Refine Search
Sort by
$499,000
5092212 MLS
Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a proven portfolio foundational asset. The property features a rock-solid financial track record with an annual net operating income (NOI) of $33,756.41, representing an exceptional 6.25% un-leveraged Cap Rate and a highly competitive 5.86 Gross Rent Multiplier (GRM). All 6 units are currently fully occupied by seasoned tenants, with all security deposits transferring securely to the new owner at closing. The asset stands out for its exceptional location and structural layout. Situated in a prime, highly walkable in-town location, it sits just minutes from vibrant downtown Brattleboro shops, dining, transit, and major local employers—positioning this building for historically near-zero vacancy rates. Operationally, the building runs like a well-oiled machine. Streamlined infrastructure is already in place with separate tenant communications and established, reliable local vendor accounts (including Dead River for fuel delivery, Mastaler Cleaning for common area upkeep, and Goodenough for weekly trash service). The structural footprint includes a solid brick facade, convenient off-street parking for multiple tenant vehicles, a secure consolidated front porch mailbox station, and coded keyless entry to the basement utility area. Whether you are seeking to execute a strict tax-deferred exchange or expand your passive income portfolio, this stabilized multifamily building offers predictable yields with clear operational upside to push rents over time. Financial disclosures and itemized expense sheets are ready for review.

16 School St, Brattleboro

$340,000
5091977 MLS
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.

50 Oak Grove Ave, Brattleboro

$335,000
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

$340,000
3 Beds 2 Baths 5091277 MLS
Perfectly situated at the top of the hill on highly desirable Carriage Hill in West Brattleboro, this delightful yellow ranch offers the perfect blend of neighborhood comfort and exceptional curb appeal, accented by a lovely stone pathway and beautiful exterior gardens. Step out back to discover your own private oasis featuring a spacious wooden deck with a gorgeous overhead pergola, custom built-in bench seating, and an attached screened-in porch that looks out over a lush green backyard complete with a handy storage shed. Inside, the home boasts a bright, expansive living room with durable flooring and a mini-split system for efficient year-round comfort. The generous eat-in kitchen features warm wood cabinetry with vibrant turquoise accent shelving, tile flooring, and a large window overlooking the serene backyard. Comfortable bedrooms with unique, colorful accent walls and a dedicated home office or study space under a cheerful blue ceiling provide a highly versatile layout. Complete with two functional bathrooms—including one full bath with a tub/shower combo and a second featuring a retro blue shower stall—this home is ready for its next chapter. Come see all this West Brattleboro gem has to offer at our upcoming open house on Sunday, May 31st from 2:00 PM to 4:00 PM!

184 Carriage Hill Rd, Brattleboro

$399,000
5090247 MLS
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.

19 Canal St, Brattleboro

$319,000
3 Beds 1 Baths 5089873 MLS
Located in one of the area’s most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a formal dining room, complemented by a retro-inspired kitchen full of personality. Just off the living room, the enclosed south-facing porch with newer windows may become your favorite place to relax and unwind. Upstairs offers 3 bedrooms, a bright and cheerful bath, and access to an incredible attic space with exciting potential for a studio, yoga room, office, or expanded living area. Outside, the landscaping is a delightful surprise, featuring striking artistic bluestone details and a peaceful water feature that create a private, zen-like setting rarely found in town. This is a wonderful opportunity to own a character-filled home in a neighborhood known for its quality homes, strong sense of community, and convenient access to restaurants, shopping, and local amenities.

117 Oak Grove Ave, Brattleboro

$1,100,000
4 Beds 4 Baths 5088064 MLS
Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting room where the current owners gather around the piano. Upstairs you'll find a generous primary suite, two bedrooms, and one with a connecting room, an ideal playroom or office. The walk-out basement is partially finished with a workout room, laundry room and abundant storage. The house includes high-speed fiber internet and a whole-house generator. The attached 2-car garage is heated and a second heated detached 2-car garage with a finished loft above is perfect for playing pool and foosball with family & friends. Relaxation comes easily by the inviting in-ground pool overlooking tranquil woodlands, the stone-terraced landscape and native wildlife. This special property is nestled in a friendly community on a country road, adjacent to 367 acres of protected land with trails perfect for hiking, biking and snowshoeing. Just 2 hrs to Boston, 3.5 hrs to NYC with direct Amtrak to NYC. Easy drive to ski mountains.

390 Pleasant Valley Rd, Brattleboro

$595,000
3 Beds 3 Baths 5086904 MLS
Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living is elevated by a light-filled sunroom overlooking a lush backyard complete with raised garden beds and blueberry bushes. Unique features include a former garage transformed into a private guest studio with a Murphy bed, and a new, oversized two-car garage with a clever "drive-through" door for garden access. There is a 40x10' attic space, perfect for tons of storage, or if more living space is needed, it may be finished. Hot water pipes are already located there. Complete with an array of solar panels,{owned}, heat pumps, a whole-house generator, and the potential for single-level living, this Brattleboro gem offers ultimate comfort and self-sufficiency.

171 Green Mdw, Brattleboro

$475,000
5086282 MLS
This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing. The financial incentives currently lined up for this project are significant. The sale includes access to VHIP funds : 8 original units $130,000 and the 5 new units $187,500. Additionally, there is a $125,000 Downtown State Tax Credit that can be used directly or sold to a bank at 90% face value, plus an estimated $60,000 in weatherization incentives. A recent appraisal supports a strong finished value, offering a clear path to equity for an investor. Located in a neighborhood with high rental demand and a low vacancy rate, this property is in an ideal location and could also be renovated one stage at a time so that units could go live and start generating cash flow. A lot of leg work has already been done, and the entire community wants to see this building come alive again with residents. This part of Brattleboro is thriving and this is truly the opportunity to take the worst house in the best neighborhood and turn it into affordable housing that generates a positive return. All project documents, including architect plans and both as-is and as-complete appraisals, are available in a shared Drive file. Please note that proof of funds or a commercial pre-approval is required before scheduling a showing or receiving the full data room.

33 Oak St, Brattleboro

$349,900
5084519 MLS
458 Williams Street, formerly the WKVT headquarters, presents an opportunity for buyers exploring potential residential or mixed-use conversion in a convenient Brattleboro location. The 3,240 SF building is currently configured for office use across two levels, with more than 10 individual rooms, multiple bathrooms, and an existing kitchenette. This layout may lend itself to reconfiguration depending on a buyer’s plans, whether for multi-unit housing, live/work spaces, or continued commercial use. Built in 2003, the structure offers the advantage of more modern construction compared to many conversion properties, with central A/C, public water and sewer, high-speed internet availability, and a standby generator system already in place. On-site parking is established, which is an important consideration for any future use. The property sits on 4.3 acres with frontage along Whetstone Brook, providing a natural setting and additional land area that could be incorporated into future plans. The building itself is set above the brook, offering privacy and separation from the surrounding area. Located in a commercial zoning district just minutes from I-91 and downtown Brattleboro, the property offers flexibility for a range of potential uses. Buyers should perform their own due diligence regarding zoning, permitting, and feasibility of any intended conversion.

458 Williams St, Brattleboro

$769,900
4 Beds 4 Baths 5081610 MLS
New updates: roof replacement with 30 year architectural shingles completed and six new skylights with remote control shades installed. 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 & 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 & beam architecture and stained glass windows. The open kitchen & 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 laundry closet complete the main level. Upstairs offers four bedrooms, including a stunning primary suite with cathedral ceiling, triple closets, fireplace, and Palladian windows. There is a tucked-away guest room that enjoys a private ¾ bath. The finished lower level includes a generous game room with wet bar, half bath, propane stove, & TV area - pool table included! A detached 2-car garage with storage, a garden shed, and timeless craftsmanship throughout make this a truly rare offering. 12/1/25 new System 2000 boiler, recently paved drive and so many beautiful appointments.

5 Hillwinds N, Brattleboro

$429,000
2 Beds 2 Baths 5081478 MLS
BLACK MOUNTAIN ESTATES where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & 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, & open green space, residents enjoy a serene setting just 1 mile from I-91, with ease of access to cultural & recreational opportunities, shopping, dining, & 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, & outdoor patio w/ fire pit. Outdoor recreational amenities incl. pickleball, bocce, shuffleboard, & horseshoes—perfect for staying active & social. Enjoy the ease of HOA-managed services & a lifestyle designed for freedom & fulfillment. Each home is single-story & ADA-compliant, offering ease, accessibility, & long-term comfort. Designed w/ energy efficiency in mind, these residences feature building materials & floor plans that minimize energy usage-providing a healthier, more affordable way to live. PRICED FROM $475,000 - $585,000. HOMES OFFER at least 5 rooms – kitchen, living, dining, primary BR w/ en-suite BA, & bonus room for office/study or guest BR – 2 BA’s, & a 1-car garage. UPGRADED HOMES OFFER: 2-car garage, sunroom, expanded living & guest rms, & larger yard. Some special touches that make BME homes beautiful & comfortable: finished 1 or 2-car garage; marble & porcelain tile; radiant floor heat; porch, private backyard, patio; marble sunken-floor showers & vanities; multi-zone heat & A/C; cherry cabinetry; granite countertops; walk-in closets; high-efficiency appliances & lighting. DO NOT MISS THIS OPPORTUNITY. Even if you are not quite ready to commit, reach out right away and ask to have your name put on the waiting list!

77 Buttonwood Dr, Brattleboro

$139,000
1 Beds 1 Baths 5081405 MLS
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.

219 High St Unit 3, Brattleboro

$135,000
1 Beds 1 Baths 5081287 MLS
Welcome to this beautifully refurbished one-bedroom, one-bath condominium in desirable West Brattleboro. Freshly updated with new flooring, fresh interior paint, vanity, and a new oven, this move-in-ready home offers comfortable, low-maintenance living in a convenient location. Ideally situated just minutes from I-91, this condominium provides easy access for commuters while placing you close to many of the area's most popular recreational and attractions. Enjoy nearby skiing, scenic walks along Whetstone Brook, outdoor activities at Living Memorial Park, the vibrant Brattleboro Farmers' Market, and the beloved Vermont Country Deli. Whether you're looking for a year-round residence, a weekend getaway, or an investment opportunity, this inviting condominium combines modern updates with an exceptional location close to recreation, dining, and everything the Brattleboro area has to offer.

39 Brookside Dr Unit 7, Brattleboro

$239,000
1 Beds 1 Baths 5077121 MLS
Price Improvement! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings, cool factory-style windows, slate siding, and 2,000 square feet of sunny living space. The second level has a bedroom and a full bath, and the third level has two spacious private rooms that have been used in the past as bedrooms or office space with a large common/recreation area in between. Beautiful double patio doors open to a private sun-filled deck for outdoor dining. Zoning allows for a multitude of uses. Whether it's a primary residence, an artist studio, or a second home, this is a must-see for those who appreciate in-town offerings with a vibe and the only condo-ized loft on the market. Centrally located you are a stones throw to our lively downtown, Co-op, Kikitta Ahki park, hospital and I91. Look for the building with the Estey clock and prepare to be enraptured.

116 Birge St Unit 3, Brattleboro

$284,000
5075171 MLS
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 included. With major updates already completed—including vinyl siding, selective window replacements, and recent interior renovations—this property is designed for low-overhead management. The separate utility configuration allows tenants to manage their own heating and electric costs, further simplifying ownership. Don't miss this opportunity to own a high-quality multifamily property in one of Brattleboro's most convenient locations. Schedule your showing today!

5 Reynolds Dr, Brattleboro

$250,000
4934983 MLS
Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation. See documents for permit comments from zoning. There is a shared maintenance agreement spelled out in the deed. Can be purchased with lot 2 for a very special homestead... two is always better for one...buy them both and preserve the wonderfully special setting. Finally, a lovely spot, just waiting for the right owner to become a neighbor.

000 Fort Dummer Hts, Brattleboro

$150,000
4934978 MLS
Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation. See documents for permit comments from zoning. There is a shared maintenance agreement spelled out in the deed. Can be purchased with lot 2 for a very special homestead... two is always better for one...buy them both and preserve the wonderfully special setting. Finally, a lovely spot, just waiting for the right owner to become a neighbor.

00 Fort Dummer Hts, Brattleboro

$125,000
4934976 MLS
Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation. See documents for permit comments from zoning. There is a shared maintenance agreement spelled out in the deed. Can be purchased with lot 2 for a very special homestead... two is always better for one...buy them both and preserve the wonderfully special setting. Finally, a lovely spot, just waiting for the right owner to become a neighbor.

Fort Dummer Hts, Brattleboro

$225,000
5024829 MLS
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".

16 Washington St, Brattleboro

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .