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Single Family Homes For Sale in Winchester, KY | Page 2

156 Homes
 
443 S Maple St, Winchester, KY 40391
  • $325,000
  • 4Bd
  • 2Ba
  • 3,261 Sq Ft
New 32 Hours
563 Constitution Dr, Winchester, KY 40391
  • $99,500
  • 2Bd
  • 2Ba
  • 924 Sq Ft
New 2 Days
59 Hillcrest Dr, Winchester, KY 40391
  • $249,000
  • 4Bd
  • 2Ba
  • 1,996 Sq Ft
$1K
42 Mockingbird Valley Rd, Winchester, KY 40391
  • $439,000
  • 3Bd
  • 3Ba
  • 2,961 Sq Ft
$6.5K
175 Magnolia St, Winchester, KY 40391
  • $169,000
  • 3Bd
  • 1Ba
  • 1,046 Sq Ft
$10K
38 Mackay Ave, Winchester, KY 40391
  • $204,900
  • 3Bd
  • 1Ba
  • 1,128 Sq Ft
30 Virginia Ave, Winchester, KY 40391
  • $229,000
  • 3Bd
  • 1Ba
  • 1,050 Sq Ft
$10K
625 Pine Ridge Rd, Winchester, KY 40391
  • $475,000
  • 3Bd
  • 2Ba
  • 2,174 Sq Ft
240 Athens Boonesboro Rd, Winchester, KY 40391
  • $419,900
  • 4Bd
  • 3Ba
  • 1,500 Sq Ft
$10K
1860 Ford Rd, Winchester, KY 40391
  • $74,950
  • 2Bd
  • 1Ba
  • 825 Sq Ft
$5K
13 Maryland Ave, Winchester, KY 40391
  • $155,000
  • 2Bd
  • 1Ba
  • 1,472 Sq Ft
$4K
55 Hillcrest Dr, Winchester, KY 40391
  • $264,900
  • 5Bd
  • 2Ba
  • 2,214 Sq Ft
$14.1K
1780 Stoner-ephesus Rd, Winchester, KY 40391
  • $498,000
  • 4Bd
  • 3Ba
  • 2,496 Sq Ft
103 Southern Ct, Winchester, KY 40391
  • $275,000
  • 3Bd
  • 2Ba
  • 1,500 Sq Ft
$4.99K
4305 Old Boonesboro Rd, Winchester, KY 40391
  • $275,000
  • 3Bd
  • 2Ba
  • 1,512 Sq Ft
$20K
11 Stoney Brook Dr, Winchester, KY 40391
  • $355,000
  • 3Bd
  • 2Ba
  • 1,990 Sq Ft
$4K
217 Wades Mill Rd, Winchester, KY 40391
  • $785,000
  • 5Bd
  • 3Ba
  • 4,676 Sq Ft
527 Hidden Hills Way, Winchester, KY 40391
  • $219,500
  • 3Bd
  • 2Ba
  • 1,130 Sq Ft
$10K
405 Nick Ln, Winchester, KY 40391
  • $280,000
  • 2Bd
  • 1Ba
  • 1,344 Sq Ft
$15K
130 Winterberry Cir, Winchester, KY 40391
  • $544,900
  • 5Bd
  • 4Ba
  • 3,741 Sq Ft
$5K
546 Constitution Dr, Winchester, KY 40391
  • $60,000
  • 2Bd
  • 2Ba
  • 924 Sq Ft
$6K
428 Waycross Dr, Winchester, KY 40391
  • $279,900
  • 4Bd
  • 3Ba
  • 1,970 Sq Ft
$10K
2725 Goshen Rd, Winchester, KY 40391
  • $385,000
  • 3Bd
  • 2Ba
  • 1,344 Sq Ft
6699 Boonesboro Rd, Winchester, KY 40391
  • $195,000
  • —Bd
  • —Ba
322 Calmes Blvd, Winchester, KY 40391
  • $379,000
  • 3Bd
  • 3Ba
  • 2,204 Sq Ft
$10K
351 Boone Ave, Winchester, KY 40391
  • $379,000
  • 4Bd
  • 2Ba
  • 3,306 Sq Ft
$16K
1024 Flanagan Station Rd, Winchester, KY 40391
  • $419,000
  • 3Bd
  • 2Ba
  • 2,942 Sq Ft
$10K
510 612 Quisenberry Ln, Winchester, KY 40391
  • $3,450,000
  • 2Bd
  • 3Ba
  • 2,725 Sq Ft
275 Runnymeade Dr, Winchester, KY 40391
  • $524,900
  • 3Bd
  • 3Ba
  • 2,514 Sq Ft
2180 Big Stoner Rd, Winchester, KY 40391
  • $749,900
  • 3Bd
  • 3Ba
  • 2,735 Sq Ft
187 Hawthorne Dr, Winchester, KY 40391
  • $415,000
  • 3Bd
  • 2Ba
  • 2,027 Sq Ft
Open SAT 2-4
107 Hibiscus Ln, Winchester, KY 40391
  • $369,900
  • 4Bd
  • 3Ba
  • 1,978 Sq Ft
Open SUN 2-4
65 Fitch Ave, Winchester, KY 40391
  • $143,900
  • 3Bd
  • 2Ba
  • 1,680 Sq Ft
$3K
455 Davis Ln, Winchester, KY 40391
  • $699,000
  • 2Bd
  • 3Ba
  • 2,361 Sq Ft
$25.9K
309 Gallahadion Ct, Winchester, KY 40391
  • $357,000
  • 3Bd
  • 3Ba
  • 1,945 Sq Ft
$2K
955 Right Angle Rd, Winchester, KY 40391
  • $258,900
  • 2Bd
  • 1Ba
  • 849 Sq Ft
$10K
122 SE Callaway Street Se Callaway St, Winchester, KY 40391
  • $124,500
  • 2Bd
  • 1Ba
  • 876 Sq Ft
$5.4K
424 Alexis Way, Winchester, KY 40391
  • $625,000
  • 3Bd
  • 3Ba
  • 2,405 Sq Ft
14 Cook Ave, Winchester, KY 40391
  • $209,000
  • 3Bd
  • 2Ba
  • 1,261 Sq Ft
$10K
3166 Colby Rd, Winchester, KY 40391
  • $1,595,000
  • 3Bd
  • 3Ba
  • 4,518 Sq Ft
$4K
287 Logan Lick Rd, Winchester, KY 40391
  • $435,000
  • 3Bd
  • 2Ba
  • 1,680 Sq Ft
$30K
20 Edgewood Dr, Winchester, KY 40391
  • $399,900
  • 3Bd
  • 3Ba
  • 2,288 Sq Ft
$13.1K
1015 Old Stone Church Rd, Winchester, KY 40391
  • $1,500,000
  • —Bd
  • —Ba
38 N Burns Ave, Winchester, KY 40391
  • $310,000
  • 4Bd
  • 3Ba
  • 2,310 Sq Ft
$10K
4664 Lexington Rd, Winchester, KY 40391
  • $2,750,000
  • 8Bd
  • 8Ba
  • 13,433 Sq Ft
229 S Highland St, Winchester, KY 40391
  • $165,000
  • 4Bd
  • 3Ba
  • 3,462 Sq Ft
$15K
110 White Conkwright Rd, Winchester, KY 40391
  • $490,000
  • 5Bd
  • 3Ba
  • 3,102 Sq Ft
$25K
404 Mount Vernon Dr, Winchester, KY 40391
  • $124,000
  • 2Bd
  • 2Ba
  • 1,360 Sq Ft
$10.9K
1494 Amster Grove Rd, Winchester, KY 40391
  • $165,000
  • 2Bd
  • 2Ba
  • 1,202 Sq Ft
$10K
3049 Ironworks Rd, Winchester, KY 40391
  • $2,999,000
  • 6Bd
  • 5Ba
  • 3,693 Sq Ft
$101K
51 - 100 of 156 Houses for sale in Winchester, KY
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Winchester, KY real estate market trends

Statistics as of October 2026
$304K
Avg. list price
$173/Sqft
Avg. price/sqft
166
Homes for sale
1,828 Sqft
Avg. home size
102 Days
Avg. days on market
Movoto makes it easy to track market trends in Winchester, KY. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Winchester, KY?
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