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Winchester
Winchester Properties
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7,959 Matches Found
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Recently Updated
$299,900
18 N Main Street, Winchester, KY
Active
Last Modified:
4:56pm, September 12, 2025
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$7.75
495 Gawthrop Drive, Winchester, KY
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5,000SF
Last Modified:
4:56pm, September 12, 2025
IDX
$1,300,000
2570 Bypass Road, Winchester, KY
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4,331SF
Last Modified:
4:56pm, September 12, 2025
IDX
$1,700
174 Pedro Way, Winchester, KY
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Last Modified:
4:56pm, September 12, 2025
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$2,500
30 N Main Street, Winchester, KY
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3,000SF
Last Modified:
4:56pm, September 12, 2025
IDX
$1,750,000
101 S Main, Winchester, KY
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20,548SF
Last Modified:
4:56pm, September 12, 2025
IDX
$429,000
39 S Main Street, Winchester, KY
Active
3,538SF
Last Modified:
4:56pm, September 12, 2025
IDX
$300,000
1045 Early Drive, Winchester, KY
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1,675SF
Last Modified:
4:56pm, September 12, 2025
IDX
$10
1946 Bypass Road, Winchester, KY
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Last Modified:
4:56pm, September 12, 2025
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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.