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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
$154,900
$225,000
$369,500
$950,000
3D Tour
$729,900
$495,000
$180,000
$579,900
$1,300,000
$335,000
$22
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$229,900
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$565,000
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$645,000
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$305,000
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$110,000
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$366,363
$334,327
$209,900
$269,000
$31,000
3D Tour
$379,900
$245,000
$205,000
$799,900
$395,000
$1,285,000
$1,680,000
$300,000
$749,000
$345,000
$277,000
$345,000
$369,900
$359,900
$645,000
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$383,500
Days on the Market
Ascending
12
Land - Farm Land
$154,900
MLS# 25004490
ACTIVE
Listing Agent: Jarran Thomas
Listing Office: The Agency
Residential
$399,900
MLS# 25004521
ACTIVE
Listing Agent: Jordan James
Listing Office: Lifstyl Real Estate
Residential
$225,000
MLS# 25004408
ACTIVE
Listing Agent: Tracey Goebel
Listing Office: Tom Goebel & Company
Residential
$369,500
MLS# 25004402
ACTIVE
Listing Agent: Mila J Ensor
Listing Office: Ensor Real Estate, LLC
Land - Farm Land
$115,000
MLS# 25004351
ACTIVE
Listing Agent: Jason Townsend
Listing Office: Kentucky Residential Real Estate, LLC
Residential
$950,000
MLS# 25004303
ACTIVE
Listing Agent: Brenda H Sipes
Listing Office: Bridgewater Real Estate
Residential
$419,900
MLS# 25004302
ACTIVE
Listing Agent: Melissa Brown
Listing Office: Keller Williams Legacy Group
Residential
$278,000
MLS# 25004212
ACTIVE
Listing Agent: Tonya Skeens
Listing Office: RE/MAX Elite Lexington
Residential
$239,000
MLS# 25004210
PENDING
Listing Agent: Amy Diamond-Kiper
Listing Office: Bluegrass Sotheby's International Realty
Residential
$729,900
MLS# 25004170
ACTIVE
Listing Agent: Holly L Goeing
Listing Office: The Agency
Residential
$495,000
MLS# 25004009
ACTIVE
Listing Agent: Garry H Milton
Listing Office: Milton and Associates Real Estate
Residential
$849,900
MLS# 25004052
ACTIVE
Listing Agent: Nora G Williams
Listing Office: Keller Williams Commonwealth
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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: 11th March, 2025 7:22 PM (UTC)