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Winchester
Winchester Properties
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7,959 Matches Found
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List price (Low to High)
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# Bathrooms
Year Built
Square Footage
Recently Updated
$210,000
1290 Two Mile Road, Winchester, KY
Closed
4BD
3BA
2,532SF
Last Modified:
1:05pm, September 23, 2025
IDX
$124,000
5335 Pine Ridge Road, Winchester, KY
Closed
2BD
1BA
1,407SF
Last Modified:
1:05pm, September 23, 2025
IDX
$333,000
3203 Ecton Road, Winchester, KY
Closed
5BD
4BA
Last Modified:
1:05pm, September 23, 2025
IDX
$140,000
179 Ryans Mill Road, Winchester, KY
Closed
3BD
3BA
1,911SF
Last Modified:
1:05pm, September 23, 2025
IDX
$159,000
175 Chatham Place, 135-2, Winchester, KY
Active
2BD
3BA
1,056SF
Last Modified:
7:15pm, September 22, 2025
IDX
$330,000
35 Mockingbird Valley Road, Winchester, KY
Pending
3BD
3BA
1,735SF
Last Modified:
7:07pm, September 22, 2025
IDX
$439,000
104 Colby Hills Drive, Winchester, KY
Active
4BD
2BA
1,950SF
Last Modified:
6:58pm, September 22, 2025
IDX
$435,000
291 Log Lick Road, Winchester, KY
Pending
4BD
3BA
2,600SF
Last Modified:
5:40pm, September 22, 2025
IDX
$950,000
1114 McCann Drive, Winchester, KY
Contingent
5,126SF
Last Modified:
5:10pm, September 22, 2025
IDX
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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.