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

$519,000
2 Beds ⋅ 3 Baths ⋅ 5108325 MLS
This well maintained 2-bedroom, 3-bathroom townhome sits beside The Pemigewasset River within Deer Park. Step inside to discover an inviting open-concept layout where the kitchen, dining, and living areas beneath soaring vaulted ceilings. Natural wood accents and a striking updated propane stove/fireplace create the New Hampshire ambiance you've been searching for. Two upper-level master bedrooms each feature private en-suite bathrooms ensures comfort for the entire family or guests. Thoughtful updates including new flooring, kitchen, baths and appliances and furnishings make this a true turnkey property. The Deer Park community is a four-season playground. The impressive clubhouse boasts an indoor pool, hot tub, cardio and weight rooms, racquetball & pickleball courts, and an inviting great room with a double-sided stone fireplace. On summer days enjoy the gorgeous 5-acre lake and sandy beach. Adventure seekers will love the proximity to Loon Mountain, complete with seasonal shuttle service, along with easy access to Cannon Mountain and the scenic Kancamagus Highway.

27 Riverfront Dr Unit Unit 265, Woodstock
$2,485,000
4 Beds ⋅ 5 Baths ⋅ 5107880 MLS
Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village’s earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern and lodging for members of Vermont’s early legislature, giving the property an uncommon connection to both the town’s and the state’s history. Over a century later, it became the Daughters of the American Revolution House Museum. Listed on the historic register, the home underwent a comprehensive restoration in 1995 by noted preservationist Doug Guest, along with a thoughtfully designed addition. Distinctive original details remain, including five teardrop ornaments above the first-floor windows and the beautiful Palladian window over the front entrance. Together with the patina of more than two centuries, they give the house an authenticity that has been carefully preserved while incorporating the comforts of contemporary living. Inside, wide-board floors, finely proportioned rooms, five working fireplaces, period millwork, and abundant natural light create a sense of warmth and character. The capacious renovated kitchen opens to a sun-filled dining area overlooking the rear stone terrace, while gracious gathering rooms retain the scale and character of the original house. All bedrooms are en suite, an unusual convenience in a home of this age. Set back from Main Street along a quieter parallel road, the property enjoys one of Woodstock Village’s most appealing locations, with dining, the theater, galleries, cultural events, and the trails of Mount Tom all within an easy walk. A detached two-bay garage and off-street parking add another uncommon convenience for a village property. Beautifully restored and turnkey, 26 The Green offers the opportunity to live in an important early Vermont home without sacrificing the ease of contemporary village life.

26 The Grn, 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
$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
$399,600
2 Beds ⋅ 3 Baths ⋅ 5105357 MLS
QUINTESSENTIAL WOODSTOCK VILLAGE LIVING: Offered at $399,600, this beautiful townhouse presents a rare opportunity to own a home in the heart of Woodstock Village at an exceptional value. Enjoy the charm, convenience, and lifestyle of Village living, with easy access to Woodstock’s shops, restaurants, recreation, and the greater Upper Valley. 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, with an open floor plan, abundant natural light, a wood-burning fireplace, and stunning hardwood floors. The flexible layout includes two spacious upstairs bedrooms and a highly versatile first-floor flex room with pocket doors, perfect as a third 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. A UNIQUE OWNERSHIP OPPORTUNITY: This home is offered under a local deed program with specific buyer qualifications, allowing eligible buyers the opportunity to own a Woodstock Village home at an exceptional value. Wondering if you qualify? Contact broker for a simple explanation of the requirements and to find out whether this opportunity could be right for you.

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
$195,000
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
$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
$450,000
3 Beds ⋅ 2 Baths ⋅ 5102664 MLS
Enjoy peace, privacy, and endless possibilities on 2 quiet acres, just 3 miles from downtown Woodstock! This adorable ranch-style double-wide offers a bright, open-concept kitchen, dining, and living area perfect for entertaining or relaxing by the wood-burning fireplace. Vaulted ceilings and abundant natural light enhance the spacious feel. The impressive kitchen features solid hickory cabinetry, stainless steel appliances, a tile backsplash, pot filler, apron-front sink, oversized island with extensive storage, and a charming window seat with additional storage. The primary suite includes a spacious bathroom with double sinks, a stand-up shower, soaking tub, and direct access from both the bedroom and bathroom to a large walk-in closet. The property’s standout feature is the nearly new, never-used, three-story barn measuring approximately 40' x 28'. With 14-foot ceilings and 13-foot entry doors, it is ideal for RV storage, classic cars, animals, a workshop, or other recreational uses. Above the barn is an additional 20' x 40' open space, accessed by interior stairs, offering approximately 800 square feet of storage or potential finished space. The barn may also offer future residential conversion possibilities, subject to all required permits and approvals. Additional features include a 30-amp electrical hookup in the driveway for an RV or hot tub, a lovely brook that feeds a private pond, and a peaceful mountain setting. Perfect for year-round living, a second-home getaway, or a potential Airbnb opportunity!

68 Russell Farm Rd, Woodstock
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