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Winchester
Winchester Properties
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8,005 Matches Found
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# Bathrooms
Year Built
Square Footage
Recently Updated
$188,900
27 Ashland Avenue, Winchester, KY
Active
3BD
2BA
1,653SF
Last Modified:
5:36pm, December 12, 2025
IDX
$220,000
2721 Pretty Run Road, Winchester, KY
Contingent
3BD
2BA
1,456SF
Last Modified:
5:20pm, December 12, 2025
IDX
New Listing
$609,900
6595 Mt Sterling Road, Winchester, KY
Active
5BD
4BA
4,515SF
Last Modified:
5:13pm, December 12, 2025
IDX
$120,000
627 Laurel Drive, Winchester, KY
Closed
4BD
2BA
1,540SF
Last Modified:
3:05pm, December 12, 2025
IDX
$120,000
627 Laura Drive, Winchester, KY
Closed
4BD
2BA
1,540SF
Last Modified:
3:05pm, December 12, 2025
IDX
$210,000
246 Geronimo Court, Winchester, KY
Pending
3BD
2BA
1,092SF
Last Modified:
3:13am, December 12, 2025
IDX
$318,000
118 Windridge Drive, Winchester, KY
Active
3BD
2BA
1,617SF
Last Modified:
10:02pm, December 11, 2025
IDX
New Listing
$229,000
394 S Main Street, Winchester, KY
Active
4BD
2BA
1,858SF
Last Modified:
8:29pm, December 11, 2025
IDX
$385,000
1731 Ford Hampton Road, Winchester, KY
Closed
4BD
3BA
2,111SF
Last Modified:
7:28pm, December 11, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
Commute
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.