Winchester, KY Homes & Real Estate for Sale

Page 1 of 10
194 listings
13 Lakeview Drive, Winchester, KY 40391New listing icon New - 18 hours ago
Single-Family Home For Sale

$315,000

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

#26011497 - RE/MAX Creative, Winchester

316 Maryland Avenue, Winchester, KY 40391New listing icon New - 18 hours ago
Single-Family Home For Sale

$260,000

  • 3 bed |
  • 2 bath |
  • 1,809 sqft |
316 Maryland Avenue Winchester, KY 40391

#26011496 - RE/MAX Creative, Winchester

2799 Pine Ridge Road, Winchester, KY 40391New listing icon New - 18 hours ago
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

137 Eastridge Drive, Winchester, KY 40391New listing icon New - 1 day ago
Single-Family Home For Sale

$289,900

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

#26011465 - Coldwell Banker McMahan

128 Bay Hill Drive, Winchester, KY 40391New listing icon New - 1 day ago
Single-Family Home For Sale

$200,000

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

#26011449 - MELIA Realty LLC

414 Fairholme Way, Winchester, KY 40391
Single-Family Home For Sale

$484,900

  • 4 bed |
  • 3 bath |
  • 2,418 sqft |
  • 0.37 acre lot
414 Fairholme Way Winchester, KY 40391

#26011136 - The Brokerage

287 Logan Lick Road, Winchester, KY 40391
Single-Family Home For Sale

$465,000

  • 3 bed |
  • 2 bath |
  • 1,680 sqft |
  • 10.02 acre lot
287 Logan Lick Road Winchester, KY 40391

#26011126 - Dream Maker Realty, LLC

1478 Donaldson Road, Winchester, KY 40391
Pending

$444,000

  • 3 bed |
  • 2 bath |
  • 2,442 sqft |
  • 5.24 acre lot
1478 Donaldson Road Winchester, KY 40391

#26011075 - RE/MAX Creative, Winchester

147 Sunset Heights, Winchester, KY 40391
Single-Family Home For Sale

$299,900

  • 3 bed |
  • 2 bath |
  • 2,128 sqft |
  • 0.36 acre lot
147 Sunset Heights Winchester, KY 40391

#26011009 - Kentucky Land and Home

209 Boone Avenue, Winchester, KY 40391
Single-Family Home For Sale

$299,900

  • 3 bed |
  • 3 bath |
  • 2,260 sqft |
209 Boone Avenue Winchester, KY 40391

#26011097 - Lois Ann Disponett Real Est

450 Jameson Way, Winchester, KY 40391
Single-Family Home For Sale

$225,000

  • 4 bed |
  • 2 bath |
  • 1,458 sqft |
450 Jameson Way Winchester, KY 40391

#26011041 - The Brokerage

217 Short Street, Winchester, KY 40391
Single-Family Home For Sale

$250,000

  • 3 bed |
  • 1 bath |
  • 1,042 sqft |
217 Short Street Winchester, KY 40391

#26010963 - Freedom Realty & Property Management

314 Snowden Drive, Winchester, KY 40391
Pending

$224,900

  • 3 bed |
  • 1 bath |
  • 1,196 sqft |
314 Snowden Drive Winchester, KY 40391

#26010943 - Freedom Realty & Property Management

301 Snowden Drive, Winchester, KY 40391
Pending

$210,000

  • 3 bed |
  • 1 bath |
  • 1,386 sqft |
301 Snowden Drive Winchester, KY 40391

#26010643 - The Brokerage

339 S Main Street, Winchester, KY 40391
Single-Family Home For Sale

$219,900

  • 4 bed |
  • 2 bath |
  • 1,848 sqft |
339 S Main Street Winchester, KY 40391

#26010684 - RE/MAX Creative, Winchester

207 Hibiscus Lane, Winchester, KY 40391
Pending

$449,900

  • 4 bed |
  • 3 bath |
  • 3,126 sqft |
  • 0.55 acre lot
207 Hibiscus Lane Winchester, KY 40391

#26010589 - HomeLand Real Estate Inc - Mt Sterling

86 Brink Avenue, Winchester, KY 40391
Pending

$230,000

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

#26010543 - RE/MAX Elite Lexington

274 Greenway Drive, Winchester, KY 40391
Pending

$350,000

  • 4 bed |
  • 2 bath |
  • 2,208 sqft |
  • 0.55 acre lot
274 Greenway Drive Winchester, KY 40391

#26010546 - RE/MAX Creative, Winchester

146 Hawthorne Drive, Winchester, KY 40391
Pending

$539,900

  • 5 bed |
  • 4 bath |
  • 2,711 sqft |
  • 0.27 acre lot
146 Hawthorne Drive Winchester, KY 40391

#26010893 - COLOR Real Estate

5865 Van Meter Road, Winchester, KY 40391
Single-Family Home For Sale

$675,000

  • 3 bed |
  • 3 bath |
  • 2,765 sqft |
  • 5.05 acre lot
5865 Van Meter Road Winchester, KY 40391

#26010445 - Keller Williams Commonwealth

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