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Homes Under $500K in Middlesboro, KY
44 listings

Homes Under $500K in Middlesboro, KY

Homes Under $500K in Middlesboro, KY

Show Map
23 of 44 Listings
Map

Homes Under $500K in Middlesboro, KY

23 of 44 Listings

  1. 406 N 25th St — photo22

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas
Active

$285,000

3 bd · 2 ba · 2,400 sqft

406 N 25th St, Middlesboro, KY

Misti McGrath · Realty Group

  • 616 Balmoral Rd — photo12Active

    $239,900

    3 bd · 3 ba · 1,710 sqft

    616 Balmoral Rd, Middlesboro, KY

    Kevin Carroll · Backwoods Realty & Development

  • 114 E Rochester Avenue — photo3Active

    $175,500

    3 bd · 1 ba · 1,066 sqft

    114 E Rochester Avenue, Middlesboro, KY

    Melanie Mullins · Backwoods Realty & Development

  • 413 S 26th St — photo18Active

    $135,000

    2 bd · 1 ba · 1,008 sqft

    413 S 26th St, Middlesboro, KY

    Brad Cawood · Backwoods Realty & Development

  • 717 S 27th Street — photoPrice Reduced37Active

    $227,000

    5 bd · 4 ba · 3,195 sqft

    717 S 27th Street, Middlesboro, KY

    Barry Turner · RE/MAX LakeTime Realty London

  • 810 1/2 Rochester Ave — photo25Active

    $169,000

    3 bd · 2 ba · 1,592 sqft

    810 1/2 Rochester Ave, Middlesboro, KY

    Brad Cawood · Backwoods Realty & Development

  • 103 Sherwood Rd — photo32Active

    $340,000

    5 bd · 3 ba · 3,000 sqft

    103 Sherwood Rd, Middlesboro, KY

    Misti McGrath · Realty Group

  • 88 Tracy Ridge Rd — photo19Active

    $235,000

    3 bd · 2 ba · 1,600 sqft

    88 Tracy Ridge Rd, Middlesboro, KY

    Mike Hensley · REMAX PROFESSIONAL'S

  • 1015 Old Wilson Lane — photo23Active

    $315,000

    4 bd · 3 ba · 2,488 sqft

    1015 Old Wilson Lane, Middlesboro, KY

    Misti McGrath · Realty Group

  • 810 W Rochester Ave — photo15Active

    $145,900

    3 bd · 2 ba · 1,386 sqft

    810 W Rochester Ave, Middlesboro, KY

    Nichole Goins · Heartland Real Estate, LLC

  • 1801 & 1801 1/2 Exeter Avenue — photo30Active

    $175,000

    2 bd · 1 ba · 700 sqft

    1801 & 1801 1/2 Exeter Avenue, Middlesboro, KY

    Victoria Allen · Century 21 Virginia Wilder Real Estate

  • 305 N 15th St — photo17Active

    $150,000

    2 bd · 1 ba · 876 sqft

    305 N 15th St, Middlesboro, KY

    Mike Hensley · REMAX PROFESSIONAL'S

  • 1102 W Chester Ave — photo20Active

    $199,000

    3 bd · 1 ba · 1,480 sqft

    1102 W Chester Ave, Middlesboro, KY

    Kevin J Bisceglia · Coldwell Banker Bisceglia Real

  • 706 Ilchester Ave — photo16Active

    $119,900

    3 bd · 2 ba · 1,260 sqft

    706 Ilchester Ave, Middlesboro, KY

    Virginia Wilder · Century 21 Virginia Wilder Real Estate

  • 412 N 24th Street — photo15Active

    $105,900

    3 bd · 2 ba · 1,966 sqft

    412 N 24th Street, Middlesboro, KY

    Dawn Risner · Turn Key Realty

  • 2004 Twin Fawn Tr — photo33Active

    $475,000

    5 bd · 3 ba · 2,542 sqft

    2004 Twin Fawn Tr, Middlesboro, KY

    Virginia Wilder · Century 21 Virginia Wilder Real Estate

  • 8 Castleford Way — photoPrice Reduced47Active

    $175,000

    3 bd · 2 ba · 1,168 sqft

    8 Castleford Way, Middlesboro, KY

    Victoria Allen · Century 21 Virginia Wilder Real Estate

  • 708 W Chester Ave — photo17Active

    $129,000

    3 bd · 1 ba · 1,404 sqft

    708 W Chester Ave, Middlesboro, KY

    Mike Hensley · REMAX PROFESSIONAL'S

  • 812 Worchester Ave — photo22Active

    $219,000

    4 bd · 2 ba · 1,544 sqft

    812 Worchester Ave, Middlesboro, KY

    Misti McGrath · Realty Group

  • 800 S 28th St — photo28Active

    $229,000

    3 bd · 2 ba · 1,400 sqft

    800 S 28th St, Middlesboro, KY

    Mike Hensley · REMAX PROFESSIONAL'S

  • 518 S 43rd St — photo15Active

    $59,000

    2 bd · 1 ba · 920 sqft

    518 S 43rd St, Middlesboro, KY

    Mike Hensley · REMAX PROFESSIONAL'S

  • 207 Arthur Heights — photoPrice Reduced35Active

    $264,900

    5 bd · 3 ba · 3,068 sqft

    207 Arthur Heights, Middlesboro, KY

    Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co

  • 209 S 19th Street — photo12Active

    $215,000

    3 bd · 2 ba · 1,352 sqft

    209 S 19th Street, Middlesboro, KY

    Megan Stanaford · Black Diamond Realty

  • 12
    Realty.com

    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

    Equal Housing OpportunityEqual Housing Lender

    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

    TO

    Thomas O'Leary

    Realty.com

    Lic. #221881

    Call Thomas

    Listing data & MLS disclosures

    East Tennessee REALTORS MLS (Knoxville)
    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
    Listing information ©2026 Knoxville Area AOR, Inc®. All Rights Reserved. Last Updated: 2026-10-14 20:06:45 UTC
    Imagine MLS (Bluegrass REALTORS)
    The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively 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. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

    Middlesboro, KY community profile

    Area
    73.6 sq. mi.

    Source: HJN community data

    Middlesboro housing market

    September 2026 · This period is still settling

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 1, 2026

    Median home size
    1,186 sq. ft.