Colonial Homes for Sale in Bennington County VT

Welcome to this well maintained 3-bedroom, 2.5-bath Colonial combining classic style with comfortable modern living. From the inviting front porch to the covered rear porch, patio, and fire pit, this home offers exceptional spaces for relaxing and entertaining both indoors and outdoors. The recently updated kitchen serves as the heart of the home with tasteful finishes and excellent

Annette Gallo Real Broker LLC

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

Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and oven hood with a butcher

Jason Saphire www.HomeZu.com

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 and offers two separate

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.

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

Move right into this turnkey Cape offering 4 bedrooms and 3 bathrooms with extensive recent updates throughout. Combining classic New England charm with modern conveniences, this thoughtfully renovated home is designed for comfortable everyday living and effortless entertaining. The main level features a bright, open concept floor plan centered around a beautifully updated kitchen with quartz

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

Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

Christiane Carroccio TPW Real Estate

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.

Charming and spacious 3-bedroom, 1-bath home situated on approximately 1.90 acres, offering warm character and generous living space. Beautiful wood floors flow throughout the home, complemented by fresh paint, making this property truly move-in ready.The expansive wrap-around porch is a standout feature, perfect for enjoying quiet mornings, relaxing afternoons, or entertaining family and

Cassandra Ehrlich BHG Masiello Brattleboro

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

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

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

Kelley Mccarthy Mahar McCarthy Real Estate

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

Nestled in the heart of the iconic Dorset village, just steps from the Dorset Field Club and the beloved local theater, this enchanting historic home has been meticulously renovated, rejuvenated, and reimagined with no expense spared. From the moment you arrive, the home's timeless charm and thoughtful updates are evident. A complete reengineering of the roof and replacement of all major systems

Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

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 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