494 houses for sale in Brattleboro

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

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

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

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

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

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!

Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for investors. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. All three units are currently occupied, providing immediate cash flow. Unit 2 also benefits from a recently installed water heater. Enjoy peace of mind with separate utilities, state lead compliance, vinyl siding, and several replacement windows. Located in a highly walkable area-just steps from downtown, grocery stores, the hospital, and public transit-this property combines low maintenance with strong income potential. The spacious 2-bedroom units feature bright living areas and comfortable bedroom sizes, while the 1-bedroom unit offers a cozy, efficient layout. Each unit is thoughtfully designed to maximize natural light and functional living space. Off-street parking inclu

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

Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

INVESTORS, LANDLORDS and 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 par

New beginnings! Just right to live in one side, fix the other and have the tenant pay for your new lifestyle or have a family duplex and lie with extended family. the north side is vacant, needs renovation, and the south side has a tenant that will transfer with the building. Corner lot, yard, off street parking. Easy to see north unit, but otherwise a 48 hour notice to show

Offered at an affordable price! An end unit townhouse in a convenient location! Just a stone's throw from the Farmers Market and Memorial Park, this condo offers two spacious bedrooms, one and a half baths, a second floor deck and a private patio. New kitchen appliances and plenty of storage with a garage, roomy closets and a laundry room. Life is a joy when someone else handles the mowing, the plowing and the building maintenance. In the summer you can go over the bridge to shop for your fresh produce and then head over to the town park next door for swimming, tennis, pickleball, basketball, skating, even a ski hill, and hiking trails for the adventurous. Come add your own touches!

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 yea

This in town 4 bedroom, 2 bath home offers the perfect blend of comfort, convenience and versatility. Ideally located close to town amenities, this property provides easy access to shopping, dining, services, schools, parks and everyday essentials while offering a spacious place to call home. Inside you'll find beautiful wood flooring, inviting living spaces and a layout that provides flexibility for both living and working. With four bedrooms there is plenty of space for family and overnight guests while the large open finished attic can be turned into a number of uses. Perhaps a studio, exercise room, meditation space, the uses are only limited by your imagination. The property is well suited for those looking to operate a home-based business, offering a prime location and functional space for work-from-home needs. Enjoy the outdoors on your deck or patio and if weather doesn't cooperate, the enclosed porch is perfect for relaxing with morning coffee or an after dinner beverage. A on

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

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 and 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, and 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 and 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,

Major price reduction! This price reduction involves the seller staying on as a tenant for up to a year after closing. Ask for details! Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. Property is being offered as is

Sited at the top of the hill in one of Brattleboro's desirable, close to town, neighborhoods, this mini victorian home is arguably one of the coolest houses in town! Offering a perfect blend of character, comfort, and convenience. Located in a quiet, leafy area close to downtown, where you'll find a vibrant arts scene, great restaurants, shops, food coop, train station, and more. The space features high ceilings, original wood floors, and great light. Currently set up and town assessed as a two family, with a 1-2 bedroom on the first floor, a one bedroom on the second floor with unique arched windows, and a turret room encompassing the third floor. One could make this a single family just by removing the second stove, opening doors, and a change of use, plenty of room for everyone! If rental income would be welcome, the detached garage offers possibility for a tiny home. The established perennial gardens are lovely and provide a tranquil retreat. This house does need exterior maintenan

First time offered, EVER. built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big bedrooms and full bath up! The full basement has room for a workshop, storage or game room. Drive and carport are paved for easy maintenance. Huge shed in the back for storage or lawn care tools. Just what you have been waiting for!

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 close by. Close to 1-91 this convenient property can be your next. home sweet home. THE SELLERS WILL CONTRIBUTE 5,000.00 FOR CLOSING COST WITH ACCEPTABLE OFFER

Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser. Seller is doing a 1031 exchange. 48 hour notice to show, mask up please!

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

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, and 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, and 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 and features a propane stove for cozy evenings. A first-floor bedroom and full bath provide an excellent option for one-level living. Upstairs, three additional bedrooms, a renovated full bath, and a separate office space provide flexibility for f

Newly improved! This is a great set up for extended family. Both units are pretty much alike one on top of the other, 2 bedrooms, good sized living room and nice south side kitchen. Both units have been renovated and are as tidy as can be. Each has it's own utilities. important if you are renting. two easy stair cases front and back if you have the x generation needing a place to crash, or mom and dad who need first floor living. This one is worth seeing with a nice front yard presentation, off street parking and a sweet deck big enough to hang out on. Fresh and waiting for the new owner

Well maintained 4-bedroom, 2 full bath In-town cape on a large open and sunny lot in a sought after West Brattleboro neighborhood. The house features a large bright living room and a well equipped eat-in kitchen with granite counter tops and stainless appliances which walks out to the large private patio. The main level also has 2 bedrooms, a tiled full bath with pedestal sink tub/shower unit, The entire main floor has gleaming hardwood floors. Upstairs are 2 carpeted bedrooms both with large walk-in closets with additional storage space. The bedrooms share a 2nd tiled full bath. The full walk-out basement has a direct entry 1 car garage open to the paved driveway, as well as laundry hookups. Green Efficiency is a major benefit of the home and the roof top solar array, Tesla Battery Wall, and hybrid water heater make the carbon footprint much smaller. One of the greatest attributes of the property is the back yard complete with a wonderful blue stone patio with built-in fire pit and pr

Motivated Seller, Make an offer! 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

This is one of the best units at Morningside with the woods, river and view of Mount Wantastiquet beyond the patio. Every season is spectacular. And the southern orientation is great for solar heat and gardening, says the seller of 78 Morningside Commons. The seller recently replaced the storm door and put new laminate flooring in a bedroom. The kitchen installation has been replaced with oak door cabinets. The living room and kitchen have ceiling fans. A wall AC unit in a bedroom and a second portable AC unit keep the condo cool. It is just a short walk to the Association swimming pool, tennis/pickleball courts and little libraries. The common area gardens and fruit orchard, and the private garden in front of this unit create a beautiful place in which to live. 78 Morningside Commons is close to downtown Brattleboro, the hospital and the high school. 78 Morningside Commons awaits you

Well maintained 4-bedroom, 2 full bath In-town cape on a large open and sunny lot in a sought after West Brattleboro neighborhood. The house features a large bright living room and a well equipped eat-in kitchen with granite counter tops and stainless appliances which walks out to the large private patio. The main level also has 2 bedrooms, a tiled full bath with pedestal sink tub/shower unit, The entire main floor has gleaming hardwood floors. Upstairs are 2 carpeted bedrooms both with large walk-in closets with additional storage space. The bedrooms share a 2nd tiled full bath. The full walk-out basement has a direct entry 1 car garage open to the paved driveway, as well as laundry hookups. Green Efficiency is a major benefit of the home and the roof top solar array, Tesla Battery Wall, and hybrid water heater make the carbon footprint much smaller. One of the greatest attributes of the property is the back yard complete with a wonderful blue stone patio with built-in fire pit and pr

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. The 3 units have been 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