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40965, KY - homes for sale
62 of 62 results displayed
- New
$210,000Active3 beds 1 baths728 sq. ft.105, 103, 120 Nutwood Road #A & B, Middlesboro, KY 40965
MLS# 26006515Listed by: BLACK DIAMOND REALTY - New
$50,000Active0.38 Acres0000 Edgewood Road, Middlesboro, KY 40965
MLS# 26006363Listed by: BLACK DIAMOND REALTY - New
$59,900Active4.24 Acres1197 Beans Fork Road, Middlesboro, KY 40965
MLS# 26006342Listed by: RE/MAX PREFERRED GROUP - New
$20,000Active0.13 Acres205 Exeter Avenue, Middlesboro, KY 40965
MLS# 26006275Listed by: BLACK DIAMOND REALTY - New
$30,000Active2 beds 1 baths1,244 sq. ft.103 Nutwood Road, Middlesboro, KY 40965
MLS# 26005898Listed by: BLACK DIAMOND REALTY - New
$50,000Active3 beds 1 baths728 sq. ft.105 Nutwood Road, Middlesboro, KY 40965
MLS# 26005884Listed by: BLACK DIAMOND REALTY - New
$175,000Active4 beds 2 baths1,664 sq. ft.102 Redwood Road #A & B, Middlesboro, KY 40965
MLS# 26005872Listed by: BLACK DIAMOND REALTY - New
$245,000Active3 beds 2 baths1,320 sq. ft.156 Wellington Drive, Middlesboro, KY 40965
MLS# 26005639Listed by: BLACK DIAMOND REALTY 
$229,000Pending3 beds 3 baths2,000 sq. ft.810 Worchester Ave, Middlesboro, KY 40965
MLS# 1333149Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$239,900Active4 beds 3 baths2,455 sq. ft.1203 Winchester Avenue, Middlesboro, KY 40965
MLS# 26004238Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$202,500Active3 beds 2 baths1,080 sq. ft.23 Castleford Way, Middlesboro, KY 40965
MLS# 1331558Listed by: TURN KEY 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
$399,000Active3 beds 3 baths3,397 sq. ft.103 Kingsbury Woods, Middlesboro, KY 40965
MLS# 26003950Listed by: LISTWITHFREEDOM.COM
$25,000Active0.3 Acres2503 Exeter Ave, Middlesboro, KY 40965
MLS# 1330573Listed by: REALTY GROUP
$455,000Active5 beds 4 baths3,146 sq. ft.523 N 30th St, Middlesboro, KY 40965
MLS# 1330109Listed by: TURN KEY REALTY
$105,000Pending3 beds 2 baths1,056 sq. ft.925 Winchester Ave, Middlesboro, KY 40965
MLS# 1329979Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$168,000Pending4 beds 2 baths1,120 sq. ft.409 Meadow Lane, Middlesboro, KY 40965
MLS# 1329538Listed by: TURN KEY REALTY
$139,900Pending3 beds 2 baths1,680 sq. ft.2523 Exeter Avenue, Middlesboro, KY 40965
MLS# 26002575Listed by: THRESHOLD REAL ESTATE SERVICES
$142,000Active3 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
$249,000Active3 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
$259,000Active4 beds 3 baths1,832 sq. ft.206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$148,000Pending2 beds 1 baths952 sq. ft.359 Beans Fork Rd, Middlesboro, KY 40965
MLS# 1327412Listed by: REALTY GROUP
$139,000Active5.33 Acres312 Blakely Lane, Middlesboro, KY 40965
MLS# 26001499Listed by: ACTION REALTY
$115,000Active2 beds 2 baths1,240 sq. ft.816 W Chester Avenue, Middlesboro, KY 40965
MLS# 26001413Listed by: CENTURY 21 PINNACLE
$159,900Active4 beds 2 baths1,908 sq. ft.405 S 37th Street, Middlesboro, KY 40965
MLS# 26000834Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$44,000Pending3 beds 2 baths1,230 sq. ft.406 Rochester Avenue, Middlesboro, KY 40965
MLS# 26000523Listed by: BLACK DIAMOND REALTY
$79,900Active-- beds -- baths2,256 sq. ft.417-A&B Avondale Ave, Middlesboro, KY 40965
MLS# 1324983Listed by: MOUNTAIN REALTY
$99,000Active1 beds 1 baths800 sq. ft.923 Winchester Ave, Middlesboro, KY 40965
MLS# 1324643Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$195,000Active3 beds 1 baths1,100 sq. ft.11 Castleford Way, Middlesboro, KY 40965
MLS# 25508059Listed by: KENTUCKY LAND AND HOME
$249,900Active3 beds 2 baths1,612 sq. ft.140 Wellington Drive, Middlesboro, KY 40965
MLS# 1323746Listed by: FATHOM REALTY TN LLC
$499,000Active5 beds 3 baths2,542 sq. ft.2004 Twin Fawn Tr, Middlesboro, KY 40965
MLS# 1323538Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$130,000Active3 beds 1 baths792 sq. ft.918 E Cumberland Avenue, Middlesboro, KY 40965
MLS# 25504336Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$79,900Pending3 beds 2 baths1,848 sq. ft.72 Happy Hollow Hill Road, Middlesboro, KY 40965
MLS# 25504175Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$155,000Pending2 beds 1 baths1,088 sq. ft.123 Upper Gibson Lane, Middlesboro, KY 40965
MLS# 25502716Listed by: BLACK DIAMOND REALTY
$249,900Active3 beds 2 baths1,200 sq. ft.807 Exeter Ave, Middlesboro, KY 40965
MLS# 1316511Listed by: FATHOM REALTY TN LLC
$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
$324,900Pending5 beds 3 baths2,250 sq. ft.805 Worchester Ave, Middlesboro, KY 40965
MLS# 1315952Listed by: REMAX PROFESSIONAL'S
$189,000Active-- beds -- baths4607 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315760Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$165,000Pending3 beds 2 baths1,056 sq. ft.4605 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1315630Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$68,000Pending2 beds 1 baths1,456 sq. ft.1720 Exeter Ave, Middlesboro, KY 40965
MLS# 1315173Listed by: REALTY GROUP
$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
$19,900Active2.32 AcresLOT 9 Brush Mountain Circle, Middlesboro, KY 40856
MLS# 25010902Listed by: CENTURY 21 ADVANTAGE REALTY
$22,500Active0.36 Acres526 Balmoral Road, Middlesboro, KY 40965
MLS# 25008692Listed by: BLACK DIAMOND REALTY
$319,900Pending6 beds 4 baths4,033 sq. ft.832 N 25th Street, Middlesboro, KY 40965
MLS# 25011376Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$285,000Active-- beds -- baths00 Highway 217 & 1344, Middlesboro, KY 40965
MLS# 25018632Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$100,000Active2 beds 1 baths910 sq. ft.310 Barkley Drive, Middlesboro, KY 40965
MLS# 1311219Listed by: REMAX PROFESSIONAL'S
$175,000Active3 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
$2,500,000Active3 beds 2 baths1,976 sq. ft.259 Watson Lane, Middlesboro, KY 40965
MLS# 1306495Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$299,000Active1.69 Acres321 Chester Avenue, Middlesboro, KY 40965
MLS# 25012296Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$170,000Active3 beds 1 baths1,200 sq. ft.180 Stevenson Branch Rd, Middlesboro, KY 40965
MLS# 1301528Listed by: TURN KEY REALTY
$115,000Pending3 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
$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:CENTURY 21 Pinnacle, CENTURY 21 Legacy
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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.
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.