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Middlesboro, KY - homes for sale
51 of 51 results displayed
- New
$249,900Active4 beds 3 baths2,456 sq. ft.1203 Winchester Ave, Middlesboro, KY 40965
MLS# 1311840Listed by: COLDWELL BANKER BISCEGLIA REAL - New
$49,900Active0.34 Acres1107 Winchester Ave, Middlesboro, KY 40965
MLS# 1311846Listed by: COLDWELL BANKER BISCEGLIA REAL - New
$169,000Active2 beds 1 baths952 sq. ft.102 Stone Creek Drive, Middlesboro, KY 40965
MLS# 1311715Listed by: REALTY GROUP 
$199,900Pending2 beds 2 baths1,059 sq. ft.206 Nottingham Drive, Middlesboro, KY 40965
MLS# 1311264Listed by: REMAX PROFESSIONAL'S- New
$105,000Active2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S - New
$105,000Active3 beds 2 baths1,104 sq. ft.101 Earle Lane, Middlesboro, KY 40965
MLS# 1311097Listed by: REMAX PROFESSIONAL'S 
$200,000Active3 beds 2 baths1,800 sq. ft.3008 State Highway 441, Middlesboro, KY 40965
MLS# 1310673Listed by: TURN KEY REALTY
$185,000Pending4 beds 2 baths1,600 sq. ft.414 SE North 24th St, Middlesboro, KY 40965
MLS# 1309991Listed by: TURN KEY REALTY
$199,900Active3 beds 2 baths1,560 sq. ft.63 Old Pineville Pike, Middlesboro, KY 40965
MLS# 1310085Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$185,000Pending4 beds 2 baths2,024 sq. ft.919 Rochester Ave, Middlesboro, KY 40965
MLS# 1309987Listed by: TURN KEY REALTY
$299,000Active3 beds 4 baths2,349 sq. ft.915 Lothbury Ave, Middlesboro, KY 40965
MLS# 1309393Listed by: TURN KEY REALTY
$249,900Active3 beds 2 baths1,221 sq. ft.5 Abbey Lane, Middlesboro, KY 40965
MLS# 1309187Listed by: COLDWELL BANKER BISCEGLIA REAL
$48,000Active3 beds 1 baths1,344 sq. ft.510 Chester Ave, Middlesboro, KY 40965
MLS# 1309021Listed by: REALTY GROUP
$159,000Active3 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
$284,900Pending3 beds 2 baths2,096 sq. ft.10 Thaxted Lane, Middlesboro, KY 40965
MLS# 1306135Listed by: COLDWELL BANKER BISCEGLIA REAL
$205,000Active3 beds 2 baths1,312 sq. ft.708 Ilchester Ave, Middlesboro, KY 40965
MLS# 1306070Listed by: REMAX PROFESSIONAL'S
$50,000Pending2 Acres739 Hwy 441, Middlesboro, KY 40965
MLS# 1306059Listed by: AAA REALTY, INC.
$399,000Pending4 beds 3 baths2,500 sq. ft.2824 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1305849Listed by: REMAX PROFESSIONAL'S
$189,000Active4 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
$275,000Pending4 beds 2 baths1,950 sq. ft.709 Balmoral Rd, Middlesboro, KY 40965
MLS# 1304232Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$349,900Active1.69 Acres321 Chester Ave, Middlesboro, KY 40965
MLS# 1304132Listed by: COLDWELL BANKER BISCEGLIA REAL
$184,999Active3 beds 1 baths996 sq. ft.105 Mudlick Rd, Middlesboro, KY 40965
MLS# 1302435Listed by: REALTY NETWORK, INC
$89,000Pending3 beds 1 baths1,296 sq. ft.3028 Highway 441, Middlesboro, KY 40965
MLS# 1302185Listed by: TURN KEY REALTY
$314,900Active3 beds 2 baths2,270 sq. ft.900 Twin Fawn Trail, Middlesboro, KY 40965
MLS# 1300789Listed by: REALTY GROUP
$145,000Active3 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
$249,900Active3 beds 2 baths1,900 sq. ft.4921 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1301589Listed by: REMAX PROFESSIONAL'S
$60,000Pending3 beds 1 baths1,100 sq. ft.515 Winchester Ave, Middlesboro, KY 40965
MLS# 1301631Listed by: REALTY GROUP
$458,000Active5 beds 4 baths3,146 sq. ft.523 N 30th St, Middlesboro, KY 40965
MLS# 1299951Listed by: TURN KEY REALTY
$249,900Active4 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
$249,900Pending3 beds 2 baths1,989 sq. ft.4922 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1295519Listed by: COLDWELL BANKER BISCEGLIA REAL
$115,000Active3 beds 2 baths1,344 sq. ft.921 Winchester Ave, Middlesboro, KY 40965
MLS# 1293786Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$650,000Active2 beds 1 baths776 sq. ft.516 S 34th St, Middlesboro, KY 40965
MLS# 1293374Listed by: REMAX PROFESSIONAL'S
$192,900Active3 beds 2 baths1,408 sq. ft.106 S 38th Street, Middlesboro, KY 40965
MLS# 1292147Listed by: COLDWELL BANKER BISCEGLIA REAL
$110,000Pending2 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
$24,000Active1.46 AcresLot 13 Venado Drive, Middlesboro, KY 40965
MLS# 1280147Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$299,000Active3 beds 3 baths3,174 sq. ft.113 Hollywood Drive, Middlesboro, KY 40965
MLS# 1277166Listed by: COLDWELL BANKER BISCEGLIA REAL
$289,900Active5 beds 4 baths3,000 sq. ft.2410 Cumberland Ave, Middlesboro, KY 40965
MLS# 1274726Listed by: COLDWELL BANKER BISCEGLIA REAL
$289,900Active3 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.
$1,250,000Pending64.84 Acres423 N 10th St, Middlesboro, KY 40965
MLS# 1247661Listed by: COLDWELL BANKER BISCEGLIA REAL
$1,200,000Active3.2 Acres2794 E E Us-25, Middlesboro, KY 40965
MLS# 1244871Listed by: COLDWELL BANKER BISCEGLIA REAL
$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 Jackson Realty
Neighborhoods near Middlesboro, KY
Zip codes near Middlesboro, KY
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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.