Winchester, TN VA-Eligible Homes & Real Estate for Sale

Page 4 of 9
178 listings
50 Pontoon Place, Winchester, TN 37398
Single-Family Home For Sale

$599,900

  • 4 bed |
  • 4 bath |
  • 2,497 sqft |
50 Pontoon Place Winchester, TN 37398

#3093533 - Onward Real Estate

714 N Cedar St, Winchester, TN 37398
Single-Family Home For Sale

$180,000

  • 2 bed |
  • 2 bath |
  • 1,150 sqft |
714 N Cedar St Winchester, TN 37398

#3111126 - Southern Middle Realty

286 Strawberry Dr, Winchester, TN 37398
Single-Family Home For Sale

$259,900

  • 3 bed |
  • 2 bath |
  • 1,150 sqft |
  • 0.28 acre lot
286 Strawberry Dr Winchester, TN 37398

#3078933 - Southern Middle Realty

279 Hammock Drive, Winchester, TN 37398
Single-Family Home For Sale

$954,000

  • 4 bed |
  • 4 bath |
  • 3,341 sqft |
  • 0.26 acre lot
279 Hammock Drive Winchester, TN 37398

#3079153 - Benchmark Realty, LLC

137 Campfire Ct, Winchester, TN 37398
Single-Family Home For Sale

$489,900

  • 5 bed |
  • 3 bath |
  • 2,052 sqft |
137 Campfire Ct Winchester, TN 37398

#3068241 - eXp Realty

101 N Shephard St, Winchester, TN 37398
Single-Family Home For Sale

$327,900

  • 3 bed |
  • 3 bath |
  • 1,358 sqft |
101 N Shephard St Winchester, TN 37398

#3079702 - Southern Middle Realty

219 Old Mill Rd, Winchester, TN 37398
Single-Family Home For Sale

$399,000

  • 3 bed |
  • 2 bath |
  • 3,050 sqft |
  • 1.05 acre lot
219 Old Mill Rd Winchester, TN 37398

#3067448 - EXIT Noble Realty Group

656 SHADOWBROOK RD, Winchester, TN 37398
Single-Family Home For Sale

$579,000

  • 3 bed |
  • 3 bath |
  • 2,946 sqft |
  • 1.01 acre lot
656 SHADOWBROOK RD Winchester, TN 37398

#3078727 - Southern Middle Realty

716 N Cedar St, Winchester, TN 37398
Single-Family Home For Sale

$154,900

  • 2 bed |
  • 1 bath |
  • 1,092 sqft |
716 N Cedar St Winchester, TN 37398

#3067138 - Steve Jernigan Realty

44 Hammock Dr, Winchester, TN 37398
Single-Family Home For Sale

$575,000

  • 3 bed |
  • 3 bath |
  • 2,296 sqft |
44 Hammock Dr Winchester, TN 37398

#3068567 - Benchmark Realty, LLC

189 Pickney Rd, Winchester, TN 37398
Single-Family Home For Sale

$380,000

  • 3 bed |
  • 2 bath |
  • 2,607 sqft |
  • 0.92 acre lot
189 Pickney Rd Winchester, TN 37398

#3067416 - Crye-Leike, Realtors

0 Blairmont Ct, Winchester, TN 37398
Single-Family Home For Sale

$699,900

  • 4 bed |
  • 3 bath |
  • 2,884 sqft |
  • 0.74 acre lot
0 Blairmont Ct Winchester, TN 37398

#3062096 - simpliHOM - The Results Team

400 Cessna Cir, Winchester, TN 37398
Single-Family Home For Sale

$315,000

  • 5 bed |
  • 3 bath |
  • 2,218 sqft |
  • 0.72 acre lot
400 Cessna Cir Winchester, TN 37398

#3080449 - Benchmark Realty, LLC

815 N High St, Winchester, TN 37398
Single-Family Home For Sale

$199,000

  • 2 bed |
  • 1 bath |
  • 936 sqft |
815 N High St Winchester, TN 37398

#3059442 - Lake Homes Realty, LLC

74 Freedom Ln, Winchester, TN 37398
Single-Family Home For Sale

$399,999

  • 2 bed |
  • 2 bath |
  • 2,244 sqft |
  • 0.99 acre lot
74 Freedom Ln Winchester, TN 37398

#3058554 - John Smith Jr Realty and Auction LLC

160 Wiseman Ln, Winchester, TN 37398
Pending

$474,900

  • 4 bed |
  • 2 bath |
  • 2,187 sqft |
  • 1.32 acre lot
160 Wiseman Ln Winchester, TN 37398

#3058512 - Better Homes & Gardens Real Estate Heritage Group

No photos available for 188 Wiseman Ln, Winchester, TN 37398
Single-Family Home For Sale

$474,900

  • 4 bed |
  • 2 bath |
  • 2,269 sqft |
  • 1.39 acre lot
188 Wiseman Ln Winchester, TN 37398

#3058511 - Better Homes & Gardens Real Estate Heritage Group

99 N Shephard St, Winchester, TN 37398
Single-Family Home For Sale

$309,900

  • 3 bed |
  • 2 bath |
  • 1,213 sqft |
99 N Shephard St Winchester, TN 37398

#3059253 - Monteagle Sewanee REALTORS

510 N Vine St, Winchester, TN 37398
Single-Family Home

$229,000

  • 3 bed |
  • 1 bath |
  • 1,360 sqft |
510 N Vine St Winchester, TN 37398

#3057671 - Harton Realty Company

17 Favre Cir, Winchester, TN 37398
Single-Family Home

$374,900

  • 3 bed |
  • 2 bath |
  • 1,615 sqft |
  • 0.55 acre lot
17 Favre Cir Winchester, TN 37398

#3051345 - Franklin County Realty

Presented by Kellie Gragg - Veterans United Realty

Veterans United Homefront
IDX Listings courtesy of RealTracs Middle Tennessee Regional MLS as distributed by MLS GRID.

All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

IDX© 2026 of the REALTRACS MLS. All rights Reserved.

The data relating to this real estate for sale on this websites comes in part courtesy of the IDX program of the REALTRACS MLS. Real estate listings held by brokerage firms other than this broker are marked with the REALTRACS IDX Logo. REALTRACS and this broker deem all information reliable but not guaranteed, and should be independently verified. REALTRACS and this broker assume no responsibility for typographical errors, misprints or misinformation.

REALTRACS, this broker and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing 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.

Based on information submitted to the MLS GRID as of date and time noted below. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. 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