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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
$399,900
$154,900
$225,000
$369,500
$950,000
3D Tour
$729,900
$495,000
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$335,000
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$275,000
$22
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$374,738
Days on the Market
Ascending
12
Land - Farm Land
$235,000
MLS# 25003893
ACTIVE
Listing Agent: Megan McCoy
Listing Office: Keller Williams Legacy Group
Land - Farm Land
$109,000
MLS# 25003894
ACTIVE
Listing Agent: Megan McCoy
Listing Office: Keller Williams Legacy Group
Land - Farm Land
$109,000
MLS# 25003895
ACTIVE
Listing Agent: Megan McCoy
Listing Office: Keller Williams Legacy Group
Residential
$990,000
MLS# 25003606
ACTIVE
Listing Agent: Kathryn M Cheuvront
Listing Office: Coldwell Banker McMahan
Residential
$229,000
MLS# 25003728
PENDING
Listing Agent: Joshua A Davis
Listing Office: The Agency
Residential
$825,000
MLS# 25003566
ACTIVE
Listing Agent: Kim Nelson
Listing Office: Keller Williams Legacy Group
Land - Farm Land
$825,000
MLS# 25003569
ACTIVE
Listing Agent: Kim Nelson
Listing Office: Keller Williams Legacy Group
Residential
$99,500
MLS# 25003481
ACTIVE
Listing Agent: A. Rebecca Woods
Listing Office: Woods Realty Group
Residential
$512,000
MLS# 25003646
ACTIVE
Listing Agent: Brenda G Murphy
Listing Office: Murphy Realty Group
Residential
$1,285,000
MLS# 25003433
ACTIVE
Listing Agent: Suzanne H Elliott
Listing Office: Berkshire Hathaway de Movellan Properties
Residential
$275,000
MLS# 25003361
PENDING
Listing Agent: James Woodrum
Listing Office: RE/MAX Creative, Winchester
Comm Prof Ind
$22
MLS# 25003366
ACTIVE
Listing Agent: Lara Thornbury
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: 11th March, 2025 11:57 PM (UTC)