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Middlesborough, KY - single-family homes for sale
22 of 22 results displayed
- New
$225,000Active2 beds 3 baths960 sq. ft.615 S 22nd Street, Middlesboro, KY 40965
MLS# 26003147Listed by: BLACK DIAMOND REALTY - New
$455,000Active5 beds 4 baths3,146 sq. ft.523 N 30th St, Middlesboro, KY 40965
MLS# 1330109Listed by: TURN KEY REALTY 
$105,000Pending3 beds 2 baths1,056 sq. ft.925 Winchester Ave, Middlesboro, KY 40965
MLS# 1329979Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$139,900Pending3 beds 2 baths1,680 sq. ft.2523 Exeter Avenue, Middlesboro, KY 40965
MLS# 26002575Listed by: THRESHOLD REAL ESTATE SERVICES
$140,000Pending4 beds 2 baths995 sq. ft.172 Beans Fork Road, Middlesboro, KY 40965
MLS# 26001939Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$259,000Active4 beds 3 baths1,832 sq. ft.206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$115,000Active2 beds 2 baths1,240 sq. ft.816 W Chester Avenue, Middlesboro, KY 40965
MLS# 26001413Listed by: CENTURY 21 PINNACLE
$159,900Active4 beds 2 baths1,908 sq. ft.405 S 37th Street, Middlesboro, KY 40965
MLS# 26000834Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$44,000Pending3 beds 2 baths1,230 sq. ft.406 Rochester Avenue, Middlesboro, KY 40965
MLS# 26000523Listed by: BLACK DIAMOND REALTY
$24,900Pending3 beds 2 baths960 sq. ft.13 Duncan Lane, Middlesboro, KY 40965
MLS# 1323130Listed by: TURN KEY REALTY
$159,900Pending3 beds 2 baths934 sq. ft.45 Fourmile Run Road, Middlesboro, KY 40965
MLS# 25506029Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$194,500Active3 beds 2 baths1,375 sq. ft.280 Parker Lane, Middlesboro, KY 40965
MLS# 1319571Listed by: REALTY GROUP
$130,000Active3 beds 1 baths792 sq. ft.918 E Cumberland Avenue, Middlesboro, KY 40965
MLS# 25504336Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$79,900Pending3 beds 2 baths1,848 sq. ft.72 Happy Hollow Hill Road, Middlesboro, KY 40965
MLS# 25504175Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$155,000Pending2 beds 1 baths1,088 sq. ft.123 Upper Gibson Lane, Middlesboro, KY 40965
MLS# 25502716Listed by: BLACK DIAMOND REALTY
$329,900Active5 beds 3 baths2,250 sq. ft.805 Worchester Ave, Middlesboro, KY 40965
MLS# 1315952Listed by: REMAX PROFESSIONAL'S
$165,000Pending3 beds 2 baths1,056 sq. ft.4605 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315630Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$68,000Pending2 beds 1 baths1,456 sq. ft.1720 Exeter Ave, Middlesboro, KY 40965
MLS# 1315173Listed by: REALTY GROUP
$359,000Active4 beds 3 baths3,885 sq. ft.2702 Cumberland Avenue, Middlesboro, KY 40965
MLS# 25500647Listed by: DIY FLAT FEE.COM
$319,900Active6 beds 4 baths4,033 sq. ft.832 N 25th Street, Middlesboro, KY 40965
MLS# 25011376Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$229,900Active4 beds 3 baths2,455 sq. ft.1203 Winchester Avenue, Middlesboro, KY 40965
MLS# 25017682Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$490,000Pending7 beds 5 baths6,276 sq. ft.142 Edgewood Rd, Middlesboro, KY 40965
MLS# 1290184Listed by: TURN KEY REALTY
Local realty services provided by:CENTURY 21 Pinnacle, CENTURY 21 Legacy
Neighborhoods near Middlesborough, KY
Zip codes near Middlesborough, KY
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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.
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.