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Middlesboro, KY - homes for sale
77 of 77 results displayed
$79,000Pending2 beds 1 baths840 sq. ft.1614 Exeter Ave, Middlesboro, KY 40965
MLS# 1351094Listed by: ACTION REALTY- New
$325,000Active5 beds 2 baths2,664 sq. ft.926 Doncaster Avenue, Middlesboro, KY 40965
MLS# 26021089Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO - New
$270,000Active3 beds 3 baths3,174 sq. ft.113 Hollywood Drive, Middlesboro, KY 40965
MLS# 26020874Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO 
$279,000Active3 beds 3 baths2,210 sq. ft.515 Englewood Road, Middlesboro, KY 40965
MLS# 26020657Listed by: BACKWOODS REALTY & DEVELOPMENT
$455,000Active5 beds 4 baths3,146 sq. ft.523 N 30th Street, Middlesboro, KY 40965
MLS# 26020660Listed by: BACKWOODS REALTY & DEVELOPMENT
$299,000Active4 beds 2 baths2,032 sq. ft.400 Gloucester Avenue, Middlesboro, KY 40965
MLS# 26020497Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$299,000Active4 beds 2 baths2,032 sq. ft.400 Gloucester Ave, Middlesboro, KY 40965
MLS# 1350232Listed by: COLDWELL BANKER BISCEGLIA REAL
$60,000Active3 beds 1 baths768 sq. ft.712 Balmoral Road, Middlesboro, KY 40965
MLS# 26019521Listed by: BLACK DIAMOND REALTY
$19,900Active3 beds 2 baths960 sq. ft.13 Duncan Lane, Middlesboro, KY 40965
MLS# 26019353Listed by: CENTURY 21 PINNACLE
$200,000Active4 beds 2 baths1,612 sq. ft.140 Wellington Drive, Middlesboro, KY 40965
MLS# 1348714Listed by: FATHOM REALTY TN LLC
$200,000Pending3 beds 1 baths1,652 sq. ft.116 N Petersborough Avenue, Middlesboro, KY 40965
MLS# 26018934Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$112,500Pending45 Acres0 Ky-1534, Pineville, KY 40977
MLS# 26018948Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$35,000Pending0.28 Acres904-A E Cumberland Ave, Middlesboro, KY 40965
MLS# 1348564Listed by: COLDWELL BANKER BISCEGLIA REAL
$112,500Pending45 AcresState Highway 1534, Pineville, KY 40977
MLS# 1348318Listed by: COLDWELL BANKER BISCEGLIA REAL
$359,500Active3 beds 2 baths2,000 sq. ft.2909 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1348099Listed by: BACKWOODS REALTY & DEVELOPMENT
$142,500Active2 beds 2 baths1,400 sq. ft.125 Cawood Lane, Middlesboro, KY 40965
MLS# 1346436Listed by: REALTY GROUP
$149,999Active2 beds 1 baths1,275 sq. ft.1010 W Chester, Middlesboro, KY 40965
MLS# 26015402Listed by: FATHOM REALTY KY LLC
$115,000Active2 beds 1 baths1,456 sq. ft.1720 Exeter Avenue, Middlesboro, KY 40965
MLS# 26014807Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$59,000Active2 beds 1 baths920 sq. ft.518 S 43rd St, Middlesboro, KY 40965
MLS# 1345724Listed by: REMAX PROFESSIONAL'S
$110,000Active3 beds 2 baths1,963 sq. ft.901 Exeter Avenue, Middlesboro, KY 40965
MLS# 26014433Listed by: FATHOM REALTY KY LLC
$142,500Active3 beds 2 baths1,100 sq. ft.908 Manchester Avenue, Middlesboro, KY 40965
MLS# 26013710Listed by: ACTION REALTY
$28,000Active0.17 Acres14 Honeycutt Lane, Middlesboro, KY 40965
MLS# 1344549Listed by: REALTY GROUP
$229,500Active6 beds 6 baths2,700 sq. ft.623 N 20th Street, Middlesboro, KY 40965
MLS# 26013646Listed by: CONTINENTAL REAL ESTATE GROUP
$19,000Active1.02 Acres1577 Beans Fork Rd, Middlesboro, KY 40965
MLS# 1344334Listed by: REALTY GROUP
$29,000Active0.9 Acres0 Bowling Rd, Middlesboro, KY 40965
MLS# 1344123Listed by: REALTY GROUP
$200,000Active3 beds 2 baths2,154 sq. ft.116 Edgewood Road, Middlesboro, KY 40965
MLS# 26013326Listed by: BLACK DIAMOND REALTY
$267,500Active5 beds 4 baths3,195 sq. ft.717 S 27th Street, Middlesboro, KY 40965
MLS# 26013256Listed by: RE/MAX LAKETIME REALTY LONDON
$159,000Active4 beds 2 baths1,440 sq. ft.64 Dunlap Hollow Rd, Middlesboro, KY 40965
MLS# 1343957Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$164,900Active2 beds 1 baths792 sq. ft.815 Dorchester Ave, Middlesboro, KY 40965
MLS# 1343066Listed by: BACKWOODS REALTY & DEVELOPMENT
$135,000Active2 beds 1 baths1,008 sq. ft.413 S 26th St, Middlesboro, KY 40965
MLS# 1342457Listed by: BACKWOODS REALTY & DEVELOPMENT
$120,000Active5 beds 4 baths2,844 sq. ft.215 S 21st Street, Middlesboro, KY 40965
MLS# 26011288Listed by: BLACK DIAMOND REALTY
$214,999Pending3 beds 2 baths3,948 sq. ft.2621 Cumberland Avenue, Middlesboro, KY 40965
MLS# 26011050Listed by: KELLER WILLIAMS LEGACY GROUP
$200,000Pending3 beds 1 baths1,652 sq. ft.116 N Petersborough Ave, Middlesboro, KY 40965
MLS# 1341032Listed by: COLDWELL BANKER BISCEGLIA REAL
$83,500Active2 beds 2 baths1,426 sq. ft.123 Cawood Lane, Middlesboro, KY 40965
MLS# 1340557Listed by: MOUNTAIN REALTY
$279,000Active5 beds 3 baths3,068 sq. ft.207 Arthur Heights, Middlesboro, KY 40965
MLS# 26010558Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$45,000Active2 beds 1 baths792 sq. ft.918 E Cumberland Ave, Middlesboro, KY 40965
MLS# 1340131Listed by: REMAX PROFESSIONAL'S
$135,000Active2 beds 1 baths1,120 sq. ft.2002 Winchester Avenue, Middlesboro, KY 40965
MLS# 26010030Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$325,000Active4 beds 3 baths2,488 sq. ft.1015 Old Wilson Lane, Middlesboro, KY 40965
MLS# 26009828Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$125,000Pending4 beds 2 baths1,664 sq. ft.120 Redwood Road #A & B, Middlesboro, KY 40965
MLS# 26005872Listed by: BLACK DIAMOND REALTY
$22,000Active0.17 Acres109 Bloomsbury Avenue, Middlesboro, KY 40965
MLS# 26009366Listed by: BLACK DIAMOND REALTY
$29,000Active0.34 Acres2107 Winchester Avenue, Middlesboro, KY 40965
MLS# 26009102Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$249,000Active3 beds 2 baths2,016 sq. ft.127 Alpine Road, Middlesboro, KY 40965
MLS# 26007901Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$249,900Pending3 beds 2 baths1,346 sq. ft.913 Doncaster St, Middlesboro, KY 40965
MLS# 1336350Listed by: FATHOM REALTY TN LLC
$165,000Pending4 beds 1 baths2,430 sq. ft.713 Exeter Avenue, Middlesboro, KY 40965
MLS# 26007393Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$182,000Active2 beds 2 baths1,608 sq. ft.414 S 24th Street, Middlesboro, KY 40965
MLS# 26007215Listed by: TURN KEY REALTY
$295,000Active5 beds 3 baths2,100 sq. ft.717 Highway 441, Middlesboro, KY 40965
MLS# 26006775Listed by: BLACK DIAMOND REALTY
$50,000Active0.38 Acres0000 Edgewood Road, Middlesboro, KY 40965
MLS# 26006363Listed by: BLACK DIAMOND REALTY
$39,900Active4.24 Acres1197 Beans Fork Road, Middlesboro, KY 40965
MLS# 26006342Listed by: RE/MAX PREFERRED GROUP
$15,000Active0.13 Acres205 Exeter Avenue, Middlesboro, KY 40965
MLS# 26006275Listed by: BLACK DIAMOND REALTY
$35,000Active3 beds 1 baths728 sq. ft.105 Nutwood Road, Middlesboro, KY 40965
MLS# 26005884Listed by: BLACK DIAMOND REALTY
$230,000Active3 beds 2 baths1,320 sq. ft.156 Wellington Drive, Middlesboro, KY 40965
MLS# 26005639Listed by: BLACK DIAMOND REALTY
$575,000Pending4 beds 4 baths3,480 sq. ft.2794 Us Hwy 25 E, Middlesboro, KY 40965
MLS# 1331334Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$369,000Active3 beds 3 baths3,397 sq. ft.103 Kingsbury Woods, Middlesboro, KY 40965
MLS# 26003950Listed by: LISTWITHFREEDOM.COM
$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
$30,000Active1.26 AcresLots 12 & 13 Sams Mountain Rd., Middlesboro, KY 40965
MLS# 1328410Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$229,500Active3 beds 3 baths2,016 sq. ft.301 Doe's Crossing, Middlesboro, KY 40965
MLS# 1328317Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$79,900Active2 beds 2 baths1,240 sq. ft.816 W Chester Avenue, Middlesboro, KY 40965
MLS# 26001413Listed by: CENTURY 21 PINNACLE
$129,900Active4 beds 2 baths1,908 sq. ft.405 S 37th Street, Middlesboro, KY 40965
MLS# 26000834Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$69,900Active-- beds -- baths2,256 sq. ft.417-A&B Avondale Ave, Middlesboro, KY 40965
MLS# 1324983Listed by: MOUNTAIN REALTY
$189,000Pending2 beds 2 baths960 sq. ft.1208 Ky-217, Middlesboro, KY 40965
MLS# 25507211Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$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
$155,000Active-- beds -- baths4607 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315760Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$22,500Active0.36 Acres526 Balmoral Road, Middlesboro, KY 40965
MLS# 25008692Listed by: BLACK DIAMOND REALTY
$285,000Active-- beds -- baths00 Highway 217 & 1344, Middlesboro, KY 40965
MLS# 25018632Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$85,000Pending2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$159,000Pending3 beds 2 baths1,560 sq. ft.63 Old Pineville Pike, Middlesboro, KY 40965
MLS# 1310085Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$250,000Active-- beds -- baths1,500 sq. ft.119 Wagon Hollow Rd, Middlesboro, KY 40965
MLS# 1327234Listed by: BLACK DIAMOND REALTY
$17,000Pending1.14 Acres0 Home Run Rd, Middlesboro, KY 40965
MLS# 1306547Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$275,000Active1.69 Acres321 Chester Avenue, Middlesboro, KY 40965
MLS# 25012296Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$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
$97,000Active3 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, Better Homes and Gardens Real Estate Fern Leaf Group
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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.