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Winchester
Winchester Properties
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7,961 Matches Found
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# Bathrooms
Year Built
Square Footage
Recently Updated
$311,500
136 Shanahan Lane, Winchester, KY
Closed
3BD
3BA
2,059SF
Last Modified:
5:55am, August 29, 2025
IDX
$189,900
303 W Washington Street, Winchester, KY
Closed
3BD
2BA
1,080SF
Last Modified:
5:55am, August 29, 2025
IDX
$179,500
230 Winn Avenue, Winchester, KY
Closed
4BD
2BA
1,400SF
Last Modified:
5:55am, August 29, 2025
IDX
$105,000
110 3rd Street, Winchester, KY
Closed
3BD
2BA
1,242SF
Last Modified:
5:54am, August 29, 2025
IDX
$240,000
714 Simba Court, Winchester, KY
Closed
3BD
2BA
1,332SF
Last Modified:
5:54am, August 29, 2025
IDX
$320,000
1831 Kiddville Road, Winchester, KY
Closed
3BD
2BA
1,756SF
Last Modified:
5:54am, August 29, 2025
IDX
$240,000
328 S Main Street, Winchester, KY
Closed
4BD
3BA
2,709SF
Last Modified:
5:54am, August 29, 2025
IDX
$230,000
120 Milwood Drive, Winchester, KY
Closed
3BD
2BA
1,853SF
Last Modified:
5:54am, August 29, 2025
IDX
$220,000
11705 Irvine Road, Winchester, KY
Closed
3BD
2BA
2,668SF
Last Modified:
5:54am, August 29, 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.