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Winchester
Winchester Properties
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7,952 Matches Found
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Year Built
Square Footage
Recently Updated
$199,000
23 Hillcrest Drive, Winchester, KY
Active
2BD
1BA
1,557SF
Last Modified:
10:22pm, November 2, 2025
IDX
Open House
$379,000
121 Fitch Avenue, Winchester, KY
Active
4BD
3BA
2,100SF
Last Modified:
8:43pm, November 2, 2025
IDX
$413,000
410 Lyon Drive, Winchester, KY
Closed
4BD
3BA
3,806SF
Last Modified:
7:33pm, November 2, 2025
IDX
$189,900
27 Ashland Avenue, Winchester, KY
Active
3BD
2BA
1,653SF
Last Modified:
7:10pm, November 2, 2025
IDX
$200,000
34 N Burns Avenue, Winchester, KY
Closed
3BD
2BA
1,500SF
Last Modified:
6:26pm, November 2, 2025
IDX
$320,000
510 Kimberly Drive, Winchester, KY
Closed
4BD
2BA
2,430SF
Last Modified:
6:26pm, November 2, 2025
IDX
$200,000
2858 Ford Hampton Road, Winchester, KY
Closed
3BD
2BA
1,294SF
Last Modified:
6:26pm, November 2, 2025
IDX
$319,900
128 Cherokee Drive, Winchester, KY
Active
5BD
2BA
2,082SF
Last Modified:
3:17pm, November 2, 2025
IDX
$545,000
445 Lynnway Drive, Winchester, KY
Closed
4BD
4BA
3,649SF
Last Modified:
3:15pm, November 2, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
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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.