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Winchester, KY - homes for sale
170 of 170 results displayed
- New
$200,000Active3 beds 2 baths1,289 sq. ft.128 Bay Hill Drive, Winchester, KY 40391
MLS# 26005243Listed by: KELLER WILLIAMS LEGACY GROUP - New
$339,900Active3 beds 2 baths1,222 sq. ft.1291-1299 Muddy Creek Road, Winchester, KY 40391
MLS# 26005152Listed by: FC TUCKER BLUEGRASS - New
$505,000Active8 beds 4 baths5,058 sq. ft.265 S Highland Street, Winchester, KY 40391
MLS# 26004961Listed by: RE/MAX ELITE LEXINGTON 
$667,700Pending5 beds 5 baths4,712 sq. ft.20 Stoney Brook Drive, Winchester, KY 40391
MLS# 26004633Listed by: UNITED REAL ESTATE BLUEGRASS- New
$297,000Active4 beds 3 baths1,693 sq. ft.327 Newcastle Lane, Winchester, KY 40391
MLS# 26004861Listed by: BLUEGRASS PROPERTY EXCHANGE 
$399,900Pending3 beds 3 baths2,475 sq. ft.601 Gilbert Court, Winchester, KY 40391
MLS# 26004646Listed by: RO&CO REAL ESTATE- New
$209,900Active3 beds 2 baths915 sq. ft.225 Buffalo Trace, Winchester, KY 40391
MLS# 26004556Listed by: THE BROKERAGE - New
$360,000Active4 beds 3 baths3,440 sq. ft.221 W Hickman Street, Winchester, KY 40391
MLS# 26004557Listed by: KELLER WILLIAMS BLUEGRASS REALTY - New
$360,000Active3 beds 3 baths2,628 sq. ft.221 Moundale Avenue, Winchester, KY 40391
MLS# 26004551Listed by: COLDWELL BANKER MCMAHAN - New
$265,000Active4 beds 3 baths2,445 sq. ft.130 E Broadway Street, Winchester, KY 40391
MLS# 26004331Listed by: MAYCA PROPERTY SOLUTIONS 
$130,000Pending3 beds 2 baths1,232 sq. ft.19 Hughes Avenue, Winchester, KY 40391
MLS# 26004216Listed by: PLUM TREE REALTY
$165,000Pending3 beds 2 baths1,312 sq. ft.52 Judy Ann Court, Winchester, KY 40391
MLS# 26004202Listed by: CENTURY 21 ADVANTAGE REALTY
$212,000Pending3 beds 1 baths1,053 sq. ft.707 Estes Drive, Winchester, KY 40391
MLS# 26004204Listed by: TOM GOEBEL & COMPANY
$209,900Active3 beds 1 baths1,050 sq. ft.59 Holiday Road, Winchester, KY 40391
MLS# 26004165Listed by: COLDWELL BANKER MCMAHAN
$364,900Active3 beds 2 baths1,858 sq. ft.23 Windridge Drive, Winchester, KY 40391
MLS# 26004120Listed by: THE AGENCY
$339,900Active3 beds 3 baths1,794 sq. ft.322 S Burns Avenue, Winchester, KY 40391
MLS# 26004053Listed by: CENTURY 21 ADVANTAGE REALTY
$155,000Active3 beds 1 baths1,160 sq. ft.730 Byrd Avenue, Winchester, KY 40391
MLS# 26004038Listed by: KENTUCKY LAND AND HOME
$204,900Pending3 beds 2 baths1,120 sq. ft.500 Hidden Hills Way, Winchester, KY 40391
MLS# 26004000Listed by: TAYLOR REAL ESTATE, LLC
$269,000Pending3 beds 2 baths1,400 sq. ft.916 Stratton Lane, Winchester, KY 40391
MLS# 26003907Listed by: THE AGENCY
$199,000Pending3 beds 3 baths1,224 sq. ft.319 Essex Court, Winchester, KY 40391
MLS# 26003610Listed by: RE/MAX CREATIVE, WINCHESTER
$243,000Active3 beds 2 baths1,502 sq. ft.357 Silverton Way, Winchester, KY 40391
MLS# 26003487Listed by: TRU LIFE REAL ESTATE
$219,000Active3 beds 2 baths1,636 sq. ft.334 S Burns Avenue, Winchester, KY 40391
MLS# 26003334Listed by: RECTOR HAYDEN REALTORS
$259,900Pending4 beds 2 baths1,405 sq. ft.6 Hart Avenue, Winchester, KY 40391
MLS# 26003316Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$305,000Active5 beds 2 baths2,214 sq. ft.55 Hillcrest Drive, Winchester, KY 40391
MLS# 26004166Listed by: RE/MAX ELITE LEXINGTON
$285,000Active3 beds 2 baths1,790 sq. ft.211 Lindsey Court, Winchester, KY 40391
MLS# 26003170Listed by: BIEDERMAN REAL ESTATE
$925,000Active5 beds 4 baths2,842 sq. ft.1150 Craig Crossing, Winchester, KY 40391
MLS# 26002724Listed by: KENTUCKY RESIDENTIAL REAL ESTATE, LLC
$434,900Pending3 beds 2 baths3,563 sq. ft.204 Delaplain Road, Winchester, KY 40391
MLS# 26002697Listed by: COLOR REAL ESTATE
$319,500Active8 beds 5 baths3,637 sq. ft.144 Holly Avenue, Winchester, KY 40391
MLS# 26002633Listed by: KELLER WILLIAMS COMMONWEALTH
$169,900Active3 beds 1 baths1,097 sq. ft.220 E Washington Street, Winchester, KY 40391
MLS# 26002506Listed by: ENSOR REAL ESTATE, LLC
$315,000Active4 beds 2 baths1,751 sq. ft.219 Woodbine Court, Winchester, KY 40391
MLS# 26002508Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$269,900Active4 beds 1 baths1,610 sq. ft.120 Windsor Drive, Winchester, KY 40391
MLS# 26002472Listed by: SOUTHERN LEGACY REALTY
$234,900Pending3 beds 2 baths1,188 sq. ft.11 Shelley Dr, Winchester, KY 40391
MLS# 26002369Listed by: CENTURY 21 ADVANTAGE REALTY
$198,000Pending2 beds 1 baths1,223 sq. ft.616 Boone Avenue, Winchester, KY 40391
MLS# 26002364Listed by: TOM GOEBEL & COMPANY
$279,950Active4 beds 3 baths2,112 sq. ft.115 Watercrest Circle, Winchester, KY 40391
MLS# 26002338Listed by: DREAM MAKER REALTY, LLC
$160,000Pending2 beds 1 baths1,088 sq. ft.233 E Washington Street, Winchester, KY 40391
MLS# 26002299Listed by: THE BROKERAGE
$199,000Pending3 beds 2 baths1,456 sq. ft.58 Hughes Avenue, Winchester, KY 40391
MLS# 26002214Listed by: RE/MAX CREATIVE REALTY
$184,000Active2 beds 2 baths1,102 sq. ft.356 Colby Ridge Boulevard, Winchester, KY 40391
MLS# 26002026Listed by: TOM GOEBEL & COMPANY
$175,000Pending2 beds 2 baths924 sq. ft.10 Pocahontas, Winchester, KY 40391
MLS# 26002018Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON
$254,900Active3 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
$354,900Active3 beds 3 baths1,628 sq. ft.538 S Maple Street, Winchester, KY 40391
MLS# 26000925Listed by: BLUEGRASS PROPERTIES GROUP
$345,000Active4 beds 4 baths2,072 sq. ft.1128-1130 Dale Drive, Winchester, KY 40391
MLS# 26000922Listed by: COLDWELL BANKER MCMAHAN
$246,400Active5 beds 3 baths3,007 sq. ft.221 S Highland Street, Winchester, KY 40391
MLS# 26000780Listed by: THE BROKERAGE
$189,500Active2 beds 3 baths1,197 sq. ft.109 Quail Ridge Road, Winchester, KY 40391
MLS# 26000647Listed by: EXP REALTY, LLC
$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
$286,000Pending12 beds 4 baths4,010 sq. ft.149 Winn Ave, Winchester, KY 40391
MLS# 26000197Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON
$452,500Active3 beds 3 baths2,961 sq. ft.42 Mockingbird Valley Road, Winchester, KY 40391
MLS# 26000113Listed by: MCCALLIE REAL ESTATE
$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# 25508389Listed by: KB REALTY GROUP
$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
$230,000Active3 beds 2 baths1,518 sq. ft.313 S Burns Avenue, Winchester, KY 40391
MLS# 25508192Listed by: RE/MAX CREATIVE, WINCHESTER
$550,000Active1.53 Acres33-41 Winn Avenue, Winchester, KY 40391
MLS# 25508043Listed by: EXP REALTY, LLC
$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
$234,900Active4 beds 2 baths2,683 sq. ft.217 S Highland Street, Winchester, KY 40391
MLS# 25507680Listed by: THE AGENCY
$298,900Pending3 beds 4 baths2,526 sq. ft.24 N Burns Avenue, Winchester, KY 40391
MLS# 25507536Listed by: KELLER WILLIAMS COMMONWEALTH
$219,000Active3 beds 1 baths1,188 sq. ft.314 E Broadway Street, Winchester, KY 40391
MLS# 25507471Listed by: KELLER WILLIAMS COMMONWEALTH
$775,000Active3 Acres609 Bullion Boulevard #3A, Winchester, KY 40391
MLS# 23015569Listed by: BLOCK + LOT REAL ESTATE
$499,000Active5 beds 4 baths3,823 sq. ft.595 Earlymeade Drive, Winchester, KY 40391
MLS# 25506943Listed by: BRIDGEWATER REAL ESTATE
$287,000Active4 beds 2 baths2,116 sq. ft.214 S Burns Avenue, Winchester, KY 40391
MLS# 25506625Listed by: KELLER WILLIAMS COMMONWEALTH
$244,900Active3 beds 2 baths1,494 sq. ft.720 Estes Drive, Winchester, KY 40391
MLS# 25506836Listed by: HOMELAND REAL ESTATE INC - MT STERLING
$188,900Active3 beds 2 baths1,116 sq. ft.41 7th Street, Winchester, KY 40391
MLS# 25506758Listed by: RE/MAX ELITE REALTY - HAMBURG
$332,700Active3 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
$235,000Pending3 beds 2 baths1,050 sq. ft.12 Linden Avenue, Winchester, KY 40391
MLS# 25506319Listed by: RE/MAX CREATIVE REALTY
$78,500Active0.22 AcresLot 3 Plantations Drive, Winchester, KY 40391
MLS# 25506247Listed by: KELLER WILLIAMS LEGACY GROUP
$78,500Active0.22 AcresLot 4 Plantations Drive, Winchester, KY 40391
MLS# 25506248Listed by: KELLER WILLIAMS LEGACY GROUP
$78,500Active0.22 AcresLot 5 Plantations Drive, Winchester, KY 40391
MLS# 25506250Listed by: KELLER WILLIAMS LEGACY GROUP
$882,000Active3.93 AcresLot 1 - 12 Plantations Drive, Winchester, KY 40391
MLS# 25506246Listed by: KELLER WILLIAMS LEGACY GROUP
$199,900Active2 beds 1 baths1,484 sq. ft.605 College Street, Winchester, KY 40391
MLS# 25506124Listed by: STEVEN D ADAMS REAL ESTATE SERVICES, LLC
$489,900Active4 beds 3 baths2,300 sq. ft.414 Fairholme Way, Winchester, KY 40391
MLS# 25505996Listed by: LIFSTYL REAL ESTATE
$600,000Active8 beds 4 baths5,046 sq. ft.101 S Burns Avenue #1,2,3,4, Winchester, KY 40391
MLS# 25505825Listed by: BIG BLUE REALTY
$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
$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
$194,000Active3 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# 26003806Listed by: THWAITES REALTORS LLC
$365,000Pending4 beds 3 baths2,105 sq. ft.114 Mallard Lane, Winchester, KY 40391
MLS# 25502189Listed by: KELLER WILLIAMS LEGACY GROUP
$10,000Active0.06 Acres75 4th Street, Winchester, KY 40391
MLS# 25501915Listed by: EXP REALTY, LLC
$335,000Pending6 beds 4 baths3,544 sq. ft.297 S Main Street, Winchester, KY 40391
MLS# 25501793Listed by: TRU LIFE REAL ESTATE
$168,500Pending3 beds 2 baths1,026 sq. ft.12 Apache Trail, Winchester, KY 40391
MLS# 25500706Listed by: KELLER WILLIAMS COMMONWEALTH
$1,200Pending2.57 Acres507 Tech Drive, Winchester, KY 40391
MLS# 24012397Listed by: KY REALTY CO
$275,000Active4 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
$100,000Active0.68 Acres100 Duclair Drive, Winchester, KY 40391
MLS# 22024061Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.38 Acres120 Duclair Drive, Winchester, KY 40391
MLS# 22024065Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.35 Acres150 Duclair Drive, Winchester, KY 40391
MLS# 22024072Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.29 Acres160 Duclair Drive, Winchester, KY 40391
MLS# 22024074Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.38 Acres200 Duclair Drive, Winchester, KY 40391
MLS# 22024092Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Pending0.34 Acres230 Duclair Drive, Winchester, KY 40391
MLS# 22024095Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.32 Acres250 Duclair Drive, Winchester, KY 40391
MLS# 22024097Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.5 Acres260 Duclair Drive, Winchester, KY 40391
MLS# 22024098Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active1.1 Acres270 Duclair Drive, Winchester, KY 40391
MLS# 22024100Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.59 Acres255 Duclair Drive, Winchester, KY 40391
MLS# 22024102Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.47 Acres139 Jacob Court, Winchester, KY 40391
MLS# 22024111Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.32 Acres135 Jacob Court, Winchester, KY 40391
MLS# 22024112Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.27 Acres125 Jacob Court, Winchester, KY 40391
MLS# 22024114Listed by: BLUEGRASS PROPERTIES GROUP
$110,000Active0.32 Acres115 Jacob Court, Winchester, KY 40391
MLS# 22024116Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.32 Acres111 Jacob Court, Winchester, KY 40391
MLS# 22024120Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.37 Acres225 Jacob Court, Winchester, KY 40391
MLS# 22024121Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.31 Acres215 Duclair Drive, Winchester, KY 40391
MLS# 22024123Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.32 Acres169 Duclair Drive, Winchester, KY 40391
MLS# 22024124Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.32 Acres165 Duclair Drive, Winchester, KY 40391
MLS# 22024126Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.32 Acres155 Duclair Drive, Winchester, KY 40391
MLS# 22024128Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.32 Acres141 Duclair Drive, Winchester, KY 40391
MLS# 22024130Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.32 Acres129 Duclair Drive, Winchester, KY 40391
MLS# 22024133Listed by: BLUEGRASS PROPERTIES GROUP
$100,000Active0.32 Acres115 Duclair Drive, Winchester, KY 40391
MLS# 22024134Listed by: BLUEGRASS PROPERTIES GROUP
$1,200,000Active24.15 Acres1395 Two Mile Road, Winchester, KY 40391
MLS# 23018853Listed by: TOM GOEBEL & COMPANY
$550,500Active20.78 Acres1395 Two Mile Road, Winchester, KY 40391
MLS# 23018854Listed by: TOM GOEBEL & COMPANY
$650,000Active3 Acres205 Codella Drive, Winchester, KY 40391
MLS# 25008456Listed by: BLOCK + LOT REAL ESTATE
$14,100,000Active274.52 Acres2395 Paris Road, Winchester, KY 40391
MLS# 25015654Listed by: KELLER WILLIAMS LEGACY GROUP
$925,000Active3.77 Acres300 Rolling Hills Lane, Winchester, KY 40391
MLS# 1805484Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$1,850,000Active17.87 Acres1509 Boonesboro Road, Winchester, KY 40391
MLS# 20101924Listed by: CMI PROPERTIES
$270,000Active0.84 Acres800 Interstate Drive, Winchester, KY 40391
MLS# 20111867Listed by: ENSOR REAL ESTATE, LLC
$500,000Active1.52 Acres1005 Early Drive, Winchester, KY 40391
MLS# 20111871Listed by: ENSOR REAL ESTATE, LLC
$400,000Active2.19 Acres145 Codella Drive, Winchester, KY 40391
MLS# 22007107Listed by: BLOCK + LOT REAL ESTATE
$150,000Active2.11 Acres125 Knox Court, Winchester, KY 40391
MLS# 22024090Listed by: BLUEGRASS PROPERTIES GROUP
$374,900Pending1.29 Acres395 Croxton Way, Winchester, KY 40391
MLS# 23015432Listed by: RECTOR HAYDEN REALTORS
$1,350,000Active3.02 Acres155 April Way, Winchester, KY 40391
MLS# 23015568Listed by: BLOCK + LOT REAL ESTATE
$775,000Active2.6 Acres529 Bullion Boulevard #3B, Winchester, KY 40391
MLS# 23015571Listed by: BLOCK + LOT REAL ESTATE
$29,000Active0.46 Acres102 Augusta Drive, Winchester, KY 40391
MLS# 24022901Listed by: DREAM MAKER REALTY, LLC
$129,300Active2.3 Acres110 Knox Court, Winchester, KY 40391
MLS# 25503832Listed by: THE AGENCY
$225,000Pending4 beds 2 baths3,295 sq. ft.133 S Burns Avenue, Winchester, KY 40391
MLS# 25005466Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
$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
$388,000Active5 beds 3 baths2,762 sq. ft.101 E Lexington Avenue, Winchester, KY 40391
MLS# 25015191Listed by: BLUEGRASS REALTY PROS, INC
$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
$251,000Pending6 beds 3 baths2,302 sq. ft.133 S Highland Street, Winchester, KY 40391
MLS# 25017462Listed 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
$1,595,000Active37 beds 20 baths26,124 sq. ft.2 N Main Street, Winchester, KY 40391
MLS# 25017572Listed by: TSUBAKI GROUP, LLC
$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
$429,000Active4 beds 2 baths1,950 sq. ft.104 Colby Hills Drive, Winchester, KY 40391
MLS# 25004009Listed by: MILTON AND ASSOCIATES REAL ESTATE
$205,000Active3 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
$515,000Active2 beds 2 baths5,054 sq. ft.808 Bypass Road, Winchester, KY 40391
MLS# 25015851Listed by: LIFSTYL REAL ESTATE
$800,000Pending4.87 Acres1108 W Lexington Avenue, Winchester, KY 40391
MLS# 25009775Listed by: KENTUCKY RESIDENTIAL REAL ESTATE, LLC
$195,500Pending2 beds 3 baths1,197 sq. ft.109 Quail Ridge Road, Winchester, KY 40391
MLS# 25503672Listed by: EXP REALTY, LLC
$215,000Pending2 beds 2 baths1,120 sq. ft.271 April Way, Winchester, KY 40391
MLS# 25016184Listed by: KELLER WILLIAMS COMMONWEALTH
$299,000Active-- beds -- baths550 E Broadway Street, Winchester, KY 40391
MLS# 25018505Listed by: COLDWELL BANKER MCMAHAN
$197,500Pending2 beds 3 baths1,197 sq. ft.111 Quail Ridge Road, Winchester, KY 40391
MLS# 25503670Listed by: EXP REALTY, LLC
$579,900Active4 beds 5 baths4,374 sq. ft.600 Boone Avenue, Winchester, KY 40391
MLS# 25018239Listed by: THE AGENCY
$50,000Active0.41 Acres308 Duclair Drive, Winchester, KY 40391
MLS# 25018185Listed by: KELLER WILLIAMS COMMONWEALTH
$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
$64,900Pending0.52 Acres101 Royal Oak Drive, Winchester, KY 40391
MLS# 25501641Listed by: KELLER WILLIAMS LEGACY GROUP
$64,900Pending0.64 Acres102 Royal Oak Drive, Winchester, KY 40391
MLS# 25501642Listed by: KELLER WILLIAMS LEGACY GROUP
$325,000Active3 beds 3 baths2,821 sq. ft.3622 Stamper Drive, Winchester, KY 40391
MLS# 26003842Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT
Local realty services provided by:CENTURY 21 Virginia Wilder Real Estate
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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.