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Homes Under $500K in Brattleboro, VT
49 listings

Homes Under $500K in Brattleboro, VT

Homes Under $500K in Brattleboro, VT

Show Map
23 of 49 Listings
Map

Homes Under $500K in Brattleboro, VT

23 of 49 Listings

  1. 9 Robin Way — photo21Active

Your local brokerage

JW

John White

Realty.com

Lic. #81.0094848

Call John

$219,000

2 bd · 2 ba · 1,248 sqft

9 Robin Way, Brattleboro, VT

John McPherson · Berkley & Veller Greenwood Country

  • 56 Fuller Drive — photo26Active

    $250,000

    2 bd · 1 ba · 1,485 sqft

    56 Fuller Drive, Brattleboro, VT

    Cassandra Ehrlich · BHG Masiello Brattleboro

  • 78 Morningside Commons — photo51Active

    $239,900

    2 bd · 2 ba · 1,056 sqft

    78 Morningside Commons, Brattleboro, VT

    Sally Fegley · BHG Masiello Brattleboro

  • 35 Fairground Road — photo14Active

    $280,000

    3 bd · 1 ba · 1,300 sqft

    35 Fairground Road, Brattleboro, VT

    A.J. Bellville · Bellville Realty

  • 311 Guilford Street — photo49Active

    $349,900

    4 bd · 2 ba · 1,152 sqft

    311 Guilford Street, Brattleboro, VT

    Steve Schoppmeyer · BHG Masiello Brattleboro

  • 9 Evergreen Lane — photo23Active

    $230,000

    2 bd · 2 ba · 1,248 sqft

    9 Evergreen Lane, Brattleboro, VT

    Peggy Winchester · ACORN REAL ESTATE GROUP LLC

  • 43 Winter Street — photo18Active

    $275,000

    3 bd · 1 ba · 1,112 sqft

    43 Winter Street, Brattleboro, VT

    Christine Lewis · Brattleboro Area Realty

  • 625 Black Mountain Road — photo14Active

    $339,000

    3 bd · 2 ba · 1,395 sqft

    625 Black Mountain Road, Brattleboro, VT

    Heidi Bernier · Berkley & Veller Greenwood Country

  • 29 Morningside Commons — photo39Active

    $189,500

    2 bd · 2 ba · 966 sqft

    29 Morningside Commons, Brattleboro, VT

    Sally Fegley · BHG Masiello Brattleboro

  • 164 Morningside Commons — photo29Active

    $229,000

    2 bd · 2 ba · 1,096 sqft

    164 Morningside Commons, Brattleboro, VT

    Sally Fegley · BHG Masiello Brattleboro

  • 627 Abbott Road — photo3Active

    $310,000

    3 bd · 2 ba · 1,536 sqft

    627 Abbott Road, Brattleboro, VT

    Ginny Read · Read Realty LTD

  • 104 Morningside Commons — photoPrice Reduced27Active

    $279,000

    2 bd · 2 ba · 1,139 sqft

    104 Morningside Commons, Brattleboro, VT

    Dan Normandeau · Berkley & Veller Greenwood Country

  • 40 Brookside Drive — photo21Active

    $179,000

    1 bd · 1 ba · 700 sqft

    40 Brookside Drive, Brattleboro, VT

    Angela Sherman · Brattleboro Area Realty

  • 36 Pine Street — photoPrice Reduced30Active

    $279,000

    3 bd · 2 ba · 1,406 sqft

    36 Pine Street, Brattleboro, VT

    Christine Lewis · Brattleboro Area Realty

  • 41 Organ Street — photo23Active

    $270,000

    2 bd · 1 ba · 1,061 sqft

    41 Organ Street, Brattleboro, VT

    Desiree Stango · Berkley & Veller Greenwood Country

  • 59 Highland Street — photo44Active

    $319,000

    2 bd · 2 ba · 1,883 sqft

    59 Highland Street, Brattleboro, VT

    Rebecca Seymour · Brattleboro Area Realty

  • 48 Wilsons Woods Road — photoPrice Reduced32Active

    $269,900

    3 bd · 1 ba · 1,104 sqft

    48 Wilsons Woods Road, Brattleboro, VT

    Cassandra Ehrlich · BHG Masiello Brattleboro

  • 14 Deepwood Park — photo34Active

    $149,900

    3 bd · 2 ba · 1,232 sqft

    14 Deepwood Park, Brattleboro, VT

    Steve Schoppmeyer · BHG Masiello Brattleboro

  • 39 Brookside Drive — photo23Active

    $190,000

    2 bd · 1 ba · 930 sqft

    39 Brookside Drive, Brattleboro, VT

    Angela Sherman · Brattleboro Area Realty

  • 77 Buttonwood Drive — photo17Active

    $439,000

    2 bd · 2 ba · 1,550 sqft

    77 Buttonwood Drive, Brattleboro, VT

    Christine M Lewis · Brattleboro Area Realty

  • 9 Village Drive — photoPrice Reduced24Active

    $52,000

    2 bd · 1 ba · 744 sqft

    9 Village Drive, Brattleboro, VT

    Rebecca Seymour · Brattleboro Area Realty

  • 11 Evergreen Lane — photoPrice Reduced27Active

    $230,000

    2 bd · 2 ba · 1,248 sqft

    11 Evergreen Lane, Brattleboro, VT

    Janet Lucier · Barrett & Valley Assoc. Inc

  • 455 South Main Street — photoPrice Reduced16Active

    $269,000

    3 bd · 1 ba · 1,050 sqft

    455 South Main Street, Brattleboro, VT

    Christine M Lewis · Brattleboro Area Realty

  • 123

    Explore Brattleboro homes

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    • Homes Under $300K
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    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Your local brokerage

    JW

    John White

    Realty.com

    Lic. #81.0094848

    Call John

    Listing data & MLS disclosures

    PrimeMLS
    Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this web site 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.

    Brattleboro, VT community profile

    Area
    146.7 sq. mi.

    Source: HJN community data

    Brattleboro housing market

    October 2026 · This period is still settling

    Selling at 97.5% of asking price

    Buyers here are paying below asking. MLS · 18 sales · as of Oct 30, 2026

    Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

    Median list price
    $319,500
    Homes for sale
    62
    Median days on market
    29 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,588 sq. ft.