496 houses for sale in Brattleboro

Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. 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 V

This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level offers a fantastic opportunity with a partially finished, extra-large bonus room that can be customized to suit your needs. Additionally, this level includes a convenient laundry/utility room and a small workshop space, offering practical solutions for storage and hobbies.Outdoor living is equally inviting with a private deck off the back of the house, leading to a fenced backyard. This space is ideal for relaxation and entertaining, complete with a firepit perfect for enjoying summer and fall evenings. You'll also appreciate the thoughtful landscape touches, particularly the delightful goldfis

Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. 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 V

Welcome to 116 Green Meadow Road, where a unique shared-meadow setting offers the feel of country living with the convenience of Brattleboro nearby. Built in 1981 and situated on a manageable.25-acre lot, this home overlooks a beautiful 22-acre meadow. The current owner holds 20 shares in the meadow, providing shared ownership, recreational use and a voice in its stewardship. Purchase of the 20 shares by the buyer is a condition of ($6,800). Step inside to a freshly painted interior with all-new flooring and new appliances. The flexible floor plan currently offers two bedrooms, including an exceptionally spacious bedroom with potential to be divided to create additional sleeping or living space. Three 3/4 baths provide convenience throughout the home, with one offering space to accommodate a future bathtub. The walk-out basement already has a 3/4 bath and offers wonderful potential for additional finished living space. Enjoy your morning coffee or unwind at the end of the day on the ba

Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. 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 V

Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck overlooking gorgeous, mature gardens - your own peaceful retreat. The property also includes a conveniently attached garage and a fully finished basement. The finished lower level includes a generous living room with a wet bar, a half bath, and a second fireplace, ready for a propane fireplace unit. With approximately 1,250 square feet of versatile space on each level, this home is a rare find. Showings begin Saturday, August 8th, with an Open House from 10-1 p.m

Welcome to 116 Green Meadow Road, where a unique shared-meadow setting offers the feel of country living with the convenience of Brattleboro nearby. Built in 1981 and situated on a manageable.25-acre lot, this home overlooks a beautiful 22-acre meadow. The current owner holds 20 shares in the meadow, providing shared ownership, recreational use and a voice in its stewardship. Purchase of the 20 shares by the buyer is a condition of sale ($6,800). Step inside to a freshly painted interior with all-new flooring and new appliances. The flexible floor plan currently offers two bedrooms, including an exceptionally spacious bedroom with potential to be divided to create additional sleeping or living space. Three 3/4 baths provide convenience throughout the home, with one offering space to accommodate a future bathtub. The walk-out basement already has a 3/4 bath and offers wonderful potential for additional finished living space. Enjoy your morning coffee or unwind at the end of the day on t

This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level offers a fantastic opportunity with a partially finished, extra-large bonus room that can be customized to suit your needs. Additionally, this level includes a convenient laundry/utility room and a small workshop space, offering practical solutions for storage and hobbies.Outdoor living is equally inviting with a private deck off the back of the house, leading to a fenced backyard. This space is ideal for relaxation and entertaining, complete with a firepit perfect for enjoying summer and fall evenings. You'll also appreciate the thoughtful landscape touches, particularly the delightful goldfis

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 ide

On offer is this tidy, three-unit multi-family home, located in a tranquil residential neighborhood on Moreland Avenue. Originally designed as a multi-family, the three units have identical floor plans with good layout flow. Each 2-bedroom unit has a large eat-in kitchen with pantry, a dining room with French doors opening to the living room and the bonus of a generous, three-season, enclosed front-porch. Each unit features the original handsome wood trim and doors, gleaming hard wood floors, good closet space, and many huge windows filling the place with glorious natural light. There are separate electric meters and boilers for each unit. Additional bonuses are the two-car garage, a small but sweet yard with trees including two pear trees, and a good basement. Great investment opportunity or owner occupied income property. Currently, the first floor is rented with a lease while the second and third floor units are vacant. Great location near high school, hospital, shopping and I-91. P

PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, and year-round comfort. Completed in July 2026 and designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner's electrical needs, including heating and cooling. Warrantied ENERGY STAR(R) appliances, two quiet high-efficiency mini-splits, and a continuous fresh-air ventilation system support healthy indoor air, low operating costs, and efficient climate control. Just minutes from Brattleboro Hospital, shopping, restaurants, downtown, and Interstate 91, the home also offers walking access to miles of peaceful forested hiking trails. Designed for one-level living, the first floor includes an inviting foyer, abundant natural light, an open-concept kitchen, dining, and living area, a primary bedroom and full bath, and a large pantry with a washer and

Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. 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

Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. 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

Easy living. This move-in-ready townhouse comes with snow removal; trash, recycling and compost removal; landscaping; a swimming pool; tennis and pickleball courts; a hiking trail and little libraries included. The seller has refurbished the entire unit by installing beautiful flooring on the first floor and in bathrooms, refinishing cabinets, painting, and cleaning carpeting in order to get the condo ready for you. It is fresh, clean and ready for you! The convenient second floor laundry has a newer energy efficient all-in-one washer/dryer unit. You can sit on your private patio and enjoy nature. Or, escape the heat with a dip in the pool. Morningside Commons is within walking distance of downtown Brattleboro with its many shops and restaurants. Your condo awaits you!

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. Come sit on the back porch and watch the sunrise over the mountain. 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

Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field, grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor space. A large barn accommodates up to two vehicles and offers excellent additional storage potential. The home features low-maintenance vinyl siding, plenty of off-street parking, and strong investment potential for both owner-occupants and investors alike. Each unit has its own private entrance and separate electric service, adding convenience for tenants and ease of management for owners

Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining area features quality KitchenAid appliances and flows seamlessly into the inviting living room. An additional full bathroom, first-floor laundry, and a walkout patio complete the main level. Large windows provide an abundance of natural light throughout the home. The finished lower level offers a spacious family room with a walkout door, a convenient half bath, and an additional large unfinished area ideal for storage, a workshop, or hobby space. Only a handful of units at Morningside Commons offer this highly desirable floor plan. Enjoy all the amenities Morningside Commons has to offer, includin

PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, and year-round comfort. Completed in July 2026 and designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner's electrical needs, including heating and cooling. Warrantied ENERGY STAR(R) appliances, two quiet high-efficiency mini-splits, and a continuous fresh-air ventilation system support healthy indoor air, low operating costs, and efficient climate control. Just minutes from Brattleboro Hospital, shopping, restaurants, downtown, and Interstate 91, the home also offers walking access to miles of peaceful forested hiking trails. Designed for one-level living, the first floor includes an inviting foyer, abundant natural light, an open-concept kitchen, dining, and living area, a primary bedroom and full bath, and a large pantry with a washer and

Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining area features quality KitchenAid appliances and flows seamlessly into the inviting living room. An additional full bathroom, first-floor laundry, and a walkout patio complete the main level. Large windows provide an abundance of natural light throughout the home. The finished lower level offers a spacious family room with a walkout door, a convenient half bath, and an additional large unfinished area ideal for storage, a workshop, or hobby space. Only a handful of units at Morningside Commons offer this highly desirable floor plan. Enjoy all the amenities Morningside Commons has to offer, includin

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 ide

Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. 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

Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting. walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the tenants. No interior photos to respect tenants privacy

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. Come sit on the back porch and watch the sunrise over the mountain. 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

Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field, grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor space. A large barn accommodates up to two vehicles and offers excellent additional storage potential. The home features low-maintenance vinyl siding, plenty of off-street parking, and strong investment potential for both owner-occupants and investors alike. Each unit has its own private entrance and separate electric service, adding convenience for tenants and ease of management for owners

On offer is this tidy, three-unit multi-family home, located in a tranquil residential neighborhood on Moreland Avenue. Originally designed as a multi-family, the three units have identical floor plans with good layout flow. Each 2-bedroom unit has a large eat-in kitchen with pantry, a dining room with French doors opening to the living room and the bonus of a generous, three-season, enclosed front-porch. Each unit features the original handsome wood trim and doors, gleaming hard wood floors, good closet space, and many huge windows filling the place with glorious natural light. There are separate electric meters and boilers for each unit. Additional bonuses are the two-car garage, a small but sweet yard with trees including two pear trees, and a good basement. Great investment opportunity or owner occupied income property. Currently, the first floor is rented with a lease while the second and third floor units are vacant. Great location near high school, hospital, shopping and I-91. P

Just around the corner! From the middle and high school, Oak grove elementary! Pop around the corner for all the high school games, exercise at the track. Interstate is minutes away for easy access to work or play! One apartment is over 1,000 square feet so tons of room for owner occupancy! 2 nice front porches. Worth looking at for either your own home or as an investment. Masks please. Owner is a licensed appraiser and is doing a 1031 exchange. 48 hour notice to show

Easy living. This move-in-ready townhouse comes with snow removal; trash, recycling and compost removal; landscaping; a swimming pool; tennis and pickleball courts; a hiking trail and little libraries included. The seller has refurbished the entire unit by installing beautiful flooring on the first floor and in bathrooms, refinishing cabinets, painting, and cleaning carpeting in order to get the condo ready for you. It is fresh, clean and ready for you! The convenient second floor laundry has a newer energy efficient all-in-one washer/dryer unit. You can sit on your private patio and enjoy nature. Or, escape the heat with a dip in the pool. Morningside Commons is within walking distance of downtown Brattleboro with its many shops and restaurants. Your condo awaits you!

This is a rare opportunity to take over a multi-family redevelopment project in the heart of Brattleboro. Situated on a 0.40-acre site, the property features a vacant three-story building that has already been gutted and fully remediated for lead paint. With municipal zoning approvals already in place to expand from 8 to 13 units and full architectural plans included with the sale, the time-consuming planning and permitting phase is behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing in a neighborhood characterized by strong rental demand and near-zero vacancy. The financial incentives lined up for this project provide substantial non-dilutive equity. The purchase includes access to $317,500 in VHIP funds ($130,000 for the 8 original units and $187,500 for the 5 expansion units), a $125,000 Downtown State Tax Credit that can be utilized directly or sold to a lender at 90% face value, and an estimated $60,000 in weatherization incentives

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank