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Middlesboro, KY - single-family homes for sale
55 of 55 results displayed
- New
$359,500Active3 beds 2 baths2,000 sq. ft.2909 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1348099Listed by: BACKWOODS REALTY & DEVELOPMENT - New
$269,000Active2 beds 2 baths1,750 sq. ft.119 S 20th Street, Middlesboro, KY 40965
MLS# 644620Listed by: KENTUCKY HOMES AND LAND LLC - New
$260,000Active3 beds 2 baths1,304 sq. ft.2802 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1347176Listed by: REALTY GROUP 
$169,900Active2 beds 1 baths853 sq. ft.371 Eagle Lane, Middlesboro, KY 40965
MLS# 26015539Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$142,500Active2 beds 2 baths1,400 sq. ft.125 Cawood Lane, Middlesboro, KY 40965
MLS# 1346436Listed by: REALTY GROUP
$149,999Pending2 beds 1 baths1,275 sq. ft.1010 W Chester, Middlesboro, KY 40965
MLS# 26015402Listed by: FATHOM REALTY KY LLC
$125,000Active2 beds 1 baths1,456 sq. ft.1720 Exeter Avenue, Middlesboro, KY 40965
MLS# 26014807Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$59,000Active2 beds 1 baths920 sq. ft.518 S 43rd St, Middlesboro, KY 40965
MLS# 1345724Listed by: REMAX PROFESSIONAL'S
$135,000Active3 beds 2 baths1,963 sq. ft.901 Exeter Avenue, Middlesboro, KY 40965
MLS# 26014433Listed by: FATHOM REALTY KY LLC
$154,900Active3 beds 2 baths1,100 sq. ft.908 Manchester Avenue, Middlesboro, KY 40965
MLS# 26013710Listed by: ACTION REALTY
$209,900Active3 beds 2 baths2,154 sq. ft.116 Edgewood Road, Middlesboro, KY 40965
MLS# 26013326Listed by: BLACK DIAMOND REALTY
$297,500Active5 beds 4 baths3,195 sq. ft.717 S 27th Street, Middlesboro, KY 40965
MLS# 26013256Listed by: RE/MAX LAKETIME REALTY LONDON
$175,000Active4 beds 2 baths1,440 sq. ft.64 Dunlap Hollow Rd, Middlesboro, KY 40965
MLS# 1343957Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$150,000Active2 beds 1 baths840 sq. ft.422 Wilderness Rd, Middlesboro, KY 40965
MLS# 1343837Listed by: REALTY GROUP
$169,000Active2 beds 1 baths792 sq. ft.815 Dorchester Ave, Middlesboro, KY 40965
MLS# 1343066Listed by: BACKWOODS REALTY & DEVELOPMENT
$155,000Pending3 beds 1 baths1,104 sq. ft.1807 Winchester Ave, Middlesboro, KY 40965
MLS# 1342793Listed by: REMAX PROFESSIONAL'S
$165,000Pending3 beds 2 baths1,242 sq. ft.1425 Highway 441, Middlesboro, KY 40965
MLS# 1342800Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$135,000Active2 beds 1 baths1,008 sq. ft.413 S 26th St, Middlesboro, KY 40965
MLS# 1342457Listed by: BACKWOODS REALTY & DEVELOPMENT
$134,000Active5 beds 4 baths2,844 sq. ft.215 S 21st Street, Middlesboro, KY 40965
MLS# 26011288Listed by: BLACK DIAMOND REALTY
$214,999Pending3 beds 2 baths3,948 sq. ft.2621 W Cumberland Avenue, Middlesboro, KY 40965
MLS# 26011050Listed by: KELLER WILLIAMS LEGACY GROUP
$200,000Active3 beds 1 baths1,652 sq. ft.116 N Petersborough Ave, Middlesboro, KY 40965
MLS# 1341032Listed by: COLDWELL BANKER BISCEGLIA REAL
$93,500Active2 beds 2 baths1,426 sq. ft.123 Cawood Lane, Middlesboro, KY 40965
MLS# 1340557Listed by: MOUNTAIN REALTY
$279,000Active5 beds 3 baths3,068 sq. ft.207 Arthur Heights, Middlesboro, KY 40965
MLS# 26010558Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$125,000Pending4 beds 2 baths2,592 sq. ft.316 Exeter Ave, Middlesboro, KY 40965
MLS# 1340116Listed by: REMAX PROFESSIONAL'S
$55,000Active2 beds 1 baths792 sq. ft.918 E Cumberland Ave, Middlesboro, KY 40965
MLS# 1340131Listed by: REMAX PROFESSIONAL'S
$135,000Active2 beds 1 baths1,120 sq. ft.2002 Winchester Avenue, Middlesboro, KY 40965
MLS# 26010030Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$325,000Active4 beds 3 baths2,488 sq. ft.1015 Old Wilson Lane, Middlesboro, KY 40965
MLS# 26009828Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$269,900Active3 beds 2 baths2,016 sq. ft.127 Alpine Road, Middlesboro, KY 40965
MLS# 26007901Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$249,900Active3 beds 2 baths1,346 sq. ft.913 Doncaster St, Middlesboro, KY 40965
MLS# 1336350Listed by: FATHOM REALTY TN LLC
$165,000Active4 beds 1 baths2,430 sq. ft.713 Exeter Avenue, Middlesboro, KY 40965
MLS# 26007393Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$349,900Pending3 beds 2 baths2,126 sq. ft.3306 W Cumberland Avenue, Middlesboro, KY 40965
MLS# 26006987Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$295,000Active5 beds 3 baths2,100 sq. ft.717 Highway 441, Middlesboro, KY 40965
MLS# 26006775Listed by: BLACK DIAMOND REALTY
$30,000Pending2 beds 1 baths1,244 sq. ft.103 Nutwood Road, Middlesboro, KY 40965
MLS# 26005898Listed by: BLACK DIAMOND REALTY
$50,000Active3 beds 1 baths728 sq. ft.105 Nutwood Road, Middlesboro, KY 40965
MLS# 26005884Listed by: BLACK DIAMOND REALTY
$230,000Active3 beds 2 baths1,320 sq. ft.156 Wellington Drive, Middlesboro, KY 40965
MLS# 26005639Listed by: BLACK DIAMOND REALTY
$239,900Pending4 beds 3 baths2,455 sq. ft.1203 Winchester Avenue, Middlesboro, KY 40965
MLS# 26004238Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$183,500Pending3 beds 2 baths1,080 sq. ft.23 Castleford Way, Middlesboro, KY 40965
MLS# 1331558Listed by: BACKWOODS REALTY & DEVELOPMENT
$575,000Pending4 beds 4 baths3,480 sq. ft.2794 Us Hwy 25 E, Middlesboro, KY 40965
MLS# 1331334Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$399,000Active3 beds 3 baths3,397 sq. ft.103 Kingsbury Woods, Middlesboro, KY 40965
MLS# 26003950Listed by: LISTWITHFREEDOM.COM
$455,000Active5 beds 4 baths3,146 sq. ft.523 N 30th St, Middlesboro, KY 40965
MLS# 1330109Listed by: BACKWOODS REALTY & DEVELOPMENT
$279,000Active3 beds 3 baths2,210 sq. ft.515 Englewood Rd, Middlesboro, KY 40965
MLS# 1329448Listed by: BACKWOODS REALTY & DEVELOPMENT
$135,000Active3 beds 1 baths1,404 sq. ft.708 W Chester Ave, Middlesboro, KY 40965
MLS# 1328773Listed by: REMAX PROFESSIONAL'S
$232,500Active3 beds 3 baths2,016 sq. ft.301 Doe's Crossing, Middlesboro, KY 40965
MLS# 1328317Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$140,000Pending4 beds 2 baths995 sq. ft.172 Beans Fork Road, Middlesboro, KY 40965
MLS# 26001939Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$89,900Active2 beds 2 baths1,240 sq. ft.816 W Chester Avenue, Middlesboro, KY 40965
MLS# 26001413Listed by: CENTURY 21 PINNACLE
$129,900Active4 beds 2 baths1,908 sq. ft.405 S 37th Street, Middlesboro, KY 40965
MLS# 26000834Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$189,000Pending2 beds 2 baths960 sq. ft.1208 Ky-217, Middlesboro, KY 40965
MLS# 25507211Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$24,900Pending3 beds 2 baths960 sq. ft.13 Duncan Lane, Middlesboro, KY 40965
MLS# 1323130Listed by: TURN KEY REALTY
$240,000Pending3 beds 3 baths1,856 sq. ft.129 Lower Gibson Lane, Middlesboro, KY 40965
MLS# 1316259Listed by: REMAX PROFESSIONAL'S
$85,000Active2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$159,000Pending3 beds 2 baths1,560 sq. ft.63 Old Pineville Pike, Middlesboro, KY 40965
MLS# 1310085Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$158,000Active3 beds 1 baths1,200 sq. ft.180 Stevenson Branch Rd, Middlesboro, KY 40965
MLS# 1301528Listed by: BACKWOODS REALTY & DEVELOPMENT
$490,000Pending7 beds 5 baths6,276 sq. ft.142 Edgewood Rd, Middlesboro, KY 40965
MLS# 1290184Listed by: TURN KEY REALTY
$270,000Active3 beds 3 baths3,174 sq. ft.113 Hollywood Drive, Middlesboro, KY 40965
MLS# 1277166Listed by: COLDWELL BANKER BISCEGLIA REAL
$99,999Active3 beds 2 baths1,296 sq. ft.252 Chasteen Drive, Middlesboro, KY 40965
MLS# 1316842Listed by: REALTY NETWORK, INC
Local realty services provided by:CENTURY 21 Legacy, CENTURY 21 Garner Properties, CENTURY 21 Advantage Realty
Information Deemed Reliable but Not Guaranteed. 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 CENTURY 21 Garner Properties 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. Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved. KY_NKMLS Member Broker: Douglas Garner
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Zip codes near Middlesboro, KY
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.