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Winchester, KY - single-family homes for sale
123 of 123 results displayed
- New
$285,000Active3 beds 2 baths1,955 sq. ft.108 Milwood Drive, Winchester, KY 40391
MLS# 26019908Listed by: DISNEY & COMPANY - New
$380,000Active3 beds 2 baths2,358 sq. ft.125 Amiens Boulevard, Winchester, KY 40391
MLS# 26019273Listed by: ERA SELECT REAL ESTATE - New
$272,900Active3 beds 2 baths1,356 sq. ft.316 Buffalo Trace, Winchester, KY 40391
MLS# 26019259Listed by: CENTURY 21 ADVANTAGE REALTY - New
$369,000Active3 beds 2 baths1,990 sq. ft.11 Stoney Brook Drive #1, Winchester, KY 40391
MLS# 26019263Listed by: MILTON AND ASSOCIATES REAL ESTATE - New
$229,000Active3 beds 2 baths1,297 sq. ft.13 Long Avenue, Winchester, KY 40391
MLS# 26019206Listed by: COLDWELL BANKER MCMAHAN - New
$429,000Active3 beds 3 baths2,204 sq. ft.322 Calmes Boulevard, Winchester, KY 40391
MLS# 26019133Listed by: DREAM MAKER REALTY, LLC - New
$410,000Active4 beds 2 baths3,306 sq. ft.351 Boone Avenue, Winchester, KY 40391
MLS# 26017258Listed by: RE/MAX CREATIVE, WINCHESTER 
$178,000Pending2 beds 1 baths1,061 sq. ft.17 Waveland Avenue, Winchester, KY 40391
MLS# 26019033Listed by: HAVEN HOMES GROUP- New
$209,900Active3 beds 1 baths1,200 sq. ft.30 Hughes Avenue, Winchester, KY 40391
MLS# 26019005Listed by: NATIONAL REAL ESTATE - New
$239,995Active3 beds 2 baths1,228 sq. ft.22 Apache Trail, Winchester, KY 40391
MLS# 26018986Listed by: RE/MAX ELITE LEXINGTON - New
$179,900Active3 beds 2 baths1,176 sq. ft.76 Clay Street, Winchester, KY 40391
MLS# 26017853Listed by: ERA SELECT REAL ESTATE 
$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
$235,000Active2 beds 2 baths1,039 sq. ft.47 Hughes Avenue, Winchester, KY 40391
MLS# 26018337Listed by: THRESHOLD REAL ESTATE SERVICES
$296,000Active3 beds 2 baths1,386 sq. ft.33 Bon-haven Avenue, Winchester, KY 40391
MLS# 26018346Listed by: PLUM TREE REALTY
$147,900Active3 beds 1 baths1,150 sq. ft.118 Park Avenue, Winchester, KY 40391
MLS# 26017859Listed by: THE BROKERAGE
$319,900Active5 beds 2 baths2,082 sq. ft.128 Cherokee Drive, Winchester, KY 40391
MLS# 26017629Listed by: OAK & ACRE
$350,000Pending4 beds 3 baths2,591 sq. ft.411 Skylark Drive, Winchester, KY 40391
MLS# 26017601Listed by: KELLER WILLIAMS COMMONWEALTH
$229,900Active3 beds 2 baths1,200 sq. ft.491 Hidden Hills Way, Winchester, KY 40391
MLS# 26017144Listed by: HOMEFIRST REAL ESTATE
$274,900Active4 beds 3 baths1,377 sq. ft.304 Sandra Drive, Winchester, KY 40391
MLS# 26016975Listed by: THE AGENCY
$374,900Active3 beds 2 baths2,269 sq. ft.15 Moundale Avenue, Winchester, KY 40391
MLS# 26016576Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$409,500Active3 beds 2 baths2,304 sq. ft.215 Delaplain Road, Winchester, KY 40391
MLS# 26016762Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON
$249,900Active3 beds 1 baths1,204 sq. ft.10 Chickadee Lane, Winchester, KY 40391
MLS# 26016217Listed by: KELLER WILLIAMS COMMONWEALTH
$329,000Active3 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
$420,000Active3 beds 2 baths2,027 sq. ft.187 Hawthorne Drive, Winchester, KY 40391
MLS# 26015824Listed by: KELLER WILLIAMS COMMONWEALTH
$315,000Active4 beds 3 baths1,840 sq. ft.209 Connie Lane, Winchester, KY 40391
MLS# 26015653Listed by: ENSOR REAL ESTATE, LLC
$419,500Active4 beds 3 baths1,978 sq. ft.107 Hibiscus Lane, Winchester, KY 40391
MLS# 26015608Listed by: KELLER WILLIAMS COMMONWEALTH
$40,000Active3 beds 1 baths1,842 sq. ft.16 Virginia Avenue, Winchester, KY 40391
MLS# 26015227Listed by: HIGH POINT REALTY & AUCTION
$359,000Active3 beds 3 baths1,803 sq. ft.608 Colby Road, Winchester, KY 40391
MLS# 26015128Listed by: RE/MAX CREATIVE REALTY
$115,000Active3 beds 1 baths900 sq. ft.25 Oliver Street, Winchester, KY 40391
MLS# 26014899Listed by: KELLER WILLIAMS BLUEGRASS REALTY
$349,900Active4 beds 3 baths2,325 sq. ft.119 Gibson Way, Winchester, KY 40391
MLS# 26014834Listed by: ENSOR REAL ESTATE, LLC
$310,000Pending4 beds 2 baths2,285 sq. ft.872 Stratton Lane, Winchester, KY 40391
MLS# 26014681Listed by: COLDWELL BANKER MCMAHAN
$139,900Pending3 beds 1 baths1,097 sq. ft.220 E Washington Street, Winchester, KY 40391
MLS# 26014553Listed by: ENSOR REAL ESTATE, LLC
$274,900Pending3 beds 3 baths1,604 sq. ft.136 Sturbridge Lane, Winchester, KY 40391
MLS# 26015181Listed by: KENTUCKY LAND AND HOME
$228,500Pending3 beds 2 baths1,210 sq. ft.122 Spruce Court, Winchester, KY 40391
MLS# 26014330Listed by: HOMEFIRST REAL ESTATE
$399,000Pending3 beds 3 baths2,235 sq. ft.19 Fontaine Boulevard, Winchester, KY 40391
MLS# 26014243Listed by: COLDWELL BANKER MCMAHAN
$277,000Pending4 beds 2 baths2,170 sq. ft.214 S Burns Avenue, Winchester, KY 40391
MLS# 26014099Listed by: EXP REALTY LLC
$324,900Active3 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
$149,900Active3 beds 2 baths1,680 sq. ft.65 Fitch Avenue, Winchester, KY 40391
MLS# 26013935Listed by: ENSOR REAL ESTATE, LLC
$375,000Active3 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
$459,000Pending4 beds 3 baths3,296 sq. ft.105 Monet Boulevard, Winchester, KY 40391
MLS# 26013041Listed by: EXP REALTY, LLC
$221,500Active2 beds 1 baths1,454 sq. ft.2 Western Avenue, Winchester, KY 40391
MLS# 26013551Listed by: WOODS REALTY GROUP
$239,000Active3 beds 1 baths1,050 sq. ft.30 Virginia Avenue, Winchester, KY 40391
MLS# 26013434Listed by: WEICHERT REALTORS - ABG PROPERTIES
$539,500Active4 beds 5 baths4,173 sq. ft.600 Boone Avenue, Winchester, KY 40391
MLS# 26013378Listed by: THE AGENCY
$247,500Active3 beds 2 baths1,533 sq. ft.377 Crescent Avenue, Winchester, KY 40391
MLS# 26013350Listed by: JOYCE MARCUM REALTY
$345,000Pending3 beds 3 baths2,266 sq. ft.107 Gibson Way, Winchester, KY 40391
MLS# 26013361Listed by: STEWART & CO REALTY LLC
$499,000Pending5 beds 3 baths3,097 sq. ft.182 Chardonnay Court, Winchester, KY 40392
MLS# 26013305Listed by: COLDWELL BANKER MCMAHAN
$899,000Active3 beds 3 baths2,200 sq. ft.330 Spencer Lane, Winchester, KY 40391
MLS# 26013217Listed by: RED RIVER GORGE REAL ESTATE
$334,900Active3 beds 2 baths1,858 sq. ft.23 Windridge Drive, Winchester, KY 40391
MLS# 26013010Listed by: THE AGENCY
$225,000Active3 beds 2 baths1,261 sq. ft.14 Cook Avenue, Winchester, KY 40391
MLS# 26011961Listed by: UNITED REAL ESTATE BLUEGRASS
$270,000Active3 beds 2 baths1,650 sq. ft.20 Jackson Street, Winchester, KY 40391
MLS# 26012820Listed by: KELLER WILLIAMS LEGACY GROUP
$329,900Active5 beds 4 baths4,456 sq. ft.410 W Lexington Avenue, Winchester, KY 40391
MLS# 26012369Listed by: BLUEGRASS HOME GROUP
$273,900Active4 beds 1 baths2,327 sq. ft.162 French Avenue, Winchester, KY 40391
MLS# 26012319Listed by: HOMELAND REAL ESTATE INC - MT STERLING
$268,900Pending4 beds 3 baths1,510 sq. ft.311 Geronimo Court, Winchester, KY 40391
MLS# 26011798Listed by: WEICHERT REALTORS - ABG PROPERTIES
$274,500Pending3 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
$484,900Pending4 beds 3 baths2,418 sq. ft.414 Fairholme Way, Winchester, KY 40391
MLS# 26011136Listed by: THE BROKERAGE
$290,000Active3 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
$449,900Pending4 beds 3 baths3,126 sq. ft.207 Hibiscus Lane, Winchester, KY 40391
MLS# 26010589Listed by: HOMELAND REAL ESTATE INC - MT STERLING
$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
$413,000Active3 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
$284,900Pending4 beds 2 baths2,116 sq. ft.618 Westmeade Drive, Winchester, KY 40391
MLS# 26009371Listed by: UNITED REAL ESTATE BLUEGRASS
$249,900Pending3 beds 2 baths1,446 sq. ft.123 Sunset Heights, Winchester, KY 40391
MLS# 26009360Listed by: COLDWELL BANKER MCMAHAN
$289,000Active3 beds 2 baths1,692 sq. ft.54 Locust Drive, Winchester, KY 40391
MLS# 26007779Listed by: BERKSHIRE HATHAWAY HOMESERVICES FOSTER REALTORS
$270,000Pending3 beds 2 baths1,779 sq. ft.720 Terry Drive, Winchester, KY 40391
MLS# 26009068Listed by: KELLER WILLIAMS COMMONWEALTH
$289,999Pending3 beds 3 baths2,648 sq. ft.414 Pueblo Court, Winchester, KY 40391
MLS# 26008330Listed by: THE LOCAL AGENTS
$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
$329,900Pending4 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
$675,000Active4 beds 3 baths4,928 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
$329,900Pending4 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
$349,500Pending4 beds 3 baths3,440 sq. ft.221 W Hickman Street, Winchester, KY 40391
MLS# 26004557Listed by: KELLER WILLIAMS BLUEGRASS REALTY
$299,999Pending3 beds 3 baths1,794 sq. ft.322 S Burns Avenue, Winchester, KY 40391
MLS# 26004053Listed by: CENTURY 21 ADVANTAGE REALTY
$204,900Pending3 beds 2 baths1,120 sq. ft.500 Hidden Hills Way, Winchester, KY 40391
MLS# 26004000Listed by: TAYLOR REAL ESTATE, LLC
$264,900Pending5 beds 2 baths2,214 sq. ft.55 Hillcrest Drive, Winchester, KY 40391
MLS# 26004166Listed by: RE/MAX ELITE LEXINGTON
$591,650Pending3 beds 3 baths2,200 sq. ft.104 Bella Shae Way, Winchester, KY 40391
MLS# 26000264Listed by: KELLER WILLIAMS COMMONWEALTH
$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
$189,900Pending2 beds 1 baths1,484 sq. ft.605 College Street, Winchester, KY 40391
MLS# 25506124Listed by: STEVEN D ADAMS REAL ESTATE SERVICES, LLC
$260,000Pending3 beds 2 baths2,127 sq. ft.213 Southwind Drive, Winchester, KY 40391
MLS# 25503904Listed by: REDFIN
$130,000Pending2 beds 1 baths1,254 sq. ft.208 4th Street, Winchester, KY 40391
MLS# 25501100Listed by: KELLER WILLIAMS BLUEGRASS REALTY
$168,500Pending3 beds 2 baths1,026 sq. ft.12 Apache Trail, Winchester, KY 40391
MLS# 25500706Listed by: KELLER WILLIAMS COMMONWEALTH
$350,000Pending3 beds 3 baths2,868 sq. ft.508 Boone Avenue, Winchester, KY 40391
MLS# 25019249Listed by: WRIGHT REALTY
$189,000Pending3 beds 2 baths1,238 sq. ft.24 Fairview Avenue, Winchester, KY 40391
MLS# 25007675Listed by: TOM GOEBEL & COMPANY
$139,000Pending2 beds 1 baths886 sq. ft.9 Linden Avenue, Winchester, KY 40391
MLS# 25007762Listed by: CENTURY 21 ADVANTAGE REALTY
$395,000Pending3 beds 2 baths1,855 sq. ft.205 Evergreen Drive, Winchester, KY 40391
MLS# 25009077Listed by: UNITED REAL ESTATE BLUEGRASS
$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
$389,000Active4 beds 2 baths1,950 sq. ft.104 Colby Hills Drive, Winchester, KY 40391
MLS# 25004009Listed by: MILTON AND ASSOCIATES REAL ESTATE
$430,000Pending3 beds 2 baths1,855 sq. ft.250 Evergreen Drive, Winchester, KY 40391
MLS# 25009082Listed by: UNITED REAL ESTATE BLUEGRASS
$380,000Pending3 beds 2 baths1,677 sq. ft.270 Evergreen Drive, Winchester, KY 40391
MLS# 25009085Listed by: UNITED REAL ESTATE BLUEGRASS
$289,000Pending2 beds 2 baths1,674 sq. ft.800-805 Country Club Court, Winchester, KY 40391
MLS# 25501029Listed by: DREAM MAKER REALTY, LLC
$239,500Active3 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: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.