4,710

Brattleboro, VT Homes

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    • 89 Oak Grove Ave, Brattleboro, VT 05301
      89 Oak Grove Ave, Brattleboro, VT 05301
      89 Oak Grove Ave, Brattleboro, VT 05301
      /24

      Est $566,840 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,592 Sq Ft

      89 Oak Grove Ave, Brattleboro, VT 05301

      89 Oak Grove 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

    $579,000

    • 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
  • 109 Washington St, Brattleboro, VT 05301
    109 Washington St, Brattleboro, VT 05301
    109 Washington St, Brattleboro, VT 05301
    /26

    $432,000 Sold Dec 30, 2024

    109 Washington St, Brattleboro, VT 05301

    • 4 Beds
    • 2.5 Baths
    • 3,080 Sq Ft
    • Built 1871

    Last Sold Summary

    • 10% Below List Price
    • $140/SF
    • 87 Days On Market

    Current Estimated Value $451,430

    Last Listing Agent Jeffrey Sheehan Cummings & Co

    109 Washington St, Brattleboro, VT 05301
    • 23 Winter Ct, Brattleboro, VT 05301
      23 Winter Ct, Brattleboro, VT 05301
      23 Winter Ct, Brattleboro, VT 05301
      /16

      Est $232,539 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,343 Sq Ft

      23 Winter Ct, Brattleboro, VT 05301

      23 Winter Ct, Brattleboro, VT 05301
  • 85 Stockwell Dr, Brattleboro, VT 05301
    85 Stockwell Dr, Brattleboro, VT 05301
    85 Stockwell Dr, Brattleboro, VT 05301
    /24

    $365,000

    • 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
  • 111 Bonnyvale Rd, Brattleboro, VT 05301
    111 Bonnyvale Rd, Brattleboro, VT 05301
    111 Bonnyvale Rd, Brattleboro, VT 05301
    /33

    $377,840 Sold Aug 19, 2025

    111 Bonnyvale Rd, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,536 Sq Ft
    • Built 2000

    Last Sold Summary

    • 8% Above List Price
    • $246/SF
    • 103 Days On Market

    Current Estimated Value $377,757

    Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty

    111 Bonnyvale Rd, Brattleboro, VT 05301
    • 91 Pine St, Brattleboro, VT 05301
      91 Pine St, Brattleboro, VT 05301
      91 Pine St, Brattleboro, VT 05301
      /21

      Est $263,558 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,252 Sq Ft

      91 Pine St, Brattleboro, VT 05301

      91 Pine 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
  • 9 Garden Dr, Brattleboro, VT 05301
    9 Garden Dr, Brattleboro, VT 05301
    9 Garden Dr, Brattleboro, VT 05301
    /26

    $207,000 Sold May 27, 2025

    9 Garden Dr, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 1920

    Last Sold Summary

    • 9% Above List Price
    • $137/SF
    • 28 Days On Market

    Current Estimated Value $220,594

    Last Listing Agent Sue Beaudet EXP Realty

    9 Garden Dr, Brattleboro, VT 05301
    • 88 Washington St, Brattleboro, VT 05301
      88 Washington St, Brattleboro, VT 05301
      88 Washington St, Brattleboro, VT 05301
      /25

      Est $258,831 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,033 Sq Ft

      88 Washington St, Brattleboro, VT 05301

      88 Washington 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

    $295,000

    • 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
  • 64 Meadowbrook Rd, Brattleboro, VT 05301
    64 Meadowbrook Rd, Brattleboro, VT 05301
    64 Meadowbrook Rd, Brattleboro, VT 05301
    /29

    $330,000 Sold Jul 25, 2025

    64 Meadowbrook Rd, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Built 1890

    Last Sold Summary

    • 3% Below List Price
    • $244/SF
    • 16 Days On Market

    Current Estimated Value $330,539

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    64 Meadowbrook Rd, Brattleboro, VT 05301
    • 10 Washington St, Brattleboro, VT 05301
      10 Washington St, Brattleboro, VT 05301
      10 Washington St, Brattleboro, VT 05301
      /27

      Est $266,053 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 900 Sq Ft

      10 Washington St, Brattleboro, VT 05301

      10 Washington St, Brattleboro, VT 05301
  • 16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    /29

    $315,000

    • 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
  • 39 Brookside Dr Unit 7, Brattleboro, VT 05301
    39 Brookside Dr Unit 7, Brattleboro, VT 05301
    39 Brookside Dr Unit 7, Brattleboro, VT 05301
    /5

    $100,000 Sold Aug 11, 2025

    39 Brookside Dr Unit 7, Brattleboro, VT 05301

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Built 1966

    Last Sold Summary

    • $143/SF
    • 19 Days On Market

    Current Estimated Value $103,611

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    39 Brookside Dr Unit 7, Brattleboro, VT 05301
    • 18 Central St, Brattleboro, VT 05301
      18 Central St, Brattleboro, VT 05301
      18 Central St, Brattleboro, VT 05301
      /17

      Est $327,838 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,927 Sq Ft

      18 Central St, Brattleboro, VT 05301

      18 Central St, Brattleboro, VT 05301
  • 162 Buttonwood Dr, Brattleboro, VT 05301
    162 Buttonwood Dr, Brattleboro, VT 05301
    162 Buttonwood Dr, Brattleboro, VT 05301
    /32

    $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
  • 155 Oak Grove Ave, Brattleboro, VT 05301
    155 Oak Grove Ave, Brattleboro, VT 05301
    155 Oak Grove Ave, Brattleboro, VT 05301
    /46

    $415,000 Sold Nov 07, 2025

    155 Oak Grove Ave, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 1,446 Sq Ft
    • Built 1932

    Last Sold Summary

    • 9% Above List Price
    • $287/SF
    • 7 Days On Market

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    155 Oak Grove Ave, Brattleboro, VT 05301
    • 39 Clark St, Brattleboro, VT 05301
      39 Clark St, Brattleboro, VT 05301
      39 Clark St, Brattleboro, VT 05301
      /31

      Est $207,199 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,592 Sq Ft

      39 Clark St, Brattleboro, VT 05301

      39 Clark St, Brattleboro, VT 05301
  • 50 Terrace St, Brattleboro, VT 05301
    50 Terrace St, Brattleboro, VT 05301
    50 Terrace St, Brattleboro, VT 05301
    /5

    $680,000 Under Contract

    • 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
  • 65 Hillwinds N, Brattleboro, VT 05301
    65 Hillwinds N, Brattleboro, VT 05301
    65 Hillwinds N, Brattleboro, VT 05301
    /42

    $925,000 Sold Oct 01, 2025

    65 Hillwinds N, Brattleboro, VT 05301

    • 5 Beds
    • 4.5 Baths
    • 4,150 Sq Ft
    • Built 1983

    Last Sold Summary

    • 9% Above List Price
    • $223/SF
    • 5 Days On Market

    Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

    65 Hillwinds N, Brattleboro, VT 05301
    • 60 Clark St, Brattleboro, VT 05301
      60 Clark St, Brattleboro, VT 05301
      60 Clark St, Brattleboro, VT 05301
      /18

      Not Listed For Sale

      • Studio
      • 1,683 Sq Ft

      60 Clark St, Brattleboro, VT 05301

      60 Clark St, 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
  • 142 Spruce St, Brattleboro, VT 05301
    142 Spruce St, Brattleboro, VT 05301
    142 Spruce St, Brattleboro, VT 05301
    /26

    $331,000 Sold Jan 07, 2025

    142 Spruce St, Brattleboro, VT 05301

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft
    • Built 1930

    Last Sold Summary

    • 11% Above List Price
    • $376/SF
    • 10 Days On Market

    Current Estimated Value $338,254

    Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

    142 Spruce St, Brattleboro, VT 05301
    • 95 Frost St, Brattleboro, VT 05301
      95 Frost St, Brattleboro, VT 05301
      95 Frost St, Brattleboro, VT 05301
      /22

      Est $257,127 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,146 Sq Ft

      95 Frost St, Brattleboro, VT 05301

      95 Frost St, 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
  • 36 Spruce St, Brattleboro, VT 05301
    36 Spruce St, Brattleboro, VT 05301
    36 Spruce St, Brattleboro, VT 05301
    /18

    $410,000 Sold Nov 06, 2025

    36 Spruce St, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1845

    Last Sold Summary

    • 9% Below List Price
    • $198/SF
    • 183 Days On Market

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    36 Spruce St, Brattleboro, VT 05301
    • 203 Elliot St, Brattleboro, VT 05301
      203 Elliot St, Brattleboro, VT 05301
      203 Elliot St, Brattleboro, VT 05301
      /20

      Est $387,253 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,012 Sq Ft

      203 Elliot St, Brattleboro, VT 05301

      203 Elliot 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
  • 70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
    /14

    $250,000 Sold Oct 31, 2025

    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1995

    Last Sold Summary

    • $200/SF
    • 5 Days On Market

    Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
    • 196 Fairview St, Brattleboro, VT 05301
      196 Fairview St, Brattleboro, VT 05301
      196 Fairview St, Brattleboro, VT 05301
      /41

      Est $341,080 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 1,714 Sq Ft

      196 Fairview St, Brattleboro, VT 05301

      196 Fairview St, Brattleboro, VT 05301
  • 1089 Marlboro Rd, Brattleboro, VT 05301
    1089 Marlboro Rd, Brattleboro, VT 05301
    1089 Marlboro Rd, Brattleboro, VT 05301
    /30

    $369,000

    • 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
  • 00 Fisch Rd, Brattleboro, VT 05301
    00 Fisch Rd, Brattleboro, VT 05301
    00 Fisch Rd, Brattleboro, VT 05301
    /8

    $87,000 Sold Nov 17, 2025

    00 Fisch Rd, Brattleboro, VT 05301

    • Land
    • 34.77 Acres
    • $2,502 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 7 Days On Market

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    00 Fisch Rd, Brattleboro, VT 05301
    • 31 Pleasant St, Brattleboro, VT 05301
      31 Pleasant St, Brattleboro, VT 05301
      31 Pleasant St, Brattleboro, VT 05301
      /35

      Est $321,557 Not Listed For Sale

      • 1 Bed
      • 2 Baths
      • 1,560 Sq Ft

      31 Pleasant St, Brattleboro, VT 05301

      31 Pleasant St, Brattleboro, VT 05301
  • 115 Country Hill, Brattleboro, VT 05301
    115 Country Hill, Brattleboro, VT 05301
    115 Country Hill, Brattleboro, VT 05301
    /24

    $389,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    115 Country Hill, Brattleboro, VT 05301

    This lovely West Brattleboro cape is located on a quiet cul-de-sac right on the outskirts of town. Built in 2002 with a spacious design, you enter through the oversized two-car garage into a contemporary kitchen. Features include granite countertops, tile floors, an elegant backsplash, and a door leading to a private terrace, ideal for family gatherings or entertaining. The first floor has

    Kristen Ziter Taylor Brattleboro Area Realty

    115 Country Hill, Brattleboro, VT 05301
  • 395 Hillwinds Rd, Brattleboro, VT 05301
    395 Hillwinds Rd, Brattleboro, VT 05301
    395 Hillwinds Rd, Brattleboro, VT 05301
    /46

    $668,000 Sold Aug 12, 2025

    395 Hillwinds Rd, Brattleboro, VT 05301

    • 4 Beds
    • 2.5 Baths
    • 2,226 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Above List Price
    • $300/SF
    • 7 Days On Market

    Current Estimated Value $658,603

    Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

    395 Hillwinds Rd, Brattleboro, VT 05301
    • 95 Maple St, Brattleboro, VT 05301
      95 Maple St, Brattleboro, VT 05301
      95 Maple St, Brattleboro, VT 05301
      /39

      Est $387,019 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,970 Sq Ft

      95 Maple St, Brattleboro, VT 05301

      95 Maple 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
  • 135 Upper Dummerston Rd, Brattleboro, VT 05301
    135 Upper Dummerston Rd, Brattleboro, VT 05301
    /2

    $525,000 Sold May 16, 2025

    135 Upper Dummerston Rd, Brattleboro, VT 05301

    • 5 Beds
    • 3.5 Baths
    • 3,600 Sq Ft
    • Built 1910

    Last Sold Summary

    • 19% Below List Price
    • $146/SF
    • 269 Days On Market

    Current Estimated Value $536,188

    Last Listing Agent Susan LeCours Barrett & Valley Assoc. Inc

    135 Upper Dummerston Rd, Brattleboro, VT 05301
    • 122 Frost St, Brattleboro, VT 05301
      122 Frost St, Brattleboro, VT 05301
      122 Frost St, Brattleboro, VT 05301
      /36

      Est $328,719 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,388 Sq Ft

      122 Frost St, Brattleboro, VT 05301

      122 Frost St, Brattleboro, VT 05301

Showing Results 81 - 120, Page 3 of 18

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