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Nestled just a stone's throw away from the famed Horse Capital of the World, Lexington, Winchester, KY, is a charming town that promises a one-of-a-kind experience unlike anything you've seen in the Bluegrass State. With many unique activities and attractions, Winchester is sure to captivate the adventurous traveler seeking an authentic slice of Kentucky life.
But that's not all – Winchester is also a gateway to the breathtaking Red River Gorge, where nature enthusiasts can get lost in the majesty of the outdoors. Red River Gorge has something for everyone, from heart-pumping activities like rock climbing and rappelling to peaceful hikes and camping trips.
Ready to explore? Head over to Winchester's Visitor Center at 61 S. Main Street, and our friendly staff will assist in crafting an unforgettable itinerary suited just for you. Discover the warm hospitality and allure of Winchester – we can't wait to have you.
Map of the area
$137,500
$67,500
$225,000
$260,000
$295,000
$295,000
$429,900
$359,900
$70,000
$67,500
$70,000
$137,500
Days on the Market
Ascending
12
land
$150,000
MLS# 24004160
ACTIVE
Listing Agent: Steven D Adams
Listing Office: Steven D Adams Real Estate Services, LLC
Land
$175,000
MLS# 22004991
ACTIVE
Listing Agent: V. Keith Wilson
Listing Office: Coldwell Banker McMahan
Land
$110,000
MLS# 22005014
ACTIVE
Listing Agent: V. Keith Wilson
Listing Office: Coldwell Banker McMahan
Land
$150,000
MLS# 22004993
ACTIVE
Listing Agent: V. Keith Wilson
Listing Office: Coldwell Banker McMahan
Residential
$329,500
MLS# 25005577
PENDING
Listing Agent: Danielle Haggard
Listing Office: Keller Williams Commonwealth
Residential
$329,500
MLS# 25005575
PENDING
Listing Agent: Danielle Haggard
Listing Office: Keller Williams Commonwealth
Commercial Lease
$10
MLS# 25005120
ACTIVE
Listing Agent: Bryan Little
Listing Office: Keller Williams Commonwealth
Commercial Sale
$250,000
MLS# 25004978
ACTIVE
Listing Agent: Lucy Martin Jenkins
Listing Office: United Real Estate Bluegrass
Land
$189,900
MLS# 25002803
PENDING
Listing Agent: Holly L Goeing
Listing Office: The Agency
Residential
$785,000
MLS# 25000149
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Residential
$825,000
MLS# 24025579
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Residential
$645,000
MLS# 24025577
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
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The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Lexington-Bluegrass Association of Realtors Multiple Listing Service. Real estate listings held by IDX Brokerage firms other than Distinctive Living are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX Brokers. Information Deemed Reliable but Not Guaranteed. © LBAR Multiple Listing Service. All rights reserved. Updated: 17th April, 2026 11:40 PM (UTC)