582 properties for sale in Bennington town, Bennington County Vermont

Escape to your own private retreat in Williamstown, 'The Village Beautiful.' This spacious 5-bedroom, 4.5-bath home sits on 7.5 private acres and offers over 4,000 sq. ft. of living space throughout three levels, plus a finished basement with full bath and sauna. This home blends classic and modern features: exposed wood beam ceilings and a new, private primary suite with soaking tub. The home features a second primary suite, a third floor bedroom or loft space, and an abundance of natural light throughout. There are two woodstoves and a wood-burning fireplace for staying warm, and mini-splits for cooling in the summer. The expansive property boasts a designated garden area, a large garage with loft space above, and two large decks for entertaining and enjoying the surrounding nature

Nestled in the highly desirable Stratton Hills community of Williamstown, MA, this rarely available ground-floor end unit offers an exceptional blend of modern comfort, privacy, and breathtaking Berkshire beauty. Surrounded by meticulously landscaped grounds and commanding mountain views, this serene retreat is designed for buyers seeking a low-maintenance luxury lifestyle in the heart of Williamstown. Bathed in natural light, the open living and dining area features a dramatic picture window that frames spectacular mountain vistas, creating a tranquil backdrop for everyday living and entertaining. The thoughtfully designed galley kitchen is fully applianced and highlighted by a unique serving window that opens directly to the patio, making outdoor dining and entertaining effortless. Step outside to your private, covered patio, a true extension of the living space. Complete with electric service and ambient exterior lighting, this inviting outdoor sanctuary overlooks lush lawns and stu

Welcome to this charming Victorian home in the heart of Williamstown, where timeless character meets an unbeatable location. Just steps from downtown, you'll enjoy easy access to local restaurants, shops, galleries, theaters, and year-round community events, with Williams College close by. Inside, this spacious home offers an abundance of living space designed to fit a variety of lifestyles. Featuring numerous generously sized bedrooms with ample closet space, there's room for everyone to spread out comfortably. Whether you're looking for dedicated home offices, creative studios, playrooms, guest accommodations, or quiet reading nooks, the home's many versatile rooms provide endless possibilities. Classic Victorian details blend seamlessly with comfortable living, creating warm and inviting spaces perfect for everyday life and entertaining alike. Large windows fill the home with natural light, while the thoughtful layout offers flexibility for modern needs. The outdoor space includes a

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

Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty of room for a dining area. The kitchen is a cook's dream with cherry cabinets, a gas range, and a large island, plus a slider that opens to a pergola for outdoor dining and relaxation. A private office and half bath complete the first floor. Upstairs, beautiful pine floors continue throughout. The primary suite offers comfort and style, joined by two additional bedrooms and a full bath. From nearly every window, take in sweeping views of the surrounding landscape. A truly special property combining timeless charm with acreage, views, and versatile outbuildings-while still being just minutes fro

Originally a gift from Williams College President Harry A. Garfield, the son of United States President James Garfield, to his daughter, this elegant and gracious South Street home is available for the first time in over thirty years. Fine architectural details abound with beautiful crown moldings and woodwork, six panel doors, gleaming oak flooring, abundant built-in shelving and cabinetry, and large, light-filled floor-to-ceiling windows. The spacious entrance hall opens on your left to a stunning wood-paneled library lined with ample book-shelving and warmed by a corner fireplace with wood mantel and slate hearth. Ahead, the lovely living room, with another handsome fireplace with decorative mantel, side pilasters and marble hearth, provides access to a covered slate side terrace. A formal dining room with a beautiful glass-doored china cabinet and a third fireplace, offers the perfect venue for hosting gatherings both large and small. Custom designed by Latson and Latson, the kitch

Steeped in history and rich with character, this remarkable 1767 residence is the oldest home still standing on its original site in Williamstown.Thoughtfully expanded over time, it preserves its historic integrity while offering comfort for modern living.Set on nearly five meticulously maintained acres in one of the town's most desirable neighborhoods, the property feels both private and timeless, with mature plantings, perennial gardens, and sweeping lawns.The classic Cape Cod-style architecture features a wood shake roof, enhancing its New England charm. Inside are 5 bedrooms and 3.5 baths, blending intimate period rooms with light-filled living spaces. A dramatic living room with cathedral ceilings and French doors opens to beautiful Goshen stone patios, ideal for outdoor entertaining

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

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

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

A rare Williamstown investment opportunity just moments from WilliamsCollege. 181 and 183 North Street combines a substantially renovated two-family residence with a newly constructed detached ADU, creating three distinct residences on one property. 181 North Apt. A offers 2 bedrooms/1 bath; Apt. B offers 4 bedrooms/1 bath; and the detached 183 North ADU offers 3 bedrooms/2 baths. All three residences feature fully applianced kitchens and in-unit laundry, with modern updates and off-street parking. The ADU is currently leased through the end of the 2026-27 academic year, providing established rental income. An exceptional opportunity for an investor seeking multiple rental streams or an owner-occupant looking to live in one residence while generating income from the others. Williams CLollege and the heart of Williamstown

Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2 more bedrooms and a full bathroom. The basement is large and could possible have finished space. The outside is where this home truly shines. Great location, large sitting porch to watch the fauna. Rear deck for relaxing and large yard space. Large barn for either shop work or you could use it as a garage, as well as a storage shed. Short walk to the creek and lots of hiking trails

Originally a gift from Williams College President Harry A. Garfield, the son of United States President James Garfield, to his daughter, this elegant and gracious South Street home is available for the first time in over thirty years. Fine architectural details abound with beautiful crown moldings and woodwork, six panel doors, gleaming oak flooring, abundant built-in shelving and cabinetry, and large, light-filled floor-to-ceiling windows. The spacious entrance hall opens on your left to a stunning wood-paneled library lined with ample book-shelving and warmed by a corner fireplace with wood mantel and slate hearth. Ahead, the lovely living room, with another handsome fireplace with decorative mantel, side pilasters and marble hearth, provides access to a covered slate side terrace. A formal dining room with a beautiful glass-doored china cabinet and a third fireplace, offers the perfect venue for hosting gatherings both large and small. Custom designed by Latson and Latson, the kitch

A welcoming, lead-compliant 3 bedroom, 2 bath home in a peaceful Williamstown neighborhood, thoughtfully updated to offer comfort, character, and easy living. The first floor features two bedrooms, a full bath, an open kitchen and dining area, and a comfortable living room with a working fireplace. Upstairs, the entire floor is dedicated to a private primary suite with its own ensuite bath. Extensively updated over the past five years, the home features improvements to the electrical and plumbing systems, heating, windows, and flooring, along with a stylishly renovated kitchen with quartz countertops, soft close cabinetry, and stainless-steel appliances. The bathrooms have also been refreshed with quartz vanities and tiled surrounds. Two fireplaces add warmth and atmosphere on crisp Berkshire evenings. Outdoor living is equally appealing, with three porches, a partially fenced yard, and a screened gazebo offering inviting spaces for morning coffee, quiet afternoons, or entertaining. Co

Vermont Home with Mountain, Meadow and Garden views Nestled in the Green Mountains of Vermont, this 3 bedroom 3 bath home offers scenic views, open spaces, and the tranquility of Vermont living. Situated on three separately surveyed lots, the beautifully maintained property features Heirloom apple trees, park like forests and lush perennial gardens bursting with color throughout the seasons and ample room to enjoy the outdoors. The property is conveniently located across from Lake Shaftsbury State Park ideal for hiking, swimming, fishing, making it an ideal year-round retreat with 5 Ski Resorts with in an hour drive. Inside, the thoughtfully designed home features an open-concept main floor centered around a cozy fireplace, creating a warm and inviting gathering space. A bright sunroom opens up to the second deck overlooking gardens and heirloom apple trees. Providing the perfect spot for relaxing, reading, or enjoying nature views. The finished basement offers additional living and en

Outdoor Living Meets In-Town Convenience! Rarely does a property offer such an exceptional balance of outdoor living and in-town accessibility. Located at the end of Elm Street, this home provides a peaceful retreat while remaining just minutes from downtown Williamstown, Williams College, and local amenities. Set on approximately 1.3 acres and bordering protected conservation land and the Green River Linear Park trail network, the property enjoys a rare sense of privacy and connection to nature, with direct trail access from the rear yard, all just moments from downtown Williamstown. At the heart of the home is a stunning cathedral-screened porch featuring exposed timber framing and mahogany flooring, creating an inviting three-season great room and a natural extension (click on more) of the home's interior living space. Designed for gathering and relaxation, it overlooks a backyard highlighted by mature landscaping, Goshen stone patios and retaining walls, a firepit area, deck, and h

Welcome to easy Vermont living in this beautifully maintained ranch-style home offering more than 2,000 finished square feet in one of North Bennington's most desirable neighborhoods. Set on a quiet cul-de-sac with lovely mountain views, Harvest Hills offers a wonderful sense of community, including a large neighborhood pond for residents to enjoy. The location is equally appealing; close to the village school, market, restaurants, and the popular Mile Around Woods trail. Inside, a spacious living room with a traditional brick fireplace flows into the bright, open dining and kitchen areas, creating an inviting layout for everyday living and entertaining. The charming kitchen features a breakfast bar, pantry, stainless steel appliances, and abundant natural light. Three comfortable bedrooms and two full baths include a primary bedroom with its own en suite bath. The finished lower level adds valuable flexibility with a generous family room, recreation space, or home office, complemented

JOIN US FOR AN OPEN HOUSE THIS COMING SATURDAY 9/12 and SUNDAY 9/13 FROM 12PM-2PM* Gracious, stately, and filled with distinct warmth, this impressive Colonial is a rare offering of exceptional scale and character. With more than 4,300 square feet, five bedrooms, two and a half baths, and an abundance of beautifully proportioned gathering spaces, the home offers an extraordinary sense of presence while remaining remarkably welcoming. Original detail remains beautifully intact, including exquisite wood trim, handsome hardwood floors, a grand stairway, and elegant bay windows. Huge windows and wonderful natural light illuminate the large, gracious rooms throughout the day, highlighting the craftsmanship and timeless beauty of the home. The indoor heated pool provides an exceptional year-round amenity, while the expansive attic offers tremendous storage and potential. A corner lot adds to the property's presence, and the oversized two-car garage with substantial storage above provides bot

Vermont Home with Mountain, Meadow and Garden views Nestled in the Green Mountains of Vermont, this 3 bedroom 3 bath home offers scenic views, open spaces, and the tranquility of Vermont living. Situated on three separately surveyed lots, the beautifully maintained property features Heirloom apple trees, park like forests and lush perennial gardens bursting with color throughout the seasons and ample room to enjoy the outdoors. The property is conveniently located across from Lake Shaftsbury State Park ideal for hiking, swimming, fishing, making it an ideal year-round retreat with 5 Ski Resorts with in an hour drive. Inside, the thoughtfully designed home features an open-concept main floor centered around a cozy fireplace, creating a warm and inviting gathering space. A bright sunroom opens up to the second deck overlooking gardens and heirloom apple trees. Providing the perfect spot for relaxing, reading, or enjoying nature views. The finished basement offers additional living and en

Welcome to 43 Spring Street, Cambridge, NY-a charming home offering comfort, character, and convenience in the heart of the Village of Cambridge. This well-maintained property features a functional layout with inviting living spaces, making it ideal for first-time homebuyers, those looking to downsize, or anyone seeking small-town living. Enjoy a spacious yard perfect for entertaining, gardening, or relaxing, along with the convenience of being just minutes from local shops, restaurants, parks, and schools. With its blend of classic charm and everyday practicality, 43 Spring Street is ready for its next owner to make it their own. Don't miss this wonderful opportunity to own a home in one of Washington County's most desirable communities

A rare Williamstown investment opportunity just moments from WilliamsCollege. 181 and 183 North Street combines a substantially renovated two-family residence with a newly constructed detached ADU, creating three distinct residences on one property. 181 North Apt. A offers 2 bedrooms/1 bath; Apt. B offers 4 bedrooms/1 bath; and the detached 183 North ADU offers 3 bedrooms/2 baths. All three residences feature fully applianced kitchens and in-unit laundry, with modern updates and off-street parking. The ADU is currently leased through the end of the 2026-27 academic year, providing established rental income. An exceptional opportunity for an investor seeking multiple rental streams or an owner-occupant looking to live in one residence while generating income from the others. Williams CLollege and the heart of Williamstown

Beautifully renovated condominium in the historic Mt Hope 'Minnie Mansion' Move right in to this three bedroom, two and one-half bathroom condominium. Offering a modern attractive kitchen with pass through to formal dining room; living room with gas fireplace, first floor laundry room and half bath. The second floor offers three bedrooms, two bathrooms and private office. Wood floors throughout plus one car attached garage. Beautiful, private, side yard

Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and welcoming space for relaxing or entertaining. The flexible floor plan provides three bedrooms plus an additional room that can easily serve as a fourth bedroom, home office, or hobby space. The walkout unfinished basement offers endless possibilities for future expansion, storage, or a workshop. Outside, you'll find an attached two-car garage along with a separate bonus garage, providing ample space for vehicles, recreational equipment, or additional storage. Set well back from the road, the property's 16.96 acres offer room to explore, garden, or simply enjoy the peace and beauty of Vermont. The home

This cozy ranch nestled in the picturesque town of Williamstown offers two bedrooms, one full bath an extra spacious family room, new kitchen, bath and furnace. The backyard is fenced in with mature landscaping, Spacious covered and non-covered deck to enjoy those beautiful days and nights on. Within minutes to The Clark Art, MASS MoCA, Williams College. This home would be a great investment, first home, retirement home or AirBnB. This is a must see!

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF home boasts 10 foot ceilings, with reclaimed antique oak pocket doors from a nearby mansion, inlaid floors, stained glass windows, arches and a custom cherry and granite eat in island kitchen. The foyer, gracious leads to the expansive living room and kitchen overlooking the fantastic spring fed pond. there is a main level primary suite, and second floor gathering space with pond-side balcony and 2 bedrooms. The finished basement hosts a family recreation room and a sauna. Equestrian facilities are comprised of a recently built barn with 4, 12 X 12 stalls boasting Thuro

Open House: Saturday, August 15th from 10 am to 12 pm. Welcome to 1955 Vermont Route 100, a character-filled 1870 farmhouse offering 4 bedrooms, 2 bathrooms, and 2,104 square feet of finished living space on a half-acre country lot in Readsboro. Abutting Vermont National Forest and close to VASA and Vast Trails. Inside, warm wood details and inviting living spaces create a classic Vermont feel. The spacious kitchen features a center island and opens to a dining area, while a wood stove adds warmth and charm. Additional highlights include first-floor laundry, a whirlpool tub, and flexible rooms ready to accommodate a variety of needs. Outside, enjoy the covered front porch, open lawn, wooded backdrop, and detached two-car garage. The home is served by a private spring and septic system, with fiber-optic internet availability, offering an appealing combination of rural surroundings and modern connectivity

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

Carefree living in this quaint Colonial in a great in-town location, a stone's throw to everything Williamstown and Williams College. Lovingly maintained, great yard, one car detached garage, wood floors and carpet, a wood stove for those chilly winter nights. Great price, priced to sell. 3 beds, 1 full bath, formal dining room, enclosed side porch, new Pella windows. Newer stainless appliances, new boiler, and new paint on the outside

Welcome to 111 North Street Street, ideally located in the heart of Williamstown and just minutes from Williams College downtown Williamstown, restaurants, shops, and all that this vibrant college town has to offer. 4 bedrooms, 2 full bathrooms, offers a wonderful opportunity for those looking for a comfortable residence in one of Berkshires most desirable communities. This home has been updated over the years, providing a great blend of character, functionality, and modern convenience. A great fulltime home, a weekend getaway, or investment opportunity awaits

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