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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
$499,900
414 Fairholme Way, Winchester, KY
Active
4BD
3BA
2,300SF
Last Modified:
2:09pm, December 9, 2025
IDX
$400,000
210 College Street, Winchester, KY
Closed
4BD
4BA
2,718SF
Last Modified:
9:26pm, December 8, 2025
IDX
$384,900
3600 Crowe Ridge Road, Winchester, KY
Active
4BD
5BA
Last Modified:
9:12pm, December 8, 2025
IDX
$349,900
3622 Stamper Drive, Winchester, KY
Active
3BD
3BA
2,821SF
Last Modified:
7:54pm, December 8, 2025
IDX
$209,900
245 Ecton Road, Winchester, KY
Pending
3BD
1BA
1,074SF
Last Modified:
7:44pm, December 8, 2025
IDX
$230,000
16 Apache Trail, Winchester, KY
Closed
5BD
2BA
1,831SF
Last Modified:
4:35pm, December 8, 2025
IDX
$114,000
338 Colby Ridge Boulevard, Winchester, KY
Closed
2BD
2BA
1,188SF
Last Modified:
4:35pm, December 8, 2025
IDX
$600,000
101 S Burns Avenue 1,2,3,4, Winchester, KY
Active
8BD
4BA
5,046SF
Last Modified:
1:32pm, December 8, 2025
IDX
$279,500
724 Terry Drive, Winchester, KY
Active
3BD
2BA
2,250SF
Last Modified:
7:32am, December 8, 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.