Winchester, KY Homes & Real Estate for Sale

Page 4 of 10
194 listings
306 Trapp-Goffs Cor Road, Winchester, KY 40391
Pending

$299,900

  • 4 bed |
  • 2 bath |
  • 1,840 sqft |
  • 2.33 acre lot
306 Trapp-Goffs Cor Road Winchester, KY 40391

#26008462 - Keller Williams Commonwealth

443 S Maple Street, Winchester, KY 40391
Single-Family Home For Sale

$350,000

  • 4 bed |
  • 2 bath |
  • 3,261 sqft |
  • 0.39 acre lot
443 S Maple Street Winchester, KY 40391

#26008225 - Keller Williams Commonwealth

110 Powe Drive, Winchester, KY 40391
Single-Family Home For Sale

$329,900

  • 4 bed |
  • 3 bath |
  • 2,010 sqft |
  • 0.25 acre lot
110 Powe Drive Winchester, KY 40391

#26008249 - The Agency

414 Pueblo Court, Winchester, KY 40391
Single-Family Home For Sale

$309,999

  • 3 bed |
  • 3 bath |
  • 2,648 sqft |
  • 0.27 acre lot
414 Pueblo Court Winchester, KY 40391

#26008330 - The Local Agents

905 Pretty Run Road, Winchester, KY 40391
Pending

$600,000

  • 3 bed |
  • 4 bath |
  • 3,391 sqft |
  • 2.19 acre lot
905 Pretty Run Road Winchester, KY 40391

#26008251 - Bluegrass Sotheby's International Realty

697 Goose Creek Road, Winchester, KY 40391
Single-Family Home For Sale

$180,000

  • 3 bed |
  • 2 bath |
  • 1,848 sqft |
  • 2.61 acre lot
697 Goose Creek Road Winchester, KY 40391

#26008440 - Dream Maker Realty, LLC

13 Maryland Avenue, Winchester, KY 40391
Single-Family Home For Sale

$169,000

  • 2 bed |
  • 1 bath |
  • 1,472 sqft |
13 Maryland Avenue Winchester, KY 40391

#26008307 - ERA Select Real Estate

432 Country Club Drive, Winchester, KY 40391
Pending

$175,000

  • 2 bed |
  • 2 bath |
  • 1,260 sqft |
432 Country Club Drive Winchester, KY 40391

#26008091 - Rector Hayden Realtors

200 Dubuy Drive, Winchester, KY 40391
Single-Family Home For Sale

$312,000

  • 3 bed |
  • 3 bath |
  • 1,858 sqft |
200 Dubuy Drive Winchester, KY 40391

#26008021 - RE/MAX Creative Realty

426 E Broadway Street, Winchester, KY 40391
Pending

$289,000

  • 5 bed |
  • 2 bath |
  • 1,838 sqft |
  • 0.43 acre lot
426 E Broadway Street Winchester, KY 40391

#26007906 - Coldwell Banker McMahan

222 Ashton Oak Way, Winchester, KY 40391
Pending

$450,000

  • 3 bed |
  • 3 bath |
  • 3,444 sqft |
  • 0.5 acre lot
222 Ashton Oak Way Winchester, KY 40391

#26008003 - Ensor Real Estate, LLC

614 Colby Ridge Boulevard, Winchester, KY 40391
Single-Family Home For Sale

$349,900

  • 4 bed |
  • 3 bath |
  • 2,100 sqft |
614 Colby Ridge Boulevard Winchester, KY 40391

#26007904 - HomeLand Real Estate Inc - Mt Sterling

19 3rd Street, Winchester, KY 40391
Single-Family Home For Sale

$148,000

  • 3 bed |
  • 1 bath |
  • 864 sqft |
19 3rd Street Winchester, KY 40391

#26007798 - ListWithFreedom.com

54 Locust Drive, Winchester, KY 40391
Single-Family Home For Sale

$299,000

  • 3 bed |
  • 2 bath |
  • 1,692 sqft |
  • 0.28 acre lot
54 Locust Drive Winchester, KY 40391

#26007779 - Berkshire Hathaway HomeServices Foster Realtors

201 Boone Avenue, Winchester, KY 40391
Pending

$335,000

  • 4 bed |
  • 3 bath |
  • 2,513 sqft |
201 Boone Avenue Winchester, KY 40391

#26007703 - Rector Hayden Realtors

720 Estes Drive, Winchester, KY 40391
Pending

$244,900

  • 3 bed |
  • 2 bath |
  • 1,494 sqft |
720 Estes Drive Winchester, KY 40391

#26007668 - HomeLand Real Estate Inc - Mt Sterling

34 Hays Street, Winchester, KY 40391
Pending

$210,000

  • 4 bed |
  • 2 bath |
  • 2,450 sqft |
34 Hays Street Winchester, KY 40391

#26007612 - RE/MAX Elite Lexington

465 Morris Road, Winchester, KY 40391
Single-Family Home For Sale

$775,000

  • 5 bed |
  • 3 bath |
  • 4,437 sqft |
  • 16.06 acre lot
465 Morris Road Winchester, KY 40391

#26007545 - United Real Estate Bluegrass

3760 Old Boonesboro Road, Winchester, KY 40391
Pending

$1,290,000

  • 5 bed |
  • 5 bath |
  • 5,666 sqft |
  • 12.98 acre lot
3760 Old Boonesboro Road Winchester, KY 40391

#26006697 - Freedom Realty & Property Management

118 Windridge Drive, Winchester, KY 40391
Pending

$307,900

  • 3 bed |
  • 2 bath |
  • 1,617 sqft |
118 Windridge Drive Winchester, KY 40391

#26006695 - Whalen & Company

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