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

$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

$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

$309,000

3 Beds ⋅ 1 Baths ⋅ 5096011 MLS

***Open House Sunday 7/19 from 11am-1pm** 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

$369,000

4 Beds ⋅ 2 Baths ⋅ 5095156 MLS

MAKE YOUR APPOINTMENT TODAY! A very sweet house in a desired West Brattleboro neighborhood on nice corner lot. Pull your car right into the 2-car oversized garage and enter through the enclosed porch which makes an excellent mudroom. First floor: beautifully updated kitchen with quartz countertops and cherry cabinets, a dining area that adjoins the light-filled large living room with lovely warm hardwood floors, exposed beam, an enormous picture window that allows for streaming sunshine throughout the morning. The centrally located Hearthstone woodstove adds to the appealing aesthetics of the home and provides for a secondary heat source that warms the entire home in the winter. Down the hall- a full bath and two good-sized bedrooms with wood floors. Upstairs, you will find an expansive primary bedroom, a half bath and a large office (or 4th bedroom). There is a full, poured concrete basement with bulkhead, where one of two rooms is finished and has served as a play/rec room through the years. The other room is used for storage with shelving, includes a washer and dryer, and an on-demand water heater and furnace that are only 6 years old. Outside you will enjoy a large back deck for summer grilling and relaxing. The yard provides areas for flowering trees, sun and natural shade, plantings and play. Garage roof is brand-new. Convenient location just minutes to downtown Brattleboro, or all of the West Brattleboro offerings such as hardware store. coffee shop, farm-stands, convenience store, restaurants and more. Make your appointment today!

120 Carriage Hill Rd, Brattleboro

$299,000

3 Beds ⋅ 3 Baths ⋅ 5094671 MLS

Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for relaxing, gardening, or outdoor gatherings. Upstairs, the bedrooms offer comfortable accommodations with the opportunity to add a full bathroom in the future, allowing the home to grow with your needs. The lower level includes a separate in-law suite complete with its own private entrance and laundry area, offering flexibility for guests, multi-generational living, a home office, or potential rental income. Conveniently located, the property is less than a block from the Vermont Country Deli and within walking distance of the Brattleboro Farmers' Market, Memorial Park, and recreation fields. Easy access to Interstate 91 makes commuting simple while keeping downtown Brattleboro's shops, restaurants, arts, and entertainment just minutes away. Whether you're searching for a primary residence, an investment property, or a home with income-producing potential, this well-priced property offers an excellent opportunity.

412 Western Ave, Brattleboro

$545,000

2 Beds ⋅ 1 Baths ⋅ 5094642 MLS

Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural Vermont charm, privacy and convenience, with easy access to town. The beautiful Pleasant Valley Reservoir and the recreational opportunities provided by its protected land, trail system and class 4 road network are an underutilized outdoor paradise just down the road. The home's striking flat roof design, redwood siding, and clean mid-century modern influences create a timeless architectural aesthetic. Inside, the open concept living/dining and kitchen area is filled with natural light from the expansive windows that frame the surrounding landscape. An East/SE facing corner deck provides the perfect setting for morning coffee and sunrise views. The main level features two bedrooms and a full bath updated in 2026. The finished walkout lower level offers a spacious additional living space. The impressive gambrel barn once housed horses in its 3-5 stall lower level and has water and power. The top level of the barn is open clear span with a drive-in door ideal for vehicles and equipment storage, a wood shop, workshop, studio space or a variety of other uses including a possible second dwelling unit with applicable permits. The open land in front of the barn was once a dressage arena and provides an excellent level outdoor space for recreation, animals or agriculture. The remainder of the property includes a mix of open field, young growth forest and established yard areas surrounding the home with abundant room for large gardens and outdoor fun. Despite its peaceful country setting skiing, golf, hiking and biking are only minutes away. A rare one-of-a-kind Vermont property.

211 Pleasant Valley Rd, Brattleboro

$339,000

4 Beds ⋅ 2 Baths ⋅ 5093467 MLS

Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting "benign neglect"—where nature and romance intertwine to create a storybook setting that will capture your heart from the moment you arrive. Inside, you will find a spacious layout featuring 4 bedrooms and 2 full baths spread across 2,250 square feet of versatile living space. The home has been thoroughly cleaned out and deep-cleaned, presenting a pristine, blank canvas with exceptional, rock-solid "bones" ready for its next chapter. Fine historic details anchor the home, from rich wood floors to timeless built-ins. At the heart of the home sits a magnificent centerpiece: a vintage Vermont Iron Stove Works stove, radiating authentic New England warmth and charm. The footprint continues to impress with a bright, beautiful sunroom perfect for morning coffee, a large attached 2-car garage providing excellent storage, and a expansive bonus space tucked away in the finished attic. This property is being offered in "as-is" condition and does not include appliances, making it the ultimate dream project for those looking to invest sweat equity into a truly remarkable historic home. Bring your vision to finish the cosmetic upgrades and unlock the true grandeur of this whimsical masterpiece. OPEN HOUSE SUNDAY, JUNE 14TH | 12:00 PM – 2:00 PM Come experience the magic and explore the incredible potential of this one-of-a-kind home in person!

65 Cedar St, Brattleboro

$250,000

3 Beds ⋅ 1 Baths ⋅ 5092993 MLS

This adorable single-level home offers easy living with a functional layout and comfortable living spaces. The warm and inviting interior is designed for everyday living. The home features a large living and dining area, a convenient laundry nook, a spacious primary bedroom, and two additional bedrooms that can accommodate guests, a home office, or other multi-purpose needs. Outside, you'll find a nicely-sized, level yard that offers plenty of space to enjoy gardening, outdoor activities, or simply relaxing without the burden of extensive maintenance. Whether you're a first-time buyer, looking to downsize, or seeking a low-maintenance property, this charming home provides the perfect blend of comfort and convenience. Enjoy the simplicity of one-level living while being conveniently located near the hospital, pharmacy, shopping, dining, and other everyday amenities.

111 Central St, Brattleboro

$325,000

4 Beds ⋅ 1 Baths ⋅ 5091728 MLS

Located in one of Brattleboro’s desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two bedrooms and a full bathroom on the first floor, the layout offers flexibility for a variety of living needs. Outside, enjoy a spacious backyard with room to garden, gather, or simply relax. A warm and welcoming home ready for its next chapter. Open house Saturday, 5/30 from 1-3 and Sunday 5/31 from 11-1

6 Sycamore St, Brattleboro

$344,900

3 Beds ⋅ 2 Baths ⋅ 5091453 MLS

Enjoy the privacy of your own space secluded from the rest of the world. Enjoy the comfort of a country setting in town. Look through the tree tops over the roofs of houses below on one side, onto a garden on another side, and onto a wooded hillside on the rest. Nature surrounds this immaculate house on a hill. Amenities include stone walls, a dog cage, a fire pit, raised gardens, a convenient 2-car garage, a mudroom with a closet off the garage, a workshop on the basement level, a pantry with spice racks, a palladian window and ceiling fan in one bedroom, and privacy, privacy, privacy. The seller spent a lot of time and money preparing the house for sale; see the list of improvements in the Documents section of this listing. Includes a 1/34 share of common interest in the Wilsons Woods land. Near the middle school and high school, hospital and shopping. Showings begin on Friday 6/5/26.

90 Wilsons Woods Rd, Brattleboro

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