Winchester, KY Homes & Real Estate for Sale

Page 4 of 10
189 listings
233 Schollsville Road, Winchester, KY 40391
Pending

$400,000

  • 3 bed |
  • 2 bath |
  • 1,347 sqft |
  • 5.48 acre lot
233 Schollsville Road Winchester, KY 40391

#26012231 - Keller Williams Legacy Group

104 Bay Hill Drive, Winchester, KY 40391
Pending

$199,000

  • 2 bed |
  • 2 bath |
  • 1,200 sqft |
104 Bay Hill Drive Winchester, KY 40391

#26012179 - Stewart & Co Realty LLC

7919 Mt Sterling Road, Winchester, KY 40391
Pending

$595,000

  • 4 bed |
  • 4 bath |
  • 3,431 sqft |
  • 3.01 acre lot
7919 Mt Sterling Road Winchester, KY 40391

#26012124 - Coldwell Banker McMahan

7300 Old Boonesboro Road, Winchester, KY 40391
Single-Family Home For Sale

$785,000

  • 4 bed |
  • 3 bath |
  • 3,311 sqft |
  • 7.4 acre lot
7300 Old Boonesboro Road Winchester, KY 40391

#26012036 - RE/MAX Elite Lexington

133 Bay Hill Drive, Winchester, KY 40391
Town Home For Sale

$280,000

  • 4 bed |
  • 4 bath |
  • 3,276 sqft |
133 Bay Hill Drive Winchester, KY 40391

#26012064 - Keller Williams Legacy Group

125 Kittison Drive, Winchester, KY 40391
Single-Family Home For Sale

$235,500

  • 3 bed |
  • 1 bath |
  • 1,100 sqft |
125 Kittison Drive Winchester, KY 40391

#26011953 - Coldwell Banker McMahan

14 Cook Avenue, Winchester, KY 40391
Single-Family Home For Sale

$225,000

  • 3 bed |
  • 2 bath |
  • 1,261 sqft |
14 Cook Avenue Winchester, KY 40391

#26011961 - United Real Estate Bluegrass

86 Brink Avenue, Winchester, KY 40391
Pending

$225,000

  • 3 bed |
  • 2 bath |
  • 1,136 sqft |
86 Brink Avenue Winchester, KY 40391

#26011897 - RE/MAX Elite Lexington

525 Colby Ridge Boulevard, Winchester, KY 40391
Pending

$219,500

  • 3 bed |
  • 2 bath |
  • 1,197 sqft |
525 Colby Ridge Boulevard Winchester, KY 40391

#26011873 - Bridgewater Real Estate

23 Wheeler Avenue, Winchester, KY 40391
Multi-Family Home For Sale

$389,900

  • 8 bed |
  • 5 bath |
  • 4,687 sqft |
23 Wheeler Avenue Winchester, KY 40391

#26011905 - Keller Williams Bluegrass Realty

311 Geronimo Court, Winchester, KY 40391
Pending

$268,900

  • 4 bed |
  • 3 bath |
  • 1,510 sqft |
  • 0.32 acre lot
311 Geronimo Court Winchester, KY 40391

#26011798 - WEICHERT REALTORS - ABG Properties

116 Sturbridge Lane, Winchester, KY 40391
Single-Family Home For Sale

$274,500

  • 3 bed |
  • 2 bath |
  • 1,260 sqft |
116 Sturbridge Lane Winchester, KY 40391

#26011782 - Wright Realty

8897 Rockwell Road, Lexington, KY 40509
Single-Family Home For Sale

$6,000,000

  • 7 bed |
  • 6 bath |
  • 9,769 sqft |
  • 66.58 acre lot
8897 Rockwell Road Lexington, KY 40509

#26011667 - Keller Williams Commonwealth

3166 Colby Road, Winchester, KY 40391
Single-Family Home For Sale

$1,695,000

  • 3 bed |
  • 3 bath |
  • 4,518 sqft |
  • 32.87 acre lot
3166 Colby Road Winchester, KY 40391

#26011538 - Coldwell Banker McMahan

225 Buffalo Trace, Winchester, KY 40391
Single-Family Home For Sale

$199,900

  • 3 bed |
  • 2 bath |
  • 915 sqft |
225 Buffalo Trace Winchester, KY 40391

#26011564 - The Brokerage

13 Lakeview Drive, Winchester, KY 40391
Pending

$315,000

  • 3 bed |
  • 2 bath |
  • 1,932 sqft |
  • 0.25 acre lot
13 Lakeview Drive Winchester, KY 40391

#26011497 - RE/MAX Creative, Winchester

6595 Mt Sterling Road, Winchester, KY 40391
Pending

$609,900

  • 5 bed |
  • 4 bath |
  • 4,515 sqft |
  • 2.59 acre lot
6595 Mt Sterling Road Winchester, KY 40391

#26011548 - RO&CO Real Estate

2799 Pine Ridge Road, Winchester, KY 40391
Single-Family Home For Sale

$99,900

  • 3 bed |
  • 2 bath |
  • 675 sqft |
  • 2.18 acre lot
2799 Pine Ridge Road Winchester, KY 40391

#26011430 - Keller Williams Commonwealth

128 Bay Hill Drive, Winchester, KY 40391
Pending

$200,000

  • 3 bed |
  • 2 bath |
  • 1,289 sqft |
128 Bay Hill Drive Winchester, KY 40391

#26011449 - MELIA Realty LLC

137 Eastridge Drive, Winchester, KY 40391
Single-Family Home For Sale

$274,500

  • 3 bed |
  • 2 bath |
  • 1,420 sqft |
137 Eastridge Drive Winchester, KY 40391

#26011465 - Coldwell Banker McMahan

Presented by Roger Browning - Veterans United Realty

Veterans United Homefront
IDX 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 this broker, 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. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. © 2026 LBAR Multiple Listing Service. All rights reserved. Data displayed may be a portion of, and not a complete set of all listings published in the MLS.

For questions call 1-833-252-8030

Copyright © 2026 Veterans United Realty and Did You Serve, LLC. Homefront.com is NOT affiliated with any government agencies, including the VA. Homefront.com is a service of Did You Serve, LLC. Veterans United and the Veterans United House logo are registered trademarks of Mortgage Research Center, LLC, used under license agreement. Terms of Use.

Connect with an Agent
Get paired with a top VA-friendly agentGet an Agent