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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
$1,800,000
$600,000
$150,000
3D Tour
$175,000
$1,200,000
$316,900
$369,900
Residential
$369,900
MLS# 26007904
ACTIVE
$259,500
$155,000
$335,000
$244,900
Days on the Market
Ascending
12
Land
$1,800,000
MLS# 26008233
ACTIVE
Listing Agent: Cheryl Moss Johnston
Listing Office: CMI Properties
Land
$600,000
MLS# 26008236
ACTIVE
Listing Agent: Cheryl Moss Johnston
Listing Office: CMI Properties
Land
$150,000
MLS# 26008075
ACTIVE
Listing Agent: Steven D Adams
Listing Office: Steven D Adams Real Estate Services, LLC
Residential
$199,900
MLS# 26007746
ACTIVE
Listing Agent: Amanda S Marcum
Listing Office: Berkshire Hathaway HomeServices Foster Realtors
Residential
$175,000
MLS# 26008091
PENDING
Listing Agent: Ryan W Sigler
Listing Office: Rector Hayden Realtors
Residential
$799,900
MLS# 26005374
ACTIVE
Listing Agent: Joshua Wood
Listing Office: Freedom Realty & Property Management
Residential Income
$1,200,000
MLS# 26007993
ACTIVE
Listing Agent: Kevin Bradley
Listing Office: KB Realty Group
Residential
$316,900
MLS# 26008021
ACTIVE
Listing Agent: Wayne Elkins
Listing Office: RE/MAX Creative Realty
Residential
$450,000
MLS# 26008003
ACTIVE
Listing Agent: Mila J Ensor
Listing Office: Ensor Real Estate, LLC
Residential
$369,900
MLS# 26007904
ACTIVE
Listing Agent: Stacey Dunaway
Listing Office: HomeLand Real Estate Inc - Mt Sterling
Residential
$259,500
MLS# 25017189
ACTIVE
Listing Agent: Darrell Tackett
Listing Office: Dream Maker Realty, LLC
Residential
$155,000
MLS# 26007798
ACTIVE
Listing Agent: Tony Giglio
Listing Office: ListWithFreedom.com
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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)