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Winchester, KY homes for sale & real estate
172 homes
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Recommended
NEW 31 HRS AGO
34 North Burns Ave, Winchester, KY 40391
34 North Burns Ave, Winchester, KY 40391
34 North Burns Ave, Winchester, KY 40391
$224,900
3 beds
2 baths
1,500
sq ft
34 North Burns Ave, Winchester, KY 40391
3,920 sq ft lot
•
Somewhat walkable
202 Dubuy Dr, Winchester, KY 40391
202 Dubuy Dr, Winchester, KY 40391
202 Dubuy Dr, Winchester, KY 40391
$309,000
3 beds
2.5 baths
1,800
sq ft
202 Dubuy Dr, Winchester, KY 40391
7,623 sq ft lot
•
2 garage spots
•
Somewhat walkable
Loading...
4040 Muddy Creek Rd, Winchester, KY 40391
4040 Muddy Creek Rd, Winchester, KY 40391
4040 Muddy Creek Rd, Winchester, KY 40391
$895,000
4 beds
3.5 baths
4,584
sq ft
4040 Muddy Creek Rd, Winchester, KY 40391
13.65 acre lot
•
Garage
•
Car-dependent
118 Strawberry Ln, Winchester, KY 40391
118 Strawberry Ln, Winchester, KY 40391
118 Strawberry Ln, Winchester, KY 40391
$340,000
4 beds
2.5 baths
2,008
sq ft
118 Strawberry Ln, Winchester, KY 40391
6,011 sq ft lot
•
2 garage spots
•
Car-dependent
2100 Irvine Rd #40391, Winchester, KY 40391
2100 Irvine Rd #40391, Winchester, KY 40391
2100 Irvine Rd #40391, Winchester, KY 40391
$1,179,000
3 beds
3.5 baths
3,672
sq ft
2100 Irvine Rd #40391, Winchester, KY 40391
28 acre lot
•
2 garage spots
•
Pool
136 College St, Winchester, KY 40391
$409,999
4 beds
4.5 baths
2,800
sq ft
136 College St, Winchester, KY 40391
111 Quail Ridge Rd, Winchester, KY 40391
$205,000
2 beds
2.5 baths
1,197
sq ft
111 Quail Ridge Rd, Winchester, KY 40391
3588 Stamper Dr, Winchester, KY 40391
$249,900
3 beds
2 baths
1,530
sq ft
3588 Stamper Dr, Winchester, KY 40391
600 Boone Ave, Winchester, KY 40391
$629,900
4 beds
4 baths
4,374
sq ft
600 Boone Ave, Winchester, KY 40391
1363 Clintonville Rd, Winchester, KY 40391
$312,975
2 beds
1 bath
1,116
sq ft
1363 Clintonville Rd, Winchester, KY 40391
223 Bartram Ct, Winchester, KY 40391
$289,000
3 beds
2.5 baths
1,606
sq ft
223 Bartram Ct, Winchester, KY 40391
313 Snowden Dr, Winchester, KY 40391
$249,900
3 beds
1 bath
1,232
sq ft
313 Snowden Dr, Winchester, KY 40391
227 Cross Brook Ln, Winchester, KY 40391
$284,900
3 beds
2 baths
1,508
sq ft
227 Cross Brook Ln, Winchester, KY 40391
420 Alexis Way, Winchester, KY 40391
$695,000
4 beds
2.5 baths
2,770
sq ft
420 Alexis Way, Winchester, KY 40391
58 Fitch Ave, Winchester, KY 40391
$275,000
4 beds
2.5 baths
1,736
sq ft
58 Fitch Ave, Winchester, KY 40391
2509 Mount Sterling Rd, Winchester, KY 40391
$899,900
4 beds
3.5 baths
4,922
sq ft
2509 Mount Sterling Rd, Winchester, KY 40391
Loading...
205 Chardonnay Ct, Winchester, KY 40391
$375,000
4 beds
2.5 baths
2,179
sq ft
205 Chardonnay Ct, Winchester, KY 40391
37 Lynnway Dr, Winchester, KY 40391
$300,000
3 beds
2.5 baths
3,220
sq ft
37 Lynnway Dr, Winchester, KY 40391
5620 Ironworks Rd, Winchester, KY 40391
$225,000
3 beds
2 baths
1,699
sq ft
5620 Ironworks Rd, Winchester, KY 40391
115 Woodford Dr, Winchester, KY 40391
$369,900
3 beds
3 baths
2,166
sq ft
115 Woodford Dr, Winchester, KY 40391
5705 Mount Sterling Rd, Winchester, KY 40391
$399,000
4 beds
2.5 baths
2,980
sq ft
5705 Mount Sterling Rd, Winchester, KY 40391
2 North Main St, Winchester, KY 40391
$1,595,000
37 beds
19.5 baths
26,124
sq ft
2 North Main St, Winchester, KY 40391
106 West Hickman St, Winchester, KY 40391
$230,000
3 beds
2 baths
1,836
sq ft
106 West Hickman St, Winchester, KY 40391
102 West Hickman St, Winchester, KY 40391
$171,000
2 beds
1 bath
870
sq ft
102 West Hickman St, Winchester, KY 40391
133 South Highland St, Winchester, KY 40391
$251,000
6 beds
3 baths
2,302
sq ft
133 South Highland St, Winchester, KY 40391
Loading...
206 Chaplin Ave, Winchester, KY 40391
$131,000
2 beds
1 bath
804
sq ft
206 Chaplin Ave, Winchester, KY 40391
16 Central Ave, Winchester, KY 40391
$290,000
6 beds
4 baths
2,511
sq ft
16 Central Ave, Winchester, KY 40391
136 Alabama St, Winchester, KY 40391
$224,000
3 beds
1 bath
1,645
sq ft
136 Alabama St, Winchester, KY 40391
1028 West Lexington Ave, Winchester, KY 40391
$426,000
5 beds
4 baths
—
sq ft
1028 West Lexington Ave, Winchester, KY 40391
5045 Van Meter Rd, Winchester, KY 40391
$3,330,000
6 beds
5.5 baths
7,274
sq ft
5045 Van Meter Rd, Winchester, KY 40391
211 College St, Winchester, KY 40391
$270,000
4 beds
2 baths
2,056
sq ft
211 College St, Winchester, KY 40391
208 Citation Ct, Winchester, KY 40391
$360,000
2 beds
2 baths
1,568
sq ft
208 Citation Ct, Winchester, KY 40391
3614 Stamper Dr, Winchester, KY 40391
$269,950
3 beds
2 baths
1,247
sq ft
3614 Stamper Dr, Winchester, KY 40391
521 Acadia Way, Winchester, KY 40391
$225,000
4 beds
2 baths
1,370
sq ft
521 Acadia Way, Winchester, KY 40391
511 Acadia Way, Winchester, KY 40391
$225,000
4 beds
2 baths
1,400
sq ft
511 Acadia Way, Winchester, KY 40391
31 Vine St, Winchester, KY 40391
$215,000
3 beds
1 bath
1,443
sq ft
31 Vine St, Winchester, KY 40391
180 Casa Landa Way, Winchester, KY 40391
$650,000
4 beds
3.5 baths
4,779
sq ft
180 Casa Landa Way, Winchester, KY 40391
210 College St, Winchester, KY 40391
$419,900
4 beds
3.5 baths
2,718
sq ft
210 College St, Winchester, KY 40391
231 Leslie Dr, Winchester, KY 40391
$250,000
3 beds
2 baths
1,438
sq ft
231 Leslie Dr, Winchester, KY 40391
1953 Cabin Creek Rd, Winchester, KY 40391
$554,900
6 beds
3.5 baths
3,846
sq ft
1953 Cabin Creek Rd, Winchester, KY 40391
306 Snowden Dr, Winchester, KY 40391
$252,500
4 beds
2 baths
1,593
sq ft
306 Snowden Dr, Winchester, KY 40391
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Redfin
Kentucky
Winchester
Average home prices near Winchester, KY
Cities
Lexington
homes for sale
$375,000
Richmond
homes for sale
$329,900
Stanton
homes for sale
$332,500
Clay City
homes for sale
$152,000
Mount Sterling
homes for sale
$275,000
Lexington-Fayette
homes for sale
$375,000
Camargo
homes for sale
$234,450
Paris
homes for sale
$291,250
Sharpsburg
homes for sale
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Zip Codes
40391
homes for sale
$334,900
Winchester, KY real estate trends
All Home Types trends in Winchester, KY
Median Sale Price
# of Homes Sold
Median Days on Market
All Home Types
All Home Types
Single Family Homes
Townhouses
Condos/Co-ops
Median Sale Price
(All Home Types)
$249,900
+6.3%
YoY | Jul 2025
1 year
3 year
5 year
Based on Redfin calculations of home data from MLS and/or public records.
Location
Data
Jul 2025
Growth
% YoY
Winchester, KY
$249,900
+6.3%
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Popular Markets in Kentucky
Louisville
homes for sale
$284,999
Lexington
homes for sale
$375,000
Bowling Green
homes for sale
$299,900
Covington
homes for sale
$250,000
Georgetown
homes for sale
$369,900
Frankfort
homes for sale
$299,000
Elizabethtown
homes for sale
$319,900
Florence
homes for sale
$279,900
Richmond
homes for sale
$329,900
Paducah
homes for sale
$201,250
Nicholasville
homes for sale
$364,638
Newport
homes for sale
$375,000
Versailles
homes for sale
$549,000
Winchester
homes for sale
$267,475
Fort Thomas
homes for sale
$400,000
Show more
225K
309K
895K
340K
1.18M
410K
205K
250K
630K
313K
289K
250K
285K
695K
275K
900K
375K
300K
225K
370K
399K
1.60M
230K
171K
251K
131K
290K
224K
426K
3.33M
270K
360K
270K
225K
225K
215K
650K
420K
250K
555K
253K
575K
350K
5.65M
220K
472K
550K
308K
295K
650K
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