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Winchester
Winchester Properties
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8,003 Matches Found
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List price (Low to High)
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# Bathrooms
Year Built
Square Footage
Recently Updated
$295,000
8 Village Drive, Winchester, KY
Active
3BD
2BA
1,979SF
Last Modified:
5:11pm, November 24, 2025
IDX
$900,000
1114 McCann Drive, Winchester, KY
Closed
5,126SF
Last Modified:
4:52pm, November 24, 2025
IDX
$320,000
104 Teakwood Court, Winchester, KY
Closed
4BD
3BA
1,970SF
Last Modified:
1:53pm, November 24, 2025
IDX
$60,000
145 Riverbend Lane, Winchester, KY
Closed
1BD
1BA
Last Modified:
6:18am, November 24, 2025
IDX
$245,000
231 Leslie Drive, Winchester, KY
Closed
3BD
2BA
1,438SF
Last Modified:
6:17am, November 24, 2025
IDX
$2,950
104 Colby Hlls Drive, Winchester, KY
Active
3BD
2BA
1,950SF
Last Modified:
7:47pm, November 23, 2025
IDX
$257,400
103 Hampton Avenue, Winchester, KY
Closed
3BD
3BA
1,715SF
Last Modified:
4:43pm, November 23, 2025
IDX
$413,000
410 Lyon Drive, Winchester, KY
Closed
4BD
3BA
3,806SF
Last Modified:
6:17am, November 23, 2025
IDX
$475,000
102 Camelot Drive, Winchester, KY
Closed
5BD
4BA
3,679SF
Last Modified:
6:17am, November 23, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
Commute
Health Care
Park & Recreation
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Two kids: assigned school quality, extracurriculars, after-school care, and safe walk/bus routes.
Working parents: drop-off logistics and before/after-school options.
Working parents:
daily time cost and reliability of commutes.
Kids:
longer travel times for school activities and after-school logistics.
Elder:
slightly longer travel for Lexington specialists.
Kids:
local pediatric coverage and urgent care access in Winchester.
Retired elder:
proximity to Clark Regional for emergencies and reliable route to Lexington for specialists.
Measure drive time to Clark Regional Medical Center and the fastest route to Lexington hospitals you’d use.
Call local primary-care/pediatric offices and home-health agencies to check patient acceptance and wait times.
If specific specialties are needed (cardiology, neurology, geriatric), confirm how often those clinics run in Winchester vs. require Lexington visits.
Kids:
sports fields, playgrounds, pool/rec programming.
Retired elder:
short walks, benches, senior programs and community events.
Visit Lykins Park, College Park, and neighborhood parks at different times to check crowding/noise.
Confirm sidewalks and safe walking routes from the street to parks/schools.
Check Parks & Rec program schedules (youth leagues, adult/senior classes).
Kids:
safe routes to school and parks.
Working parents:
secure home/garage and safe evening travel.
Retired elder:
good street lighting and reliable emergency response.