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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
$316,900
$369,900
Residential
$369,900
MLS# 26007904
ACTIVE
$259,500
$155,000
$335,000
$244,900
$209,900
Days on the Market
Ascending
12
Land
$1,200,000
MLS# 23018853
ACTIVE
Listing Agent: Garnett H Davis
Listing Office: Tom Goebel & Company
Land
$550,500
MLS# 23018854
ACTIVE
Listing Agent: Garnett H Davis
Listing Office: Tom Goebel & Company
Land
$2,500,000
MLS# 23018755
ACTIVE
Listing Agent: Garnett H Davis
Listing Office: Tom Goebel & Company
Land
$2,500,000
MLS# 23018756
ACTIVE
Listing Agent: Garnett H Davis
Listing Office: Tom Goebel & Company
Residential
$3,500,000
MLS# 25017446
ACTIVE
Listing Agent: The Prather Team - Michael Prather
Listing Office: Keller Williams Bluegrass Realty
Residential
$171,000
MLS# 25017468
ACTIVE
Listing Agent: David Espinosa
Listing Office: Bluegrass Realty Pros, Inc
Residential
$215,000
MLS# 25016184
PENDING
Listing Agent: Kimberly Fugate
Listing Office: Keller Williams Commonwealth
Commercial Sale
$780,000
MLS# 25015685
ACTIVE
Listing Agent: Dallas Hodge
Listing Office: The Gibson Company
Land
$14,100,000
MLS# 25015654
ACTIVE
Listing Agent: MELIA Realty Group - Melia Hord
Listing Office: Keller Williams Legacy Group
Residential
$102,000
MLS# 25015196
ACTIVE
Listing Agent: David Espinosa
Listing Office: Bluegrass Realty Pros, Inc
Residential Income
$388,000
MLS# 25015191
ACTIVE
Listing Agent: David Espinosa
Listing Office: Bluegrass Realty Pros, Inc
Residential
$144,000
MLS# 25015192
ACTIVE
Listing Agent: David Espinosa
Listing Office: Bluegrass Realty Pros, 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: 17th April, 2026 11:40 PM (UTC)