Woodstock Real Estate

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

$1,100,000
4 Beds ⋅ 3 Baths ⋅ 5106838 MLS
Lovely cottage nestled on the Ottauquechee River in the heart of historic Woodstock. Incredible river frontage with sprawling lawn for entertaining or just sitting enjoying the river tranquility in adirondack chairs. This charming cottage boasts 4 bedrooms with an open plan. An abundance of light, antique characteristics with wide pine floors, large fireplace in the living room and surrounded by lots of windows and French doors leading out to a large deck overlooking the river. The first floor consists of a large living room, dining room, eat-in kitchen and small bedroom/office. Second floor consists of primary suite with private bathroom and 2 more guest bedrooms with bath. The basement has a family room that has direct access to the back lawn adjacent to a good size storage room with ample space for bikes, kayaks and toys. A short walk into the village to all amenities, theatre, shops and restaurants. Just 3 miles to skiing and golf. Mt Tom trail access is across the street with miles of trails for hiking or cross country skiing. Incredible location!

2 River St, Woodstock
$412,000
3 Beds ⋅ 2 Baths ⋅ 5106266 MLS
Location is everything! Come experience this centrally located townhouse in downtown Woodstock where you are just 10 minutes from the slopes at Loon Mountain, 5 minutes from the vibrant restaurants and brewery in Woodstock, and a manageable 2-hour drive from Boston via I-93. This 3 bedroom 2 bath condo has the mountain charm lifestyle everyone is looking for. The main floor features a bright, open-concept layout anchored by a cozy wood-burning fireplace-the ideal spot to unwind after a day of adventure. The fully equipped kitchen, complete with modern stainless steel appliances, flows seamlessly into the living space, making it perfect for entertaining. Upstairs, the second level hosts two spacious bedrooms, while the third floor offers a large, versatile sleeping loft, providing plenty of room for family and guests. Step outside to your private, wooded back deck to enjoy the peaceful surroundings. Whether you are looking for a weekend retreat or a permanent mountain home, this condo delivers on every front.

8 Hayes Dr Unit 40, Woodstock
$225,000
2 Beds ⋅ 2 Baths ⋅ 5105576 MLS
Perched upon .83 acres in North Woodstock, this fantastic retreat offers the perfect balance of peaceful living and modern convenience. An open floor plan welcomes you inside to this 924-square-foot manufactured home offering two bedrooms and two full bathrooms lovingly maintained by the same family for 25 years. Step outside to a custom 31 foot back deck ideal for quiet mornings or lively gatherings overlooking a spacious, tree-lined backyard that feels like your own private escape. Also enjoy the wonderful screened in front porch and take advantage of the shade on those super sunny, summer days. All of this, just a 2 minute drive from downtown North Woodstock, major ski areas, rivers and the White Mountains make this home a rare blend of serenity and accessibility.

228 Daniel Webster Hwy, Woodstock
$1,040,000
3 Beds ⋅ 2 Baths ⋅ 5105489 MLS
Woodstock Village Home~ A rare opportunity to enjoy the best of Woodstock Village living from this charming and beautifully updated 3-bedroom, 2-bath home, once the town's blacksmith shop. Just steps from the heart of the village, you can leave the car at home and walk to shops, restaurants, galleries, cafés, and everything that makes Woodstock one of Vermont's most beloved destinations. Inside, an open-concept floor plan, beautiful wood floors, and abundant natural light create a warm and inviting atmosphere. Recent improvements include a new heat pump providing efficient heating and air conditioning, electrical upgrades, interior painting, and extensive basement work, enhancing both comfort and functionality. Outside is where this village property becomes truly special. The spacious fenced yard borders the Kedron Brook, creating a surprisingly peaceful setting in the heart of town. Relax on the deck and listen to the water, enjoy the newly planted fruit trees, or step through the yard to the nearby village footbridge spanning the brook--a picturesque connection to the surrounding neighborhood. Historic character, thoughtful improvements, a wonderful yard, and an exceptional walkable location come together in a home that captures the charm and ease of life in Woodstock Village.

13 High St, Woodstock
$26,000
2 Beds ⋅ 2 Baths ⋅ 5105461 MLS
Two bedroom, 2 bathroom, gas fireplace, fully furnished and ready to be enjoyed! Gas fireplace for ambience and A/C. Enjoy 13 weeks of ownership on a rotating basis at the highly sought-after Deer Park resort with all the amenities you could ever need. 5 acre spring fed swimming pond with beach, multi-million dollar clubhouse with indoor pool, racquetball courts, tennis, fitness room, etc. Enjoy the skating rink by the club house. Use this quarter share one week of every month, or exchange for a different location for a small fee through RCI or Intervale International. Showings from 11-1 on Fridays only.

164 Deer Park Dr Unit 178C, Woodstock
$415,000
2 Beds ⋅ 3 Baths ⋅ 5105357 MLS
QUINTESSENTIAL WOODSTOCK VILLAGE WORKFORCE HOUSING OPPORTUNITY: Offered at $415,000 through a local workforce housing covenant, providing qualifying buyers a rare opportunity to purchase in Woodstock Village at a price below comparable unrestricted-market properties. Enjoy premium Village living while preserving quality housing for qualifying members of our local and Upper Valley workforce. THE HOME: The largest layout in a peaceful 24 home community, this immaculate Federal-style brick townhouse offers 2,268 sq ft of living space across three fully finished levels. It functions seamlessly like a single-family home, boasting an open floor plan, bright natural light, a wood burning fireplace, and stunning hardwood floors. The layout features 2 spacious upstairs bedrooms and a highly versatile 1st-floor flex room with pocket doors, perfect as a 3rd bedroom, home office, or guest suite. KEY HIGHLIGHTS: Baths on every level. Private, oversized outdoor deck surrounded by mature woods and perennial gardens. Walking distance to the Woodstock Farmers’ Market and National Park trailheads. Updated electrical, plumbing, 2019 furnace, and a brand-new dryer. ELIGIBILITY: One occupant of your household works or will work locally at least 25 hours per week for a business or organization located within a 16 mile radius of the Woodstock Town Hall. The occupant can be either the homeowner or a long term tenant. Short term rentals (i.e., less than 30 days) are strictly prohibited. Covenants and Woodstock Trust eligibility documents are attached.

121 Townhouse Way Unit 20, Woodstock
$400,000
2 Beds ⋅ 3 Baths ⋅ 5104834 MLS
Welcome to your new home or home away from home located in beautiful Woodstock NH. This unique townhome offers a versatile floor plan that is warm and inviting. Cozy up by the fireplace on those cold blister days or read a book in your bright sun room that has two levels of enjoyment. Need an extra space for guest? Utilize the loft for additional sleeping space, privacy, or quiet time. This home has 2 bedrooms and an office that could be used as an additional sleeping space, office, den, or bonus space. The primary bedroom has its own on suite bathroom and two large closets for storage. It opens up to the bright sunrooms lower level making this primary suite the perfect sanctuary. Every inch of this homes space has been utilized for efficiency and functionality. Take advantage of the community amenities that include inground pool, basketball court, and tennis court. This home unlike many townhomes also has a dry functional basement that can be accessed from the interior and exterior. The current owners are using for a workout area. To top it all of this unit comes with a 2 car garage. Home is listed $15,000 below appraised value. Get instant equity! The back deck is brand new. It has been replaced by the HOA since the photos have been taken.

7 Sundance Rd Unit 4, Woodstock
$205,000
2 Beds ⋅ 2 Baths ⋅ 5104613 MLS
property being sold by trustee, seller has no knowledge of age, or systems within the home. There is no Zoning in the town Woodstock. This property will need work to make it livable.

88 Lost River Rd, Woodstock
$899,900
5 Beds ⋅ 4 Baths ⋅ 5104119 MLS
Mountainside Road really leans into the Mountain get-away theme of New Hampshire. This property is currently being used as an Air B & B, featuring a main house with 4 bedrooms that can be combined with or leased separately with a studio apartment that has its own kitchen, bath, porch and private entry. The home offers great White Mountain Views, is directly across the Street from Lost River (swimming and waterfalls) and providing easy access to all the Lincoln / Woodstock attractions and Loon Mountain skiing. This was a primary home for decades, and the apartment was added for a caretaker to live on site. It has been meticulously updated and maintained through the years and a whole house generator provided comfort on those harsh winter nights. The Cottage or shed structure offers a place for projects or additional storage.

5 & 7 Mountainside Rd, Woodstock
$238,000
1 Beds ⋅ 1 Baths ⋅ 5103476 MLS
Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. Quiet setting in a low density area. This end unit condo has had many updates and is ready for new owners to add their personal touch. A private deck looking out to woodlands and lawn. The bright kitchen is a pleasure to work in . Upstairs the den with skylight offers an opportunity for many uses. There is private storage space in the historic red barn. Woodstock Middle and High Schools are across the road. It is a short distance to all of the amenities historic Woodstock Village offers including dining , shopping and entertainment. Ski at Woodstock's own Saskadena Six or head over to Killington Ski Resort.

42 Heritage Condo Way Unit 24, Woodstock
$1,075,000
3 Beds ⋅ 3 Baths ⋅ 5103213 MLS
This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The home features a creative, livable floor plan with a mix of open gathering rooms and comfortable private spaces, accented with crown molding and 8 1/2-foot ceilings on the main level. The main level has two entries, with additional direct access from the spacious 2-car garage. A mudroom connects the front and garage entries, and the back entry near the garden barn is close to the kitchen. The generous living room centers on a wood-burning fireplace with floor-to-ceiling windows spanning the width of the room. A gracious dining room adjoins the living room, den/bedroom, kitchen, and private stairway to the primary bedroom suite. The second level includes the primary bedroom with study/dressing room, walk-in closet, private balcony, and en suite bath with Italian marble vanity, tile, and surfaces. The second bedroom is illuminated by natural light and well-appointed en suite bathroom. A second-floor family/media room is separate from the sleeping areas. The property is within easy walking distance to the Village Green, shopping, entertainment, elementary school, and all resort amenities. A gem waiting to be discovered.

648 Church Hill Rd, Woodstock
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 5102668 MLS
"BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a bright, open gathering space where spectacular mountain views are always on display. The newer gourmet kitchen features a large center island, Thermador appliances, quartz countertops, and abundant custom cabinetry. The spacious living room is centered around a handsome stone fireplace and offers multiple seating areas. French doors open to a newer southwest-facing deck with a large hot tub, creating the perfect setting to enjoy sunsets and panoramic views throughout the year. The main level also includes a generous primary suite with a walk-in closet and an ensuite bath featuring a soaking tub with mountain views and a separate shower. A mudroom with laundry connects directly to the oversized attached two-car garage. A circular staircase leads from the kitchen to a charming renovated tavern and wine room with French doors opening to a private brick patio, ideal for entertaining. Upstairs are a comfortable office, study, or media room, three additional bedrooms (two with long-range views), an updated full bath, and a separate half bath. The full concrete basement provides abundant storage and houses the mechanical systems. Additional amenities include a full-house automatic generator, ample parking for four or more vehicles in addition to the attached garage, and well-maintained grounds. BLISS HOUSE combines privacy, stunning views, quality renovations, and an exceptional location just minutes from Woodstock Village. Walk-through tour, video, drone aerials, and floor plans available online.

353 Cabot Rd, Woodstock
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