4,783

Brattleboro, VT Homes

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  • /27

    $399,000

    Sold Jun 29, 2026

    28 Wilsons Woods Rd, Brattleboro, VT 05301

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft
    • Built 2002

    Last Sold Summary

    • $162/SF
    • 5 Days On Market

    Current Estimated Value $394,291

    Last Listing Agent Cassandra Ehrlich BHG Masiello Brattleboro

    28 Wilsons Woods Rd, Brattleboro, VT 05301
    • /10

      Est $295,054

      Not Listed For Sale

      45 Speno Ct, Brattleboro, VT 05301

      • 3 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1956
      45 Speno Ct, Brattleboro, VT 05301

      Last Sold Summary

      • 13 Days On Market

  • /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
  • /20

    $190,000

    Sold Jun 17, 2026

    10 Morningside Commons, Guilford, VT 05301

    • 2 Beds
    • 1.5 Baths
    • 955 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $199/SF
    • 26 Days On Market

    Last Listing Agent Kerry Mulverhill

    10 Morningside Commons, Guilford, VT 05301
    • /27

      Not Listed For Sale

      131 Fairview St, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,606 Sq Ft
      • Built 1895
      131 Fairview St, Brattleboro, VT 05301

      Last Sold Summary

      • 90 Days On Market

  • /23

    $499,000

    Under Contract
    • 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
  • /38

    $239,000

    Sold Aug 14, 2025

    81 Morningside Commons, Guilford, VT 05301

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $226/SF
    • 13 Days On Market

    Current Estimated Value $230,638

    Last Listing Agent Victoria Woods Brattleboro Area Realty

    81 Morningside Commons, Guilford, VT 05301
    • /37

      Est $611,245

      Not Listed For Sale

      145 Greenhill Pkwy, Brattleboro, VT 05301

      • 4 Beds
      • 2.5 Baths
      • 3,044 Sq Ft
      • Built 1969
      145 Greenhill Pkwy, Brattleboro, VT 05301

      Last Sold Summary

      • 41 Days On Market

  • /33

    $359,000

    $38K PRICE DROP Pending
    • 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
  • /34

    $442,000

    Sold May 29, 2026

    176 High St, Brattleboro, VT 05301

    • 5 Beds
    • 4 Baths
    • 3,064 Sq Ft
    • Built 1850

    Last Sold Summary

    • 6% Below List Price
    • $144/SF
    • 73 Days On Market

    Current Estimated Value $455,000

    Last Listing Agent Matt Waddington Hoffman Real Estate

    176 High St, Brattleboro, VT 05301
    • /18

      Est $421,695

      Not Listed For Sale

      169 New England Dr, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,827 Sq Ft
      • Built 1954
      169 New England Dr, Brattleboro, VT 05301

      Last Sold Summary

      • 8 Days On Market

  • /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
  • /39

    $399,900

    Sold Jun 02, 2026

    16 Willow St, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,339 Sq Ft
    • Built 1911

    Last Sold Summary

    • $299/SF
    • 8 Days On Market

    Current Estimated Value $393,763

    Last Listing Agent Jamie Watson BHG Masiello Keene

    16 Willow St, Brattleboro, VT 05301
    • /39

      Est $333,010

      Not Listed For Sale

      96 Brattle St, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,758 Sq Ft
      • Built 1952
      96 Brattle St, Brattleboro, VT 05301

      Last Sold Summary

      • 49 Days On Market

  • /15

    $149,900

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 685 Sq Ft

    39 Brookside Dr Unit 7, Brattleboro, VT 05301

    Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat,

    Angela Sherman Brattleboro Area Realty

    39 Brookside Dr Unit 7, Brattleboro, VT 05301
  • /20

    $245,000

    Sold Sep 05, 2025

    14-16 Valley St, Brattleboro, VT 05301

    • 2,168 Sq Ft
    • Built 1915

    Last Sold Summary

    • 2% Below List Price
    • $113/SF
    • 18 Days On Market

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    14-16 Valley St, Brattleboro, VT 05301
    • /27

      Est $362,907

      Not Listed For Sale

      35 South St, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,683 Sq Ft
      • Built 1830
      35 South St, Brattleboro, VT 05301

      Last Sold Summary

      • 28 Days On Market

  • /47

    $545,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,576 Sq Ft

    211 Pleasant Valley Rd, Brattleboro, VT 05301

    Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural

    Chris Long BHG Masiello Brattleboro

    211 Pleasant Valley Rd, Brattleboro, VT 05301
  • /17

    $296,000

    Sold Jul 13, 2026

    110 Washington St, Brattleboro, VT 05301

    • 3,660 Sq Ft
    • Built 1880

    Last Sold Summary

    • 1% Below List Price
    • $81/SF
    • 6 Days On Market

    Current Estimated Value $367,333

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    110 Washington St, Brattleboro, VT 05301
    • /36

      Est $402,008

      Not Listed For Sale

      711 Western Ave, Brattleboro, VT 05301

      • 6 Beds
      • 3 Baths
      • 2,232 Sq Ft
      • Built 1920
      711 Western Ave, Brattleboro, VT 05301

      Last Sold Summary

      • 9 Days On Market

  • /37

    $340,000

    $10K PRICE DROP
    • 1,918 Sq Ft

    50 Oak Grove Ave, Brattleboro, VT 05301

    Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field, grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor space.

    Kerry Mulverhill

    50 Oak Grove Ave, Brattleboro, VT 05301
  • /18

    $45,000

    Sold May 07, 2026

    23 Deepwood Park, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft
    • Built 1996

    Last Sold Summary

    • 25% Below List Price
    • $49/SF
    • 28 Days On Market

    Last Listing Agent Angela Sherman Brattleboro Area Realty

    23 Deepwood Park, Brattleboro, VT 05301
    • /16

      Est $344,041

      Not Listed For Sale

      747 Western Ave, Brattleboro, VT 05301

      • 4 Beds
      • 1.5 Baths
      • 1,564 Sq Ft
      • Built 1791
      747 Western Ave, Brattleboro, VT 05301

      Last Sold Summary

      • 8 Days On Market

  • /13

    $465,500

    $50K PRICE DROP
    • 3,364 Sq Ft

    28 Brook St, Brattleboro, VT 05301

    Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. Offered at an impressive 10% cap rate, the building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    28 Brook St, Brattleboro, VT 05301
  • /2

    $570,000

    Sold Apr 29, 2026

    84 Magnolia Dr, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 2015

    Last Sold Summary

    • 3% Below List Price
    • $300/SF
    • 0 Days On Market

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    84 Magnolia Dr, Brattleboro, VT 05301
    • /8

      Est $285,246

      Not Listed For Sale

      10 Greenleaf St, Brattleboro, VT 05301

      • 2 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1947
      10 Greenleaf St, Brattleboro, VT 05301

      Last Sold Summary

      • 17 Days On Market

  • /17

    $110,000

    • Land
    • 5,227 Sq Ft
    • $916,667 per Acre

    117 * Fuller Dr, Brattleboro, VT 05301

    Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, sewer, and electric are all at the street, and the seller will help to keep the access accessible :) The subdivision has received preliminary approval from the town, with finalization to be completed prior to sale—giving you

    Rebecca Seymour Brattleboro Area Realty

    117 * Fuller Dr, Brattleboro, VT 05301
  • /23

    $356,000

    Sold Jul 28, 2025

    122 Marlboro Ave, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 1,550 Sq Ft
    • Built 1929

    Last Sold Summary

    • 3% Above List Price
    • $230/SF
    • 38 Days On Market

    Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty

    122 Marlboro Ave, Brattleboro, VT 05301
    • /35

      Est $353,796

      Not Listed For Sale

      70 Greenleaf St, Brattleboro, VT 05301

      • 3 Beds
      • 1.5 Baths
      • 1,631 Sq Ft
      • Built 1945
      70 Greenleaf St, Brattleboro, VT 05301

      Last Sold Summary

      • 62 Days On Market

  • /55

    $1,100,000

    $149K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 4,491 Sq Ft

    390 Pleasant Valley Rd, Brattleboro, VT 05301

    Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home

    Kristen Ziter Taylor Brattleboro Area Realty

    390 Pleasant Valley Rd, Brattleboro, VT 05301
  • /25

    $275,000

    Sold Nov 04, 2025

    50 Grove St, Brattleboro, VT 05301

    • 5 Beds
    • 4 Baths
    • 2,376 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $116/SF
    • 8 Days On Market

    Current Estimated Value $271,828

    Last Listing Agent Kate Barry EXP Realty

    50 Grove St, Brattleboro, VT 05301
    • /32

      Est $452,802

      Not Listed For Sale

      142 Greenleaf St, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,732 Sq Ft
      • Built 1978
      142 Greenleaf St, Brattleboro, VT 05301

      Last Sold Summary

      • 6 Days On Market

  • /60

    $795,000

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

    947 Miller Rd, Brattleboro, VT 05301

    Stunning Southern Vermont home with views, gardens and private pond on 10 acres incoveted Dummerston, Windham County. Entering the circular drive, lush perennial gardens welcome you and the magic begins. This meticulously designed 1600-square-foot home features soaring ceilings and superior craftsmanship throughout. Thespacious kitchen includes custom cabinetry, Sub-Zero and Wolf

    Kristen Ziter Taylor Brattleboro Area Realty

    947 Miller Rd, Brattleboro, VT 05301
  • /47

    $528,000

    Sold Jul 10, 2026

    25-27 Gingko Ln, Brattleboro, VT 05301

    • 1,600 Sq Ft
    • Built 1962

    Last Sold Summary

    • 1% Above List Price
    • $330/SF
    • 19 Days On Market

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    25-27 Gingko Ln, Brattleboro, VT 05301
    • /33

      Est $367,090

      Not Listed For Sale

      113 Stockwell Dr, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,754 Sq Ft
      • Built 1984
      113 Stockwell Dr, Brattleboro, VT 05301

      Last Sold Summary

      • 4 Days On Market

  • /19

    $350,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,521 Sq Ft

    82 Oak Grove Ave, Brattleboro, VT 05301

    Neighborhood home! Living in a sweet neighborhood is a lifestyle choice. Walk to schools, playgrounds, and shopping. This vintage home has an added features of roof top solar, 2 car direct entry garage, a fenced-in yard, and lots and lots of gardens. The classic front porch is on everyone's list of must haves. The neighborhood is perfect for long evening strolls or a brisk walk at dawn. Inside

    Christine Lewis Brattleboro Area Realty

    82 Oak Grove Ave, Brattleboro, VT 05301
  • /35

    $475,000

    Sold May 13, 2026

    24 Laurel St, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 2,480 Sq Ft
    • Built 1956

    Last Sold Summary

    • $192/SF
    • 93 Days On Market

    Current Estimated Value $474,801

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    24 Laurel St, Brattleboro, VT 05301
    • /21

      Est $349,356

      Not Listed For Sale

      1161 Western Ave, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,599 Sq Ft
      • Built 1880
      1161 Western Ave, Brattleboro, VT 05301

      Last Sold Summary

      • 15 Days On Market

  • /11

    $422,000

    $43K PRICE DROP
    • 3,756 Sq Ft

    820 Western Ave, Brattleboro, VT 05301

    Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. Offered at an impressive 10% cap rate, the building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    820 Western Ave, Brattleboro, VT 05301
  • /39

    $450,000

    Sold Jun 29, 2026

    44 Cedar St, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,163 Sq Ft
    • Built 1900

    Last Sold Summary

    • 16% Above List Price
    • $387/SF
    • 3 Days On Market

    Current Estimated Value $382,341

    Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

    44 Cedar St, Brattleboro, VT 05301

Showing Results 201 - 240, Page 6 of 18

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