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Winchester
Winchester Properties
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7,958 Matches Found
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# Bathrooms
Year Built
Square Footage
Recently Updated
$249,900
17 Euclid Avenue, Winchester, KY
Active
3BD
2BA
1,656SF
Last Modified:
5:53pm, October 13, 2025
IDX
$300,000
37 Lynnway Drive, Winchester, KY
Pending
3BD
3BA
3,220SF
Last Modified:
2:46pm, October 13, 2025
IDX
$168,000
4590 Four Mile Road, Winchester, KY
Active
Last Modified:
2:35pm, October 13, 2025
IDX
$186,500
31 Vine Street, Winchester, KY
Active
3BD
1BA
1,443SF
Last Modified:
12:43pm, October 13, 2025
IDX
$340,000
219 Hampton Avenue, Winchester, KY
Closed
4BD
3BA
2,929SF
Last Modified:
12:35pm, October 13, 2025
IDX
$355,000
208 Citation Court, Winchester, KY
Active
2BD
2BA
1,568SF
Last Modified:
6:32am, October 13, 2025
IDX
$510,000
130 Winterberry Circle, Winchester, KY
Closed
5BD
4BA
3,741SF
Last Modified:
5:18am, October 13, 2025
IDX
$310,900
115 Hampton Avenue, Winchester, KY
Closed
4BD
3BA
3,042SF
Last Modified:
5:18am, October 13, 2025
IDX
$244,000
252 S Highland Street, Winchester, KY
Closed
3BD
2BA
1,944SF
Last Modified:
5:17am, October 13, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
Commute
Health Care
Park & Recreation
Crime & Saftey
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.