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Brattleboro, VT Homes for Sale

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  • 137 Pleasant Valley Rd, Brattleboro, VT 05301
    137 Pleasant Valley Rd, Brattleboro, VT 05301
    137 Pleasant Valley Rd, Brattleboro, VT 05301
    /23

    $500,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    137 Pleasant Valley Rd, Brattleboro, VT 05301

    This is IT! If you are looking for an incredible small home...not tiny...but compact and just the right size, this is it. Timber framing at it's best gives you an open concept, live in every inch, light filled, high quality charming home. Nestled in a wildflower meadow, with plenty of room for a homestead garden, enough open sky for stargazers, big and flat enough for your own cross country ski

    Christine Lewis Brattleboro Area Realty

    137 Pleasant Valley Rd, Brattleboro, VT 05301
  • 141 Piney Brook Way, Brattleboro, VT 05301
    141 Piney Brook Way, Brattleboro, VT 05301
    141 Piney Brook Way, Brattleboro, VT 05301
    /44

    $599,000

    • 4 Beds
    • 4 Baths
    • 4,060 Sq Ft

    141 Piney Brook Way, Brattleboro, VT 05301

    Set on 12 acres of wooded privacy in desirable Marlboro, this spacious and versatile property offers comfort, flexibility, and stunning natural surroundings. The main home features 3 bedrooms, a large family room and first-floor laundry, offering plenty of room for a growing household, guests, or multi-generational living. Cozy up by the wood stove on chilly evenings, and enjoy the peace of mind

    Desiree Stango Berkley & Veller Greenwood Country

    141 Piney Brook Way, Brattleboro, VT 05301
  • 230 Western Ave, Brattleboro, VT 05301
    230 Western Ave, Brattleboro, VT 05301
    230 Western Ave, Brattleboro, VT 05301
    /36

    $479,000

    • 4 Beds
    • 2.5 Baths
    • 1,887 Sq Ft

    230 Western Ave, Brattleboro, VT 05301

    This beautifully renovated in-town home blends character, comfort, and convenience. From the welcoming front porch to the shaded backyard and new deck, every space has been thoughtfully updated. The sunny kitchen offers granite countertops, stainless steel appliances, and a well-planned pantry, while the living room is anchored by a handsome Italian pellet stove; efficient, warm, and the perfect

    John Hatton Berkley & Veller Greenwood Country

    230 Western Ave, Brattleboro, VT 05301
  • 162 Buttonwood Dr, Brattleboro, VT 05301
    162 Buttonwood Dr, Brattleboro, VT 05301
    162 Buttonwood Dr, Brattleboro, VT 05301
    /33

    $560,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    162 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

    162 Buttonwood Dr, Brattleboro, VT 05301
  • 24 Dogwood Dr, Brattleboro, VT 05301
    24 Dogwood Dr, Brattleboro, VT 05301
    24 Dogwood Dr, Brattleboro, VT 05301
    /35

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    24 Dogwood 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

    24 Dogwood Dr, Brattleboro, VT 05301
  • 161 Buttonwood Dr, Brattleboro, VT 05301
    161 Buttonwood Dr, Brattleboro, VT 05301
    161 Buttonwood Dr, Brattleboro, VT 05301
    /33

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    161 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

    161 Buttonwood Dr, Brattleboro, VT 05301
  • 58 Oak St, Brattleboro, VT 05301
    58 Oak St, Brattleboro, VT 05301
    58 Oak St, Brattleboro, VT 05301
    /39

    $625,000

    • 5 Beds
    • 4 Baths
    • 3,748 Sq Ft

    58 Oak St, Brattleboro, VT 05301

    Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

    Rebecca Seymour Brattleboro Area Realty

    58 Oak St, Brattleboro, VT 05301
  • 5 Hillwinds N, Brattleboro, VT 05301
    5 Hillwinds N, Brattleboro, VT 05301
    5 Hillwinds N, Brattleboro, VT 05301
    /37

    $849,000

    • 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 11 acres of landscaped grounds with lawns, stone walls, gardens, and woodland 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

    Robert Doyle Berkley & Veller Greenwood Country

    5 Hillwinds N, Brattleboro, VT 05301
  • 192 Western Ave, Brattleboro, VT 05301
    192 Western Ave, Brattleboro, VT 05301
    192 Western Ave, Brattleboro, VT 05301
    /58

    $568,000

    • 3 Beds
    • 2 Baths
    • 2,066 Sq Ft

    192 Western Ave, Brattleboro, VT 05301

    Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

    Claire Renaud Berkley & Veller Greenwood Country

    192 Western Ave, Brattleboro, VT 05301
  • 204 Meeting House Ln, Brattleboro, VT 05301
    204 Meeting House Ln, Brattleboro, VT 05301
    204 Meeting House Ln, Brattleboro, VT 05301
    /30

    $629,000

    • 4 Beds
    • 2 Baths
    • 2,656 Sq Ft

    204 Meeting House Ln, Brattleboro, VT 05301

    Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

    Desiree Stango Berkley & Veller Greenwood Country

    204 Meeting House Ln, Brattleboro, VT 05301
  • 925 Hinesburg Rd, Brattleboro, VT 05301
    925 Hinesburg Rd, Brattleboro, VT 05301
    925 Hinesburg Rd, Brattleboro, VT 05301
    /51

    $899,800

    • 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
  • 301 Maple St, Brattleboro, VT 05301
    301 Maple St, Brattleboro, VT 05301
    301 Maple St, Brattleboro, VT 05301
    /58

    $515,000

    • 4 Beds
    • 2 Baths
    • 3,090 Sq Ft

    301 Maple St, Brattleboro, VT 05301

    Fall is here! The leaves are turning, the mums are in cheerful blooming mode and soon it will be time to cozy in with the woodstove! But...not quite yet, there are still plenty of days for the sun filled deck, blooms galore and strolls around your own private gardens. This sweet home has the great construction of the 1800's...loved and cared for by generations of Vermonters who have added,

    Christine Lewis Brattleboro Area Realty

    301 Maple St, Brattleboro, VT 05301
  • 39 Brookside Dr Unit 3, Brattleboro, VT 05301
    39 Brookside Dr Unit 3, Brattleboro, VT 05301
    39 Brookside Dr Unit 3, Brattleboro, VT 05301
    /19

    $190,000

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft

    39 Brookside Dr Unit 3, Brattleboro, VT 05301

    Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the woods and a small yard space. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement for extra storage with washer/dryer hookup. The entire interior has been freshly painted, new kitchen cabinets, countertop, new flooring, new bathroom

    Angela Sherman Brattleboro Area Realty

    39 Brookside Dr Unit 3, Brattleboro, VT 05301
  • 97 Glen St, Brattleboro, VT 05301
    97 Glen St, Brattleboro, VT 05301
    97 Glen St, Brattleboro, VT 05301
    /24

    $29,900

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft

    97 Glen St, Brattleboro, VT 05301

    Finally!! Affordable!! This just right sized home is tucked into the 55 and older park for peace and quiet. Along the brook, the damaged homes have been removed and replaced with open green space with a gentle park like feel. There is an awning over the stairs, an added pitched roof, spacious front end kitchen/dining with several windows and some built-ins. Located in one of the 3 parks, making

    Angela Sherman Brattleboro Area Realty

    97 Glen St, Brattleboro, VT 05301
  • 31 Crescent Dr, Brattleboro, VT 05301
    31 Crescent Dr, Brattleboro, VT 05301
    31 Crescent Dr, Brattleboro, VT 05301
    /18

    $50,000

    • 2 Beds
    • 1 Bath
    • 828 Sq Ft

    31 Crescent Dr, Brattleboro, VT 05301

    SWEET!! This lovely little home is located on one of the best park lots available featuring a huge, level yard perfect for gardening, games and fenced for animals. This is an older home but has been well loved and nicely maintained with new windows, new electrical panel, fresh paint everywhere and is move right in. There are 2 huge sheds for tools and storage. Sit on the private screened porch

    Christine Lewis Brattleboro Area Realty

    31 Crescent Dr, Brattleboro, VT 05301
  • 290 Guilford St, Brattleboro, VT 05301
    290 Guilford St, Brattleboro, VT 05301
    290 Guilford St, Brattleboro, VT 05301
    /59

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    290 Guilford St, Brattleboro, VT 05301

    This meticulously maintained 3-bedroom, 2-bath ranch surprises with its spacious layout and thoughtfully designed interior. The kitchen is a dream for those who love to cook, featuring quartz countertops, slate flooring, solid hardwood soft-close cabinetry, a dedicated baking station, and access to the nearly 700 sq. ft. back deck—perfect for entertaining. The open main living area features

    Kate Barry EXP Realty

    290 Guilford St, Brattleboro, VT 05301
  • 131 Stark Rd, Brattleboro, VT 05301
    131 Stark Rd, Brattleboro, VT 05301
    131 Stark Rd, Brattleboro, VT 05301
    /54

    $1,400,000

    • 5 Beds
    • 4.5 Baths
    • 4,908 Sq Ft

    131 Stark Rd, Brattleboro, VT 05301

    Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, 35 acres of open meadow, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect

    Christine Lewis Brattleboro Area Realty

    131 Stark Rd, Brattleboro, VT 05301
  • 85 Stockwell Dr, Brattleboro, VT 05301
    85 Stockwell Dr, Brattleboro, VT 05301
    85 Stockwell Dr, Brattleboro, VT 05301
    /24

    $400,000

    • 5 Beds
    • 3 Baths
    • 2,254 Sq Ft

    85 Stockwell Dr, Brattleboro, VT 05301

    Motivated Seller! Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride

    Christine Lewis Brattleboro Area Realty

    85 Stockwell Dr, Brattleboro, VT 05301
  • 91 Sunny Acres Rd, Brattleboro, VT 05301
    91 Sunny Acres Rd, Brattleboro, VT 05301
    91 Sunny Acres Rd, Brattleboro, VT 05301
    /32

    $339,000

    • 3 Beds
    • 2.5 Baths
    • 1,890 Sq Ft

    91 Sunny Acres Rd, Brattleboro, VT 05301

    Lovely and updated, very low maintenance, clean, 3-bedroom, 3-bath home on .22 acre. HARDWOOD floors throughout! The kitchen is fabulous with granite countertops and island with soft-close drawers and GE appliances. The 3 bathrooms are completely renovated and attractive as well. Tons of south-facing sunlight and passive solar! Most windows have been replaced, including the french door to deck. A

    Stephanie Peduzzi-Baker Brattleboro Area Realty

    91 Sunny Acres Rd, Brattleboro, VT 05301
  • 1950 Collins Rd, Brattleboro, VT 05301
    1950 Collins Rd, Brattleboro, VT 05301
    1950 Collins Rd, Brattleboro, VT 05301
    /60

    $5,900,000

    • 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

    Margretta Fischer Wohler Realty Group

    1950 Collins Rd, Brattleboro, VT 05301
  • 1089 Marlboro Rd, Brattleboro, VT 05301
    1089 Marlboro Rd, Brattleboro, VT 05301
    1089 Marlboro Rd, Brattleboro, VT 05301
    /30

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,703 Sq Ft

    1089 Marlboro Rd, Brattleboro, VT 05301

    The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

    Christine Lewis Brattleboro Area Realty

    1089 Marlboro Rd, Brattleboro, VT 05301
  • 87 Orchard St, Brattleboro, VT 05301
    87 Orchard St, Brattleboro, VT 05301
    87 Orchard St, Brattleboro, VT 05301
    /36

    $414,500

    • 4 Beds
    • 3.5 Baths
    • 2,794 Sq Ft

    87 Orchard St, Brattleboro, VT 05301

    SELLER IS RELOCATING. It is time to pass the keys to the next owner and move closer to family. Welcome to one of the most highly sought after neighborhoods in Brattleboro – Orchard St.This spacious modern contemporary home is conveniently located just minutes from I-91 and downtown Brattleboro. There is plenty of space with four large bedrooms, 3 full baths, and wonderful open concept living

    Jim Bellville Bellville Realty

    87 Orchard St, Brattleboro, VT 05301
  • 76 Spruce St, Brattleboro, VT 05301
    76 Spruce St, Brattleboro, VT 05301
    76 Spruce St, Brattleboro, VT 05301
    /44

    $425,000

    • 4 Beds
    • 3 Baths
    • 3,314 Sq Ft

    76 Spruce St, Brattleboro, VT 05301

    Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

    Christine Lewis Brattleboro Area Realty

    76 Spruce St, Brattleboro, VT 05301
  • 78-80 Central St, Brattleboro, VT 05301
    78-80 Central St, Brattleboro, VT 05301
    78-80 Central St, Brattleboro, VT 05301
    /29

    $310,000

    • 4 Beds
    • 2 Baths
    • 2,408 Sq Ft

    78-80 Central St, Brattleboro, VT 05301

    MOTIVATED SELLER: Charming Two-Unit Multi-Family on Quiet In-Town Street – Ideal for Investors or Owner-Occupants! Tucked away on a peaceful side street yet just minutes from shopping, dining, and public transportation, this two-family property offers the perfect blend of convenience and comfort. The current owners have updated all the electrical in both units. Each unit features spacious,

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    78-80 Central St, Brattleboro, VT 05301
  • 22 Chestnut St Unit 1, Brattleboro, VT 05301
    22 Chestnut St Unit 1, Brattleboro, VT 05301
    22 Chestnut St Unit 1, Brattleboro, VT 05301
    /25

    $189,000

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    22 Chestnut St Unit 1, Brattleboro, VT 05301

    Welcome to 22 Chestnut Street, Unit #1 — a charming and fully furnished first-floor condo nestled in the lovely Chestnut Street neighborhood. This spacious 2-bedroom, 1-bath unit features a thoughtfully updated bathroom with a clawfoot tub and separate shower, a cozy mudroom entryway, and a sunny side porch that conveys with the unit — perfect for morning coffee or evening relaxation. The kitchen

    Erica Reynolds Southern Vermont Realty Group

    22 Chestnut St Unit 1, Brattleboro, VT 05301
  • 1177 Western Ave, Brattleboro, VT 05301
    1177 Western Ave, Brattleboro, VT 05301
    1177 Western Ave, Brattleboro, VT 05301
    /20

    $279,900

    • 4 Beds
    • 2 Baths
    • 1,733 Sq Ft

    1177 Western Ave, Brattleboro, VT 05301

    So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large kitchen with lots of counter space and the laundry tucked in for easy access while you cook and bake. The deck overlooks the lower yard where the solar panels live and the perfect spot for the above ground swimming pool (needs a liner). Huge lot, lots of off street parking and on the MOOVER line for non

    Christine Lewis Brattleboro Area Realty

    1177 Western Ave, 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

    Christine Lewis Brattleboro Area Realty

    109 Central St, 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,

    Christine Lewis Brattleboro Area Realty

    93 Clark St, Brattleboro, VT 05301
  • 321 Williams St, Brattleboro, VT 05301
    321 Williams St, Brattleboro, VT 05301
    /2

    $89,000

    • 4 Beds
    • 3 Baths
    • 2,108 Sq Ft

    321 Williams St, Brattleboro, VT 05301

    Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

    Susan Bellville Bellville Realty

    321 Williams St, Brattleboro, VT 05301
  • 266 Ursa Ridge Rd, Dummerston, VT 05301
    266 Ursa Ridge Rd, Dummerston, VT 05301
    266 Ursa Ridge Rd, Dummerston, VT 05301
    /60

    $895,000

    • 3 Beds
    • 3 Baths
    • 2,258 Sq Ft

    266 Ursa Ridge Rd, Dummerston, VT 05301

    This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

    Randi Ziter Brattleboro Area Realty

    266 Ursa Ridge Rd, Dummerston, VT 05301
  • 164 Chestnut St, Brattleboro, VT 05301
    164 Chestnut St, Brattleboro, VT 05301
    164 Chestnut St, Brattleboro, VT 05301
    /18

    $309,900

    • 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
  • 69-71 Elliot St, Brattleboro, VT 05301
    69-71 Elliot St, Brattleboro, VT 05301
    69-71 Elliot St, Brattleboro, VT 05301
    /23

    $1,150,000

    • 6,442 Sq Ft

    69-71 Elliot St, Brattleboro, VT 05301

    Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

    Erica Reynolds Southern Vermont Realty Group

    69-71 Elliot St, Brattleboro, VT 05301
  • 176 High St, Brattleboro, VT 05301
    176 High St, Brattleboro, VT 05301
    176 High St, Brattleboro, VT 05301
    /16

    $479,000

    • 5 Beds
    • 4 Baths
    • 3,064 Sq Ft

    176 High St, Brattleboro, VT 05301

    Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

    Susan Bellville Bellville Realty

    176 High St, Brattleboro, VT 05301
  • 1845 Hatch School Rd, Brattleboro, VT 05301
    1845 Hatch School Rd, Brattleboro, VT 05301
    1845 Hatch School Rd, Brattleboro, VT 05301
    /60

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    1845 Hatch School Rd, Brattleboro, VT 05301

    Welcome to our Contemporary Farmhouse with 100 private acres yet only 5 miles to Wilmington Center and 14 miles to Mount Snow Ski Resort. Harriman Reservoir is close for summer boating, water sports and picnics. Nestled in the heart of nature, the property offers numerous possibilities, including a well-appointed home, a working farm, various business opportunities and/or investment potential. As

    Richard Caplan Deerfield Valley Real Estate

    1845 Hatch School Rd, Brattleboro, VT 05301
  • 16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    /22

    $275,000

    • 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 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    /22

    $275,000

    • 4 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
  • 24 Summit Cir, West Brattleboro, VT 05301
    24 Summit Cir, West Brattleboro, VT 05301
    /2

    $80,000

    • 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
  • 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
  • 556 S Main St, Brattleboro, VT 05301
    556 S Main St, Brattleboro, VT 05301
    556 S Main St, Brattleboro, VT 05301
    /5

    $270,000

    • 6 Beds
    • 2 Baths
    • 2,112 Sq Ft

    556 S Main St, Brattleboro, VT 05301

    What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit ofpressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

    Christine Lewis Brattleboro Area Realty

    556 S Main St, Brattleboro, VT 05301
  • Lot #3 Peachtree Ln, Brattleboro, VT 05301
    Lot #3 Peachtree Ln, Brattleboro, VT 05301
    /2

    $84,900

    • Land
    • 4.27 Acres
    • $19,883 per Acre

    Lot #3 Peachtree Ln, Brattleboro, VT 05301

    Just off desirable Orchard Street is this beautiful 4.27+/- acre building lot. Located at roads end, the site is perfect for a beautiful new home with southerly exposure, stone walls, a gentle rise and privacy. Just minutes from downtown, yet country in feel.

    Desiree Stango Berkley & Veller Greenwood Country

    Lot #3 Peachtree Ln, 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 $495,533.
How many homes have sold over the last 12 months in Brattleboro, VT?
89 homes have sold in Brattleboro, VT over the last 12 months.
What are the most popular zip codes in Brattleboro, VT?
The most popular zip codes in Brattleboro, VT include 05301, 03451, 03466, 05354 and 05346.
How much do you need to make to afford a house in Brattleboro?
The median home price in Brattleboro is $345,000. If you put a 20% down payment of $69,000 and had a 30-year fixed mortgage with an interest rate of 6.17%, your estimated principal and interest payment would be $1,690 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $72K a year to afford the median home price in Brattleboro.
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 Guilford Central School, St. Michael Catholic School and Brattleboro Senior Uhsd #6. Browse all the schools in Brattleboro, VT to learn more.

Home Trends in Brattleboro, VT

On average, homes in Brattleboro, VT sell after 58 days on the market compared to the national average of 53 days. The median sale price for homes in Brattleboro, VT over the last 12 months is $341,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$341,000
Median Single Family Sale Price
$375,000
Median Townhouse Sale Price
$255,000
Median 2 Bedroom Sale Price
$212,150
Median 1 Bedroom Sale Price
$150,000
Average Price Per Sq Ft
$240
Number of Homes for Sale
29
Last 12 months Home Sales
89
Months of Supply
3.90
Median List Price
$345,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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Copyright 2025 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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