Browse All Woodstock NH 4 Bedroom Properties for Sale

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

$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

$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

$1,195,000

4 Beds ⋅ 3 Baths ⋅ 5100512 MLS

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children’s daycare center surrounded by community pools, basketball courts, and the Town’s recreation center. On long summer days, the joyful sounds of children enjoying the wide sand beach and swimming holes float up from the river below. Over the years, the floor plan has been adapted on all three levels to modern lifestyles. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The home, like many in Woodstock Village, was damaged in August 2011 by Hurricane Irene. The property is not in the designated 100-Year floodplain that requires insurance. Irene was a FEMA-designated 500-year flood event that affected the basement; afterward, the owners replaced the lower-level sheetrock and the heating boiler and restored the riverbank.

16 Church St, Woodstock

$1,645,000

4 Beds ⋅ 4 Baths ⋅ 5096963 MLS

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate! *Main Level Photos Have Been Electronically Decluttered*

2706 E Woodstock Rd, Woodstock

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 5095556 MLS

Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in the early 1800’s. The rooms are spacious, bright and inviting with exposed hand- hewn beams and pine plank floors running throughout. The updated country kitchen with soapstone counters connects to a cozy reading room with bookshelves and woodstove, and a utility/mudroom with ¾ bath, and laundry. The formal dining room offers plenty of space for gatherings. The front to back Living Room is anchored by a woodburning fireplace, and steps out to a private sunroom, and a guest room/office. Moving upstairs, there are four bedrooms and a bathroom. The 18thcentury hip roofed, post and beam English bank barn has a huge, sweeping loft space ideal for parties and entertaining. The lower level can accommodate animals, hobbies or a home occupation. The barn is surrounded by lush green pastures, and rail fencing which lead you to a network of beautiful trails for hiking. A short stroll to The Kedron Valley Inn, KV Pond, The South Woodstock Store, and Green Mountain Horse Assn. A five-minute drive to the Woodstock Village Green. Easy access to Hanover, DHMC, skiing, golf, dining, shopping and recreation.

473 Kendall Rd, Woodstock

$595,000

4 Beds ⋅ 2 Baths ⋅ 5088170 MLS

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

11 Maple St, Woodstock

$2,500,000

4 Beds ⋅ 4 Baths ⋅ 5087228 MLS

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler’s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies—including a whole-house generator and rooftop solar—offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont’s finest amenities.

114 Oak Ridge Way, Woodstock

$659,000

4 Beds ⋅ 3 Baths ⋅ 5077210 MLS

Historic Woodstock, Vermont - Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local regulations). Inside, you’ll find two charming fireplaces that add warmth and character, perfect for cozy Vermont evenings. The home’s classic architecture blends timeless appeal with endless possibilities for customization. Set on over 2 acres, the property features a fenced yard ideal for pets, gardening, or outdoor entertaining. A one-car garage adds convenience, while the separate potting shed - complete with electricity and a heater - offers wonderful space for gardening enthusiasts, creative projects, or additional storage. Located just minutes from Woodstock Village, you’ll enjoy easy access to boutique shopping, dining, and the renowned Woodstock Inn & Resort and its spa amenities. Vermont’s natural beauty surrounds you - world-class skiing, hiking, biking, and year-round recreation make this an exceptional place to unwind, recharge, and truly enjoy life. A unique property with space, charm, and opportunity in historic Woodstock.

598 E Woodstock Rd, Woodstock

$349,000

4 Beds ⋅ 2 Baths ⋅ 5063810 MLS

Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full time residence or a Vermont getaway , this property offers an excellent opportunity to enjoy one of Vermont's most desirable areas at an attractive price point. Call today for a private viewing.

5798 W Woodstock Rd, Woodstock

$5,950,000

4 Beds ⋅ 5 Baths ⋅ 5044620 MLS

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef’s kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby. Additional land available.

412 Skyland Ln, Woodstock

$865,000

4 Beds ⋅ 3 Baths ⋅ 5052613 MLS

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples.

1782 Randall Rd, Woodstock

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