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40965, KY - single-family homes for sale
48 of 48 results displayed
- New
$239,900Active4 beds 3 baths2,455 sq. ft.1203 Winchester Avenue, Middlesboro, KY 40965
MLS# 26004238Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO - New
$208,000Active3 beds 2 baths1,080 sq. ft.23 Castleford Way, Middlesboro, KY 40965
MLS# 1331558Listed by: TURN KEY REALTY - New
$575,000Active4 beds 4 baths3,480 sq. ft.2794 Us Hwy 25 E, Middlesboro, KY 40965
MLS# 1331334Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE - New
$399,000Active3 beds 3 baths3,397 sq. ft.103 Kingsbury Woods, Middlesboro, KY 40965
MLS# 26003950Listed by: LISTWITHFREEDOM.COM 
$210,000Active2 beds 3 baths960 sq. ft.615 S 22nd Street, Middlesboro, KY 40965
MLS# 26003147Listed by: BLACK DIAMOND REALTY
$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
$168,000Active4 beds 2 baths1,120 sq. ft.409 Meadow Lane, Middlesboro, KY 40965
MLS# 1329538Listed by: TURN KEY REALTY
$279,000Active3 beds 3 baths2,210 sq. ft.515 Englewood Rd, Middlesboro, KY 40965
MLS# 1329448Listed 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
$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
$164,900Pending3 beds 2 baths140 Hickory Lane, Middlesboro, KY 40965
MLS# 639539Listed by: RE/MAX PREFERRED GROUP
$197,000Active3 beds 2 baths1,238 sq. ft.1200 W Chester Ave, Middlesboro, KY 40965
MLS# 1327952Listed by: COLDWELL BANKER BISCEGLIA REAL
$259,000Active4 beds 3 baths1,832 sq. ft.206 Summit Drive, Middlesboro, KY 40965
MLS# 1327623Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$150,000Active2 beds 1 baths952 sq. ft.359 Beans Fork Rd, Middlesboro, KY 40965
MLS# 1327412Listed by: REALTY GROUP
$115,000Pending2 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 St, Middlesboro, KY 40965
MLS# 1326276Listed by: COLDWELL BANKER BISCEGLIA REAL
$44,000Pending3 beds 2 baths1,230 sq. ft.406 Rochester Avenue, Middlesboro, KY 40965
MLS# 26000523Listed by: BLACK DIAMOND REALTY
$199,000Active3 beds 2 baths1,400 sq. ft.908 Chester Ave, Middlesboro, KY 40965
MLS# 1325838Listed by: REMAX PROFESSIONAL'S
$369,900Pending4 beds 4 baths2,684 sq. ft.409 Fairview Rd, Middlesboro, KY 40965
MLS# 1324858Listed by: COLDWELL BANKER BISCEGLIA REAL
$99,000Active1 beds 1 baths800 sq. ft.923 Winchester Ave, Middlesboro, KY 40965
MLS# 1324643Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$217,000Active3 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
$525,000Active5 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
$159,900Pending3 beds 2 baths934 sq. ft.45 Fourmile Run Road, Middlesboro, KY 40965
MLS# 25506029Listed by: COLDWELL BANKER BISCEGLIA REALTY & AUCTION CO
$232,500Pending3 beds 2 baths1,900 sq. ft.4921 W Cumberland Ave, Middlesboro, KY 40965
MLS# 1319805Listed by: MOUNTAIN REALTY
$194,500Active3 beds 2 baths1,375 sq. ft.280 Parker Lane, Middlesboro, KY 40965
MLS# 1319571Listed by: REALTY GROUP
$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
$240,000Active3 beds 3 baths1,856 sq. ft.129 Lower Gibson Lane, Middlesboro, KY 40965
MLS# 1316259Listed by: REMAX PROFESSIONAL'S
$324,900Pending5 beds 3 baths2,250 sq. ft.805 Worchester Ave, Middlesboro, KY 40965
MLS# 1315952Listed by: REMAX PROFESSIONAL'S
$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
$319,900Pending6 beds 4 baths4,033 sq. ft.832 N 25th Street, Middlesboro, KY 40965
MLS# 25011376Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$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
$2,500,000Active3 beds 2 baths1,976 sq. ft.259 Watson Lane, Middlesboro, KY 40965
MLS# 1306495Listed by: CENTURY 21 VIRGINIA WILDER REAL ESTATE
$170,000Active3 beds 1 baths1,200 sq. ft.180 Stevenson Branch Rd, Middlesboro, KY 40965
MLS# 1301528Listed by: TURN KEY REALTY
$115,000Active3 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 Simpson & Associates, CENTURY 21 Legacy, CENTURY 21 Premiere Properties
Information Deemed Reliable but Not Guaranteed. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of NKMLS. Real estate listings held by IDX Brokerage firms other than CENTURY 21 Premiere Properties are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers. Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved.
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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.