108 houses for sale in Wilmington, Wilmington town Windham County Vermont

This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an

Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxed Vermont atmosphere that feels inviting year-round. Step outside to the front porch and enjoy the seasonal mountain views while taking in the peaceful surroundings. Set on a wooded lot, the property offers a balance of privacy and convenience, with easy access to the extensive amenities of Chimney Hill and the recreation opportunities that make Southern Vermont such a sought-after destination. As a homeowner in Chimney Hill, you'll enjoy access to a wide range of community amenities, including an indoor pool, outdoor pool, fitness and community center, pickleball courts, ice skating, tennis courts, and an extensive ne

A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake - with a private dock - just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats tend to head for the public-access Harriman Reservoir on the southern end of Wilmington, Raponda remains a predominantly owner-enjoyed lake. The result is noticeably less boat noise and wake, making it equally wonderful for kayaking, paddleboarding, and peaceful summer mornings on the water. The property sits on a generous, nicely sized parcel with sweeping level lawn space, a private yard with fire pit, ample parking, kayak racks, and a private dock - which transforms into an ice skating destination come winter. Inside the fully remodeled and expanded vintage four-bedroom, four-bath lake house, a

Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary bedroom, 2 guest bedrooms, and a half bath. There is a full unfinished basement with great storage space, laundry, and a full walkup staircase. A tremendous primary home or Vermont retreat

Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. Beautifully maintained and thoughtfully designed, this turnkey 3-bedroom, 2-bath home is ready to enjoy from day one whether as your full time residence, vacation getaway, or a highly successful short-term rental that guests absolutely love. Walking in through the covered entry you'll find soaring cathedral ceilings in the living room, abundant natural light, a cozy brick hearth with wood stove, and an inviting open kitchen and dining area perfect for gathering with family and friends. This main floor also has a full bathroom. The 3 bedrooms and another full bath are upstairs. Step back outside to a spacious deck featuring a hot tub, sauna, outdoor seating, and peaceful views and sounds of the beautiful Wardsboro Brook. The oversized two car garage includes a finished bonus room above, ideal for a studio apartment, office, or guest space. Bring ALL of your Big Wheels and Small Wheels! Complete with paved driveway and wal

Now Offered at $429,000 - Exceptional Value Near Mount Snow and Stratton. Classic Vermont Home with Stunning Hilltop Views - Minutes from Mount Snow and Stratton. Set atop a peaceful New England hill, this classic Vermont home offers beautiful local and local mountain views in one of Southern Vermont's most desirable four-season locations. Just six miles from Mount Snow, Stratton Mountain, Grout Pond, and access to the VAST snowmobile trail network, the property is perfectly positioned for skiing, hiking, boating, snowmobiling, and year-round recreation. Filled with natural light, the home features warm wood floors, large windows that capture the surrounding scenery, and a spacious 15' x 24' patio overlooking the private backyard, an ideal setting for relaxing or entertaining after a day of adventure. Thoughtful updates provide comfort and peace of mind while preserving the home's timeless Vermont character. The renovated kitchen features granite countertops and stainless-steel applian

Private 72 acre playground with 3 bedrooms, 3 bath log cabin. Lots of room to play, including a VAST trail in the rear. A great covered porch makes for enjoying the privacy just out side to large kitchen/living/dining room, or downstairs outside the equally large family room. Plenty of room for guests and a large barn or outbuildings for all your Vt outdoor stuff. Lake Whitingham is minutes down the road for boating and fishing. Wilmington shopping and dining, and even golfing and skiing is just to the north. Easy drive from down south or hit The Deli on your way from Brattleboro. Lots of outdoor fun for friends and family!

Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mt Snow ski resorts. The moment you arrive; the home's striking presence is undeniable. A porte-cochere welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chef's kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island.Douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the home's most captivating features is its silo with a winding staircase illumina

Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's craftsmanship. The open living and dining area features a brick fireplace with woodstove insert, creating a warm and welcoming setting on cold winter nights. The second floor offers five bedrooms, two baths, a cozy den, and a tucked-away upper-level retreat, ideal for reading, writing, or quiet reflection. Set on 12.80 acres, the land offers endless possibilities, ideal for a hobby farm, pastures for horses or cows, or growing your own vegetables. A vintage barn and storage shed, ready for restoration, adds to the property's timeless rural appeal

This chalet, situated conveniently by the river, is ideally located midway between the renowned Stratton and Mount Snow Resorts, making it a perfect retreat for skiing, hiking, and golfing enthusiasts. Just a brief 20-minute drive from both resorts, this three-bedroom, two-bath property presents an excellent opportunity for those looking to invest in a home that requires some updating and renovation. The surrounding area boasts the picturesque southern Vermont villages, including the quaint town of Jamaica, and is in close proximity to Dover/ Wilmington, which offers a variety of hiking trails and golf courses. The ski resorts are easily accessible, providing year-round recreational activities. The asking price of the property has been set to reflect its current condition, making it an attractive option for buyers seeking a project that can be transformed into a personal haven in this beautiful region

Discover the perfect Vermont four-season retreat in this architecturally unique round home, set on a picturesque 1-acre corner lot in Southern Vermont. Offered fully furnished and move-in ready, this 1,840-square-foot, 3-bedroom, 2-full-bath property is ideal as a year-round residence, vacation home, or turnkey getaway. The welcoming lower level features three comfortable bedrooms, a spacious full bath with a jetted soaking tub, tiled floors, and a glass-enclosed shower, along with a convenient utility room. Upstairs, abundant natural light fills the open-concept living area where the kitchen, dining, and living spaces flow seamlessly together. A cozy wood-burning fireplace creates the perfect gathering place after a day of skiing, hiking, snowmobiling, or exploring the surrounding lakes and trails. A second full bath on the main level adds convenience for both everyday living and entertaining guests. Step outside to enjoy multiple outdoor living spaces, including a sunny second-floor

Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary bedroom, 2 guest bedrooms, and a half bath. There is a full unfinished basement with great storage space, laundry, and a full walkup staircase. A tremendous primary home or Vermont retreat

Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. Beautifully maintained and thoughtfully designed, this turnkey 3-bedroom, 2-bath home is ready to enjoy from day one whether as your full time residence, vacation getaway, or a highly successful short-term rental that guests absolutely love. Walking in through the covered entry you'll find soaring cathedral ceilings in the living room, abundant natural light, a cozy brick hearth with wood stove, and an inviting open kitchen and dining area perfect for gathering with family and friends. This main floor also has a full bathroom. The 3 bedrooms and another full bath are upstairs. Step back outside to a spacious deck featuring a hot tub, sauna, outdoor seating, and peaceful views and sounds of the beautiful Wardsboro Brook. The oversized two car garage includes a finished bonus room above, ideal for a studio apartment, office, or guest space. Bring ALL of your Big Wheels and Small Wheels! Complete with paved driveway and wal

Now Offered at $429,000 - Exceptional Value Near Mount Snow and Stratton. Classic Vermont Home with Stunning Hilltop Views - Minutes from Mount Snow and Stratton. Set atop a peaceful New England hill, this classic Vermont home offers beautiful local and local mountain views in one of Southern Vermont's most desirable four-season locations. Just six miles from Mount Snow, Stratton Mountain, Grout Pond, and access to the VAST snowmobile trail network, the property is perfectly positioned for skiing, hiking, boating, snowmobiling, and year-round recreation. Filled with natural light, the home features warm wood floors, large windows that capture the surrounding scenery, and a spacious 15' x 24' patio overlooking the private backyard, an ideal setting for relaxing or entertaining after a day of adventure. Thoughtful updates provide comfort and peace of mind while preserving the home's timeless Vermont character. The renovated kitchen features granite countertops and stainless-steel applian

Presenting 144 Branch Hill Rd, Heath, MA - a rural ranch-style single-family residence built in 1988, offering approximately 1,832 square feet of living area on a scenic lot in the Hilltown community of Heath. The property features a functional layout, including a G-shaped kitchen with peninsula seating, vaulted/cathedral ceilings in the living room, and a bedroom with a walk-in closet. The home requires some repairs and updates and is being sold strictly AS IS. Buyers should perform their own due diligence regarding all systems and condition issues, including the well and septic systems. A Title V inspection has been completed and has received a Conditional Pass. Bonus, property has newer roof and new windows. This property presents an excellent opportunity for investors, contractors, or buyers seeking a renovation project in a private country setting with potential for sweat equity

Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mt Snow ski resorts. The moment you arrive; the home's striking presence is undeniable. A porte-cochere welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chef's kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island.Douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the home's most captivating features is its silo with a winding staircase illumina

Welcome home to this beautifully renovated and immaculate 3 bedroom, 2 bathroom home located off Flag Hill Road in Heath. Tucked away on a quiet road, this property offers the perfect blend of comfort, privacy, and outdoor recreation. Features include a spacious primary suite with its own private bathroom, new carpet in two bedrooms, an updated furnace, brand new wood stove, new appliances, new hot water heater, garage, two storage sheds, and a deck for your summer BBQ's! Trails are already carved through the woods right from your property, making it easy to enjoy the natural surroundings. Whether you're looking for a peaceful full-time residence or a weekend getaway, this move-in-ready home checks all the boxes. Private access to the beach, playground, and clubhouse is just a half mile down the road. With many updates throughout and a serene setting, all that's left to do is unpack, relax, and enjoy everything this neat property has to offer!

Set in the heart of Heath's charming Historic District, this extraordinary former artist loft blends character, space, and serenity in a truly one-of-a-kind setting. Offering over 3,300 square feet of thoughtfully expanded living space, the home features three bedrooms, three bathrooms, and soaring, light-filled interiors that create an inviting sense of openness throughout.A spacious kitchen wing overlooks the beautifully private grounds, while the second-floor deck provides the perfect spot to relax and take in the peaceful surroundings. Outside, the property continues to impress with over 2 acres of open meadow and a small barn-ideal for hobby farming, horses, gardening, or simply enjoying country living.Tucked away in a quiet, tranquil setting, this distinctive Heath retreat offers privacy, comfort, and timeless artistic charm just moments from the beauty of the Hilltowns

This chalet, situated conveniently by the river, is ideally located midway between the renowned Stratton and Mount Snow Resorts, making it a perfect retreat for skiing, hiking, and golfing enthusiasts. Just a brief 20-minute drive from both resorts, this three-bedroom, two-bath property presents an excellent opportunity for those looking to invest in a home that requires some updating and renovation. The surrounding area boasts the picturesque southern Vermont villages, including the quaint town of Jamaica, and is in close proximity to Dover/ Wilmington, which offers a variety of hiking trails and golf courses. The ski resorts are easily accessible, providing year-round recreational activities. The asking price of the property has been set to reflect its current condition, making it an attractive option for buyers seeking a project that can be transformed into a personal haven in this beautiful region

Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a large garage with an attached storage shed and ample paved parking

Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham's boat launch and beach areas - truly four-season enjoyment at your doorstep. Inside, the home offers 4+ bedrooms and 3.5 renovated baths across three distinct living areas. The flexible layout includes a main-floor primary suite option, a second upstairs suite with large closets and an upscale bath, plus a separate guest wing with two additional bedrooms and a full bath - perfect for hosting family and friends. You'll also find up- and down-country mudrooms with excellent storage, the original foyer and front door, a country kitchen with stainless appliances and Corian counters, gas stove with brick hearth, vintage bar area, wood floors, gorgeous su

Tucked away in a quiet corner of Chimney Hill is this gem! This 3 bedroom, 2 bath house in Section C has it all! It features a classic mudroom entry, a brick interior walkway, and an open-concept living, dining, and kitchen area with French doors leading to a screened outdoor living room and a picnic porch out back, which includes a firepit for cozy conversation on chilly evenings. More thoughtful touches include a dedicated propane grill, so you don't have to fuss with tank replacements, custom woodwork and built-in closets, vaulted bedroom ceilings with dramatic woodwork, double lot for added privacy, shed, and an outdoor shower! A metal roof, new furnace, new flooring, wood stove and flue, new appliances, shed, wood storage, and includes most furnishings are included. Enjoy all the amenities Chimney Hill offers on its 1,200-Acre Campus, with 550-Acres owned in common by the members. Amenities feature the exclusive Clubhouse with indoor and outdoor heated pools, a hot tub, fitness ce

Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's craftsmanship. The open living and dining area features a brick fireplace with woodstove insert, creating a warm and welcoming setting on cold winter nights. The second floor offers five bedrooms, two baths, a cozy den, and a tucked-away upper-level retreat, ideal for reading, writing, or quiet reflection. Set on 12.80 acres, the land offers endless possibilities, ideal for a hobby farm, pastures for horses or cows, or growing your own vegetables. A vintage barn and storage shed, ready for restoration, adds to the property's timeless rural appeal

Welcome home to this beautifully renovated and immaculate 3 bedroom, 2 bathroom home located off Flag Hill Road in Heath. Tucked away on a quiet road, this property offers the perfect blend of comfort, privacy, and outdoor recreation. Features include a spacious primary suite with its own private bathroom, new carpet in two bedrooms, an updated furnace, brand new wood stove, new appliances, new hot water heater, garage, two storage sheds, and a deck for your summer BBQ's! Trails are already carved through the woods right from your property, making it easy to enjoy the natural surroundings. Whether you're looking for a peaceful full-time residence or a weekend getaway, this move-in-ready home checks all the boxes. Private access to the beach, playground, and clubhouse is just a half mile down the road. With many updates throughout and a serene setting, all that's left to do is unpack, relax, and enjoy everything this neat property has to offer!

This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas brick fireplace adds warmth to the living room, while the mudroom includes a built-in bench for added functionality. The lower level, with direct outdoor access, includes a family room, laundry area, and open space ready for your finishing touches. Located near VAST trails, this move-in-ready home is perfect for year-round living or a weekend ski retreat, offering easy access to Vermont's outdoor adventures in every season