Colonial Homes for Sale in Bennington County VT

So many possibilities await at this recently renovated and affordable 3-bedroom, 2-bath home, featuring two full kitchens, one up and one down. Whether you're envisioning multigenerational living, a home-based business, or simply want to be close to skiing and outdoor adventure, this versatile layout adapts to fit your life. Recent renovations touch nearly every corner of the home, including both

Pam Tworig BISHOP WEST REAL ESTATE

Imagine a time where taverns were the heart of the community, where laughter echoed off thick brick walls and stories were told by firelight. Now see yourself enjoying the ease of Single Floor Living that includes an enormous primary ensuite, with laundry! Start your day in the completely updated kitchen and move effortlessly into the dining area and living room with an easy to light cozy propane

Gregory Cutler Four Seasons Sotheby's Int'l Realty

Nestled in one of Vermont's most coveted villages, this three-bedroom, two-bathroom home is a canvas waiting for your creative vision. Priced well below assessed value, this property represents a rare opportunity to build equity from day one while enjoying the charm of quintessential New England living. The generous lot gives you room to breathe, garden, or simply watch the seasons paint the

Brian Hill Remax Summit

Extensively Renovated Classic Vermont ColonialThis beautifully updated 1935 Vermont Colonial offers the perfect blend of classic charm and modern convenience, with thoughtful additions completed in 1972 and 2016. With nearly 3,900 square feet of living space, this spacious home features 4 bedrooms, 4.5 bathrooms, two dedicated office spaces, and a versatile third-story bonus room, ideal for a

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

Back on Market July 22nd! Amazing 1850s farmhouse rich in old-world charm and character. Gleaming hardwood floors, large sun-filled rooms, and timeless architectural details throughout. Distinctive features include an elegant arched doorway, a unique library with octagonal bookshelves, and a striking turret that enhances the home’s historic appeal. The spacious primary bedroom stretches 25 feet

Lisa Friedman Great American Dream Realty

“The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

Sara Buckley Josiah Allen Real Estate, Inc.

Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to

Jenifer Prouty Hoffman Hoffman Real Estate

Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

Britt Wohler

Welcome to this beautifully updated Cape offering 4 bedrooms and 3 bathrooms in one of Manchester's most desirable neighborhoods. Thoughtfully renovated with extensive recent improvements, this turnkey home blends classic New England character with modern style, comfort, and efficiency. The heart of the home is the bright, open-concept living space, where a beautifully renovated kitchen features

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

Erin McCormick KW Vermont

Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

Dana Kingsley Josiah Allen Real Estate, Inc.

Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels—over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making

Carrie Mathews Winhall Real Estate

Rare opportunity to own a well-maintained 4-unit property in the heart of Manchester, one of Southern Vermont’s most sought-after destinations. Offered at an attractive 8% cap rate, this unique investment features a charming 2-bedroom, 2-bath carriage house, two 2-bedroom, 1-bath units, and a 1-bedroom, 1-bath apartment, providing an appealing mix for a variety of tenants. Recent updates include

The Nancy Jenkins Team Nancy Jenkins Real Estate

Set back from a quiet country road in Manchester, Vermont, this spaciousFederal farmhouse style home offers a wonderful blend of comfort, privacyand Vermont charm. The classic white exterior with its attached red barncreates a welcoming first impression, while the home’s thoughtful designprovides plenty of space for everyday living, entertaining and enjoying thepeaceful

Carol O`Connor Four Seasons Sotheby's Int'l Realty

This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

Matt Waddington Hoffman Real Estate

Set on 2.85 acres with beautiful mountain views, this 4-bedroom, 2-bath Colonial offers space, comfort, and classic Vermont charm in the heart of Stamford. The home features 2,144 finished square feet with a welcoming layout that includes a bright living room, family room, dining area, and a spacious kitchen with warm cabinetry, an arched window, and great flow for everyday living or

Colt Hazell Flex Realty

Set on over 11.5 private acres, this custom-built Colonial offers the kind of comfort, craftsmanship, and peace of mind that’s increasingly hard to find. Thoughtfully designed and maintained since it was built in 2004, this home blends timeless style with practical features for everyday living. With over 4,300 square feet, the layout provides generous space without feeling overwhelming. The home

David Halligan Four Seasons Sotheby's Int'l Realty

In the heart of Manchester Village, this four-bedroom, six-bath colonial blends classic New England charm with the kind of space and flexibility that fits modern living. Set on a level 0.85-acre lot with mountain views, the property offers both privacy and easy access to everything the village has to offer. Inside, you'll find character you can't replicate - spruce and pine floors, exposed beams,

David Halligan Four Seasons Sotheby's Int'l Realty

Gorgeous, renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient

Kelley Mccarthy Mahar McCarthy Real Estate

Set on two private acres in a desirable Manchester location, this renovated four-bedroom, three-bath Colonial balances privacy and convenience with easy access to both Manchester and Dorset. Wide-plank pine floors, abundant natural light, and inviting living spaces define the interiors. The main level features a spacious living room anchored by a stone fireplace, a formal dining room, and an

Alexandra Crowley Four Seasons Sotheby's Int'l Realty

Built and thoughtfully expanded by its original owners, this substantial Winhall residence offers the scale and comfort of a true year-round home in a location made for four-season Vermont living. Set on 5.02 acres, the property stands apart for its broad, level, cleared grounds, an uncommon and highly usable setting just minutes from the Stratton Access Road. Inside, 3,644 square feet, four

Trent Stephens Wohler Realty Group

Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

Jenifer Prouty Hoffman Hoffman Real Estate

This charming two-story Colonial in Manchester offers a comfortable and functional layout with plenty of living space. The first floor features a kitchen with a wood burning fireplace, along with dining and living areas perfect for everyday living and entertaining. A mudroom provides convenient access to the attached garage. Upstairs, you’ll find three additional rooms offering flexibility for

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

Located in the beautiful countryside of Manchester, Vermont, 1613 West Road offers a peaceful setting with the kind of charm and character that makes this property truly one of a kind. Surrounded by scenic mountain views, open land, and natural surroundings, the property strikes a perfect balance of privacy and convenience. Just a short drive from the heart of Manchester, you enjoy easy access to

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

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

Laura Beckwith Josiah Allen Real Estate, Inc.

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

Dan Mason Perrott Realty