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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
$459,000
$325,000
$339,900
$205,000
$285,000
$249,900
$450,000
$384,900
$334,900
$210,000
$229,500
$2,100
$174,999
$2,100
$217,000
3D Tour
$205,000
$512,000
Residential
$512,000
MLS# 25006934
ACTIVE
$464,900
$275,000
$225,000
$430,000
$274,900
$219,000
$265,000
$240,000
3D Tour
$429,900
$3,500
$439,000
$40,000
$274,000
$349,900
$279,900
$399,000
$175,000
3D Tour
$329,900
$249,900
$249,900
$12
$349,000
$499,000
$340,000
$229,900
$330,000
$241,000
$285,000
$1,750
$355,000
$554,900
$217,000
$379,900
$299,900
$152,000
$364,900
$225,000
$950,000
3D Tour
$699,900
$465,000
$335,000
$210,000
$1,300,000
$579,900
$22
$1,500,000
$375,000
$262,500
Residential
$262,500
MLS# 25003180
ACTIVE
$239,900
$224,900
$299,900
$524,900
$179,900
$255,000
$324,900
$240,000
$645,000
$775,000
Days on the Market
Ascending
12
Residential
$459,000
MLS# 25007927
ACTIVE
Listing Agent: Melodie Lincavage
Listing Office: RE/MAX Elite Realty
Land
$35,000
MLS# 25007914
ACTIVE
Listing Agent: Cathleen Gedeon
Listing Office: CENTURY 21 Advantage Realty
Land
$40,000
MLS# 25007913
ACTIVE
Listing Agent: Cathleen Gedeon
Listing Office: CENTURY 21 Advantage Realty
Residential
$325,000
MLS# 25007800
ACTIVE
Listing Agent: Lindsay Barsotti
Listing Office: ERA Select Real Estate
Residential
$339,900
MLS# 25007846
ACTIVE
Listing Agent: Joshua Wood
Listing Office: Freedom Realty & Property Management
Residential
$205,000
MLS# 25007758
PENDING
Listing Agent: Whitney Ann Ensor
Listing Office: Ensor Real Estate, LLC
Residential
$199,000
MLS# 25007675
ACTIVE
Listing Agent: Tracey Goebel
Listing Office: Tom Goebel & Company
Residential
$285,000
MLS# 25007670
ACTIVE
Listing Agent: Susan Colwell
Listing Office: Colwell Realty Professionals, Inc.
Residential
$149,000
MLS# 25007762
ACTIVE
Listing Agent: Emily Hacker-Todd
Listing Office: CENTURY 21 Advantage Realty
Residential
$249,900
MLS# 25007779
ACTIVE
Listing Agent: Darrell Tackett
Listing Office: Dream Maker Realty, LLC
Residential
$249,900
MLS# 25007620
ACTIVE
Listing Agent: Destiny Darby
Listing Office: Keller Williams Commonwealth
Residential
$450,000
MLS# 25007660
ACTIVE
Listing Agent: Dale Hatton
Listing Office: Dream Maker Realty, LLC
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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: 21st April, 2025 5:12 PM (UTC)