586 properties for sale in Bennington County

Come home to the warmth and character of this inviting 4-bedroom, 2.5-bathroom log cabin, tucked into a desirable Bennington neighborhood on.46 acres. From the welcoming front porch to the cozy interior, this home offers the charm of log construction with plenty of space for comfortable everyday living. The living room is the heart of the home, featuring a fireplace and sliding doors that open to the back deck which creates the perfect atmosphere for relaxing, entertaining, or simply enjoying a quiet evening at home. The spacious primary bedroom offers a private retreat with its own bathroom and walk-in closet, while three additional bedrooms provide plenty of flexibility for family, guests, a home office, or hobbies. A full unfinished basement offers tons of storage and the opportunity to create additional living space, while the 2-car attached garage adds everyday convenience. With both a front porch and back deck, you'll have inviting spaces to enjoy the outdoors throughout the seas

Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home that feels both timeless and comfortable. The country kitchen has been tastefully renovated while respecting the home's heritage, and the spacious primary bath features a generous double vanity with classic farmhouse styling. Whether it's curling up beside the fireplace on a snowy evening, enjoying a quiet morning in the bright enclosed sunroom, or unwinding on the private back yard surrounded by gardens, every space invites you to linger just a little longer. Outside, the property's agricultural roots remain proudly intact. The impressive tri-level hand-hewn and pegged barn, with silo, offers

The Dexter Road Farmhouse, Circa 1800 In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write Stopping by the Woods on a Snowy Evening. Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region. Tucked away at the end of a peaceful, tree-lined town road, the property is ideally suited as a second home, creative retreat, or year-round residence. Lovingly cared for by the same family for over 70 years, the home retains much of its original character and craftsmanship. Wide pine floors, original moldings, classic woodwork, traditional wall and ceiling boards, and a gracious entrance hall create a warm and authentic farmhouse atmosphere. Set on approximately 40 acres with a picturesque skating pond, the property offers abundant space to explore, garden, walk, and enjoy the pastoral surroundings. Writer

Side-by-side duplex in a sought-after area in the heart of Bennington, offering the charm of yesteryear with modern conveniences. This well-maintained property presents an excellent investment opportunity, whether you're looking for a rental property generating substantial income or the option to owner-occupy one unit while renting the other to help offset your mortgage. Boasting many tasteful renovations and updates in recent years, both units feature gorgeous refinished hardwood floors and a spacious, functional layout. Each unit offers a living room, dining room, kitchen, and half bath on the first floor. Upstairs, you'll find three bedrooms, an office space, and a full bath. Each unit has its own large, inviting front porch with peeks of mountain views, perfect for relaxing or enjoying time with family and friends. Private back decks overlook the spacious backyard, while a three-car garage provides additional parking and storage. A full basement is divided between the two units, pr

Opportunity awaits in this three-bedroom, two-bath home set in a peaceful Vermont location near Bromley Mountain, Hapgood Pond, and the Catamount Trail. The single-level floor plan offers a comfortable living room with a brick fireplace, a separate dining area, and plenty of natural light. A new roof provides an important recent improvement, while the interior is ready for updates and a new owner's personal vision. With some TLC, this property could become a welcoming primary residence, weekend getaway, or four-season Vermont retreat. Enjoy easy access to skiing, hiking, swimming, cross-country skiing, and the many year-round recreational opportunities the area has to offer

Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace. The middle level offers three generously sized bedrooms that comfortably accommodate queen and king beds. On the ground floor, you'll find an expansive bonus room and a private office that can easily be converted into an additional sleeping area. Ample storage is found throughout the home, including a large utility room with washer and dryer and a secure storage closet, a dedicated outdoor gear closet, and additional exterior storage. Firewood stays dry and ready under the private carport just steps from your door. Community amenities have recently been redone and include a pool, tennis courts, and basket

Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4 bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont's four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful upgrades throughout, including fully renovated bathrooms and a refreshed lower level that's perfect for relaxing, entertaining, or hosting guests. The home's classic chalet-style design features an open-concept living area, warm wood accents, and abundant natural light that creates a cozy yet spacious atmosphere. Outside, enjoy the peace and privacy of your own Vermont retreat. The surrounding property is perfect for morning coffee, evening stargazing, or gathering with friends and family while taking in the natural beauty of the area. Outdoor enthusiasts will love the location - just minutes fro

Tucked into the foothill of the green mountains you will find this well constructed 3 bedroom 2 bath cape style home with oversized 2 car garage on 2.19 acres. This comfortable home features an updated kitchen with new island, updated appliances 6 burner gas range and classic tile back splash. The living room offers a beautiful soap stone wood burning stove and a new mini split for AC and heat. All windows and door are in excellent condition and sliders that our to the fenced in back yard. The first floor also features a full bathroom, laundry, pantry and office/ mudroom space. The second features three generous sized bedrooms and a three-quarter bath. The lower level is partially finished with a Rec room for a full sized pool table and a gym area. There is a also a spacious workshop, boiler room and extra storage with a door right out to the back yard. Very well thought out. Everything about the house is well done, from expansive covered front porch with mountain views, the large back

At the end of the road in Benedict Hollow, where privacy and the beauty of the Vermont woods take center stage, this completely renovated two-bedroom cabin is the perfect escape. Set within 32,000 acres of National Forest, the setting is remarkably peaceful and private, with a cascading stream visible from every window, extensive perennial gardens, stacked stone walls, and a beautifully restored stream-fed trout pond that creates a truly special retreat. A short walk to the historic Battenkill River, drop a line and hook a trout or take a float and relax in the waters of the Battenkill River. The cabin is completely renovated, offering easy, comfortable living with nothing left to do but arrive, unpack, and unwind. The kitchen is smartly designed with brand-new stainless steel appliances and granite countertops. A welcoming mudroom entry provides storage. Cathedral ceilings, tons of natural light, and many windows open to the surroundings, while the 3/4 bath, dining/sitting room overlo

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 rear yard gardens and large level recreation area. the Front Porch and Rear Deck add extended summer living. There's a large cooks kitchen that accommodates an island Kitchen with spalted wormy maple island, 6 burner propane range, Bosch refrigerator and dishwasher then the the extended dining room can also work for comfort seating around the fireplace. There's three pantry areas which truly services recycling and all kitchen storage needs. The sunroom also open to the kitchen brings the outdoors in as well as access to the expansive private decking. The Living room boasts lovely light, chair rail and double sl

Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you'll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026. What truly sets this property apart is its incredible versatility. The bonus space presents endless possibilities for a home based business, professional office, hobby space, expanded living area, or potential in-law accommodations. Whether you're looking for room to grow, work from home, or create a space tailored to your lifestyle, this home offers the flexibility to make it happen. The generous lot and rear garage access provide additional opportunities for future improvements. Buyers may appreciate the potential to enhance accessibility and functionality with a redesigned driveway configuration, such as a circular drive, while maximizing the

Set privately on 25.34 acres, this 3BR/2BA contemporary-style home offers expansive views and a peaceful setting just 15 minutes from Bennington. Kitchen with breakfast nook opens out onto a back deck and the spacious living room features a cathedral ceiling and dramatic floor-to-ceiling fieldstone fireplace, creating an impressive focal point and inviting gathering space. First floor also includes a formal dining room and first floor bedroom or office as well as a full bath. On the second floor, the primary suite includes a large bathroom with a walk-in shower and tub, with a layout that may accommodate accessibility needs and a second guest bedroom includes a half bath. Basement-level 2-car garage provides workspace and a dedicated laundry area. The property offers a wonderful combination of privacy, acreage, and convenience, with plenty of room to enjoy nature and and the surrounding landscape. There is ample room for gardening and play! The home needs some repairs and updating, pro

Set on 3 beautiful acres with fabulous views in every direction, this spacious and inviting home offers a wonderful blend of comfort, character, and versatility. The main level features a private primary bedroom, a large kitchen, and a welcoming living room with hardwood floors and a fireplace with woodstove insert. A generously sized office with built-ins provides the perfect space for working from home or a quiet retreat. The sunroom, located just off the back of the house, is an ideal spot to relax and enjoy the surrounding scenery throughout the seasons. The lower level offers three additional bedrooms, a full bath, and a spacious family room with another fireplace. Walk out directly to the patio and beautifully landscaped grounds, where you'll find established perennial gardens and fruit trees. There is plenty of room for gardening, entertaining, or simply enjoying the peaceful setting and expansive views. An attached two-car garage is conveniently located on the main level, while

Unique Dorset West Road offering. This rare opportunity beckons creativity, craft, and charm! Begs all those ready, willing and able to renovate, keeping the existing home, whilst enjoying life in an extremely beautiful and desirable location. Enjoy the beautiful framed in mountain views from most interior living spaces and from the back patio/yard. This 6.6 acre rolling property boasts excellent lawn space and vegetation and is located on the historic Dorset West Road, abutting the Dorset Field Club, with an easy walk to the Dorset village. Surveyor/engineer have confirmed that the property conforms to all zoning bylaws in the Rural Residential district should the buyer decide to subdivide the property into two lots to sell a portion and/or build a second home on the property. Architectural drawings available to ignite the creative process! Property being sold as is

Beautiful Dorset Contemporary Offering Privacy, Comfort, and Easy Living. If you've been looking for a private Vermont retreat with room to relax, entertain, and enjoy the beauty of every season, this exceptional custom home may be the perfect fit. Built in 1996 by respected Dorset builder Keith Dodson, this thoughtfully designed 5,731 sq. ft. contemporary sits on 12.15 peaceful acres with a pond and detached four-car garage. Inside, the home offers a welcoming and comfortable layout with 9 rooms, hardwood floors, radiant heat, central air with four zones, and a partial-house generator for added peace of mind. The kitchen features cherry cabinets, Corian countertops, a large island, cathedral ceiling, and easy access to the screened porch, an ideal spot for morning coffee or quiet summer evenings. The dramatic great room creates a wonderful gathering space, with its soaring two-story cathedral ceiling, skylights, exposed beams, built-ins, window seats, and balcony overlook. Throughout

Move-in ready Ranch offering comfortable one-level living in a peaceful setting with mountain views. Set on 1.89 acres and conveniently located for commuting to both Bennington and Williamstown, MA. This 3-bedroom, 1.5-bath home has been lovingly improved over the past five years. The owner has invested significant time and care into making the home warm, functional and easy to enjoy. Updates include a brand new roof and two new skylights, a fully renovated kitchen, new flooring and interior paint throughout, new exterior doors to the deck, and more. At the heart of the home, the beautifully redesigned kitchen features rich blue cabinetry, white quartz countertops, a large farmhouse sink, stainless steel appliances and subway tile backsplash, all opening naturally to the dining and living areas. Dark wood beams and a brick wood-burning fireplace create a cozy Vermont feel, while skylights and abundant windows fill the home with natural light. Step through the sliding doors to the spaci

Strong income potential and a versatile unit mix make this 4-unit property an outstanding investment opportunity. The building features two 2-bedroom, 1-bath units, a spacious 3-bedroom, 1-bath unit, and a 1-bedroom, 1-bath apartment, appealing to a wide range of tenants. This well-positioned property offers dependable rental income and the flexibility that investors seek. Whether you're adding to an established portfolio or purchasing your first multifamily asset, this property provides an excellent opportunity to capitalize on strong returns and long-term rental demand. A great addition for investors looking for solid cash flow and lasting value. 3D Virtual Tours Available Upon Request

This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to your lifestyle. Each unit is equipped with independent Utilities, ensuring privacy and convenience. Located village neighborhood, a short distance from The Bennington Bike path, the Bennington are trail system and downtown Bennington's vibrant shops and restaurants, and Southwestern Vermont Medical Center. 15 minutes to Prosepct Ski area 30 minutes to Mt Snow 1 hour to Albany Airport, Boston. Manhatten and Hartford are all within 3 hours

Introducing a charming 3-bedroom, 5-bathroom home in the picturesque town of Manchester, Vermont. This beautifully designed residence offers a perfect blend of modern comfort and classic New England charm. Nestled within a serene, open landscape, this property is an oasis of tranquility. The home's main floor features a spacious and inviting living room with a cozy fireplace, wet bar, and French doors to the patio. The den is adjacent, providing two living rooms on the main floor. A well-appointed kitchen with high-end appliances, ample counter and dining space, awaits the culinary enthusiast. A screened in porch provides a serene setting for relaxation, offering stunning views of the surrounding yard and forest. The main floor suite can be a primary suite or guest suite. Upstairs is a larger primary suite with walk in closet, and another bedroom suite. The lowest level is finished, with a tv space or game space, with a bathroom. Central air conditioning, back up generator, high end fi

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time whi

Investment opportunities like this are few and far between! Located in a desirable mixed use district, this well maintained four unit one bedroom apartment building offers an excellent opportunity for both seasoned and first time investors. The property features four one bedroom apartments with full bathrooms, each with its own unique character and appeal. Two of the front/lower units have been thoughtfully renovated within the past five years and feature updated appliances, fresh paint throughout, and modern finishes. The two rear units are occupied by long term tenants who are happy to remain, providing immediate rental income and stability. Outside, you'll find a spacious yard, ample off street parking, and a convenient walkable location close to local amenities. Tenants are responsible for their own electricity and hot water, with each unit having its own dedicated hot water heater. The owner currently pays for heat, water, sewer, trash removal, snow removal, master insurance, and

Tired of renting' Discover the charm, convenience, and value of this adorable two-bedroom bungalow - an ideal opportunity for first-time buyers, downsizers, investors, or anyone looking for a cozy second home in town. Tucked away from the hustle and bustle, this historic home is just a short walk from downtown shopping, restaurants, transportation, and everyday conveniences. Inside, you'll find a move-in-ready space with a welcoming dining area just off the kitchen, a spacious primary bedroom, and warm natural light. Step outside and enjoy the covered wraparound porch - always a Vermont favorite. Off-street parking adds an extra layer of convenience. If you're looking to simplify, this charming little jewel is ready to welcome you home!

Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create a sophisticated culinary space. An updated powder room and engineered hardwood flooring throughout further enhance the home's timeless appeal. The second level offers three well-appointed bedrooms and a tastefully renovated full bath designed with both style and comfort in mind. A walk-up attic provides abundant storage, while the partially finished lower level expands the living space with a dedicated laundry area, a versatile bonus room ideal for a home office, fitness studio, or media room, and a utility room featuring a newer heating system (2020), oil tank (2022), and upgraded 200-amp ele

Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural beauty and mountain views, this is a rare opportunity to own a truly versatile Southern Vermont property. The thoughtfully updated ranch-style home features comfortable single-level living with 2 bedrooms and 1 beautifully renovated bath. Bright, inviting interiors showcase an open-concept kitchen and living area designed for everyday comfort and effortless entertaining. Energy-efficient mini-split systems and a leased solar array add modern convenience, while the expansive rear deck offers the perfect place to relax and take in the peaceful Vermont landscape. Ideal for automotive enthusiasts, contr

Enjoy beautiful Green Mountain views from this exceptionally well-maintained home offering the perfect blend of comfort, space, and Vermont country living. The bright, inviting floor plan features a spacious living room with a gas fireplace, a well-appointed kitchen with abundant cabinetry, center island, gas range, stainless steel appliances, and direct access to the expansive rear deck overlooking the mountains. Central air conditioning and a newer heating system provide year-round comfort, while the finished lower level offers flexible space for a home office, recreation room, guests, or hobbies. The primary suite features a generous cedar-lined walk-in closet, with abundant storage found throughout the home. Outside, enjoy the covered front porch, level two-acre setting, oversized detached two-car garage/workshop, additional storage shed, and peaceful location just minutes from Arlington, Bennington, and Manchester, offering convenient access to shopping, dining, skiing, hiking, an

This Eagle Rise Condo with three bedrooms and two and half baths is in an exclusive residential area accessed off scenic Manchester West Road. The Condo offers an open floor plan design, central air, propane baseboard hot water heat, hardwood floors and elevated deck. Recent improvements include new kitchen w/ granite counter tops, hickory cabinets with soft close drawers and doors, stainless steel appliances, tile flooring, new washer/dryer and Azek front porch. The main level has a living room with propane fireplace, dining area with sliding glass door leading to elevated deck, beautifully updated kitchen, half bath and air lock mudroom entry. The second level offers two large bedrooms, full bath and linen closet. The primary bedroom has a walk-in closet, full tile bath and additional wash area. The lower level has a Den/TV Room with slider leading to second wood deck, large guest bedroom, second full bath and full-size laundry area. This unit is located at the top of a hill offering

A little piece of Vermont just waiting to be discovered! Tucked into nearly 13 surveyed acres of woods, this charming 1970s ranch offers the peace, privacy and simplicity so many look for. A stone wall outlines the parking area, with stone steps leading up and into the front screened in porch that overlooks the yard and meadows. Inside, you'll find 2 bedrooms, wood floors, built-in bookshelves, dining room that opens to kitchen and a large, bright living room featuring a stone fireplace with wood stove insert-perfect for cozy evenings after a day outdoors. The screened porch and back deck add wonderful spots to relax and enjoy the peaceful surroundings. The newer roof is an added plus, and the home is being sold as-is, with furnishings included (see more) making it easy to embrace its classic, old-fashioned Vermont character. Outdoor enthusiasts will love the location, close to thousands of acres of Green Mountain National Forest land, with opportunities for hiking, hunting and snowmob

Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be enjoyed fireside under the stars. The main residence boasts a flowing floor plan designed for entertaining, with large windows filling the home with natural light and framing water views from nearly every room. A brand-new septic system, built for seven bedrooms, ensures comfort and space for all. The oversized two-car garage provides ample storage for all your outdoor gear. Set apart among the trees, the guest cottage offers its own sense of retreat with vaulted ceilings, an open living space, two en-suite bedrooms, and an additional two-car garage. A short walking path leads directly to the water's

This Charming country home is currently being used as a primary home with a vacant 2nd in-law rental home. This property could be either a single family residence with/without an in-law house or as a 2 unit multifamily with 2 separate houses, This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement under the older portion, with a crawlspace under the addition. This main house needs some TLC including interior paint and could use new carpet and vinyl flooring. The smaller second house is located a few hundred feet from the main house and has its own separate driveway and a separate septic system (the 2 houses do share a common drilled well) This house fe

Nearly Lakefront Living in the Heart of North Bennington! Come for the space, stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600 sq. ft. primary suite, featuring energy-efficient mini-split heating and cooling, with a large main bedroom and an adjoining space ideal for a walk-in closet or private retreat. A new steel two-car garage was added, ensuring your vehicles stay protected year-round. The property's outdoor space is just as impressive with beautifully maintained perennial gardens (featuring lilacs, peonies, lilies, and phlox), fruit trees (peach and plum), and graceful white birches. A small backyard storage shed with electricity adds extra convenience. Located just steps from picturesque Lake Paran and nestled in the