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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
$100,000
$350,000
Residential
$350,000
MLS# 25012639
ACTIVE
$265,500
$2,000
$325,000
$314,900
$350,000
$350,000
$119,900
$249,900
$219,900
$2,500
$215,000
$219,900
$225,000
$379,900
$339,000
$189,900
$214,900
$295,000
$274,900
$45,000
$950,000
$260,000
$220,000
$215,000
$194,900
$293,500
$334,900
$195,000
$195,000
$175,000
$209,000
$199,900
$99,900
$69,000
$129,900
$825,000
$240,000
$244,700
$184,900
$289,000
$259,000
$430,000
$430,000
$380,000
$345,000
$345,000
$395,000
$380,000
$380,000
$430,000
$185,000
$129,000
$650,000
$179,000
$240,000
$225,000
$249,900
$339,900
$149,000
$189,000
$279,500
$215,000
$210,000
$185,000
$275,000
$3,500
$265,000
$699,000
$40,000
$12
$239,900
$239,900
$230,000
$499,000
$225,000
$135,000
$325,000
Days on the Market
Ascending
12
Residential
$100,000
MLS# 25012612
ACTIVE
Listing Agent: Rony Jo Ballou
Listing Office: Power House Realty
Residential
$350,000
MLS# 25012639
ACTIVE
Listing Agent: Kymberly M McCreary
Listing Office: EXP Realty, LLC
Residential
$524,999
MLS# 25012505
ACTIVE
Listing Agent: Julie Wiggington
Listing Office: RE/MAX Creative, Winchester
Residential
$488,000
MLS# 25012477
ACTIVE
Listing Agent: Brenda G Murphy
Listing Office: Murphy Realty Group
Residential
$265,500
MLS# 25012427
ACTIVE
Listing Agent: Joyce B Ratliff
Listing Office: Tom Goebel & Company
Comm Prof Ind
$2,000
MLS# 25012328
ACTIVE
Listing Agent: Lara Thornbury
Listing Office: Block + Lot Real Estate
Residential
$325,000
MLS# 25012179
ACTIVE
Listing Agent: Alyssa M Boley
Listing Office: Coldwell Banker McMahan
Residential
$314,900
MLS# 25012215
ACTIVE
Listing Agent: Haley Rollins
Listing Office: Dream Maker Realty, LLC
Residential
$193,900
MLS# 25012154
ACTIVE
Listing Agent: Sondra Clark
Listing Office: Taylor Real Estate, LLC
Comm Prof Ind
$350,000
MLS# 25012344
ACTIVE
Listing Agent: Melisa C McDonald
Listing Office: Wrenn Realty
Residential
$350,000
MLS# 25012400
ACTIVE
Listing Agent: Melisa C McDonald
Listing Office: Wrenn Realty
Residential
$397,500
MLS# 25012164
PENDING
Listing Agent: Robin Trimble
Listing Office: HomeFirst 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: 13th June, 2025 11:56 PM (UTC)