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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
3D Tour
$175,000
$1,200,000
$316,900
$450,000
$369,900
Residential
$369,900
MLS# 26007904
ACTIVE
$259,500
$155,000
$335,000
$244,900
Days on the Market
Ascending
12
Commercial Sale
$429,000
MLS# 25014867
PENDING
Listing Agent: Lara Thornbury
Listing Office: Block + Lot Real Estate
Commercial Sale
$300,000
MLS# 20111875
ACTIVE
Listing Agent: Whitney Ann Ensor
Listing Office: Ensor Real Estate, LLC
Land
$500,000
MLS# 20111871
ACTIVE
Listing Agent: Whitney Ann Ensor
Listing Office: Ensor Real Estate, LLC
Land
$270,000
MLS# 20111867
ACTIVE
Listing Agent: Whitney Ann Ensor
Listing Office: Ensor Real Estate, LLC
Residential
$380,000
MLS# 25009085
PENDING
Listing Agent: Rex Hall
Listing Office: United Real Estate Bluegrass
Residential
$430,000
MLS# 25009082
PENDING
Listing Agent: Rex Hall
Listing Office: United Real Estate Bluegrass
Residential
$2,650,000
MLS# 25013058
ACTIVE
Listing Agent: The Prather Team - Michael Prather
Listing Office: Keller Williams Bluegrass Realty
Land
$125,000
MLS# 25012636
ACTIVE
Listing Agent: Laura Sizemore
Listing Office: Kentucky Land and Home
Land
$800,000
MLS# 25009775
PENDING
Listing Agent: Jason Townsend
Listing Office: Kentucky Residential Real Estate, LLC
Residential
$395,000
MLS# 25009077
PENDING
Listing Agent: Rex Hall
Listing Office: United Real Estate Bluegrass
Land
$650,000
MLS# 25008456
ACTIVE
Listing Agent: Gregory Leveridge
Listing Office: Block + Lot Real Estate
Land
$400,000
MLS# 22007107
ACTIVE
Listing Agent: Gregory Leveridge
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: 17th April, 2026 11:40 PM (UTC)