Winchester, KY Homes & Real Estate for Sale

Page 5 of 15
297 listings
297 S Main Street, Winchester, KY 40391
Single-Family Home For Sale

$335,000

  • 6 bed |
  • 4 bath |
  • 3,544 sqft |
297 S Main Street Winchester, KY 40391

#25501793 - Tru Life Real Estate

536 S Maple Street, Winchester, KY 40391
Pending

$352,500

  • 3 bed |
  • 3 bath |
  • 1,832 sqft |
536 S Maple Street Winchester, KY 40391

#25501757 - Ensor Real Estate, LLC

165 Hilltop Drive, Winchester, KY 40391
Single-Family Home For Sale

$274,900

  • 3 bed |
  • 2 bath |
  • 1,454 sqft |
  • 0.28 acre lot
165 Hilltop Drive Winchester, KY 40391

#25501723 - Kassie & Associates

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

$824,900

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

#25501816 - RE/MAX Elite Lexington

211 Ashton Oak Way, Winchester, KY 40391
Single-Family Home For Sale

$215,000

211 Ashton Oak Way Winchester, KY 40391

#25501640 - Keller Williams Bluegrass Realty

102 Royal Oak Drive, Winchester, KY 40391
Land For Sale

$64,900

  • 0.64 acre lot
102 Royal Oak Drive Winchester, KY 40391

#25501642 - Keller Williams Bluegrass Realty

101 Royal Oak Drive, Winchester, KY 40391
Land For Sale

$64,900

  • 0.52 acre lot
101 Royal Oak Drive Winchester, KY 40391

#25501641 - Keller Williams Bluegrass Realty

4590 Four Mile Road, Winchester, KY 40391
Land For Sale

$168,000

  • 11.34 acre lot
4590 Four Mile Road Winchester, KY 40391

#25501424 - Tom Goebel & Company

103 Mayfair Court, Winchester, KY 40391
Pending

$350,000

  • 3 bed |
  • 2 bath |
  • 1,485 sqft |
103 Mayfair Court Winchester, KY 40391

#25501461 - Tru Life Real Estate

4700 Four Mile Road, Winchester, KY 40391
Land For Sale

$59,500

  • 5 acre lot
4700 Four Mile Road Winchester, KY 40391

#25501428 - Tom Goebel & Company

190 Privacy Lane, Winchester, KY 40391
Land For Sale

$260,000

  • 6.08 acre lot
190 Privacy Lane Winchester, KY 40391

#25501332 - Keller Williams Commonwealth

1857 Ironworks Road, Winchester, KY 40391
Pending

$429,000

  • 5 bed |
  • 3 bath |
  • 2,924 sqft |
  • 4.47 acre lot
1857 Ironworks Road Winchester, KY 40391

#25501321 - Bluegrass Sotheby's International Realty

175 Waterworks Road, Winchester, KY 40391
Single-Family Home For Sale

$250,000

  • 3 bed |
  • 2 bath |
  • 1,295 sqft |
  • 3.17 acre lot
175 Waterworks Road Winchester, KY 40391

#25501347 - Kentucky Residential Real Estate, LLC

408 Corinne Court, Winchester, KY 40391
Single-Family Home For Sale

$394,999

  • 3 bed |
  • 2 bath |
  • 1,604 sqft |
  • 0.29 acre lot
408 Corinne Court Winchester, KY 40391

#25501469 - The Brokerage

2317 Muddy Creek Road, Winchester, KY 40391
Pending

$169,000

  • 2 bed |
  • 1 bath |
  • 1,046 sqft |
  • 2 acre lot
2317 Muddy Creek Road Winchester, KY 40391

#25501241 - Coldwell Banker McMahan

130 E Broadway Street, Winchester, KY 40391
Triplex For Sale

$245,000

  • 5 bed |
  • 3 bath |
  • 2,445 sqft |
130 E Broadway Street Winchester, KY 40391

#25501480 - Lifstyl Real Estate

117 4th Street, Winchester, KY 40391
Land For Sale

$25,000

117 4th Street Winchester, KY 40391

#25501219 - Keller Williams Bluegrass Realty

208 4th Street, Winchester, KY 40391
Single-Family Home For Sale

$150,000

  • 2 bed |
  • 1 bath |
  • 1 sqft |
  • 0.27 acre lot
208 4th Street Winchester, KY 40391

#25501100 - Keller Williams Bluegrass Realty

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

$314,000

  • 2 bed |
  • 1 bath |
  • 1,170 sqft |
  • 10 acre lot
398 Pine Ridge Road Winchester, KY 40391

#25501136 - ERA Select Real Estate

398 Pine Ridge Road, Winchester, KY 40391
Ranch Property For Sale

$314,000

  • 2 bed |
  • 1 bath |
  • 1,170 sqft |
  • 10 acre lot
398 Pine Ridge Road Winchester, KY 40391

#25501259 - ERA Select Real Estate

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. © 2025 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 © 2025 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.

Get paired with a top VA-friendly agentGet an Agent