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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
$180,000
124 Cherokee Drive, Winchester, KY
Closed
3BD
1BA
1,116SF
Last Modified:
7:50pm, December 15, 2025
IDX
$450,000
233 Cunningham Lane, Winchester, KY
Active
3BD
3BA
2,258SF
Last Modified:
5:58pm, December 15, 2025
IDX
$140,000
208 4th Street, Winchester, KY
Active
2BD
1BA
1,254SF
Last Modified:
4:35pm, December 15, 2025
IDX
$3,100,000
3049 Ironworks Road, Winchester, KY
Active
3BD
3BA
3,693SF
Last Modified:
4:24pm, December 15, 2025
IDX
New Listing
$155,000
134 Hud Road, Winchester, KY
Pending
Last Modified:
4:01pm, December 15, 2025
IDX
$3,100,000
3049 Ironworks Road, Winchester, KY
Active
3BD
3BA
3,693SF
Last Modified:
3:48pm, December 15, 2025
IDX
$255,000
357 Crescent Avenue, Winchester, KY
Active
3BD
2BA
2,188SF
Last Modified:
2:56pm, December 15, 2025
IDX
$318,000
22 N Bloomfield Road, Winchester, KY
Active
3BD
2BA
1,913SF
Last Modified:
7:32am, December 15, 2025
IDX
$171,500
120 E Lexington Avenue, Winchester, KY
Closed
3BD
1BA
1,332SF
Last Modified:
6:17am, 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.