Stockbridge Real Estate

Stockbridge Real Estate

Welcome to Stockbridge, a charming town nestled in the heart of 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 its stunning views of the Green Mountains and easy access to outdoor recreational activities, Stockbridge is a nature lover's paradise. Whether you enjoy hiking, skiing, or simply taking a leisurely stroll through the countryside, this town has something for everyone.

In addition to its natural beauty, Stockbridge boasts a rich history and a vibrant cultural scene. Explore the historic buildings in the town center, browse the local art galleries, or attend one of the many community events held throughout the year.

For those considering a move to Stockbridge, the real estate market offers a variety of options, from cozy cottages to spacious family homes. Whether you're looking for a weekend retreat or a permanent residence, Stockbridge has something to suit every taste and budget.

Come and discover the beauty and charm of Stockbridge. With its small-town charm and natural beauty, it's no wonder why so many people are proud to call this place home.

Newest Listings in Stockbridge

$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

$500,000
5101648 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

$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
5099811 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 #5099792 and MLS#5099827.

3051 Vt Rte 107, 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

Start Your Search

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .