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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
$690,000
775 Sugar Ridge Road, Winchester, KY
Closed
4BD
3BA
2,860SF
Last Modified:
6:59am, August 29, 2025
IDX
$330,000
113 Holiday Road, Winchester, KY
Closed
3BD
3BA
2,090SF
Last Modified:
6:59am, August 29, 2025
IDX
$420,000
142 College Street, Winchester, KY
Closed
4BD
3BA
3,012SF
Last Modified:
6:59am, August 29, 2025
IDX
$849,900
3714 Wades Mill Road, Winchester, KY
Closed
5BD
4BA
3,818SF
Last Modified:
6:58am, August 29, 2025
IDX
$230,000
200 Bracken Court, Winchester, KY
Closed
3BD
2BA
1,252SF
Last Modified:
6:58am, August 29, 2025
IDX
$270,000
137 Summerhill Way, Winchester, KY
Closed
3BD
2BA
1,284SF
Last Modified:
6:58am, August 29, 2025
IDX
$219,900
142 Sturbridge Lane, Winchester, KY
Closed
3BD
2BA
1,220SF
Last Modified:
6:58am, August 29, 2025
IDX
$170,000
17 Hiawatha Trail, Winchester, KY
Closed
3BD
2BA
1,000SF
Last Modified:
6:58am, August 29, 2025
IDX
$110,750
745 Country Club Court, Winchester, KY
Closed
3BD
2BA
Last Modified:
6:58am, 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.