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    Middlesboro, KY
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    43 Properties Available

    43 Properties Available

    The average price in the selected areas has remained stable. Learn more
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    • Price-High To Low
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    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    64 Dunlap Hollow Rd, Middlesboro, KY 40965
    1/34
    New

    $175,000

    4 Beds2 Baths1,440 SqFt

    64 Dunlap Hollow Rd, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    422 Wilderness Rd, Middlesboro, KY 40965
    1/14
    New

    $150,000

    2 Beds1 Bath840 SqFt

    422 Wilderness Rd, Middlesboro, KY 40965

    Listed by Realty Group

    1425 Highway 441, Middlesboro, KY 40965
    1/29
    Active

    $165,000

    3 Beds2 Baths1,242 SqFt

    1425 Highway 441, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    1807 Winchester Ave, Middlesboro, KY 40965
    1/24
    Pending

    $155,000

    3 Beds1 Bath1,104 SqFt

    1807 Winchester Ave, Middlesboro, KY 40965

    Listed by REMAX PROFESSIONAL'S

    413 26th St, Middlesboro, KY 40965
    1/13
    Active

    $140,000

    2 Beds1 Bath1,008 SqFt

    413 26th St, Middlesboro, KY 40965

    Listed by Turn Key Realty

    116 Petersborough Ave, Middlesboro, KY 40965
    1/20
    Price Dropped by $5K

    $220,000

    3 Beds1 Bath1,652 SqFt

    116 Petersborough Ave, Middlesboro, KY 40965

    Listed by Coldwell Banker Bisceglia Real

    908 Chester Ave, Middlesboro, KY 40965
    1/12
    Active

    $225,000

    3 Beds2 Baths1,400 SqFt

    908 Chester Ave, Middlesboro, KY 40965

    Listed by REMAX PROFESSIONAL'S

    815 Dorchester Ave, Middlesboro, KY 40965
    1/15
    Active

    $175,000

    2 Beds1 Bath792 SqFt

    815 Dorchester Ave, Middlesboro, KY 40965

    Listed by Turn Key Realty

    123 Cawood LN, Middlesboro, KY 40965
    1/18
    Price Dropped by $16K

    $93,500

    2 Beds2 Baths1,426 SqFt

    123 Cawood LN, Middlesboro, KY 40965

    Listed by Mountain Realty

    316 Exeter Ave, Middlesboro, KY 40965
    1/30
    Pending

    $125,000

    4 Beds2 Baths2,592 SqFt

    316 Exeter Ave, Middlesboro, KY 40965

    Listed by REMAX PROFESSIONAL'S

    918 Cumberland Ave, Middlesboro, KY 40965
    1/13
    Price Dropped by $15K

    $55,000

    2 Beds1 Bath792 SqFt

    918 Cumberland Ave, Middlesboro, KY 40965

    Listed by REMAX PROFESSIONAL'S

    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

    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
    1/31
    Pending

    $183,500

    3 Beds2 Baths1,080 SqFt

    23 Castleford WAY, Middlesboro, KY 40965

    Listed by Backwoods Realty & Development

    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 Backwoods Realty & Development

    515 Englewood Rd, Middlesboro, KY 40965
    1/20
    Active

    $279,000

    3 Beds3 Baths2,210 SqFt

    515 Englewood Rd, Middlesboro, KY 40965

    Listed by Backwoods Realty & Development

    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
    Pending

    $259,000

    4 Beds3 Baths1,832 SqFt

    206 Summit DR, Middlesboro, KY 40965

    Listed by Century 21 Virginia Wilder Real Estate

    405 37th St, Middlesboro, KY 40965
    1/17
    Price Dropped by $10K

    $129,900

    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
    Pending

    $79,000

    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

    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

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    Demetri Demus License ID: 354450

    +1(865) 333-1695 demo@brickmortarproperties.com

    900 E Hill Avenue Suite 110, Knoxville, TN, 37915

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    default
        Home
        Buy
        1. All Listings
        2. Featured Listings
        3. Sold Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        About
        1. About Us
        2. Contact Us
        3. Reviews
        Market Snapshot
    Brick & Mortar Properties

    Demetri Demus License ID: 354450

    +1(865) 333-1695 demo@brickmortarproperties.com

    900 E Hill Avenue Suite 110, Knoxville, TN, 37915

    Get My App

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

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

    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.