Browse All Woodstock NH 4 Bedroom Properties for Sale

This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. 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 soothing music of the water rose to a crescendo in August 2011 as Hurricane Irene swept into Vermont as a tropical storm, resulting in a FEMA-designated 500-year flood event that inundated basements, as it did many homes in Woodstock and other river towns. Subsequently, the owners have replaced the lower-level sheetrock and boiler and have invested in an engineered barrier wall. The home is within walking distance of Village shops, restaurants, and resort amenities. A peaceful hideaway close to everything.

16 Church St, Woodstock

$1,695,000

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!

2706 E Woodstock Rd, Woodstock

$2,225,000

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

$589,900

4 Beds ⋅ 3 Baths ⋅ 5093238 MLS

Charming New Englander with Income-Producing Apartment in a Prime Location Well-maintained 4-bedroom, 3-bathroom New Englander-style single-family home featuring an attached apartment that offers excellent rental income potential or can serve as a comfortable in-law suite. This home has seen numerous updates, including a new roof with a transferable lifetime warranty, new windows, new siding, blown-in insulation, and a new propane-fueled wall furnace. All appliances are included, making this property truly move-in ready. A quality Reeds Ferry shed provides additional storage and functionality. Enjoy the convenience of being close to some of New Hampshire's most popular outdoor attractions, including golf courses, Loon Mountain Resort and Cannon Mountain Ski Area, snowmobile trails, grocery shopping, and a variety of restaurants. Experience the charm of small-town living while being just a couple of miles from the town center. Whether you're looking for a primary residence, a multi-generational living arrangement, or a property with supplemental income potential, this home offers exceptional versatility and value. Highlights: 4 bedrooms, 3 bathrooms Attached apartment/in-law suite New roof with transferable lifetime warranty New windows and siding New propane wall furnace Blown-in insulation All appliances included Reeds Ferry shed Close to skiing, golf, shopping, dining, and recreation Minutes from town center This property combines classic New England character with modern updates and outstanding income potential.

1113 Daniel Webster Hwy, Woodstock

$649,000

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

$502,000

4 Beds ⋅ 3 Baths ⋅ 5085202 MLS

Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including energy-efficient heat pumps, enhanced electrical systems, basement insulation, and newer windows—ensuring comfort and efficiency in every season. Recent capital improvements, such as updated siding, a newer drilled well, and new oil and propane tanks, underscore the home’s turnkey reliability, while generator-ready capability provides an added layer of confidence. Enjoy a kitchen built for making memories anchored by a newly installed and sleek granite island perfect for connection and celebration. Outdoors, the revitalized grounds invite both quiet relaxation and effortless entertaining, all framed by the natural splendor of this picturesque village setting. Positioned on coveted Happy Valley Road, the property offers a lifestyle as desirable as the home itself—where morning strolls and evening bike rides become part of your daily rhythm. Just minutes from the boutiques, dining, and charm of Woodstock, as well as convenient access to Interstate 89, this location perfectly balances a charming, village-like setting with accessibility. Imagine summer evenings spent beside the gently flowing stream, gathered around a glowing fire under the stars—an experience that captures the very essence of elevated Vermont living.

88 Happy Valley Rd, 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

$395,000

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.

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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