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Winchester
Winchester Properties
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7,959 Matches Found
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List price (Low to High)
# Bedrooms
# Bathrooms
Year Built
Square Footage
Recently Updated
$282,000
309 Jett Drive, Winchester, KY
Closed
3BD
2BA
1,506SF
Last Modified:
6:55am, August 29, 2025
IDX
$259,000
32 Stefanie Court, Winchester, KY
Closed
3BD
2BA
1,683SF
Last Modified:
6:55am, August 29, 2025
IDX
$175,000
7 Hiawathia Trail, Winchester, KY
Closed
3BD
1BA
1,215SF
Last Modified:
6:55am, August 29, 2025
IDX
$240,880
325 Vanover Way, Winchester, KY
Closed
3BD
3BA
1,428SF
Last Modified:
6:55am, August 29, 2025
IDX
$250,000
330-332 Belmont Avenue, Winchester, KY
Closed
6BD
2BA
Last Modified:
6:54am, August 29, 2025
IDX
$300,000
1570 Little Stoner Road, Winchester, KY
Closed
3BD
2BA
1,488SF
Last Modified:
6:54am, August 29, 2025
IDX
$163,900
412 Jameson Way, Winchester, KY
Closed
3BD
1BA
1,073SF
Last Modified:
6:54am, August 29, 2025
IDX
$555,000
196 Casa Landa Way, Winchester, KY
Closed
5BD
4BA
3,501SF
Last Modified:
6:54am, August 29, 2025
IDX
$429,900
105 Monet Boulevard, Winchester, KY
Closed
4BD
3BA
2,533SF
Last Modified:
6:54am, August 29, 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.