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Winchester
Winchester Properties
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8,005 Matches Found
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List price (Low to High)
# Bedrooms
# Bathrooms
Year Built
Square Footage
Recently Updated
$203,900
25 Hiawatha Trail, Winchester, KY
Closed
3BD
1BA
925SF
Last Modified:
7:28pm, December 11, 2025
IDX
$318,500
214 S Burns Avenue, Winchester, KY
Active
4BD
2BA
2,170SF
Last Modified:
7:15pm, December 11, 2025
IDX
$217,000
517 Acadia Way, Winchester, KY
Closed
4BD
2BA
1,400SF
Last Modified:
7:09pm, December 11, 2025
IDX
$660,000
420 Alexis Way, Winchester, KY
Closed
4BD
3BA
2,770SF
Last Modified:
12:55pm, December 11, 2025
IDX
$380,000
5705 Mount Sterling Road, Winchester, KY
Closed
4BD
3BA
2,980SF
Last Modified:
6:17am, December 11, 2025
IDX
$220,000
313 Snowden Drive, Winchester, KY
Closed
3BD
1BA
1,232SF
Last Modified:
6:17am, December 11, 2025
IDX
$260,000
113 Olde Potomac Avenue, Winchester, KY
Closed
3BD
2BA
1,928SF
Last Modified:
6:17am, December 11, 2025
IDX
$335,000
536 S Maple Street, Winchester, KY
Closed
3BD
3BA
1,832SF
Last Modified:
6:17am, December 11, 2025
IDX
$250,000
110 Vine Street, Winchester, KY
Closed
2,560SF
Last Modified:
6:17am, December 11, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
Commute
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.