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Middlesborough, KY - homes for sale
37 of 37 results displayed
- New
$215,000Active3 beds 2 baths1,800 sq. ft.140 Chasteen Drive, Middlesboro, KY 40965
MLS# 1319433Listed by: COLDWELL BANKER BISCEGLIA REAL 
$30,000Pending2 AcresArie Turner Lane, Middlesboro, KY 40965
MLS# 1316784Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$249,900Active3 beds 2 baths1,200 sq. ft.807 Exeter Ave, Middlesboro, KY 40965
MLS# 1316511Listed by: AAA REALTY, INC.
$249,900Active3 beds 3 baths1,856 sq. ft.129 Lower Gibson Lane, Middlesboro, KY 40965
MLS# 1316259Listed by: REMAX PROFESSIONAL'S
$275,000Pending3 beds 2 baths2,008 sq. ft.115 George Ann Drive, Middlesboro, KY 40965
MLS# 1316053Listed by: TURN KEY REALTY
$20,000Active0.13 Acres118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965
MLS# 1315958Listed by: REMAX PROFESSIONAL'S
$349,900Active5 beds 3 baths2,250 sq. ft.805 Worchester Ave, Middlesboro, KY 40965
MLS# 1315952Listed by: REMAX PROFESSIONAL'S
$75,000Active2 beds 1 baths1,456 sq. ft.1720 Exeter Ave, Middlesboro, KY 40965
MLS# 1315173Listed by: REALTY GROUP
$249,900Active4 beds 3 baths2,456 sq. ft.1203 Winchester Ave, Middlesboro, KY 40965
MLS# 1311840Listed by: COLDWELL BANKER BISCEGLIA REAL
$49,900Active0.34 Acres1107 Winchester Ave, Middlesboro, KY 40965
MLS# 1311846Listed by: COLDWELL BANKER BISCEGLIA REAL
$100,000Active2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$98,000Active3 beds 2 baths1,104 sq. ft.101 Earle Lane, Middlesboro, KY 40965
MLS# 1311097Listed by: REMAX PROFESSIONAL'S
$179,000Active3 beds 2 baths1,800 sq. ft.3008 State Highway 441, Middlesboro, KY 40965
MLS# 1310673Listed by: TURN KEY REALTY
$299,000Active3 beds 4 baths2,349 sq. ft.915 Lothbury Ave, Middlesboro, KY 40965
MLS# 1309393Listed by: TURN KEY REALTY
$154,900Pending3 beds 1 baths1,320 sq. ft.428 Wilderness Rd, Middlesboro, KY 40965
MLS# 1308272Listed by: TURN KEY REALTY
$17,000Active1.14 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
$180,000Active3 beds 2 baths1,312 sq. ft.708 Ilchester Ave, Middlesboro, KY 40965
MLS# 1306070Listed by: REMAX PROFESSIONAL'S
$184,900Active4 beds 2 baths1,120 sq. ft.409 Meadow Lane, Middlesboro, KY 40965
MLS# 1305300Listed by: TURN KEY REALTY
$190,000Active3 beds 2 baths1,456 sq. ft.626 S 22nd St, Middlesboro, KY 40965
MLS# 1303280Listed by: REALTY GROUP
$349,900Active1.69 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
$145,000Pending3 beds 2 baths648 sq. ft.138 Robinson Lane, Middlesboro, KY 40965
MLS# 1301207Listed by: TURN KEY REALTY
$458,000Active5 beds 4 baths3,146 sq. ft.523 N 30th St, Middlesboro, KY 40965
MLS# 1299951Listed by: TURN KEY REALTY
$249,900Pending4 beds 3 baths2,020 sq. ft.825 S 28th Street, Middlesboro, KY 40965
MLS# 1298148Listed by: COLDWELL BANKER BISCEGLIA REAL
$185,000Pending3 beds 1 baths2,000 sq. ft.515 N 25th St, Middlesboro, KY 40965
MLS# 1297570Listed by: REALTY GROUP
$650,000Active2 beds 1 baths776 sq. ft.516 S 34th St, Middlesboro, KY 40965
MLS# 1293374Listed by: REMAX PROFESSIONAL'S
$110,000Active2 beds 1 baths1,008 sq. ft.413 S 26th St, Middlesboro, KY 40965
MLS# 1290233Listed by: TURN KEY REALTY
$490,000Pending7 beds 5 baths6,276 sq. ft.142 Edgewood Rd, Middlesboro, KY 40965
MLS# 1290184Listed by: TURN KEY REALTY
$225,000Active2 beds 2 baths1,144 sq. ft.505 S South 38th St St, Middlesboro, KY 40965
MLS# 1284881Listed by: TURN KEY REALTY
$157,000Active3 beds 1 baths1,110 sq. ft.1005 Hollywood Drive, Middlesboro, KY 40965
MLS# 1283319Listed by: HEARTLAND REAL ESTATE, LLC
$299,000Pending3 beds 3 baths3,544 sq. ft.109 Hollywood Drive, Middlesboro, KY 40965
MLS# 1280901Listed by: COLDWELL BANKER BISCEGLIA REAL
$299,000Active3 beds 3 baths3,174 sq. ft.113 Hollywood Drive, Middlesboro, KY 40965
MLS# 1277166Listed by: COLDWELL BANKER BISCEGLIA REAL
$279,900Active3 beds 3 baths2,210 sq. ft.515 Englewood Rd, Middlesboro, KY 40965
MLS# 1309140Listed by: TURN KEY REALTY
$209,900Active3 beds 2 baths1,684 sq. ft.1315 Winchester Ave, Middlesboro, KY 40965
MLS# 1305513Listed by: AAA REALTY, INC.
$119,000Active3 beds 2 baths1,296 sq. ft.252 Chasteen Drive, Middlesboro, KY 40965
MLS# 1316842Listed by: REALTY NETWORK, INC
$600,000Active2.5 Acres00 00-us 25e Pineville Hwy, Middlesboro, KY 40965
MLS# 1120773Listed by: TURN KEY REALTY
Local realty services provided by:Better Homes and Gardens Real Estate Gwin Realty
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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 with an American Home Shield© home warranty. Learn more© 2025 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.