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Middlesboro, KY - single-family homes for sale
35 of 35 results displayed
- New
$142,000Active3 beds 1 baths1,404 sq. ft.708 W Chester Ave, Middlesboro, KY 40965
MLS# 1328773Listed by: REMAX PROFESSIONAL'S - New
$249,000Active3 beds 3 baths2,016 sq. ft.301 Doe's Crossing, Middlesboro, KY 40965
MLS# 1328317Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE 
$197,000Active3 beds 2 baths1,238 sq. ft.1200 W Chester Ave, Middlesboro, KY 40965
MLS# 1327952Listed by: COLDWELL BANKER BISCEGLIA REAL
$279,000Active4 beds 3 baths1,832 sq. ft.206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$150,000Active2 beds 1 baths952 sq. ft.359 Beans Fork Rd, Middlesboro, KY 40965
MLS# 1327412Listed by: REALTY GROUP
$165,000Pending2 beds 2 baths1,326 sq. ft.103 Leafwood Rd, Middlesboro, KY 40965
MLS# 1326703Listed by: REMAX PROFESSIONAL'S
$159,900Active4 beds 2 baths1,908 sq. ft.405 S 37th St, Middlesboro, KY 40965
MLS# 1326276Listed by: COLDWELL BANKER BISCEGLIA REAL
$199,000Active3 beds 2 baths1,400 sq. ft.908 Chester Ave, Middlesboro, KY 40965
MLS# 1325838Listed by: REMAX PROFESSIONAL'S
$369,900Pending4 beds 4 baths2,684 sq. ft.409 Fairview Rd, Middlesboro, KY 40965
MLS# 1324858Listed by: COLDWELL BANKER BISCEGLIA REAL
$99,000Active1 beds 1 baths800 sq. ft.923 Winchester Ave, Middlesboro, KY 40965
MLS# 1324643Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$249,900Active3 beds 2 baths1,612 sq. ft.140 Wellington Drive, Middlesboro, KY 40965
MLS# 1323746Listed by: FATHOM REALTY TN LLC
$525,000Active5 beds 3 baths2,542 sq. ft.2004 Twin Fawn Tr, Middlesboro, KY 40965
MLS# 1323538Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$24,900Active3 beds 2 baths960 sq. ft.13 Duncan Lane, Middlesboro, KY 40965
MLS# 1323130Listed by: TURN KEY REALTY
$79,900Pending3 beds 2 baths1,848 sq. ft.72 Happy Hollow Hill Rd, Middlesboro, KY 40965
MLS# 1319819Listed by: COLDWELL BANKER BISCEGLIA REAL
$232,500Active3 beds 2 baths1,900 sq. ft.4921 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1319805Listed by: MOUNTAIN REALTY
$210,000Active3 beds 2 baths1,375 sq. ft.280 Parker Lane, Middlesboro, KY 40965
MLS# 1319571Listed by: REALTY GROUP
$195,000Pending3 beds 2 baths1,800 sq. ft.140 Chasteen Drive, Middlesboro, KY 40965
MLS# 1319433Listed by: COLDWELL BANKER BISCEGLIA REAL
$249,900Active3 beds 2 baths1,200 sq. ft.807 Exeter Ave, Middlesboro, KY 40965
MLS# 1316511Listed by: FATHOM REALTY TN LLC
$240,000Active3 beds 3 baths1,856 sq. ft.129 Lower Gibson Lane, Middlesboro, KY 40965
MLS# 1316259Listed by: REMAX PROFESSIONAL'S
$334,900Active5 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
$68,000Active2 beds 1 baths1,456 sq. ft.1720 Exeter Ave, Middlesboro, KY 40965
MLS# 1315173Listed by: REALTY GROUP
$229,900Active4 beds 3 baths2,456 sq. ft.1203 Winchester Ave, Middlesboro, KY 40965
MLS# 1311840Listed by: COLDWELL BANKER BISCEGLIA REAL
$100,000Active2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$185,000Active3 beds 2 baths1,560 sq. ft.63 Old Pineville Pike, Middlesboro, KY 40965
MLS# 1310085Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$285,000Pending3 beds 3 baths2,512 sq. ft.440 Sams Mountain, Middlesboro, KY 40965
MLS# 1307361Listed by: REMAX PROFESSIONAL'S
$2,500,000Active3 beds 2 baths1,976 sq. ft.259 Watson Lane, Middlesboro, KY 40965
MLS# 1306495Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$89,000Pending3 beds 1 baths1,296 sq. ft.3028 Highway 441, Middlesboro, KY 40965
MLS# 1302185Listed by: TURN KEY REALTY
$145,000Pending3 beds 2 baths648 sq. ft.138 Robinson Lane, Middlesboro, KY 40965
MLS# 1301207Listed by: TURN KEY REALTY
$179,900Active3 beds 1 baths1,200 sq. ft.180 Stevenson Branch Rd, Middlesboro, KY 40965
MLS# 1301528Listed by: TURN KEY REALTY
$115,000Active3 beds 2 baths1,344 sq. ft.921 Winchester Ave, Middlesboro, KY 40965
MLS# 1293786Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$490,000Pending7 beds 5 baths6,276 sq. ft.142 Edgewood Rd, Middlesboro, KY 40965
MLS# 1290184Listed by: TURN KEY REALTY
$198,500Active2 beds 2 baths1,144 sq. ft.505 S South 38th St St, Middlesboro, KY 40965
MLS# 1284881Listed by: TURN KEY REALTY
$299,000Active3 beds 3 baths3,174 sq. ft.113 Hollywood Drive, Middlesboro, KY 40965
MLS# 1277166Listed by: COLDWELL BANKER BISCEGLIA REAL
$109,000Active3 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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Zip codes near Middlesboro, KY
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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.