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Middlesborough, KY - homes for sale
34 of 34 results displayed
$29,000Active0.9 Acres0 Bowling Rd, Middlesboro, KY 40965
MLS# 1344123Listed by: REALTY GROUP
$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
$175,000Active2 beds 1 baths792 sq. ft.815 Dorchester Ave, Middlesboro, KY 40965
MLS# 1343066Listed by: TURN KEY REALTY
$155,000Pending3 beds 1 baths1,104 sq. ft.1807 Winchester Ave, Middlesboro, KY 40965
MLS# 1342793Listed by: REMAX PROFESSIONAL'S
$140,000Active2 beds 1 baths1,008 sq. ft.413 S 26th St, Middlesboro, KY 40965
MLS# 1342457Listed by: TURN KEY REALTY
$215,000Active3 beds 1 baths1,652 sq. ft.116 N Petersborough Ave, Middlesboro, KY 40965
MLS# 1341032Listed by: COLDWELL BANKER BISCEGLIA REAL
$225,000Active3 beds 2 baths1,400 sq. ft.908 Chester Ave, Middlesboro, KY 40965
MLS# 1340728Listed by: REMAX PROFESSIONAL'S
$93,500Active2 beds 2 baths1,426 sq. ft.123 Cawood Lane, Middlesboro, KY 40965
MLS# 1340557Listed by: MOUNTAIN REALTY
$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
$159,000Active-- beds -- baths700 sq. ft.1801 Exeter Ave, Middlesboro, KY 40965
MLS# 1339877Listed by: REALTY GROUP
$249,900Active3 beds 2 baths1,346 sq. ft.913 Doncaster St, Middlesboro, KY 40965
MLS# 1336350Listed by: FATHOM REALTY TN LLC
$239,900Pending4 beds 3 baths2,456 sq. ft.1203 Winchester Ave, Middlesboro, KY 40965
MLS# 1331672Listed by: COLDWELL BANKER BISCEGLIA REAL
$20,000Pending0.3 Acres2503 Exeter Ave, Middlesboro, KY 40965
MLS# 1330573Listed by: REALTY GROUP
$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
$259,000Pending4 beds 3 baths1,832 sq. ft.206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$129,900Active4 beds 2 baths1,908 sq. ft.405 S 37th St, Middlesboro, KY 40965
MLS# 1326276Listed by: COLDWELL BANKER BISCEGLIA REAL
$74,200Pending-- beds -- baths2,256 sq. ft.417-A&B Avondale Ave, Middlesboro, KY 40965
MLS# 1324983Listed by: MOUNTAIN REALTY
$79,000Pending1 beds 1 baths800 sq. ft.923 Winchester Ave, Middlesboro, KY 40965
MLS# 1324643Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$15,000Active0.13 Acres118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965
MLS# 1315958Listed by: REMAX PROFESSIONAL'S
$165,000Active-- beds -- baths4607 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315760Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$85,000Active2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$17,000Pending1.14 Acres0 Home Run Rd, Middlesboro, KY 40965
MLS# 1306547Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$2,500,000Active3 beds 2 baths1,976 sq. ft.259 Watson Lane, Middlesboro, KY 40965
MLS# 1306495Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$275,000Active1.69 Acres321 Chester Ave, Middlesboro, KY 40965
MLS# 1304132Listed by: COLDWELL BANKER BISCEGLIA REAL
$89,000Pending3 beds 1 baths1,296 sq. ft.3028 Highway 441, Middlesboro, KY 40965
MLS# 1302185Listed by: TURN KEY REALTY
$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:Better Homes and Gardens Real Estate Jackson Realty
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
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 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.