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Winchester, KY - single-family homes for sale
90 of 90 results displayed
- Open Sun, 2 to 4pmNew
$249,900Active3 beds 1 baths1,204 sq. ft.10 Chickadee Lane, Winchester, KY 40391
MLS# 26016217Listed by: KELLER WILLIAMS COMMONWEALTH - New
$339,000Active3 beds 3 baths2,068 sq. ft.13 Bel Air Drive, Winchester, KY 40391
MLS# 26016008Listed by: KELLER WILLIAMS LEGACY GROUP 
$349,000Pending4 beds 3 baths3,405 sq. ft.411 Boone Avenue, Winchester, KY 40391
MLS# 26015962Listed by: INDIGO & CO
$420,000Pending3 beds 2 baths2,027 sq. ft.187 Hawthorne Drive, Winchester, KY 40391
MLS# 26015824Listed by: KELLER WILLIAMS COMMONWEALTH- New
$315,000Active4 beds 3 baths1,840 sq. ft.209 Connie Lane, Winchester, KY 40391
MLS# 26015653Listed by: ENSOR REAL ESTATE, LLC - Open Sat, 1 to 4pmNew
$419,500Active4 beds 3 baths1,978 sq. ft.107 Hibiscus Lane, Winchester, KY 40391
MLS# 26015608Listed by: KELLER WILLIAMS COMMONWEALTH - New
$275,000Active3 beds 3 baths1,787 sq. ft.304 Newcastle Lane, Winchester, KY 40391
MLS# 26015267Listed by: BRIDGEWATER REAL ESTATE - New
$40,000Active3 beds 1 baths1,842 sq. ft.16 Virginia Avenue, Winchester, KY 40391
MLS# 26015227Listed by: HIGH POINT REALTY & AUCTION 
$399,900Active3 beds 3 baths1,803 sq. ft.608 Colby Road, Winchester, KY 40391
MLS# 26015128Listed by: RE/MAX CREATIVE REALTY
$125,000Active3 beds 1 baths900 sq. ft.25 Oliver Street, Winchester, KY 40391
MLS# 26014899Listed by: KELLER WILLIAMS BLUEGRASS REALTY
$355,000Active4 beds 3 baths2,325 sq. ft.119 Gibson Way, Winchester, KY 40391
MLS# 26014834Listed by: ENSOR REAL ESTATE, LLC
$310,000Active4 beds 2 baths2,285 sq. ft.872 Stratton Lane, Winchester, KY 40391
MLS# 26014681Listed by: COLDWELL BANKER MCMAHAN
$155,000Active3 beds 1 baths1,097 sq. ft.220 E Washington Street, Winchester, KY 40391
MLS# 26014553Listed by: ENSOR REAL ESTATE, LLC- Open Sat, 1 to 3pmNew
$274,900Active3 beds 3 baths1,604 sq. ft.136 Sturbridge Lane, Winchester, KY 40391
MLS# 26015181Listed by: KENTUCKY LAND AND HOME 
$230,000Active3 beds 2 baths1,210 sq. ft.122 Spruce Court, Winchester, KY 40391
MLS# 26014330Listed by: HOMEFIRST REAL ESTATE
$289,000Pending3 beds 2 baths1,240 sq. ft.110 Buckingham Lane, Winchester, KY 40391
MLS# 26014133Listed by: UNITED REAL ESTATE BLUEGRASS
$420,000Active3 beds 3 baths2,235 sq. ft.19 Fontaine Boulevard, Winchester, KY 40391
MLS# 26014243Listed by: COLDWELL BANKER MCMAHAN
$289,000Active4 beds 2 baths2,170 sq. ft.214 S Burns Avenue, Winchester, KY 40391
MLS# 26014099Listed by: EXP REALTY LLC
$329,900Active3 beds 2 baths1,444 sq. ft.8 Monroe Avenue, Winchester, KY 40391
MLS# 26014053Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$249,900Pending3 beds 2 baths1,284 sq. ft.312 Buffalo Trace, Winchester, KY 40391
MLS# 26014058Listed by: THE AGENCY
$329,900Active3 beds 3 baths1,904 sq. ft.335 Newcastle Lane, Winchester, KY 40391
MLS# 26014026Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$152,500Active3 beds 2 baths1,680 sq. ft.65 Fitch Avenue, Winchester, KY 40391
MLS# 26013935Listed by: ENSOR REAL ESTATE, LLC
$385,000Active3 beds 3 baths1,945 sq. ft.309 Gallahadion Court, Winchester, KY 40391
MLS# 26013780Listed by: RE/MAX CREATIVE, WINCHESTER
$235,000Active4 beds 1 baths1,609 sq. ft.120 Windsor Drive, Winchester, KY 40391
MLS# 26013563Listed by: KELLER WILLIAMS COMMONWEALTH
$265,000Active3 beds 1 baths1,324 sq. ft.119 Sunset Heights, Winchester, KY 40391
MLS# 26012905Listed by: ENSOR REAL ESTATE, LLC
$464,000Active4 beds 3 baths3,296 sq. ft.105 Monet Boulevard, Winchester, KY 40391
MLS# 26013041Listed by: EXP REALTY, LLC
$229,500Active2 beds 1 baths1,454 sq. ft.2 Western Avenue, Winchester, KY 40391
MLS# 26013551Listed by: WOODS REALTY GROUP
$249,900Pending3 beds 2 baths1,161 sq. ft.17 Holiday Road, Winchester, KY 40391
MLS# 26013480Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$239,000Active3 beds 1 baths1,050 sq. ft.30 Virginia Avenue, Winchester, KY 40391
MLS# 26013434Listed by: WEICHERT REALTORS - ABG PROPERTIES
$545,900Active4 beds 5 baths4,173 sq. ft.600 Boone Avenue, Winchester, KY 40391
MLS# 26013378Listed by: THE AGENCY
$249,500Active3 beds 2 baths1,533 sq. ft.377 Crescent Avenue, Winchester, KY 40391
MLS# 26013350Listed by: JOYCE MARCUM REALTY- Open Sun, 2 to 4pm
$345,000Pending3 beds 3 baths2,266 sq. ft.107 Gibson Way, Winchester, KY 40391
MLS# 26013361Listed by: STEWART & CO REALTY LLC 
$899,000Active3 beds 3 baths2,200 sq. ft.330 Spencer Lane, Winchester, KY 40391
MLS# 26013217Listed by: RED RIVER GORGE REAL ESTATE
$339,900Active3 beds 2 baths1,858 sq. ft.23 Windridge Drive, Winchester, KY 40391
MLS# 26013010Listed by: THE AGENCY
$235,000Active3 beds 2 baths1,297 sq. ft.13 Long Avenue, Winchester, KY 40391
MLS# 26013004Listed by: COLDWELL BANKER MCMAHAN
$225,000Active3 beds 2 baths1,261 sq. ft.14 Cook Avenue, Winchester, KY 40391
MLS# 26011961Listed by: UNITED REAL ESTATE BLUEGRASS
$275,000Active3 beds 2 baths1,650 sq. ft.20 Jackson Street, Winchester, KY 40391
MLS# 26012820Listed by: KELLER WILLIAMS LEGACY GROUP
$339,900Active5 beds 4 baths4,456 sq. ft.410 W Lexington Avenue, Winchester, KY 40391
MLS# 26012369Listed by: BLUEGRASS HOME GROUP
$234,900Pending3 beds 2 baths1,904 sq. ft.528 Estes Drive, Winchester, KY 40391
MLS# 26012351Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$273,900Active4 beds 1 baths2,327 sq. ft.162 French Avenue, Winchester, KY 40391
MLS# 26012319Listed by: HOMELAND REAL ESTATE INC - MT STERLING
$235,500Active3 beds 1 baths1,100 sq. ft.125 Kittison Drive, Winchester, KY 40391
MLS# 26011953Listed by: COLDWELL BANKER MCMAHAN
$274,500Active3 beds 2 baths1,260 sq. ft.116 Sturbridge Lane, Winchester, KY 40391
MLS# 26011782Listed by: WRIGHT REALTY
$199,900Active3 beds 2 baths915 sq. ft.225 Buffalo Trace, Winchester, KY 40391
MLS# 26011564Listed by: THE BROKERAGE
$315,000Pending3 beds 2 baths1,932 sq. ft.13 Lakeview Drive, Winchester, KY 40391
MLS# 26011497Listed by: RE/MAX CREATIVE, WINCHESTER
$200,000Pending3 beds 2 baths1,289 sq. ft.128 Bay Hill Drive, Winchester, KY 40391
MLS# 26011449Listed by: MELIA REALTY LLC
$484,900Active4 beds 3 baths2,418 sq. ft.414 Fairholme Way, Winchester, KY 40391
MLS# 26011136Listed by: THE BROKERAGE
$294,900Active3 beds 3 baths2,260 sq. ft.209 Boone Avenue, Winchester, KY 40391
MLS# 26011097Listed by: LOIS ANN DISPONETT REAL EST
$294,900Pending3 beds 2 baths2,128 sq. ft.147 Sunset Heights, Winchester, KY 40391
MLS# 26011009Listed by: KENTUCKY LAND AND HOME
$210,000Pending3 beds 1 baths1,386 sq. ft.301 Snowden Drive, Winchester, KY 40391
MLS# 26010643Listed by: THE BROKERAGE- Open Sun, 1 to 3pm
$549,900Active3 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
$350,000Pending3 beds 2 baths2,835 sq. ft.27 Hampton Avenue, Winchester, KY 40391
MLS# 26010286Listed by: KELLER WILLIAMS COMMONWEALTH
$427,000Active3 beds 3 baths2,288 sq. ft.20 Edgewood Drive, Winchester, KY 40391
MLS# 26009517Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON
$350,000Active4 beds 3 baths2,310 sq. ft.38 N Burns Avenue, Winchester, KY 40391
MLS# 26009835Listed by: RE/MAX CREATIVE REALTY
$159,500Pending2 beds 1 baths842 sq. ft.22 Magnolia Street, Winchester, KY 40391
MLS# 26009730Listed by: RE/MAX CREATIVE REALTY
$284,900Pending4 beds 2 baths2,116 sq. ft.618 Westmeade Drive, Winchester, KY 40391
MLS# 26009371Listed by: UNITED REAL ESTATE BLUEGRASS
$289,000Active3 beds 2 baths1,692 sq. ft.54 Locust Drive, Winchester, KY 40391
MLS# 26007779Listed by: BERKSHIRE HATHAWAY HOMESERVICES FOSTER REALTORS
$375,000Active4 beds 3 baths3,310 sq. ft.382 S Main Street, Winchester, KY 40391
MLS# 26008931Listed by: RE/MAX CREATIVE, WINCHESTER
$312,000Active3 beds 3 baths2,648 sq. ft.412 Pueblo Court, Winchester, KY 40391
MLS# 26008794Listed by: RECTOR HAYDEN REALTORS
$169,000Active3 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
$164,000Active2 beds 1 baths1,472 sq. ft.13 Maryland Avenue, Winchester, KY 40391
MLS# 26008307Listed by: ERA SELECT REAL ESTATE
$329,900Active4 beds 3 baths2,010 sq. ft.110 Powe Drive, Winchester, KY 40391
MLS# 26008249Listed by: THE AGENCY
$312,000Active3 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
$164,900Active1 beds 2 baths1,056 sq. ft.101 Alabama Street, Winchester, KY 40391
MLS# 26007407Listed by: WOODS REALTY GROUP
$279,999Active3 beds 2 baths1,500 sq. ft.103 Southern Court, Winchester, KY 40391
MLS# 26007260Listed by: ENSOR REAL ESTATE, LLC
$699,999Active4 beds 3 baths7,058 sq. ft.186 Chardonnay Court, Winchester, KY 40391
MLS# 26006869Listed by: WEICHERT REALTORS - ABG PROPERTIES
$188,500Active3 beds 1 baths950 sq. ft.41 Hiawatha Trail, Winchester, KY 40391
MLS# 26006789Listed by: COLDWELL BANKER MCMAHAN
$329,900Active4 beds 2 baths1,843 sq. ft.228 Holiday Road, Winchester, KY 40391
MLS# 26006679Listed by: CENTURY 21 COMMONWEALTH R E
$139,900Active2 beds 1 baths986 sq. ft.174 Cook Avenue, Winchester, KY 40391
MLS# 26006389Listed by: WOODS REALTY GROUP
$264,900Active5 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
$365,900Active3 beds 2 baths1,558 sq. ft.204 Jett Drive, Winchester, KY 40391
MLS# 25507850Listed by: ENSOR REAL ESTATE, LLC
$199,900Active2 beds 1 baths1,484 sq. ft.605 College Street, Winchester, KY 40391
MLS# 25506124Listed by: STEVEN D ADAMS REAL ESTATE SERVICES, LLC
$139,000Active2 beds 1 baths886 sq. ft.9 Linden Avenue, Winchester, KY 40391
MLS# 25007762Listed by: CENTURY 21 ADVANTAGE REALTY
$365,900Active3 beds 2 baths1,635 sq. ft.206 Jett Drive, Winchester, KY 40391
MLS# 24018286Listed by: ENSOR REAL ESTATE, LLC
$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
$398,000Active4 beds 2 baths1,950 sq. ft.104 Colby Hills Drive, Winchester, KY 40391
MLS# 25004009Listed by: MILTON AND ASSOCIATES REAL ESTATE
$249,500Active3 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.