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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
$339,000
$270,000
$450,000
$260,000
$355,000
$219,000
$1,850
$189,500
$189,500
$591,650
$95,000
$452,500
Days on the Market
Ascending
12
Residential
$339,000
MLS# 26001569
ACTIVE
Listing Agent: Brittany Nester
Listing Office: RO&CO Real Estate
Residential
$270,000
MLS# 26001564
ACTIVE
Listing Agent: A. Rebecca Woods
Listing Office: Woods Realty Group
Residential
$450,000
MLS# 26001532
ACTIVE
Listing Agent: Laura Eaves
Listing Office: Berkshire Hathaway de Movellan Properties
Residential
$260,000
MLS# 26001286
ACTIVE
Listing Agent: Kenneth DeGrant
Listing Office: High Point Realty & Auction
Residential
$849,000
MLS# 26001454
ACTIVE
Listing Agent: Craig R Bridgewater
Listing Office: Bridgewater Real Estate
Residential
$215,000
MLS# 26001199
ACTIVE
Listing Agent: James Woodrum
Listing Office: RE/MAX Creative, Winchester
Residential
$199,900
MLS# 26000958
ACTIVE
Listing Agent: Dylan Justice
Listing Office: GSP Homes
Residential Income
$355,000
MLS# 26000922
ACTIVE
Listing Agent: Brian T Hatfield
Listing Office: Coldwell Banker McMahan
Residential
$365,000
MLS# 26000914
PENDING
Listing Agent: Meggan Batey
Listing Office: Keller Williams Legacy Group
Residential
$359,900
MLS# 26000925
ACTIVE
Listing Agent: Heather Kuykendoll
Listing Office: Bluegrass Properties Group
Residential
$290,000
MLS# 26001069
PENDING
Listing Agent: Craig R Bridgewater
Listing Office: Bridgewater Real Estate
Residential
$219,000
MLS# 26000887
ACTIVE
Listing Agent: Slava Furs
Listing Office: 85W 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: 22nd January, 2026 12:43 PM (UTC)