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Winchester
Winchester Properties
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7,956 Matches Found
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Year Built
Square Footage
Recently Updated
$399,000
7236 Old Boonesboro Road, Winchester, KY
Closed
3BD
2BA
2,041SF
Last Modified:
8:35pm, October 10, 2025
IDX
$234,000
209 Allan Place, Winchester, KY
Active
3BD
2BA
1,260SF
Last Modified:
2:51pm, October 10, 2025
IDX
$165,000
220 Pendleton Street, Winchester, KY
Pending
2BD
1BA
902SF
Last Modified:
12:53pm, October 10, 2025
IDX
$472,500
208 Royal Oak Drive, Winchester, KY
Closed
4BD
3BA
2,593SF
Last Modified:
5:17am, October 10, 2025
IDX
$690,500
2950 Pretty Run Road, Winchester, KY
Closed
4BD
3BA
2,912SF
Last Modified:
5:17am, October 10, 2025
IDX
$260,000
7934 Ironworks Road, Winchester, KY
Closed
3BD
1BA
1,633SF
Last Modified:
5:17am, October 10, 2025
IDX
$324,900
110 Vine Street, Winchester, KY
Pending
2,560SF
Last Modified:
1:50am, October 10, 2025
IDX
$239,900
313 Snowden Drive, Winchester, KY
Pending
3BD
1BA
1,232SF
Last Modified:
1:49am, October 10, 2025
IDX
$159,200
646 Laura Drive, Winchester, KY
Closed
4BD
2BA
1,534SF
Last Modified:
6:00pm, October 9, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
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Health Care
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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.