Brattleboro Real Estate

Welcome to Brattleboro, Vermont, a charming town nestled in the picturesque Windham County. Known for its vibrant arts scene and rich history, Brattleboro offers a unique blend of small-town charm and cultural sophistication. With the Connecticut River gracefully winding through it, this scenic town is surrounded by the stunning Green Mountains, providing a breathtaking backdrop for outdoor enthusiasts and nature lovers alike.

Brattleboro boasts a lively downtown area filled with eclectic shops, cozy cafes, and farm-to-table restaurants that highlight the region’s local produce. The town is home to a thriving arts community, featuring galleries, theaters, and live music venues that regularly host events, making it a cultural hub in southern Vermont. Be sure to visit the Brattleboro Museum & Art Center, where contemporary exhibitions and community events are always on display.

For those who appreciate outdoor activities, Brattleboro does not disappoint. The nearby trails and parks offer endless opportunities for hiking, biking, and winter sports, while the Connecticut River is perfect for kayaking and fishing during the warmer months.

With its friendly residents, a strong sense of community, and a commitment to sustainability, Brattleboro is not just a place to live; it’s a lifestyle. Whether you’re looking for a quaint home in a historic neighborhood or a modern property with stunning views, Brattleboro has something to offer everyone. Discover the magic of this enchanting town, where every day is an opportunity to embrace the beauty of nature and the warmth of community.

Newest Listings in Brattleboro

$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

$59,000

2 Beds ⋅ 1 Baths ⋅ 5102920 MLS

Sweet little mobile home! Large mudroom or multi purpose sun room, eat in kitchen separated from the living room with open shelving. Two bedrooms, the larger used to be two smaller bedrooms which could become that again if you need 3 bedrooms, otherwise a great bedroom with a sitting area, and a second bedroom at the end! Stackable washer/dryer in the bathroom. A large shed is great for storage, plenty of room in the yard for flowers or veggies, and you even have your own private beach on the Whetstone Brook! Comer take a look! Must be park approved!

9 Village Dr, Brattleboro

$198,000

5102764 MLS

It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant Valley, but a right of way to take you to the rear lot. You can't miss this opportunity to join the neighborhood, become a part of something special. Don't compromise any longer, build that energy efficient, Vermont home and be the influencer for the next generation of homes.

Pleasant Valley Rd, 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

$680,000

5102102 MLS

SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and public water and sewer. Many units have private entrances – wow! On-site laundry, too! It’s time to diversify, and acquiring a steady income stream is the best way forward!!! Excellent investment with superb ROI potential. LOCATION & OPPORTUNITY. This is THE ONE for you. Do NOT miss out! Private showings on request.

50 Terrace St, Brattleboro

$350,000

5100544 MLS

Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident throughout, with the property having been carefully maintained over the years. Come sit on the back porch and watch the sunrise over the mountain. Whether you're looking to expand your investment portfolio or live in one unit while generating income from the other, this well-kept duplex offers convenience, versatility, and lasting value in a desirable location.

120 Western Ave, Brattleboro

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