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

$425,000

5100788 MLS

Outstanding investment opportunity! This well-maintained 5-unit apartment building offers strong income in a highly desirable neighborhood close to downtown, shopping, schools, and the hospital. The property features five 1-bedroom apartments and has seen some updates, including some new vinyl replacement windows, one unit fully renovated, recently painted porches, and improvements to portions of the plumbing and electrical systems. Two car garage, off-street parking, and rear yard, adding to the property's long-term appeal and rental demand. With its prime location, valuable updates, and excellent cash-flow, this is a turnkey addition to any investment portfolio or a great opportunity for an owner looking to grow their rental holdings. Don't miss your chance to own this exceptional income-producing property! No interior photos due to tenant privacy.

126 Oak Grove Ave, Brattleboro

$279,000

2 Beds ⋅ 1 Baths ⋅ 5100548 MLS

Sweet ranch home with 2 car attached garage. A lovely and level lot for gardening or outdoor entertaining, this location provides a country feel but only minutes from vibrant West Brattleboro events and businesses and a short trip brings you into downtown Brattleboro with lots of opportunities. This home with a generous living/dining space, good sized kitchen, 2 bedrooms and 1 full bathroom is great for a starter home or people looking to down size. The attached two car garage has automatic garage doors and an attached breezeway provides direct entry into the house and makes a great mud room with storage. The full basement has storage, the washer and dryer, the pellet stove and an oil hot air furnace. There is also a place to install a bathroom if you want. Use some of the basement as a workshop for projects and fix-it shop. Recent upgrades include new windows and a standing seam metal roof and hot water heater.

98 Greenleaf 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. 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

$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

$265,000

2 Beds ⋅ 2 Baths ⋅ 5099429 MLS

Nestled next to Brattleboro's favorite public park, this end unit is wrapped in coveted out door space ,wrapping from the coffee deck all the way around to the back brick patio It also features a private garage with auto open, and laundry and storage neatly behind, The parking is paved with plenty of room for guests. Inside the ample galley kitchen has everything you need including a large top doing double duty as prep space and an extension of the dining room with stools to sit and sip. Just the right size for entertaining or family time, the living room is bathed in light from the large windows and the slider to the deck. A refuge from every day life, the huge main bedroom has room for a cozy chair, lots of closets and direct access to the bath. So special in it's location, so close to I91 north and south and east/west travel on RT 9, you can easily access health care, shopping, and all the fun things Vermont has to offer. Worth a visit for affordability, location and ease of lifestyle.

9 Evergreen Ln, Brattleboro

$250,000

2 Beds ⋅ 2 Baths ⋅ 5099302 MLS

This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2 bedrooms with vaulted ceilings. Just next door is the Living Memorial Park offering swimming, baseball games, pickleball, skiing, skating and annual events, The popular Farmer's Market is also close by. Close to 1-91 this convenient property can be your next ....home sweet home.

11 Evergreen Ln, Brattleboro

$110,000

5099250 MLS

Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, sewer, and electric are all at the street, and the seller will help to keep the access accessible :) The subdivision has received preliminary approval from the town, with finalization to be completed prior to sale—giving you peace of mind as you plan. Downtown Brattleboro is just about a mile away, while everyday essentials are close by as well. Close to hospital, public transportation, schools, and shopping! Perhaps the best perk of all? Fantastic neighbors and a rare opportunity: buyers have the option to rent the seller's ADU while building their new home, making the transition seamless and stress-free. Whether you're a first-time builder, downsizing, or a dreamer chasing simplicity, this thoughtfully positioned and convenient lot is a rare find. Come imagine the possibilities and stake your claim in wonderful Brattleboro, Vermont. Deed, taxes, and final acreage to be determined but will be at least .12 acres. NOTE- BS&L offers special tiny home loans!

117 Fuller Dr, Brattleboro

$495,000

5099165 MLS

Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water heater, spray foam insulation, and new cellulose insulation in the attic. The building offers six rental units, including three efficiency apartments, (2) two-bedroom units, and (1) one-bedroom unit (please note the bedroom does not have a window). Three units are currently occupied by long-term tenants. The two-bedroom and one-bedroom units each have separate electric service, while the three efficiency units are on the owner's electric meter. Heat and hot water are included for all tenants. The property also offers plenty of off-street parking with a convenient location close to shopping, the hospital, public transportation, Interstate 91, and other local amenities. A turnkey investment with many major capital improvements already completed.

1309 Putney Rd, 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

$465,500

5097401 MLS

Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. Offered at an impressive 10% cap rate, the building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the property offers exciting upside with attic space that may provide opportunities for additional living area or future expansion, subject to local approvals. Ideally located in Brattleboro, tenants enjoy the convenience of a thriving downtown known for its eclectic shops, restaurants, arts scene, and year-round community events, as well as easy access to Interstate 91 and the outdoor recreation that Southern Vermont is known for. Whether you're seeking stable cash flow or long-term value-add potential, this property delivers both in one of Vermont’s most desirable communities. 3D Virtual Tours Available Upon Request.

28 Brook St, Brattleboro

$422,000

5097400 MLS

Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. Offered at an impressive 10% cap rate, the building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term maintenance. Located in vibrant Brattleboro, tenants enjoy easy access to the town’s eclectic mix of restaurants, coffee shops, galleries, and local events, along with convenient access to Interstate 91 and nearby outdoor recreation. Known for its strong sense of community and thriving arts scene, Brattleboro continues to attract residents seeking both small-town charm and everyday conveniences. Whether you're expanding an existing portfolio or looking for a high-yield investment in one of Southern Vermont’s most dynamic communities, this property offers strong returns and lasting appeal. 3D Virtual Tours Available Upon Request.

820 Western Ave, Brattleboro

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