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Winchester Real Estate & Winchester, KY Homes For Sale | Page 2

242 Homes
 
30 Virginia Ave, Winchester, KY 40391
  • $229,000
  • 3Bd
  • 1Ba
  • 1,050 Sq Ft
New 3 Days
563 Constitution Dr, Winchester, KY 40391
  • $99,500
  • 2Bd
  • 2Ba
  • 924 Sq Ft
New 5 Days
625 Pine Ridge Rd, Winchester, KY 40391
  • $475,000
  • 3Bd
  • 2Ba
  • 2,174 Sq Ft
33 Bon-haven Ave, Winchester, KY 40391
  • $249,000
  • 3Bd
  • 2Ba
  • 1,386 Sq Ft
$10K
345 Providence Ln, Winchester, KY 40391
  • $950,000
  • 120 Acre
1780 Stoner-ephesus Rd, Winchester, KY 40391
  • $498,000
  • 4Bd
  • 3Ba
  • 2,496 Sq Ft
4305 Old Boonesboro Rd, Winchester, KY 40391
  • $275,000
  • 3Bd
  • 2Ba
  • 1,512 Sq Ft
$20K
225 Buffalo Trce, Winchester, KY 40391
  • $189,900
  • 3Bd
  • 2Ba
  • 915 Sq Ft
$10K
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
528 Estes Dr, Winchester, KY 40391
  • $234,900
  • 3Bd
  • 2Ba
  • 1,904 Sq Ft
59 Hillcrest Dr, Winchester, KY 40391
  • $250,000
  • 4Bd
  • 2Ba
  • 1,996 Sq Ft
$6K
106 Quail Ridge Rd, Winchester, KY 40391
  • $226,900
  • 3Bd
  • 2Ba
  • 1,665 Sq Ft
$3K
380 Howard Creek Rd, Winchester, KY 40391
  • $326,000
  • 48.54 Acre
$1K
209 Boone Ave, Winchester, KY 40391
  • $265,000
  • 3Bd
  • 3Ba
  • 2,260 Sq Ft
$15K
546 Constitution Dr, Winchester, KY 40391
  • $60,000
  • 2Bd
  • 2Ba
  • 924 Sq Ft
$6K
428 Waycross Dr, Winchester, KY 40391
  • $289,900
  • 4Bd
  • 3Ba
  • 1,970 Sq Ft
$5.1K
267 Runnymeade Dr, Winchester, KY 40391
  • $529,900
  • 4Bd
  • 3Ba
  • 2,732 Sq Ft
$6.1K
2725 Goshen Rd, Winchester, KY 40391
  • $385,000
  • 3Bd
  • 2Ba
  • 1,344 Sq Ft
2379 Big Stoner Rd, Winchester, KY 40391
  • $259,900
  • 3Bd
  • 1Ba
  • 2,444 Sq Ft
$10K
5039 Combs Ferry Rd, Winchester, KY 40391
  • $2,299,000
  • 5Bd
  • 5Ba
  • 6,284 Sq Ft
32 Jackson St, Winchester, KY 40391
  • $189,000
  • 3Bd
  • 1Ba
  • 1,152 Sq Ft
$10K
443 Oxford Dr, Winchester, KY 40391
  • $495,000
  • 2Bd
  • 2Ba
  • 1,054 Sq Ft
$34K
322 Calmes Blvd, Winchester, KY 40391
  • $399,000
  • 3Bd
  • 3Ba
  • 2,204 Sq Ft
$20K
351 Boone Ave, Winchester, KY 40391
  • $379,000
  • 4Bd
  • 2Ba
  • 3,306 Sq Ft
$16K
102 Royal Oak Dr, Winchester, KY 40391
  • $64,900
  • 0.64 Acre
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
2395 Paris Rd, Winchester, KY 40391
  • $100,000
  • 0.52 Acre
$21.5K
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
  • $420,000
  • 3Bd
  • 2Ba
  • 2,027 Sq Ft
128 Cherokee Dr, Winchester, KY 40391
  • $299,900
  • 5Bd
  • 2Ba
  • 2,082 Sq Ft
$10K
491 Hidden Hills Way, Winchester, KY 40391
  • $219,500
  • 3Bd
  • 2Ba
  • 1,200 Sq Ft
$10.4K
3686 Crowe Ridge Rd, Winchester, KY 40391
  • $219,900
  • 23.83 Acre
107 Hibiscus Ln, Winchester, KY 40391
  • $379,000
  • 4Bd
  • 3Ba
  • 1,978 Sq Ft
$20K
4095 Basin Springs Rd, Winchester, KY 40391
  • $350,000
  • 7.31 Acre
$50K
65 Fitch Ave, Winchester, KY 40391
  • $146,900
  • 3Bd
  • 2Ba
  • 1,680 Sq Ft
$3K
309 Gallahadion Ct, Winchester, KY 40391
  • $357,000
  • 3Bd
  • 3Ba
  • 1,945 Sq Ft
$2K
750 Craig Xing, Winchester, KY 40391
  • $154,900
  • 2.53 Acre
955 Right Angle Rd, Winchester, KY 40391
  • $258,900
  • 2Bd
  • 1Ba
  • 849 Sq Ft
$10K
14 Cook Ave, Winchester, KY 40391
  • $219,000
  • 3Bd
  • 2Ba
  • 1,261 Sq Ft
$6K
410 W Lexington Ave, Winchester, KY 40391
  • $325,000
  • 5Bd
  • 4Ba
  • 4,456 Sq Ft
$4.9K
0 Fairholme Way, Winchester, KY 40391
  • $399,000
  • 11.3 Acre
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
502 W Lexington Ave, Winchester, KY 40391
  • $340,000
  • 4Bd
  • 5Ba
  • 4,798 Sq Ft
$10K
20 Edgewood Dr, Winchester, KY 40391
  • $399,900
  • 3Bd
  • 3Ba
  • 2,288 Sq Ft
$13.1K
42 Mockingbird Valley Rd, Winchester, KY 40391
  • $445,500
  • 3Bd
  • 3Ba
  • 2,961 Sq Ft
38 N Burns Ave, Winchester, KY 40391
  • $310,000
  • 4Bd
  • 3Ba
  • 2,310 Sq Ft
$10K
51 - 100 of 242 Homes for sale in Winchester, KY
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Winchester, KY real estate market trends

Statistics as of September 2026
$304K
Avg. list price
$176/Sqft
Avg. price/sqft
174
Homes for sale
1,792 Sqft
Avg. home size
95 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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