the resort. Enjoy the beautiful surroundings and four-season recreation that make this community such a desirable place to own. Whether you’re looking for a mountain getaway, a place to gather with family and friends, or a property with rental potential, this condo offers plenty of possibilities. Ask about the local rental management options and the popular Stay & Play packages offered in partnership with the Jack Golf Course. Owners enjoy access to a great selection of resort amenities, including an indoor heated pool, hot tub, outdoor pool, recreation room, basketball hoop, new playground, and tennis/pickleball courts. Outdoor enthusiasts will love the direct access to Corridor 11 for snowmobiling, with trailer storage available in the resort’s overflow lot. Located right next to the Jack Golf Course, restaurant, and bar, this property is set up to be enjoyed in every season, whether you’re golfing in the summer, enjoying the fall foliage, or hitting the slopes in winter.

19 Jack O Lantern Dr Unit Unit 16, Woodstock
45 Pleasant St, Woodstock
$1,595,000
5 Beds ⋅ 6 Baths ⋅ 5115063 MLS
Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!

45 Pleasant St, Woodstock
18 Pleasant St, 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
Lot 206-044 Lost River, 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
121 Townhouse Way Unit 20, Woodstock
$495,000
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.

121 Townhouse Way Unit 20, Woodstock
75 Riverfront Dr Unit 208, Woodstock
$449,900
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
156 Deer Park Dr Unit 128TD, 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 lower level garden-style condo at Deer Park Resort features 1 bedroom, 1 full bath, propane fireplace 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
1190 Long Hill Rd, 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
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
139 Doe Hill Way, 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
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