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

$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

$245,000

2 Beds ⋅ 2 Baths ⋅ 5112140 MLS

Don't miss your chance to own this well-cared for , low-maintenance home. Move-in ready condominium located less than a mile to downtown Brattleboro. This home offers a bright, freshly painted kitchen and dining area. Beautiful Kraft Maid cabinetry with plenty of storage. 2 bedrooms, 1.5 baths and convenient second floor laundry. New double hung windows installed last year along with recent carpeting throughout. If you enjoy gardening, two perennial beds are awaiting your special touch. Relax on your private patio or enjoy the trails right in your backyard. Are you looking for lower maintenance? This condominium includes snow removal and landscaping as well as trash, recycling and compost removal; swimming pool, pickleball courts and a carport. Don't miss this opportunity!!

92 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

$300,000

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

$289,000

3 Beds ⋅ 1 Baths ⋅ 5108845 MLS

Whether you are a first time home buyer or looking for an investment property, this is a home you will not want to miss. This property’s location, which abuts Brattleboro Memorial Hospital, offers the best of both worlds as it sits atop a quiet road within a half mile of grocery stores, schools, pharmacies and shopping. The home’s interior offers three bedrooms, a built in fireplace and hardwood floors. The basement features walk out access, a dedicated laundry space, ample dry storage with tons of potential to renovate into more living space. In the winter you’ll love the pull-in garage with a sheltered breezeway leading inside your home, never having been exposed to the elements. The back yard is fenced in with a gate opening to a wooded area on your land with a walking trail to the hospital. With a bone dry basement, on town septic and sewer, and a new standing seam metal roof installed by the previous owner, this home is ready to be moved into and enjoyed with peace of mind for years to come! Please come to our open house at this property on Saturday, September 12 from 10 am to 1 pm!

145 Belmont Ave, Brattleboro

$284,000

3 Beds ⋅ 1 Baths ⋅ 5108647 MLS

PRICE IMPROVEMENT! Sunny and inviting, this classic ranch offers easy single-level living with 3 bedrooms, 1 full bath, and a spacious living/dining area. Classic wainscoting adds charm and character to the hallway and bathroom. Recent updates include a roof replaced in 2019 and water heater replaced in 2022. The back deck overlooks a large yard with plenty of room for gardening, pets, and entertaining, plus a shed for additional storage. The full, unfinished basement offers versatile space for storage, a workshop, hobbies, or future living space, with a propane heating stove that provides supplemental warmth and an added measure of comfort and peace of mind during a power outage. Conveniently located near schools, shopping, and the hospital.

48 Wilsons Woods Rd, Brattleboro

$479,000

2 Beds ⋅ 2 Baths ⋅ 5106580 MLS

It has all you wanted! Shiny wood floors to celebrate New England building, plenty of windows to capture every inch of light possible, granite tops on a multitude of cabinets, a step in shower but also a tub for long soaks or the little ones who visit....total one floor living, so rare locally, even no stairs to the direct entry garage. A service that plows, shovels and mows.....a playground for adults with pickle ball, dedicated exercise room, meeting room and kitchen, and a cozy place by the fire to sit and visit. If you are at an age when you can appreciate an easier lifestyle, come take a look and see if this is your next adventure. This property is being subdivided from a larger parcel.

162 Buttonwood Dr, Brattleboro

$439,000

2 Beds ⋅ 2 Baths ⋅ 5106541 MLS

You've earned it.....the right to easy living.....have someone to do the heavy lifting...This community has become a much needed addition to the housing community. All are designed for the 55 and over who are looking for an easy way to settle in. Just think, the snowplowing, shoveling and salting are all taken care of, as well as the summer mowing and hedge trimming. One level living with no steps, a step in shower...no hopping over the tub rim...no cleaning off the car when you park in the garage...Besides all this there is a community center featuring exercise equipment, a function room, cozy fireplace and kitchen. A great place for walking, meeting the neighbors and making friends. Pickle Ball anyone? Located right off I91, you CAN get there from here. No mud season, no fuss. You have earned it! This property is being subdivided from a larger parcel.

77 Buttonwood Dr, Brattleboro

$585,000

4 Beds ⋅ 3 Baths ⋅ 5106451 MLS

You don't have to wear pearls to live here! This home oozes classic charm, memories of Thanksgivings and every holiday celebrated. The first step in has a welcoming wood stove for winter chill and glass french doors to fling open the first day of spring....Bring them home to the heart of the house with a dining room big enough for a feast...living room with a fireplace....warm hardwood floors, a lovely staircase and windows everywhere. Inside or out... every season will capture your heart....you will find them on the patio surrounded by blooms and summer sounds, tucked in reading a book while the snow swirls, taking in a game while the snacks flow. There is room for it all, and they will come home.

354 Orchard St, Brattleboro

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