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Single Family Homes For Sale in Winchester, KY

158 Homes
 
25 W Hickman St, Winchester, KY 40391
  • $325,000
  • 5Bd
  • 3Ba
  • 3,378 Sq Ft
New 12 Hours
26 Holiday Rd, Winchester, KY 40391
  • $255,000
  • 3Bd
  • 1Ba
  • 1,135 Sq Ft
New 30 Hours
5825 Combs Ferry Rd, Winchester, KY 40391
  • $4,895,000
  • 3Bd
  • 4Ba
  • 5,800 Sq Ft
New 2 Days
214 Center Dr, Winchester, KY 40391
  • $199,500
  • 3Bd
  • 1Ba
  • 1,193 Sq Ft
New 2 Days
410 W Lexington Ave, Winchester, KY 40391
  • $299,900
  • 5Bd
  • 4Ba
  • 4,456 Sq Ft
New 3 Days
122 Sunset Hts, Winchester, KY 40391
  • $265,000
  • 3Bd
  • 2Ba
  • 1,715 Sq Ft
New 4 Days
5039 Combs Ferry Rd, Winchester, KY 40391
  • $2,299,000
  • 5Bd
  • 4Ba
  • 8,389 Sq Ft
New 5 Days
47 Cherokee Ct, Winchester, KY 40391
  • $289,900
  • 3Bd
  • 2Ba
  • 1,254 Sq Ft
New 6 Days
444 Wellington Way, Winchester, KY 40391
  • $314,900
  • 4Bd
  • 3Ba
  • 1,963 Sq Ft
New 7 Days
9930 Mount Sterling Rd, Winchester, KY 40391
  • $639,000
  • 3Bd
  • 1Ba
  • 1,962 Sq Ft
New 7 Days
15 Maryland Ave, Winchester, KY 40391
  • $220,000
  • 3Bd
  • 1Ba
  • 1,140 Sq Ft
109 5th St, Winchester, KY 40391
  • $265,000
  • 5Bd
  • 4Ba
  • 1,714 Sq Ft
213 E Broadway St, Winchester, KY 40391
  • $200,000
  • 3Bd
  • 1Ba
  • 1,453 Sq Ft
107 S Burns Ave, Winchester, KY 40391
  • $367,700
  • 4Bd
  • 2Ba
  • 2,352 Sq Ft
330 Spencer Ln, Winchester, KY 40391
  • $769,900
  • 3Bd
  • 3Ba
  • 2,200 Sq Ft
2100 Irvine Rd, Winchester, KY 40391
  • $1,125,000
  • 3Bd
  • 4Ba
  • 3,672 Sq Ft
326 W Lexington Ave, Winchester, KY 40391
  • $225,000
  • 3Bd
  • 1Ba
  • 2,244 Sq Ft
14 Shelley Dr, Winchester, KY 40391
  • $215,000
  • 3Bd
  • 1Ba
  • 1,134 Sq Ft
600 College St, Winchester, KY 40391
  • $220,000
  • 3Bd
  • 2Ba
  • 1,737 Sq Ft
$5K
609 W Barlow Dr, Winchester, KY 40391
  • $375,000
  • 4Bd
  • 2Ba
  • 1,828 Sq Ft
1039 Cole Rd, Winchester, KY 40391
  • $939,000
  • 4Bd
  • 3Ba
  • 3,103 Sq Ft
$58K
335 Newcastle Ln, Winchester, KY 40391
  • $304,900
  • 3Bd
  • 3Ba
  • 1,904 Sq Ft
1477 Sewell Shop Rd, Winchester, KY 40391
  • $675,000
  • 4Bd
  • 4Ba
  • 2,659 Sq Ft
102 Quail Ridge Rd, Winchester, KY 40391
  • $239,000
  • 3Bd
  • 3Ba
  • 1,856 Sq Ft
Open SAT 2-4
6 French Ave, Winchester, KY 40391
  • $296,000
  • 4Bd
  • 2Ba
  • 1,953 Sq Ft
$23.9K
4578 Combs Ferry Rd, Winchester, KY 40391
  • $1,500,000
  • 3Bd
  • 2Ba
  • 1,860 Sq Ft
7353 Ironworks Rd, Winchester, KY 40391
  • $390,000
  • 4Bd
  • 1Ba
  • 2,063 Sq Ft
317 Vanover Way, Winchester, KY 40391
  • $249,900
  • 3Bd
  • 2Ba
  • 1,492 Sq Ft
5960 Van Meter Rd, Winchester, KY 40391
  • $855,000
  • 3Bd
  • 3Ba
  • 2,872 Sq Ft
11304 Irvine Rd, Winchester, KY 40391
  • $248,900
  • 3Bd
  • 1Ba
  • 2,249 Sq Ft
$11K
420 Calmes Blvd, Winchester, KY 40391
  • $349,900
  • 3Bd
  • 3Ba
  • 1,846 Sq Ft
$10K
209 E Washington St, Winchester, KY 40391
  • $159,000
  • 3Bd
  • 1Ba
  • 1,249 Sq Ft
$6K
119 Tower Ln, Winchester, KY 40391
  • $229,900
  • 3Bd
  • 1Ba
  • 1,272 Sq Ft
$5.1K
54 Locust Dr, Winchester, KY 40391
  • $244,000
  • 3Bd
  • 2Ba
  • 1,692 Sq Ft
104 Teal Ln, Winchester, KY 40391
  • $629,000
  • 5Bd
  • 4Ba
  • 5,011 Sq Ft
$10K
3208 Ford Hampton Rd, Winchester, KY 40391
  • $135,000
  • 2Bd
  • 1Ba
  • 807 Sq Ft
1400 Craig Xing, Winchester, KY 40391
  • $1,400,000
  • 4Bd
  • 4Ba
  • 5,613 Sq Ft
198 Hilltop Dr, Winchester, KY 40391
  • $269,500
  • 4Bd
  • 2Ba
  • 1,752 Sq Ft
$5.5K
125 Kittison Dr, Winchester, KY 40391
  • $219,900
  • 3Bd
  • 1Ba
  • 1,100 Sq Ft
$10K
15 Moundale Ave, Winchester, KY 40391
  • $359,900
  • 3Bd
  • 2Ba
  • 2,269 Sq Ft
410 Fairholme Way, Winchester, KY 40391
  • $484,900
  • 4Bd
  • 3Ba
  • 2,381 Sq Ft
204 Jett Dr, Winchester, KY 40391
  • $365,900
  • 3Bd
  • 2Ba
  • 1,558 Sq Ft
206 Jett Dr, Winchester, KY 40391
  • $365,900
  • 3Bd
  • 2Ba
  • 1,635 Sq Ft
3 Nunnelly Ct, Winchester, KY 40391
  • $205,000
  • 3Bd
  • 2Ba
  • 1,319 Sq Ft
$10K
24 Spring St, Winchester, KY 40391
  • $160,000
  • 3Bd
  • 1Ba
  • 1,173 Sq Ft
$15K
16 Denny Ave, Winchester, KY 40391
  • $78,500
  • 3Bd
  • 1Ba
  • 1,152 Sq Ft
$20K
127 Bay Hill Dr, Winchester, KY 40391
  • $249,000
  • 3Bd
  • 3Ba
  • 1,664 Sq Ft
$5.9K
606 College St, Winchester, KY 40391
  • $199,000
  • 2Bd
  • 1Ba
  • 1,154 Sq Ft
$6.4K
15 Kittison Dr, Winchester, KY 40391
  • $265,000
  • 3Bd
  • 2Ba
  • 1,776 Sq Ft
$5K
108 Franklin Ave, Winchester, KY 40391
  • $140,000
  • 2Bd
  • 1Ba
  • 630 Sq Ft
$10K
1 - 50 of 158 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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