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Middlesboro, KY Homes for Sale | Realty.com
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3 beds
40 listings
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New construction
With a pool

Homes for Sale in Middlesboro, KY

Homes for Sale in Middlesboro, KY

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21 of 40 Listings
Map

Homes for Sale in Middlesboro, KY

21 of 40 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas
  1. 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

  2. 518 S 43rd St — photo15Active

    $59,000

    2 bd · 1 ba · 920 sqft

    518 S 43rd St, Middlesboro, KY

    Mike Hensley · REMAX PROFESSIONAL'S

  3. 207 Arthur Heights — photoPrice Reduced29Active

    $279,000

    5 bd · 3 ba · 3,068 sqft

    207 Arthur Heights, Middlesboro, KY

    Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co

  4. 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

  5. 1102 W Chester Avenue — photo23Active

    $199,000

    3 bd · 1 ba · 1,480 sqft

    1102 W Chester Avenue, Middlesboro, KY

    David Gambrell · Coldwell Banker Bisceglia Realty & Auction Co

  6. 1015 Old Wilson Lane — photoPrice Reduced46Active

    $315,000

    4 bd · 3 ba · 2,488 sqft

    1015 Old Wilson Lane, Middlesboro, KY

    David Gambrell · Coldwell Banker Bisceglia Realty & Auction Co

  7. 110 Danbury Ave — photo3Active

    $17,000

    2 bd · 1 ba · 936 sqft

    110 Danbury Ave, Middlesboro, KY

    Misti McGrath · Realty Group

  8. 142 Edgewood Rd — photo1Active

    $595,000

    7 bd · 5 ba · 6,276 sqft

    142 Edgewood Rd, Middlesboro, KY

    Lisa Stacy-Gibbs · Backwoods Realty & Development

  9. 105 Nutwood Road — photoPrice Reduced11Active

    $35,000

    3 bd · 1 ba · 728 sqft

    105 Nutwood Road, Middlesboro, KY

    Megan Stanaford · Black Diamond Realty

  10. 515 Englewood Road — photo1Active

    $279,000

    3 bd · 3 ba · 2,210 sqft

    515 Englewood Road, Middlesboro, KY

    Kevin Carroll · Backwoods Realty & Development

  11. 926 Doncaster Avenue — photoPrice Reduced46Active

    $315,000

    5 bd · 2 ba · 2,664 sqft

    926 Doncaster Avenue, Middlesboro, KY

    Kevin Bisceglia · Coldwell Banker Bisceglia Realty & Auction Co

  12. 523 N 30th Street — photo1Active

    $455,000

    5 bd · 4 ba · 3,146 sqft

    523 N 30th Street, Middlesboro, KY

    Kevin Carroll · Backwoods Realty & Development

  13. 400 Gloucester Avenue — photoPrice Reduced44Active

    $279,000

    4 bd · 2 ba · 2,032 sqft

    400 Gloucester Avenue, Middlesboro, KY

    Sheila Durham · Coldwell Banker Bisceglia Realty & Auction Co

  14. 712 Balmoral Road — photo16Active

    $60,000

    3 bd · 1 ba · 768 sqft

    712 Balmoral Road, Middlesboro, KY

    Megan Stanaford · Black Diamond Realty

  15. 13 Duncan Lane — photo17Active

    $19,900

    3 bd · 2 ba · 960 sqft

    13 Duncan Lane, Middlesboro, KY

    James Martin · Century 21 Pinnacle

  16. 140 Wellington Drive — photo26Active

    $199,900

    4 bd · 2 ba · 1,612 sqft

    140 Wellington Drive, Middlesboro, KY

    Janice Pratt · Fathom Realty TN LLC

  17. 2909 W Cumberland Ave — photo34Active

    $359,500

    3 bd · 2 ba · 2,000 sqft

    2909 W Cumberland Ave, Middlesboro, KY

    Lisa Stacy-Gibbs · Backwoods Realty & Development

  18. 119 S 20th Street — photoPrice Reduced26Active

    $250,000

    2 bd · 2 ba · 1,750 sqft

    119 S 20th Street, Middlesboro, KY

    Tina Eades · Kentucky Homes and Land LLC

  19. 125 Cawood Lane — photo16Active

    $142,500

    2 bd · 2 ba · 1,400 sqft

    125 Cawood Lane, Middlesboro, KY

    Misti McGrath · Realty Group

  20. 908 Manchester Avenue — photoPrice Reduced9Active

    $137,900

    3 bd · 2 ba · 1,100 sqft

    908 Manchester Avenue, Middlesboro, KY

    Jonathan Evans · Action Realty

  21. 116 Edgewood Road — photoPrice Reduced30Active

    $200,000

    3 bd · 2 ba · 2,154 sqft

    116 Edgewood Road, Middlesboro, KY

    Megan Stanaford · Black Diamond Realty

12

Explore Middlesboro homes

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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: 2026-08-29 02:04:39 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.
Northern Kentucky Multiple Listing Service
The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of NKMLS. Real estate listings held by IDX Brokerage firms other than Realty.com, Inc. are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers.
Listing information is deemed reliable, but not guaranteed.
Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved. Last Updated: 2026-08-20 23:57:00 UTC
  • By feature

    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #221881

    Call Thomas

    Middlesboro, KY community profile

    Area
    73.6 sq. mi.

    Source: HJN community data

    Nearby areas

    ZIP codes

    • 40701 (51)
    • 40965 (40)
    • 40906 (28)
    • 40977 (28)
    • 40734 (8)
    • 40769 (6)
    • 40759 (5)
    • 40806 (5)

    Cities

    • Corbin (51)
    • Barbourville (28)
    • Pineville (28)
    • Gray (8)
    • Williamsburg (6)
    • Baxter (5)
    • Rockholds (5)
    • Flat Lick (4)

    Middlesboro housing market

    August 2026 · This period is still settling

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,186 sq. ft.