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Winchester
Winchester Properties
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7,952 Matches Found
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# Bathrooms
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Square Footage
Recently Updated
$635,000
315 The Woods Lane, Winchester, KY
Closed
5BD
5BA
5,524SF
Last Modified:
5:20am, October 31, 2025
IDX
New Listing
$219,900
245 Ecton Road, Winchester, KY
Active
3BD
1BA
1,074SF
Last Modified:
11:21pm, October 30, 2025
IDX
$299,900
729 Wayland Drive, Winchester, KY
Active
3BD
2BA
1,966SF
Last Modified:
11:14pm, October 30, 2025
IDX
New Listing
$399,717
300 Calmes Boulevard, Winchester, KY
Active
3BD
3BA
2,636SF
Last Modified:
8:17pm, October 30, 2025
IDX
$340,000
356 Boone Avenue, Winchester, KY
Closed
4BD
3BA
3,200SF
Last Modified:
7:37pm, October 30, 2025
IDX
New Listing
$265,000
433 Wellington Way, Winchester, KY
Active
3BD
2BA
1,234SF
Last Modified:
6:57pm, October 30, 2025
IDX
$319,000
410 Corinne Court, Winchester, KY
Active
3BD
2BA
1,604SF
Last Modified:
6:01pm, October 30, 2025
IDX
New Listing
$363,000
614 S Maple Street, Winchester, KY
Closed
2BD
3BA
1,734SF
Last Modified:
4:19pm, October 30, 2025
IDX
$260,000
190 Privacy Lane, Winchester, KY
Active
Last Modified:
3:29pm, October 30, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
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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.