Stratton, VT Classified Ad Listings

Stunning updated and expanded chalet just a short drive out of the village of Wilmington. This home sits privately on a wooded double lot, nestled in the Chimney Hill community with easy access to the amenities building, as well as nearby access to Mount Snow and Lake Whitingham. The home was extensively renovated and expanded and now has tremendous unique one of a kind space featuring a gorgeo...

58 Red Hawk Rise. Single Family Home for sale in Stratton, VT for $2,700,000 with 5 bedrooms and 5 full baths, 1 half bath. This 5,390 square foot home was built in 2004 on a lot size of 5.12.. Crafted by Vermont Barns / Wadsworth Design Build, this custom timber frame home in Stratton, Vermont, brings together beautiful craftsmanship, generous living spaces, and a peaceful National Forest sett...

1073 Chapel Rd. Unlock the potential of this spectacular 58.1 +/- acre woodland property in historic Bennington. The groundwork for your future home or getaway is already laid with a State-approved wastewater permit in place for a three-bedroom single-family residence, allowing you the flexibility to design your build. Further simplifying your plans, the property offers the rare advantage of co...

390 Fairview St. Situated just outside historic Old Bennington and near the Bennington Battle Monument, this property offers the privacy and natural setting of a larger country parcel while remaining convenient to downtown Bennington and area amenities. With approximately 318 feet of road frontage, the wooded property offers plenty of room to create a private homesite surrounded by nature. Much...

9 Brown Rd. Nice private almost 17 acre site with driveway, dug well, dug pond, sitework and ski area and Mountain views. Log cabin or post and beam home is a great fit. VAST snowmobile trail runs through the property. Beautiful bright and sunny exposure.

116-118 S Branch St. Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a d...

232 Depot St. Charming in-town 3-bedroom, 1-bath home situated on a low-maintenance 0.09-acre lot. Enjoy a private, fully fenced backyard with views of Mt Anthony, which is perfect for relaxing, entertaining, or pets. Shared driveway with off-street parking. Conveniently located within walking distance to shopping, restaurants, parks, and local amenities. This home offers the perfect blend of c...

153 Northside Dr. Level,.53-acre lot situated in Bennington's high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more stre...

2436 Mad Tom Rd. Picture yourself on 12 private wooded acres along one of Vermont's most scenic country roads in a classic 4-bedroom, 3-bath Colonial offering the perfect blend of comfort, character, and outdoor adventure. Built in 1977 and thoughtfully maintained, the home welcomes you with warm hardwood floors, a beautifully renovated kitchen featuring soapstone countertops, abundant cabinetr...

19 View Road. Single Family Home for sale in Wilmington, VT for $335,000 with 3 bedrooms and 2 full baths. This 1,400 square foot home was built in 1982 on a lot size of 0.5.. Come take a look at this three bedroom and two bath chalet in the B Section of Chimney Hill with terrific amenities. Relax on the main level in an open concept living, dining and kitchen space, living room has a woodstove...

710 Main St. Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental...

4880 Pikes Falls Rd. Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for se...

655 Squirrel Hollow Rd. This contemporary residence by acclaimed architect Jeff Barnes offers a versatile floor plan with abundant living options, set on 23 private acres that balance tranquility with equal proximity to Manchester Center and Dorset Village. A quick trip to Bromley Mountain and Stratton, the home is set amidst professional landscaping with sweeping Green Mountain views. The main...

215 Main St. IN THE HEART OF THE HAMLET that is South Londonderry, VT, sits this exquisitely charming 1820s home, where historic Vermont character meets thoughtful updates and remarkable future potential. From the moment you arrive, the curb appeal, spacious private lot, and classic architecture set the tone. Inside, freshly professionally refinished wood floors gleam alongside beautiful staine...

34 Rock Split Way. Perched atop Chimney Hill, this 3-bedroom, 3-bathroom home is perfectly suited as a vacation retreat or a primary residence, offering fantastic indoor and outdoor entertaining spaces. Enter the main level via the newly expanded staircase and deck. Inside, a spacious tile entryway provides ample room for gear and clothing storage. The sunken living room, with stone fireplace, ...

This West Wardsboro chalet is looking for someone to bring it back to life! Full of potential and ready for renovation, this property offers the perfect opportunity to create your own Vermont mountain getaway. The town lists the property as a three-bedroom, though it currently features one bedroom plus a loft, offering flexibility for future improvements. Set on a nice lot in a convenient locat...

26 Highlands Ave Unit J2. Elevated Mountain Living at Haystack Highlands. Discover the ultimate four-season retreat in this exceptional townhome, ideally positioned along the 11th fairway of Haystack Golf Course and framed by distant mountain views. Designed for effortless entertaining and memorable gatherings, this beautifully appointed home offers an exceptional blend of finishes, generous li...

99 Mirror Lake Xing. Old Mill on Haystack Mountain is a mountain residence designed for the next chapter of family life, set on 3.58 acres within the gates of The Hermitage Club with views of the Haystack trails. With over 6,000 square feet of finished living space, the home offers the scale and flexibility to comfortably accommodate children, grandchildren, friends, and extended family while s...

215 VT Route 30. Opportunities are Knocking! Welcome to an extraordinary 50+ acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta location, natural beauty, and limitless potential. Bordering a gentle brook and featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in o...

37 Stowe Hill Rd. OPEN HOUSE Saturday, October 10th 2pm-4pm. Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 picturesque acres just minutes from the charming village of Wilmington, Lake Raponda, Lake Whitingham, Mount Snow Ski Resort, and The Hermitage Club at Haystack. Lovingly renovated by its current owners since 1997, this exceptional property seamlessl...