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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
$344.9K
$294K
$325K
$90K
$45K
$45K
Days on the Market
Ascending
12
Residential
$344,900
MLS# 25000868
ACTIVE
Listing Agent: Derrick A Simpson
Listing Office: CENTURY 21 Advantage Realty
Residential
$208,000
MLS# 25000856
ACTIVE
Listing Agent: Phillip Neeley-Morrison
Listing Office: Bluegrass Home Group
Residential
$989,000
MLS# 25000871
ACTIVE
Listing Agent: Alysia Niva
Listing Office: Century 21 Advantage Realty - Georgetown
Land - Farm Land
$989,000
MLS# 25000869
ACTIVE
Listing Agent: Alysia Niva
Listing Office: Century 21 Advantage Realty - Georgetown
Residential
$1,375,000
MLS# 25000814
ACTIVE
Listing Agent: Jenny B Ray
Listing Office: RE/MAX Elite Lexington
Residential
$189,000
MLS# 25000799
ACTIVE
Listing Agent: Dale Hatton
Listing Office: Dream Maker Realty, LLC
Residential
$275,000
MLS# 25000803
ACTIVE
Listing Agent: Michelle R Blackburn
Listing Office: RE/MAX Creative, Winchester
Residential
$775,000
MLS# 25000683
ACTIVE
Listing Agent: John L Wilson
Listing Office: Bluegrass Properties Group
Residential
$380,000
MLS# 24025302
PENDING
Listing Agent: Mila J Ensor
Listing Office: Ensor Real Estate, LLC
Land - Farm Land
$546,000
MLS# 25000537
ACTIVE
Listing Agent: Jason B Robinson
Listing Office: Kentucky Real Estate Sales and Finance
Residential
$699,000
MLS# 25000515
PENDING
Listing Agent: Cassie Foley
Listing Office: CENTURY 21 Advantage Realty
Land - Farm Land
$195,000
MLS# 25000480
ACTIVE
Listing Agent: Jenny B Ray
Listing Office: RE/MAX Elite Lexington
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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: 19th January, 2025 10:06 PM (UTC)