430 properties for sale in Brattleboro town

Beautifully cared-for 3 bedroom, 3 bath single family condo in a desirable small association, conveniently located near town, golf course and major road access. This spacious home features a sought after first-floor primary suite with en-suite bath, skylights that fill the home with natural light, and elegant cherry flooring throughout the main living areas. The remodeled kitchen offers modern finishes and functionality, while the family room boasts brand new carpeting for added comfort. a perfect blend of privacy, convenience, and tasteful updates in an exceptional location. Open house Sunday May 31st 11am-2pm

BLACK MOUNTAIN ESTATES where your next chapter begins! Welcome to Brattleboro's premier 55+ active lifestyle community, where nature, connection, and comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, and open green space, residents enjoy a serene setting just 1 mile from I-91, with ease of access to cultural and recreational opportunities, shopping, dining, and medical care. Nestled on 33 acres of pristine Vermont landscape, this premier neighborhood is thoughtfully designed, offering a vibrant community center w/ library, fireplace lounge, fitness center, full kitchen, and outdoor patio w/ fire pit. Outdoor recreational amenities incl. pickleball, bocce, shuffleboard, and horseshoes-perfect for staying active and social. Enjoy the ease of HOA-managed services and a lifestyle designed for freedom and fulfillment. Each home is single-story and ADA-compl

Distinguished brick country estate built for William R. Moody, eldest son and successor of Dwight L. Moody, founder of the Northfield Seminary School. Thoughtfully updated while preserving its original character. Three-and-a-half levels of living space featuring exquisite architectural details, period craftsmanship, timeless millwork, custom cabinetry, exceptional built-ins, and three working fireplaces. A gracious foyer with original staircases introduces living spaces rich in character and craftsmanship. The kitchen is complemented by a walk-in pantry and butler's pantry, while south-facing windows and a sun-filled conservatory overlook gardens, fruit trees, pool, and gazebo. Set on 5.67 acres with paddocks, a four-stall stable, and a carriage-style barn with one stall, tack room, run-in shed, and two-car garage, the property borders state land with miles of trails. Minutes to Northfield Center and the New Hampshire border. A rare opportunity to own a piece of Northfield's history

Opportunity, flexibility, and character come together in this exceptional bungalow style multi family property offering over 2,300 sq ft of living space and endless possibilities for owner occupants, investors, multi generational living, or those seeking a live/work lifestyle. The spacious main residence features 4 to 5 bedrooms and 1 full bath, showcasing the timeless charm of a classic bungalow with beautiful hardwood floors, original woodwork, tall ceilings, abundant natural light, and generously sized rooms throughout. The well appointed kitchen features granite countertops, stainless steel appliances, custom cabinetry, and exposed brick accents, blending modern convenience with the home's character and craftsmanship. The oversized living room serves as the heart of the home, highlighted by a gas fireplace, expansive windows, and views overlooking the stunning covered front porch. The primary bedroom also features its own gas fireplace, creating a warm and inviting retreat. A stand

Elegant Post-and-Beam! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls and gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass windows. Adjacent, opens into a warm, spacious family room with cherry wainscoting, a gas stone fireplace, curved architectural accents and mud room access. The formal living room features a brick fireplace and is surrounded by classic post and beam architecture and stained glass windows. The open kitchen and dining area are ideal for entertaining and impress with cherry cabinetry, quartz countertops, stainless appliances, and sliders to an expansive deck with serene views. A den, half bath, and

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

Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an exceptional occupancy history with very little vacancy. The building has been well maintained and features newer windows, vinyl siding, two oil tanks, and two boilers. Tenants pay their own electric while the owner covers heat, water, sewer, and taxes. Conveniently located just moments from downtown shopping, restaurants, entertainment, and public transportation, the property is ideally situated to support continued strong rental demand. A unique opportunity to acquire a proven income-producing property with a long track record of stable occupancy and excellent cash flow potential

Enjoy peaceful country living in this to-be-built Full Dormer Cape, thoughtfully situated on a beautiful 1-acre lot. This well-designed home offers the convenience of a first-floor bedroom with a walk-in closet and a full bath nearby - perfect for flexible living arrangements. The open-concept kitchen and living area create a bright, welcoming space ideal for both everyday living and entertaining. The kitchen will feature granite countertops, a center island, abundant cabinetry, and a sliding glass door leading to the back deck - a perfect spot to relax and take in the surrounding landscape. Upstairs, you'll find two generously sized bedrooms and a second full bath, providing comfortable space for family, guests, or a home office. A charming covered front porch enhances the home's curb appeal, while the attached 24x24 garage offers ample room for vehicles, storage, or hobbies. Outdoor enthusiasts will appreciate being close to Pisgah State Park, a breathtaking 13,300-acre public recrea

Nestled in the sought-after Orchard Street neighborhood, this beautiful townhouse offers bright, sun-filled living spaces and a serene wooded backdrop. The rear deck extends into the backyard, creating the peaceful feeling of living in a private treehouse retreat

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

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

Tucked away on a quiet hilltop, this charming home offers the perfect escape with views over the Connecticut river and mountains afar. A 900-foot private driveway welcomes you home with many opportunities any spacious parking. Designed with true first floor living, the main residence offers everyday functionality without compromise. Expansive windows flood the home with natural light. The open layout flows seamlessly for comfortable living and effortless entertaining. Step outside your own private oasis-featuring a stone patio, charming screened in gazebo, and relaxing hot tub. This home is also equipped with solar panels, helping reduce energy costs while supporting sustainable living. Adding even more versatility, the attached dwelling unit provides ideal space for multigenerational living, extended guest, a private office, or rental income potential which is currently in place. Primary residence and ADU have separate entrances, utilities and both have full basements. Do not miss out

A rare combination of recreation and convenience in one of Brattleboro's most desirable neighborhoods. This home is designed for living and entertaining! The property sits on 1.6 acres of landscaped grounds with sweeping views of Mt. Wantastiquet showcasing spectacular sunrises and 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. Adj

Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and year-round recreation. Inside, the chef's kitchen is both stylish and functional, featuring a farmhouse sink, generous walk-in pantry, and a sunlit eat-in area that opens to a screened porch that's perfect for hosting and relaxing. A formal dining room includes a custom Vermont live-edge farm table (conveying with the ), while three inviting living spaces provide flexibility and comfort, including a spacious main living room with a wood-burning fireplace and a separate TV room. The home offers versatile living options with several bonus rooms ideal for home offices or guest accommodations, along

Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors magical in combination and truly beautiful. A home, an artist loft. so many uses, so unique, so inspiring. A Joy to own

Bordered by classic stone walls, an ornamental arched gate welcomes you to this enchanting Folk Victorian home, rich in character and timeless appeal. Decorative scalloped gables and inviting spindled porches reflect an era of exceptional craftsmanship. Thoughtfully maintained and updated, the home features wood floors, pocket doors, and stained-glass accents. A newer deck w/ stairs extends from the original side porch, ideal for relaxing or entertaining. The grounds offer established gardens and a pergola set behind the oversized 2-car garage w/ attached barn (1994), perfect for storage or workshop use. A Buderus boiler provides a single heating system. Ductless mini-splits provide heating and cooling on the 1st floor, w/ a separate ducted heat pump system and thermostat upstairs. Although zoned as a two-unit property, the home has long been used as a single-family and offers excellent potential for multi-generational living or Airbnb. Ideally located on sought-after Highland Ave near

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 lifestyl

Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. 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. Shared basement with assigned storage space. Association fees include heat, water/sewer, landscaping and more

Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share the lovely gardens and enjoy your spacious covered porch. It is heated and air-conditioned with a highly efficient, state-of-the-art heat pump, ensuring comfort in every season. The location is ideal, offering close proximity to several access points for the retreat trails, including an extensive system of hiking trails, with the closest at the nearby Chestnut Reservoir. Very short walk to downtown. The home owners fee is $170.00/month

Discover this special location and versatile home! Built in 1989, the current owners have updated almost everything from the brand NEW roof, rebuilt chimney, new composite front porch, to the double walled oil tank and new bulkhead cover. The home has been upgraded with quality components and design. The well-planned kitchen boasts cherry cabinets, silestone counters, new S/S DW and Refrig and the spacious Dining/LR extends the full depth of the house, featuring oak floors and a fireplace w/woodstove insert. Thoughtfully appointed baths w/tile finishes, one deep tub, and dbl vanity in the primary. First floor den/office can also serve as a main level BR. Well-done lower-level bonus room is great for game room or theater. Outside, the partially covered expansive composite deck is a great space to relax while overlooking the acre-sized yard. Sweet location, walkable to Thomas Aquinas campus, Northfield Golf Course, and quick access to Main St shops, school and library. More info attached

Spacious and Inviting Home in a Convenient Location! Ideally located just minutes from Brattleboro and I-91, this wonderful home offers the perfect blend of comfort, space, and convenience. The first floor features a bright bedroom with abundant natural light and a handicap-accessible bath complete with a beautiful walk-in tile shower - ideal for single-level living or guests. Enjoy cooking and entertaining in the large eat-in kitchen, featuring generous cabinet and counter space, and direct access to the back deck and yard for outdoor dining or relaxation. The spacious living room offers plenty of room for seating and gathering, while the delightful three-season porch, surrounded by windows, provides a sunny retreat throughout much of the year. Upstairs, you'll find three comfortable bedrooms and a full bath, offering flexibility for family, guests, or a home office. With its versatile layout, natural light, and easy access to area amenities, this move-in ready home is a wonderful opp

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 hos

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; 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

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders to the back for grilling and a living room with a picture window to the front yard, you can tuck in and enjoy. Half of the lower level is finished and is perfect for a den, at home office or playroom. Plenty of storage in the unfinished portion, so stock up on those items! Please be prequalified before making an appointment to view

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 within walking distances. Close to 1-91 this convenient property can be your next. home sweet home