4,769

Brattleboro, VT Homes

Section Image
    • /38

      Est $360,223

      Not Listed For Sale

      106 Western Ave, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 2,061 Sq Ft
      • Built 1924
      106 Western Ave, Brattleboro, VT 05301

      Last Sold Summary

      • 25 Days On Market

  • /5

    $270,000

    Pending
    • 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
  • /39

    $312,450

    Sold Jul 03, 2025

    96 Brattle St, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • Built 1952

    Last Sold Summary

    • 2% Below List Price
    • $178/SF
    • 49 Days On Market

    Current Estimated Value $335,185

    Last Listing Agent Darlene Conca

    96 Brattle St, Brattleboro, VT 05301
    • /38

      Est $396,000

      Not Listed For Sale

      24 Oak Crest Unit 1, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,715 Sq Ft
      • Built 1920
      24 Oak Crest Unit 1, Brattleboro, VT 05301

      Last Sold Summary

      • 76 Days On Market

  • /21

    $179,000

    Pending
    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    40 Brookside Dr Unit 8, Brattleboro, VT 05301

    Don't wait to come view this newly remodeled, low maintenance, affordable and desirable ground floor end unit. Inviting circular flow, the spacious living room has a brand new slider with a view of the rear yard and the Whetstone brook. Plus, you have a brand new kitchen and appliances. The large bedroom with double closet has direct access to the newly renovated bath. This condo is located in a

    Angela Sherman Brattleboro Area Realty

    40 Brookside Dr Unit 8, Brattleboro, VT 05301
  • /58

    $568,000

    Sold Apr 20, 2026

    192 Western Ave, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 2,066 Sq Ft
    • Built 1855

    Last Sold Summary

    • $275/SF
    • 0 Days On Market

    Current Estimated Value $552,673

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    192 Western Ave, Brattleboro, VT 05301
    • /27

      Est $487,960

      Not Listed For Sale

      39 Western Ave, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 2,300 Sq Ft
      • Built 1890
      39 Western Ave, Brattleboro, VT 05301

      Last Sold Summary

      • 61 Days On Market

  • /33

    $235,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    116 Morningside Commons, Brattleboro, VT 05301

    Yes! A coveted first floor single level unit! And not only that but an end unit, sweetly tucked away for privacy! Just follow the tree and flower lined path right to your door!2 bedrooms, one ensuite, with an additional bedroom, bath, large eat in kitchen, living room, and a stackable washer/dryer, all on the first floor! There are only a few condos here that have finished basement space and

    Rebecca Seymour Brattleboro Area Realty

    116 Morningside Commons, Brattleboro, VT 05301
  • /41

    $439,000

    Sold May 13, 2026

    387 Meadowbrook Rd, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1965

    Last Sold Summary

    • 2% Above List Price
    • $280/SF
    • 6 Days On Market

    Current Estimated Value $422,493

    Last Listing Agent Chris Long BHG Masiello Brattleboro

    387 Meadowbrook Rd, Brattleboro, VT 05301
    • /18

      Est $300,544

      Not Listed For Sale

      48 Speno Ct, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 1950
      48 Speno Ct, Brattleboro, VT 05301

      Last Sold Summary

      • 21 Days On Market

  • /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
  • /2

    $145,000

    Sold Jul 18, 2025

    29 Elliot Terrace, Brattleboro, VT 05301

    • 6 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1885

    Last Sold Summary

    • 12% Above List Price
    • $60/SF
    • 45 Days On Market

    Current Estimated Value $149,388

    Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

    29 Elliot Terrace, Brattleboro, VT 05301
    • /10

      Est $298,012

      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

  • /57

    $259,900

    $40K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,248 Sq Ft

    552 - 554 Hinesburg Rd, Brattleboro, VT 05301

    Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

    Steve Schoppmeyer BHG Masiello Brattleboro

    552 - 554 Hinesburg Rd, Brattleboro, VT 05301
  • /40

    $447,700

    Sold Dec 08, 2025

    10 Ethan Hill, Brattleboro, VT 05301

    • 3 Beds
    • 2.5 Baths
    • 2,399 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $187/SF
    • 7 Days On Market

    Current Estimated Value $450,839

    Last Listing Agent John Mcpherson Berkley & Veller Greenwood Country

    10 Ethan Hill, Brattleboro, 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

  • /2

    $95,000

    $5K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 2,108 Sq Ft

    321 Williams St, Brattleboro, VT 05301

    Opportunity to live and invest in upgrades for your new home.

    Susan Bellville Bellville Realty

    321 Williams St, Brattleboro, VT 05301
  • /50

    $659,000

    Sold Sep 29, 2025

    86 Stark Rd, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 2018

    Last Sold Summary

    • $412/SF
    • 4 Days On Market

    Current Estimated Value $677,184

    Last Listing Agent Victoria Woods Brattleboro Area Realty

    86 Stark Rd, Brattleboro, VT 05301
    • /15

      Est $318,096

      Not Listed For Sale

      6 Sycamore St, Brattleboro, VT 05301

      • 4 Beds
      • 1 Bath
      • 1,578 Sq Ft
      • Built 1956
      6 Sycamore St, Brattleboro, VT 05301

      Last Sold Summary

      • 14 Days On Market

  • /54

    $899,000

    $501K PRICE DROP Under Contract
    • 4 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, rolling meadows, 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 location...minutes to town,

    Christine Lewis Brattleboro Area Realty

    131 Stark Rd, Brattleboro, VT 05301
  • /39

    $395,000

    Sold Nov 20, 2025

    105 Chestnut St, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft
    • Built 1895

    Last Sold Summary

    • $145/SF
    • 10 Days On Market

    Current Estimated Value $381,139

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    105 Chestnut St, Brattleboro, VT 05301
    • /37

      Est $577,320

      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

  • /26

    $395,000

    • 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
  • /12

    $79,000

    Sold Dec 11, 2025

    13 Winding Hill Rd, West Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,222 Sq Ft
    • Built 1988

    Last Sold Summary

    • $65/SF
    • 2 Days On Market

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    13 Winding Hill Rd, West Brattleboro, VT 05301
    • /18

      Est $386,769

      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

  • /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
  • /30

    $497,408

    Sold Apr 10, 2026

    204 Meeting House Ln, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 2,656 Sq Ft
    • Built 1970

    Last Sold Summary

    • 14% Below List Price
    • $187/SF
    • 230 Days On Market

    Current Estimated Value $572,443

    Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

    204 Meeting House Ln, Brattleboro, VT 05301
    • /34

      Est $301,140

      Not Listed For Sale

      56 Orchard St, Brattleboro, VT 05301

      • 2 Beds
      • 1.5 Baths
      • 1,038 Sq Ft
      • Built 1949
      56 Orchard St, Brattleboro, VT 05301

      Last Sold Summary

      • 25 Days On Market

  • /34

    $387,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft

    87 Orchard St, Brattleboro, VT 05301

    If you love light, this is your new home! This condo is special, in that it is one of only 2 homes in the complex. Easy to manage, make an agreement for next year's expenses and you are done. This 4 bedroom, 3.5 bath unit is extraordinary for the area, with an attached 2 car garage, back deck, nice yard, and minutes to everything... hospital, Co-op, schools, interstate. Open concept first floor

    Christine Lewis Brattleboro Area Realty

    87 Orchard St, Brattleboro, VT 05301
  • /30

    $330,000

    Sold Aug 07, 2025

    116 Edward Heights, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 2,146 Sq Ft
    • Built 1952

    Last Sold Summary

    • 2% Above List Price
    • $154/SF
    • 56 Days On Market

    Current Estimated Value $349,112

    Last Listing Agent Stephanie Wilde

    116 Edward Heights, Brattleboro, VT 05301
    • /35

      Est $357,986

      Not Listed For Sale

      83 Brattle St, Brattleboro, VT 05301

      • 3 Beds
      • 1.5 Baths
      • 1,799 Sq Ft
      • Built 1935
      83 Brattle St, Brattleboro, VT 05301

      Last Sold Summary

      • 8 Days On Market

  • /17

    $339,000

    • 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
  • /26

    $347,000

    Sold Jul 25, 2025

    157 Pine St, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,435 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Above List Price
    • $242/SF
    • 22 Days On Market

    Current Estimated Value $349,989

    Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty

    157 Pine St, Brattleboro, VT 05301
    • /27

      Est $330,153

      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

  • /15

    $159,500

    • 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
  • /45

    $93,000

    Sold Mar 31, 2026

    26 Lynwood Dr, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1985

    Last Sold Summary

    • 19% Below List Price
    • $92/SF
    • 35 Days On Market

    Last Listing Agent Jon Tourville

    26 Lynwood Dr, Brattleboro, VT 05301
    • /16

      Est $310,724

      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

  • /37

    $639,000

    • 4 Beds
    • 2.5 Baths
    • 2,573 Sq Ft

    11 Strawberry Hill, Brattleboro, VT 05301

    Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed

    Dan Normandeau Berkley & Veller Greenwood Country

    11 Strawberry Hill, Brattleboro, VT 05301
  • /26

    $714,000

    Sold Oct 06, 2025

    29 Canal St, Brattleboro, VT 05301

    • 18 Beds
    • 8 Baths
    • 4,932 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $145/SF
    • 135 Days On Market

    Last Listing Agent Michael Gilman 3GEN Real Estate Inc

    29 Canal St, Brattleboro, VT 05301
    • /8

      Est $283,936

      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

Showing Results 161 - 200, Page 5 of 18

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