Stratton, VT Classified Ad Listings

1886 Winhall Hollow Rd. Great New Price, Great VALUE, Great Location, New Roof, New Septic, recent exterior painting! This turn key residence is ideally located between three ski areas and near schools and shopping. Gourmet kitchen, wood floors, upscale baths and a huge 3 car garage/ barn with finished office space. Tucked amidst the forest with views of Magic Mountain's ridge line, whether you...

2036 VT Route 30. A cozy base for days spent enjoying Vermont country life warmed by a cozy wood stove and enjoying countless meals prepared together in the upgraded cherry and tile kitchen. Property has direct access to the West River. a nice deck to sit on in the back and a nice sitting platform overlooking river. Two bedroom one bath mobile home. Six months occupancy per year. New tenants mu...

336 Kirby Hollow Rd. Set in a premier Dorset country setting with sweeping 360-degree views of rolling pastures, mountains, and neighboring farmland, this charming single-level ranch offers a rare opportunity to enjoy the beauty and tranquility of Southern Vermont. The home offers over 1,568 square feet of comfortable living space, including an open-concept kitchen, dining, and living area, an ...

Water St. A rare opportunity to own over 91 private acres just a short walk from the charming Village of Jamaica. Tucked away off a private right-of-way, this remarkable parcel offers the perfect balance of peaceful seclusion and convenient access to local shops, dining, and community events. The property features a beautiful mix of mature forest, gently rolling terrain, and serene natural surr...

113 Main St. Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry. Step inside to find gleaming newly upgraded flooring, a warm and...

157 Newfane Hill Rd. Welcome to a home with a story. Originally the 1787 residence of local blacksmith Marshall Newton, this property has been a cherished family retreat for the last fifty years. One of only two original settlements on Newfane Hill that are still there. It's a place with "old world" charm-like centuries-old wall paneling -but also a new 2025 standing-seam roof and extensive ins...

72 Depot St. Step into classic New England charm with this cozy 1900 Cape, available for seasonal rental from mid-November to mid-April. Nestled in a peaceful setting, you are just a short stroll from the heart of picturesque Jamaica Village and a quick 15-minute drive to Stratton Mountain, 23 minutes to Mount Snow and 38 minutes to Okemo. Featuring 3 bedrooms and 2 baths, this home is the rela...

Beautifully renovated inside and out, this 3-bedroom, 2-bath Ranch offers 1,788 square feet of comfortable single-level living in a highly coveted Bennington location. Tucked into an established neighborhood on the outskirts of town, the property feels private and peaceful while remaining just minutes from major shopping, services, and everyday conveniences. Thoughtfully remodeled with a gorgeo...

310 Longview Drive. Single Family Home for sale in Manchester, VT for $1,200,000 with 5 bedrooms and 4 full baths. This 4,450 square foot home was built in 1970 on a lot size of 2.9.. In the heart of Manchester Village, with Equinox Mountain as Your Backdrop Set gracefully on 2.9, this beautifully maintained Cape-style home captures the timeless charm and natural beauty of Vermont living. With ...

29 Markham Ln. This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store,...

498 Townline Rd. If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home wa...

127 Dewey St. Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again. Inside, you'll find generous living space ready for your vision and u...

2 Hamlin Ave. 2-Unit Multi-Family with Professional-Grade Workshop! Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotiv...

3269 Route 30. Historic District, Dorset Village 4 Bedroom Colonial Farmhouse located with both residential and commercial zoning walk to every village amenity such as the Dorset Inn, Barrows House and Pool, Dorset Bakery, The Union Store, The Field Club, Dorset Library, Theater, Historic Society, and the Pinnacle walking trail. Recently restored this residence lives comfortably with extensive ...

2 Belvedere St. Here is the blank slate for your Vermont home, offering beautiful views of the Green Mountains and a location that is just steps from a 160-acre wildlife preserve with numerous hiking trails, wetland viewing platforms, and abundant wildlife. This cute corner lot is mostly level, cleared, and ready to build, with town water and sewer available at the street. Bring your imaginatio...

1944 Monument Ave. Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-squa...

3148 Route 11. More than a Vermont home, this is a property built for the way you want to live here. Set on 14 acres in Londonderry, this versatile Southern Vermont property combines a 3-bedroom, 2-bath home with something increasingly difficult to find near the mountains: acreage, substantial storage, multiple outbuildings and room for all the gear that comes with the Vermont lifestyle. The pr...

2200 Chapel Rd. Well maintained and updated 2011 double wide with 3 bedrooms and 2 full bathrooms situated on 1.33 acres in Bennington. Offering new flooring through most of the house and new appliances. Large living room, kitchen and laundry room. Primary bedroom has a private full bath. Nice property and great location.

Scattered Timber Rd. Build your dream mountain retreat on this exceptional 1.4-acre double lot (Lots 494 and 495) in the highly desirable Chimney Hill community. Gently sloping and situated at approximately 2,400 feet in elevation, this unique parcel offers outstanding privacy with seasonal winter valley views while directly abutting Green Mountain National Forest and HOA common land, helping p...

118 Foster Dr. Invest in the potential with this unique split-level ranch and guest house. This property presents an exceptional opportunity for anyone looking to roll up their sleeves and bring a property back to life. Set on expansive acreage surrounded by peaceful woodlands, the property offers a tranquil rural setting while remaining just a short drive from town amenities. The main residenc...