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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
$799,900
3D Tour
$54,900
$129,900
$1,115,000
$429,900
$69,900
$79,950
$531,000
$195,000
$1,250,000
$139,000
Days on the Market
Ascending
12
Residential
$550,000
MLS# 24025578
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Residential
$700,000
MLS# 24025582
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Residential
$635,000
MLS# 24025583
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Residential
$625,000
MLS# 24025584
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Residential
$665,000
MLS# 24025581
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Residential
$670,000
MLS# 24025580
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Land
$1,850,000
MLS# 20101924
ACTIVE
Listing Agent: Cheryl Moss Johnston
Listing Office: CMI Properties
Land
$1,200
MLS# 24012397
PENDING
Listing Agent: Holly Spradlin
Listing Office: KY Realty Co
Land
$1,350,000
MLS# 23015568
ACTIVE
Listing Agent: Gregory Leveridge
Listing Office: Block + Lot Real Estate
Land
$775,000
MLS# 23015571
ACTIVE
Listing Agent: Gregory Leveridge
Listing Office: Block + Lot Real Estate
Land
$775,000
MLS# 23015569
ACTIVE
Listing Agent: Gregory Leveridge
Listing Office: Block + Lot Real Estate
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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)