54

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

    1950 Collins Rd, Brattleboro, VT 05301
  • 1309 Putney Rd, Brattleboro, VT 05301
    1309 Putney Rd, Brattleboro, VT 05301
    1309 Putney Rd, Brattleboro, VT 05301
    /32

    $495,000

    • 3,882 Sq Ft

    1309 Putney Rd, Brattleboro, VT 05301

    Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water

    Kerry Mulverhill

    1309 Putney Rd, Brattleboro, VT 05301
  • 33 Oak St, Brattleboro, VT 05301
    33 Oak St, Brattleboro, VT 05301
    33 Oak St, Brattleboro, VT 05301
    /32

    $475,000

    $75K 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
  • 131,133,141 Green St, Brattleboro, VT 05301
    131,133,141 Green St, Brattleboro, VT 05301
    131,133,141 Green St, Brattleboro, VT 05301
    /26

    $1,350,000

    • 7,660 Sq Ft

    131,133,141 Green St, Brattleboro, VT 05301

    What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

    Susan Bellville Bellville Realty

    131,133,141 Green St, 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
    • 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
  • 120 Western Ave, Brattleboro, VT 05301
    120 Western Ave, Brattleboro, VT 05301
    120 Western Ave, Brattleboro, VT 05301
    /42

    $350,000

    • 2,745 Sq Ft

    120 Western Ave, Brattleboro, VT 05301

    Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    120 Western Ave, Brattleboro, VT 05301
  • 10 Birge St, Brattleboro, VT 05301
    10 Birge St, Brattleboro, VT 05301
    /2

    $350,000

    $20K PRICE DROP
    • 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
  • 68 E Bonnyvale Ln, Brattleboro, VT 05301
    68 E Bonnyvale Ln, Brattleboro, VT 05301
    68 E Bonnyvale Ln, Brattleboro, VT 05301
    /30

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    68 E Bonnyvale Ln, Brattleboro, VT 05301

    Looking for your first home, ready to downsize, or seeking single level living? This one is for you. Set in a peaceful rural location near the end of a quiet dead end road, this single level ranch offers comfort, privacy, and great potential on 6.5+ acres just outside the village of West Brattleboro. Enjoy an in ground swimming pool with a pool house and bathroom - perfect for summer relaxation.

    Dan Normandeau Berkley & Veller Greenwood Country

    68 E Bonnyvale Ln, Brattleboro, VT 05301
  • 461 South Rd, Brattleboro, VT 05301
    461 South Rd, Brattleboro, VT 05301
    461 South Rd, Brattleboro, VT 05301
    /24

    $280,000

    $30K PRICE DROP
    • 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, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the

    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
  • 4303 Hinesburg Rd, Brattleboro, VT 05301
    4303 Hinesburg Rd, Brattleboro, VT 05301
    4303 Hinesburg Rd, Brattleboro, VT 05301
    /44

    $475,000

    • 6 Beds
    • 2.5 Baths
    • 3,682 Sq Ft

    4303 Hinesburg Rd, Brattleboro, VT 05301

    Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambiance and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of

    Christine Lewis Brattleboro Area Realty

    4303 Hinesburg Rd, 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

    $769,900

    $25K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,600 Sq Ft

    5 Hillwinds N, Brattleboro, VT 05301

    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.

    Robert Doyle Berkley & Veller Greenwood Country

    5 Hillwinds N, Brattleboro, VT 05301
  • 116 Birge St Unit 2, Guilford, VT 05301
    116 Birge St Unit 2, Guilford, VT 05301
    116 Birge St Unit 2, Guilford, VT 05301
    /17

    $255,000

    $30K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 1,320 Sq Ft

    116 Birge St Unit 2, Guilford, VT 05301

    Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

    Christine Lewis Brattleboro Area Realty

    116 Birge St Unit 2, Guilford, VT 05301
  • 179 Hillwinds N, Brattleboro, VT 05301
    179 Hillwinds N, Brattleboro, VT 05301
    179 Hillwinds N, Brattleboro, VT 05301
    /36

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 3,576 Sq Ft

    179 Hillwinds N, Brattleboro, VT 05301

    This handsome Contemporary Colonial is beautifully set on over an acre of level land in the desirable Hillwinds community, w/access to 200 acres of woodland featuring 3.7 miles of trails. Designed for comfort and efficiency, the property includes 24 solar panels for substantial energy savings, 2 Tesla Powerwalls and large rear decking for outdoor living. A 24' x 24' attached garage with overhead

    Robert Doyle Berkley & Veller Greenwood Country

    179 Hillwinds N, Brattleboro, VT 05301
  • 50 Terrace St, Brattleboro, VT 05301
    50 Terrace St, Brattleboro, VT 05301
    50 Terrace St, Brattleboro, VT 05301
    /14

    $680,000

    • 5,540 Sq Ft

    50 Terrace St, Brattleboro, VT 05301

    SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and

    Dan Normandeau Berkley & Veller Greenwood Country

    50 Terrace St, Brattleboro, VT 05301
  • 72 Green Meadow Rd, West Brattleboro, VT 05301
    72 Green Meadow Rd, West Brattleboro, VT 05301
    72 Green Meadow Rd, West Brattleboro, VT 05301
    /27

    $450,000

    • 3 Beds
    • 2 Baths
    • 2,530 Sq Ft

    72 Green Meadow Rd, West Brattleboro, VT 05301

    Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck

    Thomas Dahlin Berkley & Veller Greenwood Country

    72 Green Meadow Rd, West Brattleboro, VT 05301
  • 136 Morningside Dr, Brattleboro, VT 05301
    136 Morningside Dr, Brattleboro, VT 05301
    136 Morningside Dr, Brattleboro, VT 05301
    /30

    $305,000

    $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,607 Sq Ft

    136 Morningside Dr, Brattleboro, VT 05301

    Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining

    Desiree Stango Berkley & Veller Greenwood Country

    136 Morningside Dr, Brattleboro, VT 05301
  • 455 S Main St, Brattleboro, VT 05301
    455 S Main St, Brattleboro, VT 05301
    455 S Main St, Brattleboro, VT 05301
    /12

    $285,000

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    455 S Main St, Brattleboro, VT 05301

    Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

    Christine Lewis Brattleboro Area Realty

    455 S Main St, 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
  • 110 Western Ave, Brattleboro, VT 05301
    110 Western Ave, Brattleboro, VT 05301
    110 Western Ave, Brattleboro, VT 05301
    /29

    $289,000

    • 4 Beds
    • 2 Baths
    • 1,860 Sq Ft

    110 Western Ave, Brattleboro, VT 05301

    This in town 4 bedroom, 2 bath home offers the perfect blend of comfort, convenience and versatility. Ideally located close to town amenities, this property provides easy access to shopping, dining, services, schools, parks and everyday essentials while offering a spacious place to call home. Inside you’ll find beautiful wood flooring, inviting living spaces and a layout that provides flexibility

    Wilma Skovinski Berkley & Veller Greenwood Country

    110 Western Ave, Brattleboro, VT 05301
  • 16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    /33

    $225,000

    $75K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,209 Sq Ft

    16 Washington St, Brattleboro, VT 05301

    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

    Rebecca Seymour Brattleboro Area Realty

    16 Washington St, Brattleboro, VT 05301
  • 0 Pleasant Valley Rd, Brattleboro, VT 05301
    0 Pleasant Valley Rd, Brattleboro, VT 05301
    0 Pleasant Valley Rd, Brattleboro, VT 05301
    /9

    $198,000

    • Land
    • 3.27 Acres
    • $60,550 per Acre

    0 Pleasant Valley Rd, Brattleboro, VT 05301

    It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant

    Christine Lewis Brattleboro Area Realty

    0 Pleasant Valley Rd, Brattleboro, VT 05301
  • 16 School St, Brattleboro, VT 05301
    16 School St, Brattleboro, VT 05301
    16 School St, Brattleboro, VT 05301
    /23

    $499,000

    $41K PRICE DROP
    • 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

    • 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
  • 116 Birge St Unit 3, Brattleboro, VT 05301
    116 Birge St Unit 3, Brattleboro, VT 05301
    116 Birge St Unit 3, Brattleboro, VT 05301
    /35

    $239,000

    $50K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 2,000 Sq Ft

    116 Birge St Unit 3, Brattleboro, VT 05301

    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,

    Liz LaVorgna Brattleboro Area Realty

    116 Birge St Unit 3, Brattleboro, VT 05301
  • 11 Evergreen Ln, Brattleboro, VT 05301
    11 Evergreen Ln, Brattleboro, VT 05301
    11 Evergreen Ln, Brattleboro, VT 05301
    /25

    $250,000

    • 2 Beds
    • 1.5 Baths
    • 2,496 Sq Ft

    11 Evergreen Ln, Brattleboro, VT 05301

    This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2

    Janet Lucier Barrett & Valley Assoc. Inc

    11 Evergreen Ln, Brattleboro, VT 05301
  • 23 Williams St, Brattleboro, VT 05301
    23 Williams St, Brattleboro, VT 05301
    23 Williams St, Brattleboro, VT 05301
    /4

    $182,000

    • 3 Beds
    • 1.5 Baths
    • 1,114 Sq Ft

    23 Williams St, Brattleboro, VT 05301

    Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting........walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the

    Christine Lewis Brattleboro Area Realty

    23 Williams St, Brattleboro, VT 05301
  • 203 Fairview St, Brattleboro, VT 05301
    203 Fairview St, Brattleboro, VT 05301
    203 Fairview St, Brattleboro, VT 05301
    /35

    $350,000

    New Construction
    • 2 Beds
    • 1 Bath
    • 640 Sq Ft

    203 Fairview St, Brattleboro, VT 05301

    Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, and year-round comfort. Completed in July 2026 and designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner’s electrical needs, including heating and cooling. Warrantied ENERGY STAR®

    Kristen Ziter Taylor Brattleboro Area Realty

    203 Fairview St, Brattleboro, VT 05301
  • 39 Atwood St, Brattleboro, VT 05301
    39 Atwood St, Brattleboro, VT 05301
    39 Atwood St, Brattleboro, VT 05301
    /20

    $320,000

    $34K 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 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

    Kate Barry EXP Realty

    5 Reynolds Dr, Brattleboro, VT 05301
  • 9 Evergreen Ln, Brattleboro, VT 05301
    9 Evergreen Ln, Brattleboro, VT 05301
    9 Evergreen Ln, Brattleboro, VT 05301
    /35

    $245,000

    • 2 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    9 Evergreen Ln, Brattleboro, VT 05301

    Welcome to Brookside Condominiums! This 2-bedroom, 1.5-bath end-unit townhome offers a comfortable, low-maintenance lifestyle in a convenient Brattleboro location. Natural light fills the living areas throughout, while the thoughtfully designed galley kitchen offers ample cabinet and counter space, a breakfast bar, and an easy flow into the dining area. Upstairs, two spacious bedrooms feature

    Ayden Hardy BHG Masiello Keene

    9 Evergreen Ln, Brattleboro, VT 05301
  • 109 Central St, Brattleboro, VT 05301
    109 Central St, Brattleboro, VT 05301
    /2

    $350,000

    $50K PRICE INCREASE
    • 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
  • 556 S Main St, Brattleboro, VT 05301
    556 S Main St, Brattleboro, VT 05301
    556 S Main St, Brattleboro, VT 05301
    /5

    $250,000

    $20K PRICE DROP
    • 2,112 Sq Ft

    556 S Main St, Brattleboro, VT 05301

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

    Christine Lewis Brattleboro Area Realty

    556 S Main St, Brattleboro, VT 05301
  • 90 Wilsons Woods Rd, Brattleboro, VT 05301
    90 Wilsons Woods Rd, Brattleboro, VT 05301
    90 Wilsons Woods Rd, Brattleboro, VT 05301
    /60

    $335,000

    $14K PRICE DROP
    • 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
  • 9 Village Dr, Brattleboro, VT 05301
    9 Village Dr, Brattleboro, VT 05301
    9 Village Dr, Brattleboro, VT 05301
    /24

    $59,000

    • 2 Beds
    • 1 Bath
    • 744 Sq Ft

    9 Village Dr, Brattleboro, VT 05301

    Sweet little mobile home! Large mudroom or multi purpose sun room, eat in kitchen separated from the living room with open shelving. Two bedrooms, the larger used to be two smaller bedrooms which could become that again if you need 3 bedrooms, otherwise a great bedroom with a sitting area, and a second bedroom at the end! Stackable washer/dryer in the bathroom. A large shed is great for storage,

    Rebecca Seymour Brattleboro Area Realty

    9 Village Dr, Brattleboro, VT 05301
  • 77 Buttonwood Dr, Brattleboro, VT 05301
    77 Buttonwood Dr, Brattleboro, VT 05301
    77 Buttonwood Dr, Brattleboro, VT 05301
    /32

    $429,000

    $70K 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 mile

    Dan Normandeau Berkley & Veller Greenwood Country

    77 Buttonwood Dr, Brattleboro, VT 05301

Showing Results 1 - 40, Page 1 of 2

Vermont Windham County

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 $486,192.
How many homes have sold over the last 12 months in Brattleboro, VT?
102 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, 05362 and 05354.
How much do you need to make to afford a house in Brattleboro?
The median home price in Brattleboro is $350,000. If you put a 20% down payment of $70,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $1,800 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $77K 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 Dummerston School. Browse all the schools in Brattleboro, VT to learn more.

Home Prices in Brattleboro, VT

The median home sale price in Brattleboro, VT is $367,500, up 10% year-over-year. Homes in Brattleboro sell in 52 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$367,500
Median Single Family Sale Price
$399,000
Median Townhouse Sale Price
$323,000
Median 2 Bedroom Sale Price
$272,320
Median 1 Bedroom Sale Price
$175,000
Average Price Per Sq Ft
$244
Number of Homes for Sale
28
Last 12 months Home Sales
102
Months of Supply
3.30
Median List Price
$350,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
10%
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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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