Brattleboro Homes for Sale

Welcome to Brattleboro, Vermont – a hidden gem nestled in the picturesque Windham County. This charming town, steeped in history and culture, offers a vibrant community atmosphere that is both welcoming and warm. With its stunning landscapes, including the rolling hills and the serene Connecticut River, Brattleboro is a haven for those who appreciate nature and outdoor activities.

Brattleboro boasts a rich artistic scene, featuring local galleries, theaters, and an array of festivals that celebrate the creativity of its residents. The downtown area is lined with unique shops, cozy cafes, and farm-to-table restaurants, making it a delightful place to explore or unwind. Whether you’re enjoying a leisurely stroll along the riverbank or taking in the views from the nearby Mount Wantastiquet, Brattleboro’s natural beauty is sure to captivate you.

For those considering a move to this enchanting town, there are a variety of homes for sale that cater to different lifestyles and budgets. From charming historic homes with character to modern condos with all the amenities, Brattleboro offers diverse real estate options. Each neighborhood has its own unique charm, whether you prefer the bustling downtown vibe or the tranquility of a suburban setting.

With its combination of natural beauty, artistic flair, and a strong sense of community, Brattleboro is more than just a place to live – it’s a lifestyle. Discover your dream home in this vibrant town, and experience the magic of Brattleboro for yourself!

Newest Brattleboro Homes for Sale

$350,000

2 Beds ⋅ 1 Baths ⋅ 5103959 MLS

Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, and year-round comfort. Completed in July 2026 and designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner’s electrical needs, including heating and cooling. Warrantied ENERGY STAR® appliances, two quiet high-efficiency mini-splits, and a continuous fresh-air ventilation system support healthy indoor air, low operating costs, and efficient climate control. Just minutes from Brattleboro Hospital, shopping, restaurants, downtown, and Interstate 91, the home also offers walking access to miles of peaceful forested hiking trails. Designed for one-level living, the first floor includes an inviting foyer, abundant natural light, an open-concept kitchen, dining, and living area, a primary bedroom and full bath, and a large pantry with a washer and dryer. The cozy loft offers flexible space for a second bedroom, office, studio, or guests. Southeast-facing windows and double glass doors open to a rear deck overlooking the Connecticut River Valley. Enjoy autumn foliage, mountain views, classic winter landscapes, colorful sunrises, and warm-weather privacy from mature maple, oak, and locust trees. The poured-concrete walk-out basement is plumbed for radiant heat and includes two windows and double glass doors, offering potential for a workshop, recreation room, studio, guest suite, or possible efficiency apartment, subject to local approvals. The backyard offers room for gardens and outdoor enjoyment. Solar credits are available for purchase separately, creating an exceptional opportunity for long-term energy savings. Every major design decision reflects quality, durability, energy performance, and ease of living. Whether as a year-round residence, Vermont retreat, or simplified one-level home, this home offers thoughtful design, modern comfort, and long-term value.

203 Fairview St, Brattleboro

$299,000

3 Beds ⋅ 2 Baths ⋅ 5103897 MLS

Looking for your first home, ready to downsize, or seeking single level living? This one is for you. Set in a peaceful rural location near the end of a quiet dead end road, this single level ranch offers comfort, privacy, and great potential on 6.5+ acres just outside the village of West Brattleboro. Enjoy an in ground swimming pool with a pool house and bathroom - perfect for summer relaxation. High speed internet keeps you connected, a reliable Buderus boiler provides heat and hot water, and most windows have been updated to double glazed vinyl for improved efficiency. Inside, the layout is practical and inviting. Enter from the attached 24x24 two car garage into a substantial mudroom/laundry room - a huge perk in Vermont. The kitchen offers ample workspace and storage, opening to the dining and living areas with a wall of west facing windows. The living room fireplace is an ideal candidate for a woodstove insert, offering efficient heat with the ambiance of a traditional hearth. Off the central living area are three bedrooms, including a primary bedroom with full bath. Two additional bedrooms - or office/studio/workout spaces - plus a second full bath complete the floor plan. Outside, there’s room to garden, play, and enjoy the land. The price reflects the opportunity for a new owner to perform work and updates to build meaningful equity while enjoying a cozy home in a rural setting close to everyday necessities. Minutes from Memorial Park, trail networks, shopping, schools, the hospital, and I 91, this property delivers outstanding value at a competitive price. Don’t let it get away.

68 E Bonnyvale Ln, Brattleboro

$289,000

4 Beds ⋅ 2 Baths ⋅ 5103506 MLS

This in town 4 bedroom, 2 bath home offers the perfect blend of comfort, convenience and versatility. Ideally located close to town amenities, this property provides easy access to shopping, dining, services, schools, parks and everyday essentials while offering a spacious place to call home. Inside you’ll find beautiful wood flooring, inviting living spaces and a layout that provides flexibility for both living and working. With four bedrooms there is plenty of space for family and overnight guests while the large open finished attic can be turned into a number of uses. Perhaps a studio, exercise room, meditation space, the uses are only limited by your imagination. The property is well suited for those looking to operate a home-based business, offering a prime location and functional space for work-from-home needs. Enjoy the outdoors on your deck or patio and if weather doesn’t cooperate, the enclosed porch is perfect for relaxing with morning coffee or an after dinner beverage. A one-car garage adds convenience while the minimal exterior maintenance allows more time to just enjoy a little down time relaxing. A rare combination of location, flexibility and affordability are just a few of the reasons to take a look at this property. Showings begin Sunday 8/9 with OPEN HOUSE 12pm-3pm.

110 Western Ave, Brattleboro

$182,000

3 Beds ⋅ 2 Baths ⋅ 5103420 MLS

Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting........walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the tenants. No interior photos to respect tenants privacy.

23 Williams St, Brattleboro

$295,000

3 Beds ⋅ 1 Baths ⋅ 5103014 MLS

Welcome to this charming, well maintained ranch built with character, exceptional functionality, and comfort on a desirable dead end street. Classic curb appeal and the timeless design allow for first-floor living with spacious living and dining areas. It is flooded with natural light from the oversized windows and features original hardwood trim, solid wood doors, built-ins, and vintage light fixtures. Currently carpeted, but beautiful oak floors are underneath. The sunroom is welcoming and bright, offering the perfect space for an artist or an afternoon retreat while connecting with nature. The floor plan includes 3 bedrooms all of which look out to the expansive, level backyard. The vintage bathroom has warm accents, featuring original cream tiles with delicate pink surrounding the tub and shower, along with a laundry chute to the basement. The outside is impressive with a large open backyard offering endless possibilities for entertaining, gardening, recreation, or future outdoor additions. There is a charming rustic outbuilding that is the perfect garden shed or potential workshop. An oversized one-car garage connects to the home via a comfortable breezeway. There's an expansive full basement with cold storage room and flexibility for hobbies or a workshop. This home is rich in character yet full of opportunity for the next special owners to add their touches. Very close to the hospital, shopping, schools, bus route, and I-91.

30 Lexington Ave, Brattleboro

$450,000

3 Beds ⋅ 2 Baths ⋅ 5103012 MLS

Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck overlooking gorgeous, mature gardens - your own peaceful retreat. The property also includes a conveniently attached garage and a fully finished basement. The finished lower level includes a generous living room with a wet bar, a half bath, and a second fireplace, ready for a propane fireplace unit. With approximately 1,250 square feet of versatile space on each level, this home is a rare find. Showings begin Saturday, August 8th, with an Open House from 10-1 p.m.

72 Green Mdw, Brattleboro

$599,000

4 Beds ⋅ 3 Baths ⋅ 5102586 MLS

This handsome Contemporary Colonial is beautifully set on over an acre of level land in the desirable Hillwinds community, w/access to 200 acres of woodland featuring 3.7 miles of trails. Designed for comfort and efficiency, the property includes 24 solar panels for substantial energy savings, 2 Tesla Powerwalls and large rear decking for outdoor living. A 24' x 24' attached garage with overhead electric doors and finished sheetrock walls provides excellent space for vehicles or a workshop. The bright, inviting interior offers spacious principal rooms, large windows throughout, and has been recently painted. A generous mudroom with terracotta and ceramic tile flooring provides access to the garage, laundry room, and half bath before leading into the open kitchen and dining area. The well-appointed kitchen features cherry cabinetry, granite countertops, stainless steel appliances and recessed lighting. The dining room offers hardwood flooring, a charming bay window with window seat, and sliders to the rear deck. The expansive living room features hardwood flooring, a fireplace with pellet stove, and sliders to the deck. A formal entry with terracotta flooring and a private office with built-in shelving and glass-fronted folding doors complete the main level. Upstairs are four spacious bedrooms. The primary suite includes two large closets and a beautifully renovated en-suite bath with a soaking tub, glass-enclosed shower, and ceramic flooring. 3 additional bedrooms offer generous closet space and share an updated full bath. One bedroom provides access to a large finished bonus room with skylights, built-in shelving, and eaves storage. The walkout lower level is mostly finished, providing space for a family room or game room, along with utility closets and a large storage room. Located in one of Southern Vermont's most sought-after neighborhoods, this exceptional home offers energy efficiency, quality finishes, abundant natural light & outstanding access to nature.

179 Hillwinds N, Brattleboro

$415,000

3 Beds ⋅ 2 Baths ⋅ 5102500 MLS

Finally! A rare offering in a neighborhood with a waiting list!! And....a rare ranch style for either aging in place or just starting out!! Nice open concept living/dining features a fireplace that has been converted to a wood stove hook up for efficient use. Private primary bath, wood floors, big mud room/ breakfast nook are some of the sweet features to look forward to. Finished basement adds family area and fitness room. Huge yard features a cute raised studio, sunny deck ad is partially fenced. Join us for an Open House Saturday, August 1st from 11 am -1 pm.

138 Wantastiquet Dr, Brattleboro

$729,000

3 Beds ⋅ 3 Baths ⋅ 5100444 MLS

A rare combination of recreation & convenience in one of Brattleboro's most desirable neighborhoods. This home is designed for living & entertaining! The property sits on 1.6 acres of landscaped grounds with sweeping views of Mt. Wantastiquet showcasing spectacular sunrises & front-row views of Brattleboro's 4th of July fireworks. Tucked beside Living Memorial Park on a quiet cul-de-sac where skiing, tennis, baseball, swimming, playgrounds and year-round recreation are just steps away. Inside, oversized windows fill the home with natural light while viewing the spectacular setting. A welcoming foyer with beveled glass doors and three generous closets opens to the elegant living room with hardwood floors, propane fireplace, and expansive windows. The heart of the home is the stunning kitchen / dining area featuring ash flooring, a massive center island, custom Schrock cabinetry, granite countertops, and large sliding doors opening to the patio w/ firepit overlooking the views. Adjacent is an oversized walk-in butler's pantry offering abundant cabinetry, workspace and storage. The first floor features a guest bedroom with private en-suite bath featuring tile flooring and glass enclosed shower. Designed for entertaining, the year-round cabana room opens directly to a 2nd patio and 40x20 saltwater pool and includes a custom bar, full refrigerator, custom wine cabinet, plus an adjacent bath with concrete countertops, tile flooring and exposed brick accents. Upstairs, the primary suite offers a wall of windows framing the mountain views, a spa-inspired bath with double vanity & designer tiled rain shower, adjoining custom laundry room w/folding station, & an oversized walk-in dressing room with built-in organization. A 2nd spacious bedroom also includes a walk-in closet. Extensive updates, quality craftsmanship, beautiful outdoor living spaces, and an unbeatable location combine to create a rare offering of a truly move-in-ready home. Simply Stunning. Showings begin 7/24.

219 Hillcrest Ter, Brattleboro

$295,000

3 Beds ⋅ 1 Baths ⋅ 5100010 MLS

Timeless Character on Coveted Oak Grove Avenue! There's something special about an American Foursquare. Built for comfort and designed to stand the test of time, this quintessential early 20th-century home welcomes you with classic architecture, generous room sizes, and the warmth of original craftsmanship. Set on a desirable in-town lot along Oak Grove Avenue, this 3-bedroom home showcases beautiful hardwood floors, rich natural woodwork, and a cozy fireplace that anchors the inviting living room. The screened front porch is the perfect place to enjoy your morning coffee, greet neighbors, or unwind on warm summer evenings. Upstairs, you'll find three comfortable bedrooms and a full bath, while the unfinished attic offers exciting possibilities - whether you envision a studio, home office, playroom, or additional living space. Outside, there's room to garden, entertain, or simply enjoy the yard, along with the convenience of a one-car garage. Combining timeless character with everyday practicality, this home is just minutes from schools, the hospital, restaurants, shopping, and all the conveniences of in-town living. Come experience everything this Oak Grove Avenue gem has to offer.

136 Oak Grove Ave, Brattleboro

$285,000

3 Beds ⋅ 1 Baths ⋅ 5097858 MLS

Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

455 S Main St, Brattleboro

$299,000

3 Beds ⋅ 1 Baths ⋅ 5096011 MLS

Welcome to a home where everyday living feels just a little more special. Offering three comfortable bedrooms and a functional, inviting layout, this property is designed for everything from quiet evenings at home to hosting family and friends. The true highlight is the incredible backyard, a rare, fully fenced, level oasis that's ready for every season of life. Fire up the grill on the spacious back deck, let the kids and pets roam freely, plant the garden you've always wanted, or gather around a fire pit under the Vermont stars. This is the kind of outdoor space buyers dream about and seldom find. In addition to the incredible yard. A fully paved driveway with room for multiple cars, space for RV's Boats and other recreational items is at your service. Located in one of Brattleboro's most convenient neighborhoods, you'll love being just minutes from vibrant downtown shops, local restaurants, schools, parks, and minutes from I-91 leaving you 30 minutes to major MA and NH Hubs. Enjoy year-round community events while still enjoying the peace and privacy of your own backyard retreat. Whether you're grabbing a morning coffee, exploring the local arts scene, or taking advantage of nearby hiking and recreation, everything you love about Brattleboro is right at your fingertips. This isn't just a place to live, it's a place to make memories. This home offers the lifestyle you've been waiting for. Don't miss your chance to experience everything this exceptional property has to offer. List Agent is related to the Sellers

48 Carriage Hill Rd, Brattleboro

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