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Winchester
Winchester Properties
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8,004 Matches Found
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# Bathrooms
Year Built
Square Footage
Recently Updated
$200,000
612 Boone Avenue, Winchester, KY
Pending
2BD
2BA
1,262SF
Last Modified:
7:02pm, November 17, 2025
IDX
$182,000
6 Monroe Avenue, Winchester, KY
Active
3BD
2BA
1,305SF
Last Modified:
6:12pm, November 17, 2025
IDX
$319,900
128 Cherokee Drive, Winchester, KY
Active
5BD
2BA
2,082SF
Last Modified:
7:32am, November 17, 2025
IDX
$269,000
222 Bracken Court, Winchester, KY
Active
3BD
3BA
1,456SF
Last Modified:
7:32am, November 17, 2025
IDX
$824,900
7300 Old Boonesboro Road, Winchester, KY
Active
4BD
3BA
3,311SF
Last Modified:
7:32am, November 17, 2025
IDX
$360,000
309 Gallahadion Court, Winchester, KY
Closed
3BD
3BA
1,920SF
Last Modified:
6:17am, November 17, 2025
IDX
$320,000
3431 Colby Road, Winchester, KY
Closed
4BD
2BA
Last Modified:
6:17am, November 17, 2025
IDX
$10,000
117 4th Street, Winchester, KY
Active
Last Modified:
1:08am, November 17, 2025
IDX
$300,000
115 College Street, Winchester, KY
Contingent
3BD
2BA
1,839SF
Last Modified:
6:40pm, November 15, 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.