Brattleboro, VT Houses for Sale

Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden

Christine Lewis Brattleboro Area Realty

Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a

John Hatton Berkley & Veller Greenwood Country

Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed

Dan Normandeau Berkley & Veller Greenwood Country

Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

Kristen Ziter Taylor Brattleboro Area Realty

Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through

Robert Doyle Berkley & Veller Greenwood Country

BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

Dan Normandeau Berkley & Veller Greenwood Country

First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

Christine Lewis Brattleboro Area Realty

Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

Steve Schoppmeyer BHG Masiello Brattleboro

Opportunity to live and invest in upgrades for your new home.

Susan Bellville Bellville Realty

This well-maintained three-bedroom, two-bath single-family home is set on a level, fenced-in lot in a coveted neighborhood close to downtown, with convenient access to major highways. The home features radiant flooring, central air, and a finished basement offering flexible living or recreational space. A spacious kitchen provides ample cabinetry and storage, ideal for everyday living and

Kelly Agrillo Southern Vermont Realty Group

Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, 35 acres of open meadow, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect location...minutes

Christine Lewis Brattleboro Area Realty

The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

Christine Lewis Brattleboro Area Realty

Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to

Christine Lewis Brattleboro Area Realty

An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only

Christine Lewis Brattleboro Area Realty

Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

Christine Lewis Brattleboro Area Realty

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders

Christine Lewis Brattleboro Area Realty

Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

Rebecca Seymour Brattleboro Area Realty

Great location in the heart of Brattleboro. This 3-bedroom, 1-bathroom Jewel of a home is as efficient as it is charming. Very well maintained, with gorgeous maple floors, built-ins, original natural woodwork, elegant marble countertops, and an open kitchen/dining/living space that shines with a southern exposure. Snug little wood stove adds to the uplifting spirit in this home. Large upstairs

Kristen Ziter Taylor Brattleboro Area Realty