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Middlesboro, KY - homes for sale
85 of 85 results displayed
- New
$315,000Active4 beds 3 baths2,488 sq. ft.1015 Old Wilson Lane, Middlesboro, KY 40965
MLS# 1356915Listed by: REALTY GROUP - New
$145,900Active3 beds 2 baths1,386 sq. ft.810 W Rochester Ave, Middlesboro, KY 40965
MLS# 1356828Listed by: HEARTLAND REAL ESTATE, LLC - New
$158,000Active3 beds 1 baths1,200 sq. ft.180 Stevenson Branch Rd, Middlesboro, KY 40965
MLS# 1356645Listed by: BACKWOODS REALTY & DEVELOPMENT - New
$175,000Active2 beds 1 baths700 sq. ft.1801 & 1801 1/2 Exeter Avenue, Middlesboro, KY 40965
MLS# 26026368Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE - New
$299,900Active4 beds 3 baths2,968 sq. ft.412 Englewood Road, Middlesboro, KY 40965
MLS# 26026235Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO - New
$1,750,000Active0.5 Acres113 N 18th St, Middlesboro, KY 40965
MLS# 1356342Listed by: REALTY GROUP - New
$158,000Active2 beds 1 baths876 sq. ft.305 N 15th St, Middlesboro, KY 40965
MLS# 1356312Listed by: REMAX PROFESSIONAL'S - New
$139,000Active5.33 Acres312 Blakely Lane, Middlesboro, KY 40965
MLS# 26025959Listed by: MOUNTAIN REALTY GROUP LLC 
$99,900Pending3 beds 3 baths2,800 sq. ft.141 Lick Fork Road, Middlesboro, KY 40965
MLS# 26025732Listed by: CONTINENTAL REAL ESTATE GROUP
$175,000Pending - Continue To Show4 beds 2 baths1,590 sq. ft.808 N 28th St, Middlesboro, KY 40965
MLS# 1355737Listed by: REALTY GROUP
$475,000Active5 beds 3 baths2,542 sq. ft.2004 Twin Fawn Tr, Middlesboro, KY 40965
MLS# 1355491Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$105,900Active3 beds 2 baths1,966 sq. ft.412 N 24th Street, Middlesboro, KY 40965
MLS# 26025309Listed by: TURN KEY REALTY
$175,000Active3 beds 2 baths1,168 sq. ft.8 Castleford Way, Middlesboro, KY 40965
MLS# 26025315Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$575,000Active3 beds 2 baths2,016 sq. ft.2010 Twin Fawn Trail, Middlesboro, KY 40965
MLS# 1355383Listed by: BACKWOODS REALTY & DEVELOPMENT
$15,000Pending - Continue To Show0.29 Acres23 Martin Lane, Middlesboro, KY 40965
MLS# 1355171Listed by: REALTY GROUP
$60,000Pending3 beds 2 baths1,490 sq. ft.834 S 31st Street, Middlesboro, KY 40965
MLS# 26024908Listed by: JOANN BAKER & ASSOCIATES
$129,000Active3 beds 1 baths1,404 sq. ft.708 W Chester Ave, Middlesboro, KY 40965
MLS# 1354572Listed by: REMAX PROFESSIONAL'S
$235,000Active3 beds 2 baths1,400 sq. ft.800 S 28th St, Middlesboro, KY 40965
MLS# 1354108Listed by: REMAX PROFESSIONAL'S
$119,900Active3 beds 2 baths1,260 sq. ft.706 Ilchester Ave, Middlesboro, KY 40965
MLS# 1353618Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$39,900Pending3.69 AcresLot 103 Doe's Crossing, Middlesboro, KY 40965
MLS# 1353110Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$215,000Active3 beds 2 baths1,352 sq. ft.209 S 19th Street, Middlesboro, KY 40965
MLS# 26022968Listed by: BLACK DIAMOND REALTY
$219,000Active4 beds 2 baths1,544 sq. ft.812 Worchester Ave, Middlesboro, KY 40965
MLS# 1352799Listed by: REALTY GROUP
$199,000Active3 beds 1 baths1,480 sq. ft.1102 W Chester Avenue, Middlesboro, KY 40965
MLS# 26022803Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$299,000Active6 beds 4 baths3,594 sq. ft.312 W Chester Avenue, Middlesboro, KY 40965
MLS# 26022575Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$17,000Active2 beds 1 baths936 sq. ft.110 Danbury Ave, Middlesboro, KY 40965
MLS# 1352038Listed by: REALTY GROUP
$79,000Pending - Continue To Show2 beds 1 baths840 sq. ft.1614 Exeter Ave, Middlesboro, KY 40965
MLS# 1351094Listed by: ACTION REALTY
$299,900Active5 beds 2 baths2,664 sq. ft.926 Doncaster Avenue, Middlesboro, KY 40965
MLS# 26021089Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$270,000Pending3 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
$279,000Active4 beds 2 baths2,032 sq. ft.400 Gloucester Avenue, Middlesboro, KY 40965
MLS# 26020497Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$279,000Active4 beds 2 baths2,032 sq. ft.400 Gloucester Ave, Middlesboro, KY 40965
MLS# 1350232Listed by: COLDWELL BANKER BISCEGLIA REAL
$19,900Pending3 beds 2 baths960 sq. ft.13 Duncan Lane, Middlesboro, KY 40965
MLS# 26019353Listed by: CENTURY 21 PINNACLE
$199,900Active4 beds 2 baths1,612 sq. ft.140 Wellington Drive, Middlesboro, KY 40965
MLS# 1348714Listed by: FATHOM REALTY TN LLC
$112,500Pending45 Acres0 Ky-1534, Pineville, KY 40977
MLS# 26018948Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$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
$135,000Active2 beds 2 baths1,400 sq. ft.125 Cawood Lane, Middlesboro, KY 40965
MLS# 1346436Listed by: REALTY GROUP
$59,000Active2 beds 1 baths920 sq. ft.518 S 43rd St, Middlesboro, KY 40965
MLS# 1345724Listed by: REMAX PROFESSIONAL'S
$110,000Pending3 beds 2 baths1,963 sq. ft.901 Exeter Avenue, Middlesboro, KY 40965
MLS# 26014433Listed by: FATHOM REALTY KY LLC
$229,500Active6 beds 6 baths2,700 sq. ft.623 N 20th Street, Middlesboro, KY 40965
MLS# 26013646Listed by: CONTINENTAL REAL ESTATE 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
$227,000Pending5 beds 4 baths3,195 sq. ft.717 S 27th Street, Middlesboro, KY 40965
MLS# 26013256Listed by: RE/MAX LAKETIME REALTY LONDON
$149,000Active4 beds 2 baths1,440 sq. ft.64 Dunlap Hollow Rd, Middlesboro, KY 40965
MLS# 1343957Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$155,000Active2 beds 1 baths792 sq. ft.815 Dorchester Ave, Middlesboro, KY 40965
MLS# 1343066Listed by: BACKWOODS REALTY & DEVELOPMENT
$135,000Pending - Continue To Show - Inspection2 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
$70,000Active2 beds 2 baths1,426 sq. ft.123 Cawood Lane, Middlesboro, KY 40965
MLS# 1340557Listed by: MOUNTAIN REALTY
$264,900Active5 beds 3 baths3,068 sq. ft.207 Arthur Heights, Middlesboro, KY 40965
MLS# 26010558Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$35,000Active2 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
$125,000Pending4 beds 2 baths1,664 sq. ft.120 Redwood Road #A & B, Middlesboro, KY 40965
MLS# 26005872Listed by: BLACK DIAMOND REALTY
$21,000Active0.17 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
$349,900Pending3 beds 2 baths2,126 sq. ft.3306 W Cumberland Avenue, Middlesboro, KY 40965
MLS# 26006987Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$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
$35,000Pending3 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
$575,000Pending - Continue To Show - Financing4 beds 4 baths3,480 sq. ft.2794 Us Hwy 25 E, Middlesboro, KY 40965
MLS# 1331334Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$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
$140,000Pending4 beds 2 baths995 sq. ft.172 Beans Fork Road, Middlesboro, KY 40965
MLS# 26001939Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$79,900Pending2 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
$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
$149,900Pending-- beds -- baths4607 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315760Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$1,250,000Pending64.84 Acres423 N 10th Street, Middlesboro, KY 40965
MLS# 23023309Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$189,000Pending2 beds 2 baths960 sq. ft.1208 Hwy 217 Highway #217, Middlesboro, KY 40965
MLS# 24013050Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$598,000Active3 Acres0 Us Highway 25, Middlesboro, KY 40965
MLS# 25008609Listed by: SALLIE DAVIDSON, REALTORS
$22,500Active0.36 Acres526 Balmoral Road, Middlesboro, KY 40965
MLS# 25008692Listed by: BLACK DIAMOND REALTY
$85,000Pending2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$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
$595,000Active7 beds 5 baths6,276 sq. ft.142 Edgewood Rd, Middlesboro, KY 40965
MLS# 1290184Listed by: BACKWOODS REALTY & DEVELOPMENT
$270,000Pending - Continue To Show3 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:CENTURY 21 Legacy, CENTURY 21 Simpson & Associates
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.