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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
$399,000
4530 Ironworks Road, Winchester, KY
Pending
4BD
3BA
2,518SF
Last Modified:
2:36am, December 16, 2025
IDX
$274,900
407 Corinne Court, Winchester, KY
Contingent
3BD
2BA
1,352SF
Last Modified:
12:50am, December 16, 2025
IDX
Open House
$260,000
21 Virginia Avenue, Winchester, KY
Active
3BD
2BA
1,749SF
Last Modified:
11:48pm, December 15, 2025
IDX
$4,880,000
2090 Pretty Run Road, Winchester, KY
Closed
Last Modified:
10:39pm, December 15, 2025
IDX
$399,550
397 Calmes Boulevard, Winchester, KY
Pending
4BD
4BA
2,637SF
Last Modified:
9:36pm, December 15, 2025
IDX
$210,500
40 Garner Street, Winchester, KY
Active
3BD
1BA
1,354SF
Last Modified:
8:02pm, December 15, 2025
IDX
$180,000
124 Cherokee Drive, Winchester, KY
Closed
3BD
1BA
1,116SF
Last Modified:
7:50pm, December 15, 2025
IDX
New Listing
$825,000
455 Davis Lane, Winchester, KY
Active
2BD
2BA
2,361SF
Last Modified:
6:04pm, December 15, 2025
IDX
New Listing
$450,000
233 Cunningham Lane, Winchester, KY
Active
3BD
3BA
2,258SF
Last Modified:
5:58pm, December 15, 2025
IDX
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Nearby Areas
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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.