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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
$154,200
720 Terry Drive, Winchester, KY
Closed
3BD
2BA
1,852SF
Last Modified:
7:50pm, October 2, 2025
IDX
$205,000
635 Lisletown Lane, Winchester, KY
Closed
2BD
2BA
1,826SF
Last Modified:
6:50pm, October 2, 2025
IDX
$68,000
690 Lisletown Lane, Winchester, KY
Closed
Last Modified:
6:50pm, October 2, 2025
IDX
$333,500
543 S Maple Street, Winchester, KY
Closed
3BD
2BA
1,527SF
Last Modified:
5:29pm, October 2, 2025
IDX
$225,000
363 S Main Street, Winchester, KY
Active
3BD
2BA
2,142SF
Last Modified:
10:47pm, October 1, 2025
IDX
$250,000
10 Upper Street, Winchester, KY
Active
3BD
3BA
2,380SF
Last Modified:
9:17pm, October 1, 2025
IDX
$925,000
1150 Craig Crossing, Winchester, KY
Active
5BD
4BA
2,842SF
Last Modified:
8:44pm, October 1, 2025
IDX
$1,350,000
115 Hud Road, Winchester, KY
Closed
19,500SF
Last Modified:
6:44pm, October 1, 2025
IDX
$259,900
315 Newcastle Lane, Winchester, KY
Closed
3BD
3BA
1,544SF
Last Modified:
5:37am, October 1, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
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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.