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Winchester
Winchester Properties
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7,951 Matches Found
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# Bathrooms
Year Built
Square Footage
Recently Updated
$204,000
133 S Burns Avenue, Winchester, KY
Closed
4BD
2BA
3,295SF
Last Modified:
7:06pm, October 31, 2025
IDX
Open House
$899,000
2447 Clintonville Road, Winchester, KY
Active
5BD
4BA
4,058SF
Last Modified:
4:31pm, October 31, 2025
IDX
New Listing
$275,000
103 Hampton Avenue, Winchester, KY
Contingent
3BD
3BA
1,715SF
Last Modified:
3:47pm, October 31, 2025
IDX
New Listing
$349,000
212 Woodbine Court, Winchester, KY
Active
3BD
3BA
2,475SF
Last Modified:
3:23pm, October 31, 2025
IDX
New Listing
Open House
$355,000
145 Shanahan Lane, Winchester, KY
Active
4BD
3BA
2,520SF
Last Modified:
3:08pm, October 31, 2025
IDX
$186,000
205 Arbor Court, Winchester, KY
Closed
3BD
2BA
1,188SF
Last Modified:
3:05pm, October 31, 2025
IDX
$366,363
140 Gibson Way, Winchester, KY
Closed
4BD
3BA
2,269SF
Last Modified:
3:05pm, October 31, 2025
IDX
$575,000
842 Bypass Road, Winchester, KY
Pending
1,950SF
Last Modified:
2:21pm, October 31, 2025
IDX
$273,000
727 Terry Drive, Winchester, KY
Closed
3BD
2BA
1,958SF
Last Modified:
1:35pm, October 31, 2025
IDX
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Nearby Areas
Explore popular things to do in the areas.
Education
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Health Care
Park & Recreation
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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.