Stockbridge Homes for Sale

Welcome to Stockbridge, a charming town nestled in Windsor County, Vermont. Known for its picturesque landscapes and tight-knit community, Stockbridge offers a tranquil and idyllic setting for those looking to escape the hustle and bustle of city life.

With a variety of homes for sale in Stockbridge, you can find the perfect property to suit your needs. Whether you're looking for a cozy cottage, a spacious family home, or a secluded retreat in the woods, Stockbridge has something for everyone. From historic properties with character to modern homes with all the amenities, the real estate market in Stockbridge is diverse and vibrant.

Imagine waking up to the sound of birds chirping and the fresh mountain air filling your lungs. In Stockbridge, you can enjoy a peaceful and serene lifestyle, surrounded by nature's beauty. Take a leisurely stroll through the town center, explore the nearby hiking trails, or simply relax on your porch and soak in the stunning views.

If you're ready to make Stockbridge your home, now is the perfect time to explore the homes for sale in this charming town. Let us help you find your dream property in Stockbridge, where you can create lasting memories and live the life you've always imagined.

Newest Stockbridge Homes for Sale

$105,000

2 Beds ⋅ 5107947 MLS

For those who believe the best weekends begin where the pavement ends, this charming off-grid seasonal camp offers a genuine back-to-basics escape on 23.7 acres of remote Vermont wilderness. Comprised of two adjacent parcels - 11.4 acres with the camp plus an additional 12.3-acre lot - the property provides plenty of room to roam, explore and simply get away from it all. The rustic cabin is all about simplicity and character, with a bright, open living space beneath vaulted rustic pine ceilings, no-frills plywood walls and warm hardwood floors. A compact kitchenette with gas range and sink provides the essentials, while a cozy woodstove and gas lights create an inviting atmosphere when the sun goes down. There is no running water, so you'll bring your own or pump it from the outdoor storage tank. An outhouse completes the setup. Step outside and the adventure begins. Off-roading, hunting, hiking and mountain biking are all part of the experience, with trails leading directly into the surrounding woods. A deer stand sits up the trail, offering an added bonus for the outdoor enthusiast. Or simply leave the gear behind, settle in by the woodstove and listen to the sounds of nature. This is not a property for those seeking polished amenities or turnkey luxury. It is something far more elemental: a private place to unplug, reconnect with the outdoors and enjoy Vermont on its most authentic terms. Bring your 4WD, your sense of adventure and your appreciation for the simple life.

243 Thompson Rd, Stockbridge

$319,000

3 Beds ⋅ 1 Baths ⋅ 5106102 MLS

Sweet 3-bedroom home with a wraparound deck and covered porch in a country setting. Hardwood flooring and natural wood window casings, cathedral ceiling, a walkout basement w/shop area and office space. . Current owner only uses between 3-4 cords of wood and less than 1 tank of oil to heat the home. Only minutes to downtown Bethel eateries and grocery market and convenient to the I-89 corridor. (

2147 River Rd, Stockbridge

$649,000

3 Beds ⋅ 2 Baths ⋅ 5103851 MLS

Charming timber frame cottage on 15 private acres with nearly 500 feet of frontage along the pristine White River, where world-class fly fishing, crystal-clear swimming holes, and the soothing sounds of flowing water create an unforgettable Vermont retreat. Rich in authentic character, this extraordinary home showcases hand-hewn posts and beams, beautifully refinished wide pine floors, vaulted ceilings, and a welcoming living room anchored by a traditional fieldstone fireplace. Cozy bedrooms and gently uneven floors aren't imperfections - they're reminders of a time when homes were built by hand and meant to last. The spacious country kitchen blends timeless charm with modern convenience, featuring a large breakfast bar, farmhouse sink, six-burner gas range beneath a handcrafted stucco and tile hood, and contemporary skylights. A whimsical loft overlooks the living room, while the primary suite offers vaulted ceilings, woodland views, and a classic clawfoot soaking tub. Outside, enjoy a wraparound porch, perennial gardens, open lawns, a private spring-fed pond, wooded trails, an outdoor stone fireplace, and a small barn for recreational gear. Fish, swim, tube, hike, bike, or snowshoe directly from your own property. Rarely does a home so perfectly capture the spirit of Vermont, where history, privacy, and outdoor adventure come together in one remarkable setting. Offer deadline 8/18/26.

333 Childrens Camp Rd, Stockbridge

$500,000

4 Beds ⋅ 4 Baths ⋅ 5101647 MLS

Welcome to Camp Treetops, a one-of-a-kind mountaintop estate perched high above the White River Valley. This fully operating, high-performing retreat conveys COMPLETELY FURNISHED and turnkey, with panoramic mountain and White River views, total privacy, and a proven income stream already in place. At its heart is the original Sears Roebuck kit hunting cabin, beautifully renovated with warm wood interiors, an open living and dining area, a cozy wood stove, and expansive windows framing the mountains. The covered deck is built for sunrises, sunsets, and brilliant fall foliage. Two additional cabins, newly built in 2023 and 2024, are themed to the roaring 1920s and the classic 1950s, each furnished with authentic antiques for a true blast from the past. A vintage camper adds a memorable glamping stay, and a shared communal space brings guests together. The retreat has offered fresh breakfast and dinner service, and the property runs as a thriving Airbnb with strong, established revenue. Smart, low-impact engineering makes it all work. A dedicated septic design serves the main cabin, while the additional cabins are outfitted with NASA-designed bag-system toilets and outdoor showers. There is also potential room to grow: sites for two more cabins are already cleared with construction under way, maybe allowing a future owner to operate up to five cabins in total, every one capturing the same sweeping mountain and White River views. The setting delivers seclusion with easy access. Close to Route 107 with quick connections to Route 100 and I-89, it sits roughly 30 minutes from Killington Ski Resort and under an hour from Sugarbush Ski Resort. Surrounded by mature forest and dramatic rock outcroppings, Camp Treetops offers rare privacy without sacrificing those long-range views. Whether you want a private family compound, a recreational basecamp, or a turnkey investment with a track record to prove it, 544 Vulture Mountain Road is a truly unforgettable piece of Vermont.

544 Vulture Mountain Rd, Stockbridge

$385,000

3 Beds ⋅ 1 Baths ⋅ 5099792 MLS

A rare chance to own a substantial slice of Vermont's countryside, with commercial upside built in. This 62-acre property spans both sides of VT Route 107, offering a diverse landscape along with the flexibility of a commercial zoning designation, opening the door to a range of business and development possibilities. On the south side, mature forested acreage includes a former sugarbush offering privacy, recreational potential, and timber value. On the north side, you'll find stunning riverfront acreage where the property abuts both the White River and Stony Brook, offering exceptional access to fishing, swimming, and peaceful water views that are hard to come by. The property includes an existing house in need of rehab, a blank canvas ready for your vision, and made all the more appealing by a drilled well and up-to-date septic system already in place. Plenty of locations on the property to build away from the road. A large 4-bay equipment garage adds valuable storage and workspace,ideal for tractors, toys, vehicles, or a commercial operation. Whether you're envisioning a commercial venture, a working sugarbush, a renovation project with income potential, or a long-term investment in Vermont land, this property offers the space, natural beauty, water frontage, and zoning flexibility to make it happen. With Route 107 frontage for easy access and two distinct landscapes to explore, the possibilities here are as varied as the terrain itself. This property has been in the same family for generations, and the heirs have retained a section of the riverfront for family get-togethers and summertime camping. Don't miss your chance to own this exceptional piece of the Green Mountains, zoned for opportunity, ready for your ideas. Also being marketed as MLS #5099811 and #5099827.

3051 Vt Rt 107, Stockbridge

$459,000

3 Beds ⋅ 2 Baths ⋅ 5097518 MLS

Beautifully maintained and thoughtfully updated, this classic Vermont Cape is nestled on five private, sun-drenched acres in the heart of the Green Mountains. Whether you're searching for a centrally located primary residence or a peaceful mountain retreat, this inviting property offers comfort, privacy, and year-round recreation. Surrounded by forest, the open homesite enjoys abundant sunshine, a partially fenced yard, mature perennial gardens, and space to garden or simply enjoy the outdoors. A welcoming wraparound deck leads to a spacious mudroom with built-in cubbies, creating the ideal everyday entry after hiking, skiing, or working in the yard. Inside, the bright, open main level features gleaming hardwood floors and an updated kitchen with stainless steel appliances, striking soapstone countertops, a butcher block center island, and ample workspace for cooking and entertaining. The adjoining living area is anchored by a cozy wood stove for crisp Vermont evenings, while a convenient powder room with laundry completes the first floor. Upstairs, the expansive primary bedroom offers a generous walk-in closet, complemented by two guest bedrooms and a full bath. Skylights fill the second level with natural light, while energy-efficient mini-splits on both floors provide year-round comfort. The full basement offers abundant storage and flexible space for a workshop, hobby studio, recreation room, or play area. Outside, the charming red barn is perfect for lawn equipment, gardening supplies, and all the gear needed to enjoy Vermont's four-season lifestyle, with nearby access to snowmobile and ATV trails. Just across the road, the White River offers renowned fly fishing, kayaking, and summer tubing, while Killington and Pico are just a short drive away. With seasonal winter views, exceptional privacy, and a tranquil setting, this special property captures the very best of Vermont living. Seller motivated!

38 Stony Brook Rd, Stockbridge

$424,500

2 Beds ⋅ 3 Baths ⋅ 5072031 MLS

EXTRA ACRE! EXTRA VALUE. PROPERTY NOW INCLUDES one more acre than previously listed. Take a look at this home in central Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 3 acre lot with plenty of sun and space for pets, gardens, greenhouses or farm animals. This Stockbridge home has an in-law apartment below- accessible by a separate driveway. It provides options for extended family, short or long term renters or vacationers, and allows space to spread out or mom and pop to have privacy. While technically it's a 2 bedroom, the layout could accommodate 6-8 with a little creativity. Or make it your forever home in the heart of Vermont with small towns Stockbridge and Rochester providing quality living: Summer tubing and river activities, hiking the Green Mountains, golf, local food and art scenes, Mad River, Sugarbush and Killington ski resorts- there is a lot to do in Vermont! Tenant occupied, please provide 12 hour notice for showings. Some of the room pictures are virtually staged.

339 Ranney Rd, Stockbridge

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