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Winchester, KY - single-family homes for sale
101 of 101 results displayed
- New
$329,000Active3 beds 2 baths1,480 sq. ft.358 Hanover Drive, Winchester, KY 40391
MLS# 26024503Listed by: DREAM MAKER REALTY, LLC - New
$359,900Active3 beds 3 baths1,846 sq. ft.420 Calmes Boulevard, Winchester, KY 40391
MLS# 26024212Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT - New
$150,000Active3 beds 1 baths1,842 sq. ft.5 S Burns Avenue, Winchester, KY 40391
MLS# 26024165Listed by: THE HOWARD REALTY CO - New
$165,000Active3 beds 1 baths1,249 sq. ft.209 E Washington Street, Winchester, KY 40391
MLS# 26024016Listed by: RE/MAX CREATIVE, WINCHESTER - New
$244,000Active3 beds 2 baths1,692 sq. ft.54 Locust Drive, Winchester, KY 40391
MLS# 26023633Listed by: BERKSHIRE HATHAWAY HOMESERVICES FOSTER REALTORS - New
$639,000Active5 beds 4 baths5,011 sq. ft.104 Teal Lane, Winchester, KY 40391
MLS# 26023607Listed by: RE/MAX ELITE LEXINGTON 
$519,900Pending4 beds 3 baths3,792 sq. ft.123 Winterberry Circle, Winchester, KY 40391
MLS# 26023537Listed by: NATIONAL REAL ESTATE
$275,000Pending3 beds 2 baths1,444 sq. ft.204 Lindsey Court, Winchester, KY 40391
MLS# 26023105Listed by: RE/MAX CREATIVE, WINCHESTER
$359,900Active3 beds 2 baths2,269 sq. ft.15 Moundale Avenue, Winchester, KY 40391
MLS# 26023052Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$229,900Active3 beds 1 baths1,100 sq. ft.125 Kittison Drive, Winchester, KY 40391
MLS# 26023054Listed by: COLDWELL BANKER MCMAHAN
$484,900Active4 beds 3 baths2,381 sq. ft.410 Fairholme Way, Winchester, KY 40391
MLS# 26022505Listed by: THE BROKERAGE
$365,900Active3 beds 2 baths1,558 sq. ft.204 Jett Drive, Winchester, KY 40391
MLS# 26022830Listed by: ENSOR REAL ESTATE, LLC
$365,900Active3 beds 2 baths1,635 sq. ft.206 Jett Drive, Winchester, KY 40391
MLS# 26022825Listed by: ENSOR REAL ESTATE, LLC
$259,500Pending3 beds 2 baths1,403 sq. ft.503 Kimberly Drive, Winchester, KY 40391
MLS# 26022796Listed by: RE/MAX ELITE LEXINGTON
$225,000Active3 beds 2 baths1,319 sq. ft.3 Nunnelly Court, Winchester, KY 40391
MLS# 26022771Listed by: BLACK MOUNTAIN REALTY
$279,500Active3 beds 3 baths1,963 sq. ft.304 Newcastle Lane, Winchester, KY 40391
MLS# 26022702Listed by: BRIDGEWATER REAL ESTATE
$489,000Active4 beds 4 baths3,584 sq. ft.1137 Lafayette Boulevard, Winchester, KY 40391
MLS# 26022723Listed by: RO&CO REAL ESTATE
$175,000Active3 beds 1 baths1,173 sq. ft.24 Spring Street, Winchester, KY 40391
MLS# 26022678Listed by: EXIT TOWN & COUNTRY REALTORS
$254,900Active3 beds 3 baths1,664 sq. ft.127 Bay Hill Drive, Winchester, KY 40391
MLS# 26022409Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$98,500Active3 beds 1 baths1,152 sq. ft.16 Denny Avenue, Winchester, KY 40391
MLS# 26022585Listed by: HOMEFIRST REAL ESTATE
$168,000Pending3 beds 1 baths950 sq. ft.41 Hiawatha Trail, Winchester, KY 40391
MLS# 26022281Listed by: COLDWELL BANKER MCMAHAN
$265,000Active3 beds 2 baths1,776 sq. ft.15 Kittison Drive, Winchester, KY 40391
MLS# 26022208Listed by: LIFSTYL REAL ESTATE
$140,000Active2 beds 1 baths630 sq. ft.108 Franklin Avenue, Winchester, KY 40391
MLS# 26022182Listed by: LIFSTYL REAL ESTATE
$724,889Active4 beds 5 baths4,255 sq. ft.132 Lana Lane, Winchester, KY 40391
MLS# 26022150Listed by: NAPIER REALTORS
$234,500Active3 beds 2 baths1,130 sq. ft.527 Hidden Hills Way, Winchester, KY 40391
MLS# 26022078Listed by: THE AGENCY
$410,000Active4 beds 2 baths2,435 sq. ft.406 Lynnway Drive, Winchester, KY 40391
MLS# 26021961Listed by: RE/MAX CREATIVE, WINCHESTER
$194,900Active3 beds 1 baths1,046 sq. ft.143 Spruce Court, Winchester, KY 40391
MLS# 26021903Listed by: BLUEGRASS PROPERTIES GROUP
$300,000Active4 beds 2 baths2,479 sq. ft.224 W Hickman Street, Winchester, KY 40391
MLS# 26021718Listed by: EXP REALTY, LLC
$204,900Pending3 beds 1 baths1,128 sq. ft.38 Mackay Avenue, Winchester, KY 40391
MLS# 26021864Listed by: TOM GOEBEL & COMPANY
$544,900Active5 beds 4 baths3,741 sq. ft.130 Winterberry Circle, Winchester, KY 40391
MLS# 26021642Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$205,400Active2 beds 1 baths1,154 sq. ft.606 College Street, Winchester, KY 40391
MLS# 26021605Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON
$258,900Pending4 beds 1 baths2,327 sq. ft.162 French Avenue, Winchester, KY 40391
MLS# 26021028Listed by: HOMELAND REAL ESTATE INC - MT STERLING
$250,000Active4 beds 2 baths1,996 sq. ft.59 Hillcrest Drive, Winchester, KY 40391
MLS# 26020680Listed by: THE AGENCY
$295,000Active4 beds 3 baths1,970 sq. ft.428 Waycross Drive, Winchester, KY 40391
MLS# 26020651Listed by: RE/MAX CREATIVE REALTY
$536,000Active3 beds 3 baths2,732 sq. ft.267 Runnymeade Drive, Winchester, KY 40391
MLS# 26019672Listed by: RE/MAX CREATIVE REALTY
$149,900Pending3 beds 1 baths1,775 sq. ft.60 Fitch Avenue, Winchester, KY 40391
MLS# 26020511Listed by: ENSOR REAL ESTATE, LLC
$199,000Active3 beds 1 baths1,152 sq. ft.32 Jackson Street, Winchester, KY 40391
MLS# 26020135Listed by: DREAM MAKER REALTY, LLC
$380,000Pending3 beds 2 baths2,358 sq. ft.125 Amiens Boulevard, Winchester, KY 40391
MLS# 26019273Listed by: ERA SELECT REAL ESTATE
$272,900Pending3 beds 2 baths1,356 sq. ft.316 Buffalo Trace, Winchester, KY 40391
MLS# 26019259Listed by: CENTURY 21 ADVANTAGE REALTY
$359,000Active3 beds 2 baths1,990 sq. ft.11 Stoney Brook Drive #1, Winchester, KY 40391
MLS# 26019263Listed by: MILTON AND ASSOCIATES REAL ESTATE
$219,000Active3 beds 2 baths1,297 sq. ft.13 Long Avenue, Winchester, KY 40391
MLS# 26019206Listed by: COLDWELL BANKER MCMAHAN
$399,000Active3 beds 3 baths2,204 sq. ft.322 Calmes Boulevard, Winchester, KY 40391
MLS# 26019133Listed by: DREAM MAKER REALTY, LLC
$395,000Active4 beds 2 baths3,306 sq. ft.351 Boone Avenue, Winchester, KY 40391
MLS# 26017258Listed by: RE/MAX CREATIVE, WINCHESTER
$205,000Pending3 beds 1 baths1,200 sq. ft.30 Hughes Avenue, Winchester, KY 40391
MLS# 26019005Listed by: NATIONAL REAL ESTATE
$229,500Pending3 beds 2 baths1,228 sq. ft.22 Apache Trail, Winchester, KY 40391
MLS# 26018986Listed by: RE/MAX ELITE LEXINGTON
$234,900Active3 beds 2 baths1,904 sq. ft.528 Estes Drive, Winchester, KY 40391
MLS# 26018492Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$524,900Active3 beds 3 baths2,514 sq. ft.275 Runnymeade Drive, Winchester, KY 40391
MLS# 26018460Listed by: BRIDGEWATER REAL ESTATE
$220,000Pending2 beds 2 baths1,039 sq. ft.47 Hughes Avenue, Winchester, KY 40391
MLS# 26018337Listed by: THRESHOLD REAL ESTATE SERVICES
$259,000Active3 beds 2 baths1,386 sq. ft.33 Bon-haven Avenue, Winchester, KY 40391
MLS# 26018346Listed by: PLUM TREE REALTY
$309,900Active5 beds 2 baths2,082 sq. ft.128 Cherokee Drive, Winchester, KY 40391
MLS# 26017629Listed by: OAK & ACRE
$219,500Active3 beds 2 baths1,200 sq. ft.491 Hidden Hills Way, Winchester, KY 40391
MLS# 26017144Listed by: HOMEFIRST REAL ESTATE
$239,900Pending3 beds 1 baths1,204 sq. ft.10 Chickadee Lane, Winchester, KY 40391
MLS# 26016217Listed by: KELLER WILLIAMS COMMONWEALTH
$329,000Pending3 beds 3 baths2,068 sq. ft.13 Bel Air Drive, Winchester, KY 40391
MLS# 26016008Listed by: KELLER WILLIAMS LEGACY GROUP
$420,000Active3 beds 2 baths2,027 sq. ft.187 Hawthorne Drive, Winchester, KY 40391
MLS# 26015824Listed by: KELLER WILLIAMS COMMONWEALTH
$299,900Active4 beds 3 baths1,840 sq. ft.209 Connie Lane, Winchester, KY 40391
MLS# 26015653Listed by: ENSOR REAL ESTATE, LLC
$379,000Active4 beds 3 baths1,978 sq. ft.107 Hibiscus Lane, Winchester, KY 40391
MLS# 26015608Listed by: KELLER WILLIAMS COMMONWEALTH
$360,000Pending3 beds 3 baths1,803 sq. ft.608 Colby Road, Winchester, KY 40391
MLS# 26015128Listed by: RE/MAX CREATIVE REALTY
$344,900Pending4 beds 3 baths2,325 sq. ft.119 Gibson Way, Winchester, KY 40391
MLS# 26014834Listed by: ENSOR REAL ESTATE, LLC
$319,900Active3 beds 2 baths1,444 sq. ft.8 Monroe Avenue, Winchester, KY 40391
MLS# 26014053Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$309,900Active3 beds 3 baths1,904 sq. ft.335 Newcastle Lane, Winchester, KY 40391
MLS# 26014026Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$149,900Active3 beds 2 baths1,680 sq. ft.65 Fitch Avenue, Winchester, KY 40391
MLS# 26013935Listed by: ENSOR REAL ESTATE, LLC
$359,000Active3 beds 3 baths1,945 sq. ft.309 Gallahadion Court, Winchester, KY 40391
MLS# 26013780Listed by: RE/MAX CREATIVE, WINCHESTER
$249,900Pending3 beds 1 baths1,324 sq. ft.119 Sunset Heights, Winchester, KY 40391
MLS# 26012905Listed by: ENSOR REAL ESTATE, LLC
$229,000Active3 beds 1 baths1,050 sq. ft.30 Virginia Avenue, Winchester, KY 40391
MLS# 26013434Listed by: WEICHERT REALTORS - ABG PROPERTIES
$519,900Active4 beds 5 baths4,173 sq. ft.600 Boone Avenue, Winchester, KY 40391
MLS# 26013378Listed by: THE AGENCY
$239,900Active3 beds 2 baths1,533 sq. ft.377 Crescent Avenue, Winchester, KY 40391
MLS# 26013350Listed by: JOYCE MARCUM REALTY
$319,900Active3 beds 2 baths1,858 sq. ft.23 Windridge Drive, Winchester, KY 40391
MLS# 26013010Listed by: THE AGENCY
$219,000Active3 beds 2 baths1,261 sq. ft.14 Cook Avenue, Winchester, KY 40391
MLS# 26011961Listed by: UNITED REAL ESTATE BLUEGRASS
$329,900Active5 beds 4 baths4,456 sq. ft.410 W Lexington Avenue, Winchester, KY 40391
MLS# 26012369Listed by: BLUEGRASS HOME GROUP
$189,900Active3 beds 2 baths915 sq. ft.225 Buffalo Trace, Winchester, KY 40391
MLS# 26011564Listed by: THE BROKERAGE
$280,000Active3 beds 3 baths2,260 sq. ft.209 Boone Avenue, Winchester, KY 40391
MLS# 26011097Listed by: LOIS ANN DISPONETT REAL EST
$539,900Pending3 beds 2 baths2,280 sq. ft.108 Bella Shae Way, Winchester, KY 40391
MLS# 26010352Listed by: RE/MAX ELITE LEXINGTON
$499,900Active4 beds 3 baths5,646 sq. ft.16 Manor Drive, Winchester, KY 40391
MLS# 26010312Listed by: TOM GOEBEL & COMPANY
$413,000Active3 beds 3 baths2,288 sq. ft.20 Edgewood Drive, Winchester, KY 40391
MLS# 26009517Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON
$320,000Active4 beds 3 baths2,310 sq. ft.38 N Burns Avenue, Winchester, KY 40391
MLS# 26009835Listed by: RE/MAX CREATIVE REALTY
$375,000Pending4 beds 3 baths3,310 sq. ft.382 S Main Street, Winchester, KY 40391
MLS# 26008931Listed by: RE/MAX CREATIVE, WINCHESTER
$312,000Pending3 beds 3 baths2,648 sq. ft.412 Pueblo Court, Winchester, KY 40391
MLS# 26008794Listed by: RECTOR HAYDEN REALTORS
$169,000Pending3 beds 1 baths1,046 sq. ft.175 Magnolia Street, Winchester, KY 40391
MLS# 26008759Listed by: WOODS REALTY GROUP
$165,000Active4 beds 3 baths3,462 sq. ft.229 S Highland Street, Winchester, KY 40391
MLS# 26008701Listed by: RE/MAX CREATIVE, WINCHESTER
$340,000Active4 beds 2 baths3,261 sq. ft.443 S Maple Street, Winchester, KY 40391
MLS# 26008225Listed by: KELLER WILLIAMS COMMONWEALTH
$159,000Active2 beds 1 baths1,472 sq. ft.13 Maryland Avenue, Winchester, KY 40391
MLS# 26008307Listed by: ERA SELECT REAL ESTATE
$316,900Active3 beds 3 baths1,858 sq. ft.200 Dubuy Drive, Winchester, KY 40391
MLS# 26008021Listed by: RE/MAX CREATIVE REALTY
$139,900Active3 beds 1 baths864 sq. ft.19 3rd Street, Winchester, KY 40391
MLS# 26007798Listed by: LISTWITHFREEDOM.COM
$155,900Active1 beds 2 baths1,056 sq. ft.101 Alabama Street, Winchester, KY 40391
MLS# 26007407Listed by: WOODS REALTY GROUP
$279,999Pending3 beds 2 baths1,500 sq. ft.103 Southern Court, Winchester, KY 40391
MLS# 26007260Listed by: ENSOR REAL ESTATE, LLC
$649,000Active4 beds 3 baths4,928 sq. ft.186 Chardonnay Court, Winchester, KY 40391
MLS# 26006869Listed by: WEICHERT REALTORS - ABG PROPERTIES
$138,000Active2 beds 1 baths986 sq. ft.174 Cook Avenue, Winchester, KY 40391
MLS# 26006389Listed by: WOODS REALTY GROUP
$324,900Pending3 beds 2 baths1,222 sq. ft.1291-1299 Muddy Creek Road, Winchester, KY 40391
MLS# 26005152Listed by: FC TUCKER BLUEGRASS
$264,900Pending5 beds 2 baths2,214 sq. ft.55 Hillcrest Drive, Winchester, KY 40391
MLS# 26004166Listed by: RE/MAX ELITE LEXINGTON
$124,500Active2 beds 1 baths876 sq. ft.122 Callaway Street SE Callaway Street, Winchester, KY 40391
MLS# 26000228Listed by: DREAM MAKER REALTY, LLC
$445,500Active3 beds 3 baths2,961 sq. ft.42 Mockingbird Valley Road, Winchester, KY 40391
MLS# 26009944Listed by: MCCALLIE REAL ESTATE
$825,000Active3 beds 3 baths2,995 sq. ft.111 Bella Shae Way, Winchester, KY 40391
MLS# 24025579Listed by: KELLER WILLIAMS COMMONWEALTH
$625,000Active3 beds 3 baths2,405 sq. ft.424 Alexis Way, Winchester, KY 40391
MLS# 24025584Listed by: KELLER WILLIAMS COMMONWEALTH
$239,500Pending3 beds 2 baths1,247 sq. ft.3614 Stamper Drive, Winchester, KY 40391
MLS# 25017189Listed by: DREAM MAKER REALTY, LLC
$785,000Active4 beds 3 baths2,476 sq. ft.425 Alexis Way, Winchester, KY 40391
MLS# 25000149Listed by: KELLER WILLIAMS COMMONWEALTH
$645,000Active4 beds 3 baths2,526 sq. ft.106 Bella Shae Way, Winchester, KY 40391
MLS# 24025577Listed by: KELLER WILLIAMS COMMONWEALTH
$550,000Active3 beds 3 baths2,200 sq. ft.107 Bella Shae Way, Winchester, KY 40391
MLS# 24025578Listed by: KELLER WILLIAMS COMMONWEALTH
$670,000Active3 beds 2 baths2,261 sq. ft.113 Bella Shae Way, Winchester, KY 40391
MLS# 24025580Listed by: KELLER WILLIAMS COMMONWEALTH
$665,000Active3 beds 3 baths2,643 sq. ft.414 Alexis Way, Winchester, KY 40391
MLS# 24025581Listed by: KELLER WILLIAMS COMMONWEALTH
$700,000Active3 beds 2 baths2,400 sq. ft.415 Alexis Way, Winchester, KY 40391
MLS# 24025582Listed by: KELLER WILLIAMS COMMONWEALTH
$635,000Active4 beds 3 baths2,537 sq. ft.422 Alexis Way, Winchester, KY 40391
MLS# 24025583Listed by: KELLER WILLIAMS COMMONWEALTH
Local realty services provided by: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.