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Brattleboro, VT Homes for Sale

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  • 1950 Collins Rd, Brattleboro, VT 05301
    1950 Collins Rd, Brattleboro, VT 05301
    1950 Collins Rd, Brattleboro, VT 05301
    /60

    $3,800,000

    $2M PRICE DROP
    • 4 Beds
    • 8 Baths
    • 16,736 Sq Ft

    1950 Collins Rd, Brattleboro, VT 05301

    Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 317-7158

    1950 Collins Rd, Brattleboro, VT 05301
  • 33 Oak St, Brattleboro, VT 05301
    33 Oak St, Brattleboro, VT 05301
    33 Oak St, Brattleboro, VT 05301
    /24

    $495,000

    $55K PRICE DROP
    • 4,116 Sq Ft

    33 Oak St, Brattleboro, VT 05301

    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

    Kate Barry EXP Realty

    33 Oak St, Brattleboro, VT 05301
  • 1041 Church Hollow Rd, Brattleboro, VT 05301
    1041 Church Hollow Rd, Brattleboro, VT 05301
    1041 Church Hollow Rd, Brattleboro, VT 05301
    /51

    $538,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    1041 Church Hollow Rd, Brattleboro, VT 05301

    Country quiet and tranquility! Sun dappled trees and seventeen woodland acres surround this comfortable seven room, four bedroom, two and half bath house and two car garage. A peaceful setting where views from the deck, porch and every window take in the richness of nature and give a feeling of solitude. Built in 1987, this 2567 SF home has been much loved and well cared for. Designed for easy

    Kathy Dowd Bellville Realty

    1041 Church Hollow Rd, Brattleboro, VT 05301
  • 48 Pleasant St, Brattleboro, VT 05301
    48 Pleasant St, Brattleboro, VT 05301
    48 Pleasant St, Brattleboro, VT 05301
    /6

    $295,000

    • 4 Beds
    • 2 Baths
    • 1,744 Sq Ft

    48 Pleasant St, Brattleboro, VT 05301

    This handsome two unit home is located on desirable Pleasant Street and includes a large yard with plenty of parking. Each unit is 2 bedrooms, bath, living room and kitchen and they feature softwood flooring, bulls eye molding, replacement windows, decking and a covered front porch. Tenant pays for Electric and Heat and each unit has new Buderus boilers. W&D hookup up and Coin washer and dryer in

    Robert Doyle Berkley & Veller Greenwood Country

    48 Pleasant St, Brattleboro, VT 05301
  • 69 Grove St, Brattleboro, VT 05301
    69 Grove St, Brattleboro, VT 05301
    /2

    $245,000

    • 4 Beds
    • 2 Baths
    • 2,148 Sq Ft

    69 Grove St, Brattleboro, VT 05301

    69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent

    Robert Doyle Berkley & Veller Greenwood Country

    69 Grove St, Brattleboro, VT 05301
  • 219 High St Unit 3, Brattleboro, VT 05301
    219 High St Unit 3, Brattleboro, VT 05301
    219 High St Unit 3, Brattleboro, VT 05301
    /23

    $139,000

    $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 592 Sq Ft

    219 High St Unit 3, Brattleboro, VT 05301

    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

    Kristen Ziter Taylor Brattleboro Area Realty

    219 High St Unit 3, Brattleboro, VT 05301
  • 117 Oak Grove Ave, Brattleboro, VT 05301
    117 Oak Grove Ave, Brattleboro, VT 05301
    117 Oak Grove Ave, Brattleboro, VT 05301
    /27

    $339,000

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft

    117 Oak Grove Ave, Brattleboro, VT 05301

    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

    Liz LaVorgna Brattleboro Area Realty

    117 Oak Grove Ave, Brattleboro, VT 05301
  • 19 Canal St, Brattleboro, VT 05301
    19 Canal St, Brattleboro, VT 05301
    19 Canal St, Brattleboro, VT 05301
    /22

    $399,000

    • 9 Beds
    • 4 Baths
    • 3,286 Sq Ft

    19 Canal St, Brattleboro, VT 05301

    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

    Karen Hoppe Berkley & Veller Greenwood Country

    19 Canal St, Brattleboro, VT 05301
  • 573 S Main St, Brattleboro, VT 05301
    573 S Main St, Brattleboro, VT 05301
    /2

    $350,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 3,312 Sq Ft

    573 S Main St, Brattleboro, VT 05301

    Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

    Christine Lewis Brattleboro Area Realty

    573 S Main St, Brattleboro, VT 05301
  • 0 Cooke Rd, Brattleboro, VT 05301
    0 Cooke Rd, Brattleboro, VT 05301
    0 Cooke Rd, Brattleboro, VT 05301
    /8

    $48,000

    $4K PRICE DROP
    • Land
    • 6.1 Acres
    • $7,869 per Acre

    0 Cooke Rd, Brattleboro, VT 05301

    Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

    Victoria Woods Brattleboro Area Realty

    0 Cooke Rd, Brattleboro, VT 05301
  • 10 Birge St, Brattleboro, VT 05301
    10 Birge St, Brattleboro, VT 05301
    /2

    $370,000

    • 5 Beds
    • 4 Baths
    • 3,002 Sq Ft

    10 Birge St, Brattleboro, VT 05301

    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.

    Christine Lewis Brattleboro Area Realty

    10 Birge St, Brattleboro, VT 05301
  • 461 South Rd, Brattleboro, VT 05301
    461 South Rd, Brattleboro, VT 05301
    461 South Rd, Brattleboro, VT 05301
    /24

    $310,000

    • 2 Beds
    • 2 Baths
    • 1,451 Sq Ft

    461 South Rd, Brattleboro, VT 05301

    This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, fresh paint inside and out and a new septic system! There's been quite a bit done to this lovely home that's a stone's throw from the Marlboro town office and post office and a few minutes ride down to Brattleboro. There's good lawn space on the back

    Susan Bellville Bellville Realty

    461 South Rd, Brattleboro, VT 05301
  • 925 Hinesburg Rd, Brattleboro, VT 05301
    925 Hinesburg Rd, Brattleboro, VT 05301
    925 Hinesburg Rd, Brattleboro, VT 05301
    /51

    $899,800

    $49K PRICE DROP
    • 5 Beds
    • 8 Baths
    • 7,430 Sq Ft

    925 Hinesburg Rd, Brattleboro, VT 05301

    Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

    Christine Lewis Brattleboro Area Realty

    925 Hinesburg Rd, Brattleboro, VT 05301
  • 39 Locust St, Brattleboro, VT 05301
    39 Locust St, Brattleboro, VT 05301
    39 Locust St, Brattleboro, VT 05301
    /28

    $369,900

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    39 Locust St, Brattleboro, VT 05301

    Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog,

    Christine Lewis Brattleboro Area Realty

    39 Locust St, Brattleboro, VT 05301
  • 171 Green Meadow, Brattleboro, VT 05301
    171 Green Meadow, Brattleboro, VT 05301
    171 Green Meadow, Brattleboro, VT 05301
    /37

    $595,000

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft

    171 Green Meadow, Brattleboro, VT 05301

    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

    Thomas Dahlin Berkley & Veller Greenwood Country

    171 Green Meadow, Brattleboro, VT 05301
  • 0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
    /3

    $125,000

    $50K PRICE DROP
    • Land
    • 1.75 Acres
    • $71,429 per Acre

    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

    Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould 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

    Christine Lewis Brattleboro Area Realty

    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
  • 5 Hillwinds N, Brattleboro, VT 05301
    5 Hillwinds N, Brattleboro, VT 05301
    5 Hillwinds N, Brattleboro, VT 05301
    /38

    $795,000

    • 4 Beds
    • 4 Baths
    • 3,600 Sq Ft

    5 Hillwinds N, Brattleboro, VT 05301

    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

    Robert Doyle Berkley & Veller Greenwood Country

    5 Hillwinds N, Brattleboro, VT 05301
  • 164 Chestnut St, Brattleboro, VT 05301
    164 Chestnut St, Brattleboro, VT 05301
    164 Chestnut St, Brattleboro, VT 05301
    /18

    $285,000

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,323 Sq Ft

    164 Chestnut St, Brattleboro, VT 05301

    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

    Christine Lewis Brattleboro Area Realty

    164 Chestnut St, Brattleboro, VT 05301
  • 108 Morningside Commons, Brattleboro, VT 05301
    108 Morningside Commons, Brattleboro, VT 05301
    108 Morningside Commons, Brattleboro, VT 05301
    /10

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,139 Sq Ft

    108 Morningside Commons, Brattleboro, VT 05301

    Take a deep breath...enjoy your free time...sit back and wait for the walks to be clear, the lawn mowed and the flowers to bloom...without lifting a finger! Take a dip in the clear waters of the fenced, private pool or have a game of friendly tennis or pickleball! No clean up there either! The best of the best! Top floor, end unit 2nd floor deck for looking down at the world, and windows

    Christine Lewis Brattleboro Area Realty

    108 Morningside Commons, Brattleboro, VT 05301
  • 24 Summit Cir, West Brattleboro, VT 05301
    24 Summit Cir, West Brattleboro, VT 05301
    /2

    $80,000

    $10K PRICE DROP
    • Land
    • 1.97 Acres
    • $40,609 per Acre

    24 Summit Cir, West Brattleboro, VT 05301

    Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

    Claire Renaud Berkley & Veller Greenwood Country

    24 Summit Cir, West Brattleboro, VT 05301
  • 16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    /28

    $325,000

    $25K PRICE INCREASE
    • 5 Beds
    • 3 Baths
    • 2,209 Sq Ft

    16 Washington St, Brattleboro, VT 05301

    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

    Rebecca Seymour Brattleboro Area Realty

    16 Washington St, Brattleboro, VT 05301
  • 16 School St, Brattleboro, VT 05301
    16 School St, Brattleboro, VT 05301
    16 School St, Brattleboro, VT 05301
    /4

    $540,000

    • 6,000 Sq Ft

    16 School St, Brattleboro, VT 05301

    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

    Kate Barry EXP Realty

    16 School St, Brattleboro, VT 05301
  • 00 Fort Dummer Heights, Brattleboro, VT 05301
    00 Fort Dummer Heights, Brattleboro, VT 05301
    /2

    $150,000

    • Land
    • 2.05 Acres
    • $73,171 per Acre

    00 Fort Dummer Heights, Brattleboro, VT 05301

    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.

    Christine Lewis Brattleboro Area Realty

    00 Fort Dummer Heights, Brattleboro, VT 05301
  • 25 Cottage St, Brattleboro, VT 05301
    25 Cottage St, Brattleboro, VT 05301
    25 Cottage St, Brattleboro, VT 05301
    /5

    $380,000

    • 6 Beds
    • 4 Baths
    • 3,264 Sq Ft

    25 Cottage St, Brattleboro, VT 05301

    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

    Christine Lewis Brattleboro Area Realty

    25 Cottage St, Brattleboro, VT 05301
  • 197 Western Ave, Brattleboro, VT 05301
    197 Western Ave, Brattleboro, VT 05301
    197 Western Ave, Brattleboro, VT 05301
    /24

    $399,000

    • 7 Beds
    • 3 Baths
    • 3,700 Sq Ft

    197 Western Ave, Brattleboro, VT 05301

    Excellent opportunity to own a well-maintained and fully occupied 3-unit investment property in the heart of Brattleboro. Located in-town with convenient access to shopping, restaurants, entertainment, and everyday amenities, this property offers strong in-place income with additional upside potential. The building consists of two 2-bedroom units and one spacious 3-bedroom unit and has been

    Karen Hoppe Berkley & Veller Greenwood Country

    197 Western Ave, Brattleboro, VT 05301
  • 39 Atwood St, Brattleboro, VT 05301
    39 Atwood St, Brattleboro, VT 05301
    39 Atwood St, Brattleboro, VT 05301
    /20

    $345,000

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    39 Atwood St, Brattleboro, VT 05301

    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

    Christine Lewis Brattleboro Area Realty

    39 Atwood St, Brattleboro, VT 05301
  • 5 Reynolds Dr, Brattleboro, VT 05301
    5 Reynolds Dr, Brattleboro, VT 05301
    5 Reynolds Dr, Brattleboro, VT 05301
    /51

    $284,000

    $15K PRICE DROP
    • 2,360 Sq Ft

    5 Reynolds Dr, Brattleboro, VT 05301

    Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for both investors and owner-occupants. 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. One of these renovated units is currently occupied, while

    Kate Barry EXP Realty

    5 Reynolds Dr, Brattleboro, VT 05301
  • 184 Carriage Hill Rd, Brattleboro, VT 05301
    184 Carriage Hill Rd, Brattleboro, VT 05301
    184 Carriage Hill Rd, Brattleboro, VT 05301
    /43

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft

    184 Carriage Hill Rd, Brattleboro, VT 05301

    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

    Kate Barry EXP Realty

    184 Carriage Hill Rd, Brattleboro, VT 05301
  • 25-27 Gingko Ln, Brattleboro, VT 05301
    25-27 Gingko Ln, Brattleboro, VT 05301
    25-27 Gingko Ln, Brattleboro, VT 05301
    /46

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    25-27 Gingko Ln, Brattleboro, VT 05301

    Welcome to an amazing, unique opportunity on Gingko Lane in a very special location. Located on a quiet side street in this beloved neighborhood, you are in close proximity to the Retreat trails, which offer extensive hiking, and close to our vibrant downtown, a short walk away. The adorable 1,600-square-foot home has 3 bedrooms and 2 baths. The light-filled, open-concept kitchen/dining area is

    Kristen Ziter Taylor Brattleboro Area Realty

    25-27 Gingko Ln, Brattleboro, VT 05301
  • 109 Central St, Brattleboro, VT 05301
    109 Central St, Brattleboro, VT 05301
    /2

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft

    109 Central St, Brattleboro, VT 05301

    Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to

    Christine Lewis Brattleboro Area Realty

    109 Central St, Brattleboro, VT 05301
  • 40 Brookside Dr Unit 6, Brattleboro, VT 05301
    40 Brookside Dr Unit 6, Brattleboro, VT 05301
    40 Brookside Dr Unit 6, Brattleboro, VT 05301
    /23

    $210,000

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft

    40 Brookside Dr Unit 6, Brattleboro, VT 05301

    Rare to find an in-town condo with a waterfront view like this! Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the tranquil Whetstone Brook. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement with washer/dryer hookup and extra storage. The entire interior has been freshly painted,

    Angela Sherman Brattleboro Area Realty

    40 Brookside Dr Unit 6, Brattleboro, VT 05301
  • 90 Wilsons Woods Rd, Brattleboro, VT 05301
    90 Wilsons Woods Rd, Brattleboro, VT 05301
    90 Wilsons Woods Rd, Brattleboro, VT 05301
    /54

    $349,000

    • 3 Beds
    • 1.5 Baths
    • 1,550 Sq Ft

    90 Wilsons Woods Rd, Brattleboro, VT 05301

    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

    Sally Fegley BHG Masiello Brattleboro

    90 Wilsons Woods Rd, Brattleboro, VT 05301
  • 6 Sycamore St, Brattleboro, VT 05301
    6 Sycamore St, Brattleboro, VT 05301
    6 Sycamore St, Brattleboro, VT 05301
    /36

    $335,000

    • 4 Beds
    • 1 Bath
    • 1,040 Sq Ft

    6 Sycamore St, Brattleboro, VT 05301

    Located in one of Brattleboro’s desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two

    Wendie Wright Coldwell Banker LIFESTYLES - Hanover

    6 Sycamore St, Brattleboro, VT 05301
  • 77 Buttonwood Dr, Brattleboro, VT 05301
    77 Buttonwood Dr, Brattleboro, VT 05301
    77 Buttonwood Dr, Brattleboro, VT 05301
    /32

    $469,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,550 Sq Ft

    77 Buttonwood Dr, Brattleboro, VT 05301

    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

    Dan Normandeau Berkley & Veller Greenwood Country

    77 Buttonwood Dr, Brattleboro, VT 05301
  • 93 Clark St, Brattleboro, VT 05301
    93 Clark St, Brattleboro, VT 05301
    /2

    $90,000

    • 3 Beds
    • 1 Bath
    • 1,030 Sq Ft

    93 Clark St, Brattleboro, VT 05301

    An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only

    Christine Lewis Brattleboro Area Realty

    93 Clark St, Brattleboro, VT 05301
  • 458 Williams St, Brattleboro, VT 05301
    458 Williams St, Brattleboro, VT 05301
    458 Williams St, Brattleboro, VT 05301
    /26

    $349,900

    $45K PRICE DROP
    • 3,240 Sq Ft

    458 Williams St, Brattleboro, VT 05301

    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

    Neil Goldberg Brattleboro Area Realty

    458 Williams St, Brattleboro, VT 05301
  • 000 Fort Dummer Heights, Brattleboro, VT 05301
    000 Fort Dummer Heights, Brattleboro, VT 05301
    000 Fort Dummer Heights, Brattleboro, VT 05301
    /9

    $250,000

    • Land
    • 3.79 Acres
    • $65,963 per Acre

    000 Fort Dummer Heights, Brattleboro, VT 05301

    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.

    Christine Lewis Brattleboro Area Realty

    000 Fort Dummer Heights, Brattleboro, VT 05301
  • 94 Brets Rd, Brattleboro, VT 05301
    94 Brets Rd, Brattleboro, VT 05301
    94 Brets Rd, Brattleboro, VT 05301
    /23

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 2,594 Sq Ft

    94 Brets Rd, Brattleboro, VT 05301

    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

    Oona Madden Berkley & Veller Greenwood Country

    94 Brets Rd, Brattleboro, VT 05301
  • 87 Orchard St, Brattleboro, VT 05301
    87 Orchard St, Brattleboro, VT 05301
    87 Orchard St, Brattleboro, VT 05301
    /33

    $359,000

    $38K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft

    87 Orchard St, Brattleboro, VT 05301

    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.

    Christine Lewis Brattleboro Area Realty

    87 Orchard St, Brattleboro, VT 05301
  • 550 S Main St, Brattleboro, VT 05301
    550 S Main St, Brattleboro, VT 05301
    550 S Main St, Brattleboro, VT 05301
    /17

    $329,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    550 S Main St, Brattleboro, VT 05301

    Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways,

    Christine Lewis Brattleboro Area Realty

    550 S Main St, Brattleboro, VT 05301

Showing Results 1 - 40, Page 1 of 2

Vermont Windham County Brattleboro

Real Estate & Homes for Sale in Brattleboro, VT

Why Live in Brattleboro

Brattleboro, Vermont, is a small town of about 12,000 residents located on the southeastern edge of the state, along the Connecticut River. Known for its artsy and outdoorsy lifestyle, Brattleboro has transformed from an industrial hub to a haven for artists, musicians, and authors. The town features a variety of things to do, including hiking trails, ski slopes, and boat ramps. Downtown Brattleboro is vibrant, with Main Street lined with trendy boutiques, eateries, and art galleries. Popular dining spots include Echo with its river views, Superfresh Organic Cafe, Mocha Joe’s, and Peter Havens. For nightlife, Kipling’s Tavern offers an intimate Irish pub experience. The town also hosts cultural events like the Brattleboro Literary Festival and monthly gallery walks. Outdoor enthusiasts can enjoy Living Memorial Park, which offers athletic fields, a disc golf course, and winter sports facilities. Retreat Farm provides 500 acres of preserved land with interactive nature experiences and historic landmarks. Housing styles in Brattleboro range from historic Victorians and eclectic bungalows to spacious farmhouses known as New Englanders. The town is served by the Windham Southeast Supervisory Union, with schools receiving mid-range ratings. Commuters benefit from Interstate 91, U.S. Route 5, and State Route 9, with Bradley International Airport about 80 miles away and Boston Logan International Airport approximately 110 miles southeast. Public transportation includes Amtrak Vermonter service and the free MOOver bus shuttle.

Learn more about living in Brattleboro

Frequently Asked Questions

What is the average home price in Brattleboro, VT?
Homes for sale in Brattleboro, VT have an average home price of $470,800.
How many homes have sold over the last 12 months in Brattleboro, VT?
100 homes have sold in Brattleboro, VT over the last 12 months.
What is the average household income in Brattleboro, VT?
The average household income in Brattleboro, VT is $71K.
What are the most popular zip codes in Brattleboro, VT?
The most popular zip codes in Brattleboro, VT include 05301, 03466, 03451, 05351 and 05354.
How much do you need to make to afford a house in Brattleboro?
The median home price in Brattleboro is $349,000. If you put a 20% down payment of $69,800 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $1,730 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $74K a year to afford the median home price in Brattleboro. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Brattleboro is $71K.
How are the schools in Brattleboro, VT?
Brattleboro, VT has highly rated public and private schools. Some of the best schools in Brattleboro based on Niche Grades are St. Michael Catholic School, Guilford Central School and Brattleboro Senior Uhsd #6. Browse all the schools in Brattleboro, VT to learn more.

Home Prices in Brattleboro, VT

The median home sale price in Brattleboro, VT is $350,000, up 6% year-over-year. Homes in Brattleboro sell in 47 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$350,000
Median Single Family Sale Price
$370,000
Median Townhouse Sale Price
$320,000
Median 2 Bedroom Sale Price
$312,500
Median 1 Bedroom Sale Price
$149,950
Average Price Per Sq Ft
$243
Number of Homes for Sale
28
Last 12 months Home Sales
100
Months of Supply
3.40
Median List Price
$349,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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