369 total properties
View 2124 Boswell Rd Winchester, TN MLS# 2990003
$990,000
4

Beds

3.1

Baths

6,803

Sq.Ft.

2124 Boswell Rd

Winchester, TN

MiddleTennessee
View 995 Dripping Springs Rd Winchester, TN MLS# 3044907
$964,900
3

Beds

2.1

Baths

2,256

Sq.Ft.

995 Dripping Springs Rd

Winchester, TN

MiddleTennessee
View 279 Hammock Drive Winchester, TN MLS# 3079153
  • New Construction
1 of 89
$954,000
4

Beds

3.1

Baths

3,341

Sq.Ft.

279 Hammock Drive

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 73 Cypress Point Dr Winchester, TN MLS# 3118220
$899,000
4

Beds

3.1

Baths

2,684

Sq.Ft.

73 Cypress Point Dr

Winchester, TN

MiddleTennessee
View 494 Cascade Dr Winchester, TN MLS# 2993628
$889,000
4

Beds

3.1

Baths

3,361

Sq.Ft.

494 Cascade Dr

Winchester, TN

MiddleTennessee
View 282 Owl Hollow Ln Winchester, TN MLS# 3123764
  • Recently Listed
1 of 57
$877,000
4

Beds

3.0

Baths

3,484

Sq.Ft.

282 Owl Hollow Ln

Winchester, TN

MiddleTennessee
View 101 Cypress Point Dr Winchester, TN MLS# 3045267
$849,900
4

Beds

3.1

Baths

3,738

Sq.Ft.

101 Cypress Point Dr

Winchester, TN

MiddleTennessee
View 0 College St Winchester, TN MLS# 2975107
$800,000

0 College St

Winchester, TN

MiddleTennessee
View 364 Blair Pond Rd Winchester, TN MLS# 3133833
  • Recently Listed
1 of 6
$800,000
2,306

Sq.Ft.

364 Blair Pond Rd

Winchester, TN

MiddleTennessee
View 20 Windjammer Ct Winchester, TN MLS# 3078990
$799,900
4

Beds

3.0

Baths

3,032

Sq.Ft.

20 Windjammer Ct

Winchester, TN

MiddleTennessee
View 16 Blairmont Ct Winchester, TN MLS# 3128456
  • Recently Listed
1 of 71
$780,900
4

Beds

3.1

Baths

4,109

Sq.Ft.

16 Blairmont Ct

Winchester, TN

MiddleTennessee
View 347 Campfire Court Winchester, TN MLS# 3037409
$779,900
4

Beds

3.0

Baths

2,930

Sq.Ft.

347 Campfire Court

Winchester, TN

MiddleTennessee
View 74 Summerlake Ct Winchester, TN MLS# 2944564
  • New Construction
1 of 38
$775,000
3

Beds

3.1

Baths

2,504

Sq.Ft.

74 Summerlake Ct

Winchester, TN

MiddleTennessee
View 71 Windjammer Ct Winchester, TN MLS# 3073936
$775,000
4

Beds

3.1

Baths

3,017

Sq.Ft.

71 Windjammer Ct

Winchester, TN

MiddleTennessee
View 397 Campfire Ct Winchester, TN MLS# 3059004
$774,900
5

Beds

3.1

Baths

2,805

Sq.Ft.

397 Campfire Ct

Winchester, TN

MiddleTennessee
View 82 Hammock Dr Winchester, TN MLS# 3048125
$749,000
4

Beds

3.1

Baths

3,118

Sq.Ft.

82 Hammock Dr

Winchester, TN

MiddleTennessee
View 117 1st Ave NE Winchester, TN MLS# 3118418
$749,000
4,848

Sq.Ft.

117 1st Ave NE

Winchester, TN

MiddleTennessee
View 265 Shasteen Bend Dr Winchester, TN MLS# 3121476
  • Recently Listed
1 of 49
$749,000
3

Beds

2.0

Baths

2,349

Sq.Ft.

265 Shasteen Bend Dr

Winchester, TN

MiddleTennessee
View 814 River Watch Way Winchester, TN MLS# 3132232
  • Recently Listed
1 of 66
$729,900
3

Beds

3.1

Baths

2,650

Sq.Ft.

814 River Watch Way

Winchester, TN

MiddleTennessee
View 102 Summer Lake Ct Winchester, TN MLS# 2979668
  • New Construction
1 of 35
$725,000
4

Beds

3.1

Baths

2,688

Sq.Ft.

102 Summer Lake Ct

Winchester, TN

MiddleTennessee

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Upper Cumberland Association of REALTORS. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be reproduced or redistribute. Its sole purpose is to be used for no other purpose than to identify prospective properties consumers may be interested in purchasing. p>

Data is updated as of 2/23/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (MLS Data Share) Program of The Multiple Listing Service of Chattanooga, Inc. Real estate listings held by brokerage firms other than WEICHERT are marked with the MLS Datashare Logo and detailed information about them includes the name of the listing brokers. The information being provided is 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.

The information being provided is 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.