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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
$155,000
MLS# 23023339
2 Beds
1 Baths
1,584 Sq ft
Listing Agent: Peter M doCouto
Listing Office: Plum Tree Realty
$4,800,000
MLS# 23023296
57,050 Sq ft
Listing Agent: Lara Thornbury
Listing Office: Block + Lot Real Estate
$329,900
MLS# 23023292
3 Beds
2 Baths
1,715 Sq ft
Listing Agent: Mila J Ensor
Listing Office: Ensor Real Estate, LLC
$259,900
MLS# 23023250
3 Beds
2 Baths
1,588 Sq ft
Listing Agent: Michael R Hilario
Listing Office: The Agency
$525,000
MLS# 23022697
4 Beds
2 Baths
2,500 Sq ft
Listing Agent: Megan McCoy
Listing Office: Keller Williams Legacy Group
$260,000
MLS# 23023132
Listing Agent: Heather G Penichet
Listing Office: United Real Estate Lexington KY
$134,900
MLS# 23023084
3 Beds
1 Baths
1,708 Sq ft
Listing Agent: Darrell Lewis
Listing Office: DIYFlatFee.com
$85,000
MLS# 23022951
Listing Agent: Crystal Gail Smith
Listing Office: Keller Williams Bluegrass Realty
$275,000
MLS# 23022967
3 Beds
3 Baths
2,318 Sq ft
Listing Agent: W Preston Martin
Listing Office: Biller Homes
$375,000
MLS# 23022919
3 Beds
2 Baths
1,966 Sq ft
Listing Agent: Blake Todd
Listing Office: Big Blue Realty
$510,000
MLS# 23022793
3 Beds
2 Baths
2,405 Sq ft
Listing Agent: Megan McCoy
Listing Office: Keller Williams Legacy Group
$245,000
MLS# 23022895
4 Beds
3 Baths
2,042 Sq ft
Listing Agent: V. Keith Wilson
Listing Office: Coldwell Banker McMahan
$185,000
MLS# 23022671
2 Beds
1 Baths
1,456 Sq ft
Listing Agent: Michelle R Blackburn
Listing Office: RE/MAX Creative, Winchester
$329,900
MLS# 23022662
3 Beds
2 Baths
2,248 Sq ft
Listing Agent: W Patrick Arvin
Listing Office: Keller Williams Commonwealth
$580,000
MLS# 23022661
3 Beds
3 Baths
2,546 Sq ft
Listing Agent: Craig R Bridgewater
Listing Office: Bridgewater Real Estate
$200,000
MLS# 23022577
4 Beds
2 Baths
1,502 Sq ft
Listing Agent: Brenda H Sipes
Listing Office: Bridgewater Real Estate
$200,000
MLS# 23022573
4 Beds
2 Baths
1,502 Sq ft
Listing Agent: Brenda H Sipes
Listing Office: Bridgewater Real Estate
$200,000
MLS# 23022176
5 Beds
3 Baths
1,828 Sq ft
Listing Agent: Bob Sophiea
Listing Office: eXp Realty, LLC
$320,000
MLS# 23022422
4 Beds
3 Baths
2,513 Sq ft
Listing Agent: Matt Metts
Listing Office: LexHomes Real Estate
$215,000
MLS# 23022416
3 Beds
1 Baths
1,465 Sq ft
Listing Agent: Jason Townsend
Listing Office: Kentucky Residential Real Estate, LLC
$475,000
MLS# 23022402
4 Beds
3 Baths
4,108 Sq ft
Listing Agent: Kathryn M Cheuvront
Listing Office: Coldwell Banker McMahan
$205,000
MLS# 23022351
4 Beds
2 Baths
1,989 Sq ft
Listing Agent: V. Keith Wilson
Listing Office: Coldwell Banker McMahan
$259,900
MLS# 23022282
3 Beds
2 Baths
1,486 Sq ft
Listing Agent: Greg E Wood
Listing Office: Freedom Realty & Property Management
$249,000
MLS# 23022189
3 Beds
2 Baths
1,746 Sq ft
Listing Agent: Christa Joynt
Listing Office: Keller Williams Commonwealth
$244,500
MLS# 23022190
3 Beds
2 Baths
2,078 Sq ft
Listing Agent: Christa Joynt
Listing Office: Keller Williams Commonwealth
$189,900
MLS# 23022158
3 Beds
2 Baths
1,080 Sq ft
Listing Agent: A. Jo Gawthrop
Listing Office: Keller Williams Bluegrass Realty
$263,900
MLS# 23022159
3 Beds
2 Baths
1,780 Sq ft
Listing Agent: Cheri Shaffer
Listing Office: Keller Williams Commonwealth
$247,900
MLS# 23022121
4 Beds
3 Baths
2,183 Sq ft
Listing Agent: Joshua Lynch
Listing Office: The Brokerage
$269,900
MLS# 23022012
5 Beds
3 Baths
2,480 Sq ft
Listing Agent: Andrew Fugitt
Listing Office: Coldwell Banker McMahan
$995,000
MLS# 23021911
5 Beds
5 Baths
4,698 Sq ft
Listing Agent: Gregory Leveridge
Listing Office: Block + Lot Real Estate
$225,000
MLS# 23021767
3 Beds
3 Baths
1,488 Sq ft
Listing Agent: Gregory Leveridge
Listing Office: Block + Lot Real Estate
$2,199,000
MLS# 23021846
9 Beds
6 Baths
11,230 Sq ft
Listing Agent: Gregory Leveridge
Listing Office: Block + Lot Real Estate
$189,900
MLS# 23021842
3 Beds
2 Baths
1,080 Sq ft
Listing Agent: A. Jo Gawthrop
Listing Office: Keller Williams Bluegrass Realty
$619,000
MLS# 23021769
4 Beds
4 Baths
3,200 Sq ft
Listing Agent: Brenda G Murphy
Listing Office: Murphy Realty Group
$205,000
MLS# 23021665
3 Beds
2 Baths
1,050 Sq ft
Listing Agent: Ashley Spencer
Listing Office: Keller Williams Commonwealth
$145,000
MLS# 23021615
3 Beds
1 Baths
1,476 Sq ft
Listing Agent: Andrew Fugitt
Listing Office: Coldwell Banker McMahan
$169,900
MLS# 23021600
3 Beds
1 Baths
1,517 Sq ft
Listing Agent: Larry E Moore
Listing Office: CENTURY 21 Simpson & Associates
$149,900
MLS# 23021520
3 Beds
2 Baths
1,200 Sq ft
Listing Agent: Whitney Ann Ensor
Listing Office: Ensor Real Estate, LLC
$313,000
MLS# 23021463
5 Beds
3 Baths
3,372 Sq ft
Listing Agent: Craig R Bridgewater
Listing Office: Bridgewater Real Estate
$399,000
MLS# 23021418
4 Beds
3 Baths
3,610 Sq ft
Listing Agent: Kathryn M Cheuvront
Listing Office: Coldwell Banker McMahan
$240,000
MLS# 23021386
4 Beds
2 Baths
1,626 Sq ft
Listing Agent: Cheri Shaffer
Listing Office: Keller Williams Commonwealth
$190,000
MLS# 23020593
3 Beds
2 Baths
1,740 Sq ft
Listing Agent: Michelle R Blackburn
Listing Office: RE/MAX Creative, Winchester
$675,000
MLS# 23020748
5 Beds
5 Baths
5,139 Sq ft
Listing Agent: V. Keith Wilson
Listing Office: Coldwell Banker McMahan
$239,000
MLS# 23021094
4 Beds
3 Baths
1,968 Sq ft
Listing Agent: Emily Hacker-Todd
Listing Office: CENTURY 21 Advantage Realty
$219,000
MLS# 23015737
3 Beds
2 Baths
1,569 Sq ft
Listing Agent: Christa Joynt
Listing Office: Keller Williams Commonwealth
$214,000
MLS# 23020845
3 Beds
2 Baths
1,234 Sq ft
Listing Agent: Laura Triplett
Listing Office: Christie's International Real Estate Bluegrass
$349,000
MLS# 23020525
3 Beds
2 Baths
1,550 Sq ft
Listing Agent: Patrick Doyle
Listing Office: National Real Estate
$310,000
MLS# 23020380
2 Beds
2 Baths
1,676 Sq ft
Listing Agent: Kymberly M Clem
Listing Office: Keller Williams Commonwealth
$259,900
MLS# 23020369
4 Beds
3 Baths
2,709 Sq ft
Listing Agent: Joshua Wood
Listing Office: Freedom Realty & Property Management
$340,000
MLS# 23020263
3 Beds
2 Baths
2,183 Sq ft
Listing Agent: Michelle R Blackburn
Listing Office: RE/MAX Creative, Winchester
$150,000
MLS# 23020161
3 Beds
2 Baths
1,620 Sq ft
Listing Agent: A. Rebecca Woods
Listing Office: Woods Realty Group
$189,900
MLS# 23020134
4 Beds
2 Baths
1,400 Sq ft
Listing Agent: Cindy Walker
Listing Office: Sandy Stuart Realty
$219,500
MLS# 23019877
3 Beds
2 Baths
1,360 Sq ft
Listing Agent: Chris B Campbell
Listing Office: United Real Estate Lexington KY
$289,900
MLS# 23019794
4 Beds
2 Baths
1,680 Sq ft
Listing Agent: Whitney Ann Ensor
Listing Office: Ensor Real Estate, LLC
$289,900
MLS# 23019792
4 Beds
2 Baths
1,680 Sq ft
Listing Agent: Whitney Ann Ensor
Listing Office: Ensor Real Estate, LLC
$189,500
MLS# 23019781
3 Beds
2 Baths
1,340 Sq ft
Listing Agent: Tony Giglio
Listing Office: ListWithFreedom.com
$355,000
MLS# 23019679
3 Beds
2 Baths
1,676 Sq ft
Listing Agent: Dale Hatton
Listing Office: Dream Maker Realty, LLC
$288,000
MLS# 23019567
4 Beds
2 Baths
1,870 Sq ft
Listing Agent: Charles Dean Stamper
Listing Office: Stamper Real Estate Group
$187,000
MLS# 23019497
3 Beds
1 Baths
1,169 Sq ft
Listing Agent: Garry H Milton
Listing Office: Milton and Associates Real Estate
$325,000
MLS# 23019350
3 Beds
2 Baths
1,621 Sq ft
Listing Agent: A. Jo Gawthrop
Listing Office: Keller Williams Bluegrass Realty
$323,500
MLS# 23019347
3 Beds
2 Baths
1,565 Sq ft
Listing Agent: A. Jo Gawthrop
Listing Office: Keller Williams Bluegrass Realty
$125,000
MLS# 23019330
3 Beds
1 Baths
1,107 Sq ft
Listing Agent: Marcus D Hammond
Listing Office: Bluegrass Sotheby's International Realty
$125,000
MLS# 23019329
2 Beds
1 Baths
1,032 Sq ft
Listing Agent: Marcus D Hammond
Listing Office: Bluegrass Sotheby's International Realty
$429,000
MLS# 23018983
4 Beds
3 Baths
2,462 Sq ft
Listing Agent: James Woodrum
Listing Office: RE/MAX Creative, Winchester
$499,900
MLS# 23018940
3 Beds
3 Baths
2,841 Sq ft
Listing Agent: Kymberly M Clem
Listing Office: Keller Williams Commonwealth
$574,000
MLS# 23018802
3 Beds
3 Baths
2,511 Sq ft
Listing Agent: Craig R Bridgewater
Listing Office: Bridgewater Real Estate
Days on the Market
Ascending
12
2 Beds
1 Baths
1,584 Sq ft
Listing Agent: Peter M doCouto
Listing Office: Plum Tree Realty
57,050 Sq ft
Listing Agent: Lara Thornbury
Listing Office: Block + Lot Real Estate
3 Beds
2 Baths
1,715 Sq ft
Listing Agent: Mila J Ensor
Listing Office: Ensor Real Estate, LLC
3 Beds
2 Baths
1,588 Sq ft
Listing Agent: Michael R Hilario
Listing Office: The Agency
4 Beds
2 Baths
2,500 Sq ft
Listing Agent: Megan McCoy
Listing Office: Keller Williams Legacy Group
Listing Agent: Heather G Penichet
Listing Office: United Real Estate Lexington KY
3 Beds
1 Baths
1,708 Sq ft
Listing Agent: Darrell Lewis
Listing Office: DIYFlatFee.com
Listing Agent: Crystal Gail Smith
Listing Office: Keller Williams Bluegrass Realty
3 Beds
3 Baths
2,318 Sq ft
Listing Agent: W Preston Martin
Listing Office: Biller Homes
3 Beds
2 Baths
1,966 Sq ft
Listing Agent: Blake Todd
Listing Office: Big Blue Realty
3 Beds
2 Baths
2,405 Sq ft
Listing Agent: Megan McCoy
Listing Office: Keller Williams Legacy Group
4 Beds
3 Baths
2,042 Sq ft
Listing Agent: V. Keith Wilson
Listing Office: Coldwell Banker McMahan
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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. © 2022 LBAR Multiple Listing Service. All rights reserved. Updated: 10th December, 2023 1:25 AM (UTC)
