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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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3D Tour
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Days on the Market
Ascending
12
Comm Prof Ind
$350,000
MLS# 25012344
ACTIVE
Listing Agent: Melisa C McDonald
Listing Office: Wrenn Realty
Residential
$350,000
MLS# 25012400
ACTIVE
Listing Agent: Melisa C McDonald
Listing Office: Wrenn Realty
Residential
$210,000
MLS# 25012156
ACTIVE
Listing Agent: Dale Hatton
Listing Office: Dream Maker Realty, LLC
Comm Prof Ind
$249,900
MLS# 25012086
ACTIVE
Listing Agent: Joshua Wood
Listing Office: Freedom Realty & Property Management
Multi-Housing
$5,646,000
MLS# 25012023
ACTIVE
Listing Agent: Garry H Milton
Listing Office: Milton and Associates Real Estate
Residential
$3,175,000
MLS# 25011994
ACTIVE
Listing Agent: Zach Davis
Listing Office: Kirkpatrick & Company
Land
$3,175,000
MLS# 25011995
ACTIVE
Listing Agent: Zach Davis
Listing Office: Kirkpatrick & Company
Residential
$119,900
MLS# 25012385
ACTIVE
Listing Agent: Jason L Szaks
Listing Office: EXIT TOWN & COUNTRY REALTORS
Residential
$219,900
MLS# 25011839
ACTIVE
Listing Agent: Tyler I Back
Listing Office: The Brokerage
Comm Prof Ind
$2,500
MLS# 25011931
ACTIVE
Listing Agent: Lara Thornbury
Listing Office: Block + Lot Real Estate
Residential
$215,000
MLS# 25011770
ACTIVE
Listing Agent: Jason Townsend
Listing Office: Kentucky Residential Real Estate, LLC
Residential
$219,900
MLS# 25011691
ACTIVE
Listing Agent: Chaney A Hughes
Listing Office: Guide Realty, Inc.
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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)