Most expensive homes for sale in Winchester, KY

$2,995,000

6 beds • 5.5 baths

5045 Van Meter Rd, Winchester, KY 40391

#25013058, Listing office: Keller Williams Bluegrass Realty

$1,249,500

3 beds • 2.5 baths

700 Nick Ln, Winchester, KY 40391

#25013735, Listing office: Dream Maker Realty, LLC

$1,200,000

5 beds • 6 baths

6237 Bybee Rd, Winchester, KY 40391

#25012707, Listing office: Berkshire Hathaway HomeServices Foster Realtors

$999,900

5 beds • 4 baths

2447 Clintonville Rd, Winchester, KY 40391

#25003433, Listing office: Berkshire Hathaway de Movellan Properties

$985,000

4 beds • 4.5 baths

511 Boone Ave, Winchester, KY 40391

#24007462, Listing office: Block + Lot Real Estate

$890,000

4 beds • 3.5 baths

1701 Gay Evans Rd, Winchester, KY 40391

#25003606, Listing office: Coldwell Banker McMahan

$885,000

4 beds • 2.5 baths

186 Chardonnay Ct, Winchester, KY 40391

#25004303, Listing office: WEICHERT REALTORS - ABG Properties

$829,900

2 beds • 3 baths

8129 Wades Mill Rd, Winchester, KY 40391

#25009567, Listing office: The Agency

$825,000

3 beds • 2.5 baths

111 Bella Shae Way, Winchester, KY 40391

#24025579, Listing office: Keller Williams Commonwealth

$799,000

5 beds • 3 baths

1183 The Ridings, Winchester, KY 40391

#25009591, Listing office: Marshall Lane Real Estate - Lexington

$785,000

4 beds • 2.5 baths

425 Alexis Way, Winchester, KY 40391

#25000149, Listing office: Keller Williams Commonwealth

$724,900

4 beds • 2.5 baths

420 Alexis Way, Winchester, KY 40391

#24013314, Listing office: McCormick Realty Inc.

$713,500

6 beds • 4.5 baths

418 David Ln, Winchester, KY 40391

#25014801, Listing office: Bridgewater Real Estate

$700,000

3 beds • 2 baths

415 Alexis Way, Winchester, KY 40391

#24025582, Listing office: Keller Williams Commonwealth

$699,000

6 beds • 4.5 baths

4455 Colby Rd, Winchester, KY 40391

#25014453, Listing office: Keller Williams Legacy Group

$699,000

3 beds • 4 baths

1775 Irvine Rd, Winchester, KY 40391

#25005803, Listing office: Lifstyl Real Estate

$670,000

3 beds • 2 baths

113 Bella Shae Way, Winchester, KY 40391

#24025580, Listing office: Keller Williams Commonwealth

$650,000

3 beds • 3 baths

2085 Hancock Valley Dr, Winchester, KY 40391

#25010192, Listing office: Premier Property Consultants

$649,000

5 beds • 4.5 baths

315 The Woods Ln, Winchester, KY 40391

#25013173, Listing office: FC Tucker Bluegrass

$645,000

4 beds • 2.5 baths

106 Bella Shae Way, Winchester, KY 40391

#24025577, Listing office: Keller Williams Commonwealth

$635,000

4 beds • 2.5 baths

422 Alexis Way, Winchester, KY 40391

#24025583, Listing office: Keller Williams Commonwealth

$635,000

6 beds • 3.5 baths

439 Lynnway Dr, Winchester, KY 40391

#25001107, Listing office: Dream Maker Realty, LLC

$629,000

3 beds • 3.5 baths

433 Fairholme Way, Winchester, KY 40391

#25015409, Listing office: Coldwell Banker McMahan

$610,000

3 beds • 2 baths

4560 Pine Ridge Rd, Winchester, KY 40391

#25015431, Listing office: Berkshire Hathaway HomeServices Foster Realtors

$599,500

4 beds • 2 baths

102 Bella Shae Way, Winchester, KY 40391

#25011310, Listing office: Keller Williams Commonwealth

$599,500

3 beds • 2 baths

2615 Crowe Ridge Rd, Winchester, KY 40391

#25013731, Listing office: HomeFirst Real Estate

$598,000

3 beds • 2.5 baths

160 Agawam Rd, Winchester, KY 40391

#25014461, Listing office: Keller Williams Legacy Group

$574,000

5 beds • 3 baths

110 White Conkwright Rd, Winchester, KY 40391

#25006067, Listing office: Omega Real Estate Brokerage LLC

$570,000

5 beds • 3 baths

594 Earlymeade Dr, Winchester, KY 40391

#25011592, Listing office: Coldwell Banker McMahan

$559,000

4 beds • 3 baths

5 Fairwood Ln, Winchester, KY 40391

#25014569, Listing office: Coldwell Banker McMahan

$555,000

4 beds • 2 baths

5515 Van Meter Rd, Winchester, KY 40391

#25012984, Listing office: Woods Realty Group

$550,000

4 beds • 2.5 baths

31 W Hickman St, Winchester, KY 40391

#23016936, Listing office: Block + Lot Real Estate

$549,000

4 beds • 2.5 baths

415 David Ln, Winchester, KY 40391

#25003821, Listing office: Bridgewater Real Estate

$530,000

3 beds • 2.5 baths

1778 Elkin Station Rd, Winchester, KY 40391

#25007319, Listing office: Pacesetters Real Estate

$499,000

3 beds • 2.5 baths

600 Ferry Rd, Winchester, KY 40391

#25013698, Listing office: CENTURY 21 Advantage Realty

$494,000

8 beds • 5 baths

1731 Ford Hampton Rd, Winchester, KY 40391

#25012505, Listing office: RE/MAX Creative, Winchester

$465,000

2 beds • 2.5 baths

701 Lisletown Ln, Winchester, KY 40391

#25014697, Listing office: Keller Williams Legacy Group

$455,000

3 beds • 2.5 baths

42 Mockingbird Valley Rd, Winchester, KY 40391

#24015067, Listing office: Ensor Real Estate, LLC

$450,000

4 beds • 2 baths

104 Colby Hills Dr, Winchester, KY 40391

#25004009, Listing office: Milton and Associates Real Estate

$445,000

4 beds • 2 baths

17 Hampton Ave, Winchester, KY 40391

#25013712, Listing office: Bridgewater Real Estate