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    Middlesboro, KY
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    38 Properties Available

    38 Properties Available

    The average price in the selected areas has remained stable. Learn more
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    • Newest Listings
    • Beds (Most)
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    • Square Feet (Biggest)
    1009 Cumberland Ave, Middlesboro, KY 40965
    1/18
    New

    $115,000

    2 Beds1 Bath850 SqFt

    1009 Cumberland Ave, Middlesboro, KY 40965

    Listed by REMAX PROFESSIONAL'S

    707 Gloucester Ave, Middlesboro, KY 40965
    1/21
    Pending

    $169,900

    3 Beds2 Baths1,184 SqFt

    707 Gloucester Ave, Middlesboro, KY 40965

    Listed by Turn Key Realty

    913 Doncaster St, Middlesboro, KY 40965
    1/19
    Active

    $249,900

    3 Beds2 Baths1,346 SqFt

    913 Doncaster St, Middlesboro, KY 40965

    Listed by Fathom Realty TN LLC

    3306 Cumberland Ave, Middlesboro, KY 40965
    1/33
    Pending

    $349,900

    3 Beds2 Baths2,126 SqFt

    3306 Cumberland Ave, Middlesboro, KY 40965

    Listed by Coldwell Banker Bisceglia Real

    1005 Hollywood DR, Middlesboro, KY 40965
    1/14
    Active

    $1,200

    3 Beds1 Bath1,110 SqFt

    1005 Hollywood DR, Middlesboro, KY 40965

    Listed by Heartland Real Estate, LLC

    810 Worchester Ave, Middlesboro, KY 40965
    1/17
    Pending

    $229,000

    3 Beds3 Baths2,000 SqFt

    810 Worchester Ave, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    1203 Winchester Ave, Middlesboro, KY 40965
    1/32
    Pending

    $239,900

    4 Beds3 Baths2,456 SqFt

    1203 Winchester Ave, Middlesboro, KY 40965

    Listed by Coldwell Banker Bisceglia Real

    23 Castleford WAY, Middlesboro, KY 40965
    1/29
    Pending

    $192,500

    3 Beds2 Baths1,080 SqFt

    23 Castleford WAY, Middlesboro, KY 40965

    Listed by Turn Key Realty

    2794 US HWY 25 E, Middlesboro, KY 40965
    1/48
    Pending

    $575,000

    4 Beds4 Baths3,480 SqFt

    2794 US HWY 25 E, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    523 30th St, Middlesboro, KY 40965
    1/13
    Active

    $455,000

    5 Beds4 Baths3,146 SqFt

    523 30th St, Middlesboro, KY 40965

    Listed by Turn Key Realty

    409 Meadow LN, Middlesboro, KY 40965
    1/18
    Pending

    $168,000

    4 Beds2 Baths1,120 SqFt

    409 Meadow LN, Middlesboro, KY 40965

    Listed by Turn Key Realty

    708 Chester Ave, Middlesboro, KY 40965
    1/15
    Price Dropped by $7K

    $135,000

    3 Beds1 Bath1,404 SqFt

    708 Chester Ave, Middlesboro, KY 40965

    Listed by REMAX PROFESSIONAL'S

    301 Doe's Crossing, Middlesboro, KY 40965
    1/40
    Price Dropped by $10K

    $239,000

    3 Beds3 Baths2,016 SqFt

    301 Doe's Crossing, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    206 Summit DR, Middlesboro, KY 40965
    1/29
    Price Dropped by $20K

    $259,000

    4 Beds3 Baths1,832 SqFt

    206 Summit DR, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    359 Beans Fork Rd, Middlesboro, KY 40965
    1/23
    Pending

    $148,000

    2 Beds1 Bath952 SqFt

    359 Beans Fork Rd, Middlesboro, KY 40965

    Listed by Realty Group

    405 37th St, Middlesboro, KY 40965
    1/17
    Active

    $159,900

    4 Beds2 Baths1,908 SqFt

    405 37th St, Middlesboro, KY 40965

    Listed by Coldwell Banker Bisceglia Real

    923 Winchester Ave, Middlesboro, KY 40965
    1/2
    Price Dropped by $14K

    $85,000

    1 Bed1 Bath800 SqFt

    923 Winchester Ave, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    140 Wellington DR, Middlesboro, KY 40965
    1/21
    Price Dropped by $30K

    $219,900

    4 Beds2 Baths1,612 SqFt

    140 Wellington DR, Middlesboro, KY 40965

    Listed by Fathom Realty TN LLC

    2004 Twin Fawn Tr, Middlesboro, KY 40965
    1/33
    Price Dropped by $26K

    $499,000

    5 Beds3 Baths2,542 SqFt

    2004 Twin Fawn Tr, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    13 Duncan LN, Middlesboro, KY 40965
    1/27
    Pending

    $24,900

    3 Beds2 Baths960 SqFt

    13 Duncan LN, Middlesboro, KY 40965

    Listed by Turn Key Realty

    252 Chasteen DR, Middlesboro, KY 40965
    1/22
    Active

    $109,000

    3 Beds2 Baths1,296 SqFt

    252 Chasteen DR, Middlesboro, KY 40965

    Listed by Realty Network, Inc

    129 Lower Gibson LN, Middlesboro, KY 40965
    1/53
    Pending

    $240,000

    3 Beds3 Baths1,856 SqFt

    129 Lower Gibson LN, Middlesboro, KY 40965

    Listed by REMAX PROFESSIONAL'S

    4605 Cumberland Ave, Middlesboro, KY 40965
    1/2
    Pending

    $165,000

    3 Beds2 Baths1,056 SqFt

    4605 Cumberland Ave, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    1720 Exeter Ave, Middlesboro, KY 40965
    1/15
    Pending

    $68,000

    2 Beds1 Bath1,456 SqFt

    1720 Exeter Ave, Middlesboro, KY 40965

    Listed by Realty Group

    • 1
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    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
    SCALE w Large LPT
    SCALE brokered by LPT Realty
    Brandon Williams
    +1(877) 366-2213
    brandonwlms@gmail.com
    9041 Executive Park Dr, Knoxville, TN, 37923, USA

    Get My App

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    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
    SCALE w Large LPT
    SCALE brokered by LPT Realty
    Brandon Williams
    +1(877) 366-2213
    brandonwlms@gmail.com
    9041 Executive Park Dr, Knoxville, TN, 37923, USA

    Get My App

      • Home
        Market Snapshot
        Blogs
      • Buy
        1. All Listings
        2. Featured Listings
        3. Calculator
        Our Standard
        1. Our Network
        2. Inside SCALE
        3. Reviews
      • Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Contact Us

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility