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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
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Days on the Market
Ascending
12
Residential
$2,150,000
MLS# 25011536
ACTIVE
Listing Agent: Abby A Jones
Listing Office: Bluegrass Sotheby's International Realty
Residential
$849,900
MLS# 25011566
PENDING
Listing Agent: Emily Miller
Listing Office: Bluegrass Sotheby's International Realty
Residential
$260,000
MLS# 25011586
PENDING
Listing Agent: Craig R Bridgewater
Listing Office: Bridgewater Real Estate
Residential
$575,000
MLS# 25011592
ACTIVE
Listing Agent: Alyssa M Boley
Listing Office: Coldwell Banker McMahan
Land
$2,150,000
MLS# 25011526
ACTIVE
Listing Agent: Abby A Jones
Listing Office: Bluegrass Sotheby's International Realty
Residential
$259,900
MLS# 25011454
PENDING
Listing Agent: Michael R Hilario
Listing Office: The Agency
Residential
$230,000
MLS# 25011446
ACTIVE
Listing Agent: John L Wilson
Listing Office: Bluegrass Properties Group
Residential
$599,500
MLS# 25011310
ACTIVE
Listing Agent: Shane T Underwood
Listing Office: Keller Williams Commonwealth
Comm Prof Ind
$575,000
MLS# 25011326
ACTIVE
Listing Agent: Diana C Brooker
Listing Office: Lifstyl Real Estate
Residential
$225,000
MLS# 25011235
PENDING
Listing Agent: Alyssa M Boley
Listing Office: Coldwell Banker McMahan
Land
$315,000
MLS# 25011265
PENDING
Listing Agent: Mila J Ensor
Listing Office: Ensor Real Estate, LLC
Residential
$269,900
MLS# 25011266
ACTIVE
Listing Agent: Melodie Lincavage
Listing Office: RE/MAX Elite Realty
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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: 13th June, 2025 11:56 PM (UTC)