Brattleboro Real Estate

Welcome to Brattleboro, Vermont – a charming town nestled in the picturesque Windham County, where the beauty of nature meets a rich tapestry of culture and community. Known for its vibrant arts scene and stunning landscapes, Brattleboro is a hidden gem that offers a unique blend of small-town charm and modern amenities.

As you stroll through the historic downtown area, you'll be captivated by the eclectic mix of shops, galleries, and eateries that line the streets. Whether you're indulging in a locally brewed coffee or exploring the works of talented artisans, Brattleboro's creative spirit is palpable. The town is also home to the renowned Brattleboro Museum & Art Center, showcasing contemporary art and engaging exhibitions that reflect the community’s artistic flair.

Nature enthusiasts will find themselves in paradise, with the Connecticut River and the surrounding Green Mountains providing endless opportunities for outdoor adventures. From hiking and biking in the warmer months to skiing and snowshoeing in winter, Brattleboro's natural beauty is a year-round playground for all ages.

In addition to its cultural and recreational offerings, Brattleboro boasts a strong sense of community, with numerous festivals and events that bring residents together. The annual Brattleboro Literary Festival and the vibrant farmers market are just a couple of highlights that showcase the town's commitment to fostering connections among its residents.

With its welcoming atmosphere, rich history, and breathtaking scenery, Brattleboro is not just a place to live – it's a place to thrive. Discover your dream home in this enchanting town and become a part of its wonderful community!

Newest Listings in Brattleboro

$275,000

3 Beds ⋅ 1 Baths ⋅ 5114102 MLS

Just right! All spiffed up, shinny and ready to move right in. Sweet aging in place home on one level, level back yard, and minutes from grocery stores, hospital and Memorial Park! Just starting out? 3 bedrooms gives you room for expansion, hobbies or an aging parent. This affordable home should go most programs, has lots of light, and is a perfect beginner home. Check it out and start a new chapter; leave the rentals behind and invest in your future!

43 Winter St, Brattleboro

$129,000

5114033 MLS

INVESTORS, LANDLORDS & OWNER-OCCUPANTS - HERE’S YOUR OPPORTUNITY! Whether you’re looking to expand your rental portfolio, create two income-producing units, or live in one unit while the other helps offset your mortgage, this two-unit, up-and-down multifamily property is ready for its next chapter. The heavy lifting has already begun! The current owner has completed the deconstruction, removing all drywall and taking the interior down to the studs, creating a true blank canvas for your vision. Building permits were issued for the deconstruction work already completed. Additional improvements have been made throughout the property, including replacement of the existing chimney with an insulated stainless steel chimney, as well as upgrades to the roof, heating, and electrical systems. The first-floor unit has its existing systems in place, while the second-floor unit will require systems to be installed as part of the renovation. Outside, enjoy a nice, flat yard and plenty of paved parking. With much of the initial demolition already completed, you can focus on designing and finishing the property to fit your investment goals. Bring your contractor, bring your vision, and bring your plans - this clean slate is ready for its next transformation! Come take a look and see what you can create.

139 Frost St, Brattleboro

$339,000

3 Beds ⋅ 2 Baths ⋅ 5113538 MLS

Located in the desirable Black Mountain Road area, this cozy log home includes an attached two-car garage with a workshop area, a three-season porch, and a wraparound deck. The lower level is accessible from the garage and opens into a spacious tiled mudroom. An open staircase leads to the main floor, which features three bedrooms, 1¾ baths, a living room, and a country kitchen with a dining area. The basement provides abundant unfinished space for a workshop, studio, or other creative pursuits, along with laundry, sink and a workbench. Additional outbuildings include small storage sheds. The home needs some TLC but offers worthwhile potential in a country setting, so close to town. The owners are continuing the cleanout process, and additional photos will follow. Please note that the large stones are not included.

625 Black Mountain Rd, Brattleboro

$189,500

2 Beds ⋅ 2 Baths ⋅ 5112756 MLS

This cozy condo faces a hillside, landscaped with beautiful mature hydrangeas. Besides beauty, the hillside offers privacy and quiet. And no headlights will shine in your windows. The seller has totally renewed the unit with a new hot water heater, newer boiler, new gas range, new microwave, new closet doors and new flooring, and it was newly painted throughout. Then it was professionally cleaned. It is ready for you to move in. Association amenities include a swimming pool, tennis/pickleball courts, basketball, hiking trails, little libraries and common area gardens. The Association takes care of all outside maintenance. Downtown Brattleboro is within walking distance. Easy living awaits you at 29 Morningside Commons.

29 Morningside Commons, Brattleboro

$229,000

2 Beds ⋅ 2 Baths ⋅ 5111836 MLS

In this second floor condo you will not be bothered by steps overhead. You can relax on the back deck overlooking nature. You can spread out in the comfort of a living room, eat-in kitchen, 2 bedrooms and 1.5 bathrooms all on one floor. The seller replaced the double stainless steel refrigerator, the gas range, the dishwasher and the kitchen floor 2 years ago. The washer and dryer are 5 years old. The boiler and hot water heater were replaced 10 years ago. A wall air conditioning unit and 3 ceiling fans add to the ambiance. The Morningside Commons Association takes care of everything outside and provides a swimming pool, tennis/pickleball courts, a basketball area, hiking trails, little libraries and common area gardens for your enjoyment. Downtown Brattleboro is within walking distance. 164 Morningside Commons awaits you.

164 Morningside Commons, Brattleboro

$310,000

3 Beds ⋅ 2 Baths ⋅ 5111605 MLS

This is an estate sale. Entry into the property is forbidden. While the land is beautiful and in a very pastoral rural setting, the dwelling is considered to be a tear down. This property is being sold "as is where is." Accompanied showings only preferably on Wednesday when the caretaker will be available.

627 Abbott Rd, Brattleboro

$129,000

2 Beds ⋅ 1 Baths ⋅ 5111023 MLS

Tiny-home ready for the next owner to make their own! The property offers a solid start to creating a comfortable, 2-bedroom tiny-home. The original log cabin sugarhouse features the kitchen, the dining area and ¾ bath while the unfinished addition houses the living room and the two-bedrooms. With the property’s basic infrastructure already in place - town water and sewer, 100 amp service and new roofing, the next owner can focus on completing the remaining exterior / interior work. Enjoy the outdoors from the deck or the yard. Tucked away at the end of a private road extension in a sought-after west Brattleboro residential neighborhood, the setting is tranquil but super convenient, only minutes to downtown Brattleboro and the highway. Sold As-Is. Cash or Rehab Financing Buyers Only.

50 Lawton Dr, Brattleboro

$279,000

2 Beds ⋅ 2 Baths ⋅ 5110840 MLS

Quite simply, one of the finest units ever offered at Morningside Commons. This beautifully updated 2nd-FL condominium combines thoughtful design, quality upgrades, and true move-in-ready convenience in one of the association's most desirable locations. A priv. 1st-FL entry provides a practical mudroom area before leading upstairs to a bright, welcoming living space. The spacious LR flows seamlessly into the kitchen and opens to a priv. rear deck, creating an ideal setting for everyday living & entertaining. The standout kitchen features abundant cabinetry w/ soft-close drawers, brilliant under-cabinet lighting, a new butcher block island w/ seating, 5-burner gas range, pantry, & adjoining nook perfect for meals, work, or reading. The well-designed floor plan separates living areas from BR’s. The generous primary BR incl. a walk-in closet & updated en-suite BA, while a second BR w/ oversized closet is ideal for guests, hobbies, or a home office. A second full BA, laundry closet, & add’l storage complete the layout. Gleaming maple hdwd floors, attractive tile & vinyl finishes, large sliding windows, & abundant nat. light create a warm & inviting atmosphere throughout. Many recent improvements, incl. an on-demand heat & hot water sys., recessed lighting & paint thru-out, walk-in shower, & more. Situated on a desirable outside corner of the community, this unit enjoys exceptional privacy while remaining just steps from a charming footpath providing direct access to Morningside Cemetery for peaceful daily walks. This offering incl. a dedicated covered carport w/ a priv. shed large enough for bicycles, tools, seasonal tires, & more. Association amenities incl. a swimming pool, tennis/pickleball courts, community gardens, & little libraries. Conveniently located near the hospital, shopping, pharmacies, I-91, Amtrak, & downtown Brattleboro, this exceptional condominium delivers the perfect blend of comfort, style, convenience, & value. A rare opportunity not to be missed!

104 Morningside Commons, Brattleboro

$179,000

1 Beds ⋅ 1 Baths ⋅ 5110478 MLS

Don't wait to come view this newly remodeled, low maintenance, affordable and desirable ground floor end unit. Inviting circular flow, the spacious living room has a brand new slider with a view of the rear yard and the Whetstone brook. Plus, you have a brand new kitchen and appliances. The large bedroom with double closet has direct access to the newly renovated bath. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Association fees include heat, water/sewer, landscaping and more. Come visit this sweet home with an attractive price.

40 Brookside Dr Unit 2, Brattleboro

$295,000

3 Beds ⋅ 2 Baths ⋅ 5110381 MLS

In the heart of it all! Just minutes to everything Brattleboro...Day or night, there is something fun to do....movies, eats, hiking and so may other choices....3 generations have lived in and loved this home, gardening, sipping on the back deck, saying hello on the Vermont front porch. An era when homes were built with good bones, craftsmanship and quality hard to afford today. A pretty face to the street, the lot is double with lots of room in the back for family and friends. Lots of updates, nice eat in kitchen, dining room with built in china cabinet and lots of windows, an attic with heat just waiting for finishing, sweet period stair case to take you to bed at night. This is a sweet find, comfortable, well maintained, waiting for a new generation, ready for love of home and new adventures. Open house Saturday, September 19th from 11 am - 1 pm

36 Pine St, Brattleboro

$379,000

4 Beds ⋅ 2 Baths ⋅ 5109984 MLS

Welcome to this classic in-town gem, where timeless architectural character meets thoughtful updates and beautifully cultivated outdoor spaces. Offering approximately 1,700 square feet, 3–4 bedrooms, and 2 full baths, this special home is filled with original details, including hardwood floors, handsome built-ins, & lovely wainscoting. Light-filled rooms paired with warm natural wood create an inviting atmosphere with personality at every turn. The first floor offers an easy, comfortable flow with a spacious kitchen overlooking the gardens, a convenient walk-in pantry, laundry room, & access to the private back porch. The dining room is beautifully illuminated by bay style windows, while the living room enjoys views toward the front porch & features a propane stove for cozy evenings. A first-floor bedroom & full bath provide an excellent option for one-level living. Upstairs, three additional bedrooms, a renovated full bath, & a separate office space provide flexibility for family, guests, or working from home. Both bathrooms have been thoughtfully renovated with a fresh, sleek aesthetic. The third-floor attic offers abundant storage & exciting potential for future finished space. With two separate entrances/exits & two sets of stairs, the home also presents intriguing possibilities for other flexible living arrangement. The gardens are truly exceptional. The current owner has spent years lovingly cultivating a lush, private landscape filled with mature greenery & vibrant seasonal blooms. The result is a peaceful backyard oasis—beautiful, inviting, & wonderfully secluded. Ideally situated in a quiet, friendly in-town neighborhood close to the heart of downtown, this distinctive property offers an uncommon combination of character, flexibility, & outdoor beauty. Whether you're looking for the ease of first-floor living, room for a growing household, work-from-home space, or a home with soul & history, this property may be perfect for you.

19 Blakeslee St, Brattleboro

$270,000

2 Beds ⋅ 1 Baths ⋅ 5109722 MLS

A Home Filled With Possibilities! For the first time in 43 years, this charming and comfortable Organ Street home is ready to welcome its next owner. Offering a spacious, open-concept layout and the possibility of first-floor living, this home is both functional and full of potential. The main level features a generous kitchen that flows naturally into the spacious living and dining area, creating an inviting space for everyday living and entertaining. A full bathroom with both a bathtub and walk-in stall shower, along with a first-floor washer and dryer, adds to the ease and convenience of single-level living. A versatile first-floor den could serve as a bedroom, home office, or additional living space. Upstairs, you'll find a partially finished area with a two-bedroom layout already in place, offering the opportunity to finish the space and make it your own. Whether you envision additional bedrooms, a home office, hobby space, or a combination of uses, there is room to bring your ideas to life. Step outside to enjoy the spacious, fenced-in yard perfect for gardening, entertaining, relaxing, or giving pets room to roam. Whether you're looking for comfortable one-level living or a home with room to grow, this Organ Street property offers a wonderful combination of charm, space, and opportunity. After 43 years, this beloved home is ready for its next chapter. Come see the possibilities for yourself!

41 Organ St, Brattleboro

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