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Winchester, KY - single-family homes for sale
92 of 92 results displayed
$378,000Pending4 beds 3 baths2,269 sq. ft.140 Gibson Way, Winchester, KY 40391
MLS# 26003011Listed by: STEWART & CO REALTY LLC- New
$925,000Active5 beds 4 baths2,842 sq. ft.1150 Craig Crossing, Winchester, KY 40391
MLS# 26002724Listed by: KENTUCKY RESIDENTIAL REAL ESTATE, LLC - New
$434,900Active3 beds 2 baths3,563 sq. ft.204 Delaplain Road, Winchester, KY 40391
MLS# 26002697Listed by: COLOR REAL ESTATE - New
$169,900Active3 beds 1 baths1,097 sq. ft.220 E Washington Street, Winchester, KY 40391
MLS# 26002506Listed by: ENSOR REAL ESTATE, LLC - New
$329,900Active4 beds 2 baths1,751 sq. ft.219 Woodbine Court, Winchester, KY 40391
MLS# 26002508Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT - New
$269,900Active4 beds 1 baths1,610 sq. ft.120 Windsor Drive, Winchester, KY 40391
MLS# 26002472Listed by: SOUTHERN LEGACY REALTY - New
$234,900Active3 beds 2 baths1,188 sq. ft.11 Shelley Dr, Winchester, KY 40391
MLS# 26002369Listed by: CENTURY 21 ADVANTAGE REALTY - New
$198,000Active2 beds 1 baths1,223 sq. ft.616 Boone Avenue, Winchester, KY 40391
MLS# 26002364Listed by: TOM GOEBEL & COMPANY - New
$279,950Active4 beds 3 baths2,112 sq. ft.115 Watercrest Circle, Winchester, KY 40391
MLS# 26002338Listed by: DREAM MAKER REALTY, LLC - New
$165,000Active2 beds 1 baths1,088 sq. ft.233 E Washington Street, Winchester, KY 40391
MLS# 26002299Listed by: THE BROKERAGE 
$199,000Active3 beds 2 baths1,456 sq. ft.58 Hughes Avenue, Winchester, KY 40391
MLS# 26002214Listed by: RE/MAX CREATIVE REALTY
$175,000Pending2 beds 2 baths924 sq. ft.10 Pocahontas, Winchester, KY 40391
MLS# 26002018Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON
$259,900Active3 beds 2 baths1,251 sq. ft.414 Wellington Way, Winchester, KY 40391
MLS# 26002092Listed by: ERA SELECT REAL ESTATE
$270,000Active4 beds 2 baths1,984 sq. ft.108 Ashley Drive, Winchester, KY 40391
MLS# 26001564Listed by: WOODS REALTY GROUP
$429,900Active3 beds 3 baths2,652 sq. ft.107 Woodduck Court, Winchester, KY 40391
MLS# 26001532Listed by: BERKSHIRE HATHAWAY DE MOVELLAN PROPERTIES
$260,000Pending4 beds 3 baths1,855 sq. ft.313 Carolina Avenue, Winchester, KY 40391
MLS# 26001286Listed by: HIGH POINT REALTY & AUCTION
$189,900Pending3 beds 2 baths1,328 sq. ft.357 E Washington Street, Winchester, KY 40391
MLS# 26000958Listed by: GSP HOMES
$354,900Active3 beds 3 baths1,628 sq. ft.538 S Maple Street, Winchester, KY 40391
MLS# 26000925Listed by: BLUEGRASS PROPERTIES GROUP
$591,650Pending3 beds 3 baths2,200 sq. ft.104 Bella Shae Way, Winchester, KY 40391
MLS# 26000264Listed by: KELLER WILLIAMS COMMONWEALTH
$129,900Active2 beds 1 baths876 sq. ft.122 Callaway Street SE Callaway Street, Winchester, KY 40391
MLS# 26000228Listed by: DREAM MAKER REALTY, LLC
$452,500Active3 beds 3 baths2,961 sq. ft.42 Mockingbird Valley Road, Winchester, KY 40391
MLS# 26000113Listed by: MCCALLIE REAL ESTATE
$275,000Pending3 beds 2 baths1,440 sq. ft.120 Sunset Heights, Winchester, KY 40391
MLS# 26000061Listed by: COLDWELL BANKER MCMAHAN
$367,000Pending4 beds 3 baths2,811 sq. ft.446 Tremont Lane, Winchester, KY 40391
MLS# 25508633Listed by: THE AGENCY
$269,900Pending8 beds 3 baths3,393 sq. ft.146 W Lexington Avenue, Winchester, KY 40391
MLS# 25508390Listed by: KB REALTY GROUP
$530,000Active4 beds 4 baths3,848 sq. ft.125 Casa Landa Way, Winchester, KY 40391
MLS# 25508316Listed by: NAPIER REALTORS
$295,000Pending3 beds 3 baths1,738 sq. ft.420 Willowbrook Road, Winchester, KY 40391
MLS# 25508189Listed by: RE/MAX CREATIVE, WINCHESTER
$230,000Active3 beds 2 baths1,518 sq. ft.313 S Burns Avenue, Winchester, KY 40391
MLS# 25508192Listed by: RE/MAX CREATIVE, WINCHESTER
$260,000Active4 beds 2 baths2,332 sq. ft.35 Cherokee Court, Winchester, KY 40391
MLS# 25508113Listed by: KELLER WILLIAMS BLUEGRASS REALTY
$369,900Active3 beds 2 baths1,558 sq. ft.204 Jett Drive, Winchester, KY 40391
MLS# 25507850Listed by: ENSOR REAL ESTATE, LLC
$298,900Active3 beds 4 baths2,526 sq. ft.24 N Burns Avenue, Winchester, KY 40391
MLS# 25507536Listed by: KELLER WILLIAMS COMMONWEALTH
$379,000Active3 beds 2 baths2,000 sq. ft.133 Shala-mar Rue, Winchester, KY 40391
MLS# 25507513Listed by: TOM GOEBEL & COMPANY
$219,000Active3 beds 1 baths1,188 sq. ft.314 E Broadway Street, Winchester, KY 40391
MLS# 25507471Listed by: KELLER WILLIAMS COMMONWEALTH
$349,900Active3 beds 3 baths2,821 sq. ft.3622 Stamper Drive, Winchester, KY 40391
MLS# 25507430Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$499,000Active5 beds 4 baths3,823 sq. ft.595 Earlymeade Drive, Winchester, KY 40391
MLS# 25506943Listed by: BRIDGEWATER REAL ESTATE- Open Sun, 1 to 4pm
$287,000Active4 beds 2 baths2,116 sq. ft.214 S Burns Avenue, Winchester, KY 40391
MLS# 25506625Listed by: KELLER WILLIAMS COMMONWEALTH 
$249,900Active3 beds 2 baths1,494 sq. ft.720 Estes Drive, Winchester, KY 40391
MLS# 25506836Listed by: HOMELAND REAL ESTATE INC - MT STERLING
$189,900Active3 beds 2 baths1,116 sq. ft.41 7th Street, Winchester, KY 40391
MLS# 25506758Listed by: RE/MAX ELITE REALTY - HAMBURG
$255,000Pending3 beds 2 baths1,749 sq. ft.21 Virginia Avenue, Winchester, KY 40391
MLS# 25506127Listed by: EXP REALTY, LLC
$341,900Active3 beds 3 baths3,868 sq. ft.225 Plantations Drive, Winchester, KY 40391
MLS# 25506523Listed by: BLUEGRASS PROPERTIES GROUP
$99,000Active2 beds 1 baths910 sq. ft.114 Magnolia Street, Winchester, KY 40391
MLS# 25506511Listed by: RE/MAX CREATIVE, WINCHESTER
$235,000Active3 beds 2 baths1,050 sq. ft.12 Linden Avenue, Winchester, KY 40391
MLS# 25506319Listed by: RE/MAX CREATIVE REALTY
$230,000Active2 beds 1 baths1,484 sq. ft.605 College Street, Winchester, KY 40391
MLS# 25506124Listed by: STEVEN D ADAMS REAL ESTATE SERVICES, LLC
$115,000Active4 beds 3 baths2,131 sq. ft.205 E Washington Street, Winchester, KY 40391
MLS# 25506086Listed by: KELLER WILLIAMS COMMONWEALTH
$499,900Active4 beds 3 baths2,300 sq. ft.414 Fairholme Way, Winchester, KY 40391
MLS# 25505996Listed by: LIFSTYL REAL ESTATE
$215,000Active4 beds 1 baths1,743 sq. ft.218 E Washington Street, Winchester, KY 40391
MLS# 25505534Listed by: RECTOR HAYDEN REALTORS
$275,700Active3 beds 2 baths1,682 sq. ft.404 Wellington Way, Winchester, KY 40391
MLS# 25505330Listed by: BRIDGEWATER REAL ESTATE
$200,000Pending2 beds 2 baths1,262 sq. ft.612 Boone Avenue, Winchester, KY 40391
MLS# 25505318Listed by: TOM GOEBEL & COMPANY
$379,717Pending3 beds 3 baths2,636 sq. ft.300 Calmes Boulevard, Winchester, KY 40391
MLS# 25504889Listed by: DREAM MAKER REALTY, LLC
$260,000Pending3 beds 2 baths2,127 sq. ft.213 Southwind Drive, Winchester, KY 40391
MLS# 25503904Listed by: REDFIN
$249,900Active3 beds 2 baths1,656 sq. ft.17 Euclid Avenue, Winchester, KY 40391
MLS# 26000917Listed by: THWAITES REALTORS LLC
$194,900Active3 beds 1 baths1,046 sq. ft.175 Magnolia Street, Winchester, KY 40391
MLS# 25503492Listed by: WOODS REALTY GROUP
$235,000Active3 beds 2 baths1,346 sq. ft.23 Kittison Drive, Winchester, KY 40391
MLS# 25503252Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$249,900Active3 beds 2 baths1,904 sq. ft.528 Estes Drive, Winchester, KY 40391
MLS# 25503055Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$325,000Pending4 beds 3 baths1,776 sq. ft.213 Orchid Court, Winchester, KY 40391
MLS# 25502706Listed by: 5.23 REAL ESTATE
$175,000Active3 beds 2 baths1,305 sq. ft.6 Monroe Avenue, Winchester, KY 40391
MLS# 25502677Listed by: BERKSHIRE HATHAWAY DE MOVELLAN PROPERTIES
$319,900Active5 beds 2 baths2,082 sq. ft.128 Cherokee Drive, Winchester, KY 40391
MLS# 25502349Listed by: THWAITES REALTORS LLC
$429,500Active4 beds 3 baths2,747 sq. ft.134 Fontaine Boulevard, Winchester, KY 40391
MLS# 25502273Listed by: BRIDGEWATER REAL ESTATE
$365,000Active4 beds 3 baths2,105 sq. ft.114 Mallard Lane, Winchester, KY 40391
MLS# 25502189Listed by: KELLER WILLIAMS LEGACY GROUP
$335,000Active6 beds 4 baths3,544 sq. ft.297 S Main Street, Winchester, KY 40391
MLS# 25501793Listed by: TRU LIFE REAL ESTATE
$140,000Active2 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
$275,000Pending4 beds 3 baths1,850 sq. ft.20 Bon-haven Avenue, Winchester, KY 40391
MLS# 25500083Listed by: LIFSTYL REAL ESTATE
$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
$139,000Active2 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
$144,000Active3 beds 1 baths805 sq. ft.150 Cook Avenue, Winchester, KY 40391
MLS# 25015192Listed by: BLUEGRASS REALTY PROS, INC
$146,000Active3 beds 1 baths1,020 sq. ft.228 Jackson Street, Winchester, KY 40391
MLS# 25015194Listed by: BLUEGRASS REALTY PROS, INC
$102,000Active2 beds 1 baths552 sq. ft.39 S Highland Street, Winchester, KY 40391
MLS# 25015196Listed by: BLUEGRASS REALTY PROS, INC
$171,000Active2 beds 1 baths870 sq. ft.102 W Hickman Street, Winchester, KY 40391
MLS# 25017468Listed by: BLUEGRASS REALTY PROS, INC
$369,900Active3 beds 2 baths1,635 sq. ft.206 Jett Drive, Winchester, KY 40391
MLS# 24018286Listed by: ENSOR REAL ESTATE, LLC
$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
$825,000Active3 beds 3 baths2,995 sq. ft.111 Bella Shae Way, Winchester, KY 40391
MLS# 24025579Listed 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
$625,000Active3 beds 3 baths2,405 sq. ft.424 Alexis Way, Winchester, KY 40391
MLS# 24025584Listed by: KELLER WILLIAMS COMMONWEALTH
$432,000Active4 beds 2 baths1,950 sq. ft.104 Colby Hills Drive, Winchester, KY 40391
MLS# 25004009Listed by: MILTON AND ASSOCIATES REAL ESTATE
$799,999Active4 beds 3 baths5,290 sq. ft.186 Chardonnay Court, Winchester, KY 40391
MLS# 25004303Listed by: WEICHERT REALTORS - ABG PROPERTIES
$240,000Active3 beds 3 baths2,380 sq. ft.10 Upper Street, Winchester, KY 40391
MLS# 25004895Listed by: REAL ESTATE APPRAISAL SERVICES
$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
$525,000Active2 beds 2 baths5,054 sq. ft.808 Bypass Road, Winchester, KY 40391
MLS# 25015851Listed by: LIFSTYL REAL ESTATE
$345,000Pending2 beds 2 baths1,568 sq. ft.208 Citation Court, Winchester, KY 40391
MLS# 25017361Listed by: TOM GOEBEL & COMPANY
$589,900Active4 beds 5 baths4,374 sq. ft.600 Boone Avenue, Winchester, KY 40391
MLS# 25018239Listed by: THE AGENCY
$289,000Pending2 beds 2 baths1,674 sq. ft.800-805 Country Club Court, Winchester, KY 40391
MLS# 25501029Listed by: DREAM MAKER REALTY, LLC
$259,500Active3 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
$220,000Pending3 beds 2 baths1,680 sq. ft.37 7th Street, Winchester, KY 40391
MLS# 24025642Listed by: COLDWELL BANKER MCMAHAN
$215,000Active-- beds -- baths211 Ashton Oak Way, Winchester, KY 40391
MLS# 25501640Listed by: KELLER WILLIAMS LEGACY GROUP
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.