368 total properties
View 1657 Boswell Rd Winchester, TN MLS# 2746411
$3,800,000
6

Beds

6.2

Baths

8,002

Sq.Ft.

1657 Boswell Rd

Winchester, TN

MiddleTennessee
View 7542 Chestnut Ridge Rd Winchester, TN MLS# 3058553
$2,000,000
Studio

Beds

0.0

Baths

7542 Chestnut Ridge Rd

Winchester, TN

MiddleTennessee
View 3819 Tullahoma Hwy Winchester, TN MLS# 3000595
$1,800,000
Studio

Beds

0.0

Baths

3819 Tullahoma Hwy

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 410 Dinah Shore Blvd Winchester, TN MLS# 2901941
$1,600,000
11,588

Sq.Ft.

410 Dinah Shore Blvd

Winchester, TN

MiddleTennessee
View 1000 N Vine St Winchester, TN MLS# 3015965
$1,600,000
4

Beds

2.0

Baths

2,164

Sq.Ft.

1000 N Vine St

Winchester, TN

MiddleTennessee
View 1750 Awalt Dr Winchester, TN MLS# 2868246
$1,599,000
5

Beds

4.1

Baths

3,797

Sq.Ft.

1750 Awalt Dr

Winchester, TN

MiddleTennessee
View 160 Wakeboard Way Winchester, TN MLS# 3098820
  • Virtual Tour
1 of 58
$1,579,900
4

Beds

4.0

Baths

3,720

Sq.Ft.

160 Wakeboard Way

Winchester, TN

MiddleTennessee
View 71 Slalom Cir Winchester, TN MLS# 3112698
$1,525,000
4

Beds

4.0

Baths

4,500

Sq.Ft.

71 Slalom Cir

Winchester, TN

MiddleTennessee
View 0 Cowan Highway Winchester, TN MLS# 2795751
$1,500,000
999,999

Sq.Ft.

0 Cowan Highway

Winchester, TN

MiddleTennessee
View 405 Sharp Springs Rd Winchester, TN MLS# 3056561
$1,500,000
Studio

Beds

0.0

Baths

405 Sharp Springs Rd

Winchester, TN

MiddleTennessee
View 61 Joy Cir Winchester, TN MLS# 3046246
$1,499,500
6

Beds

5.1

Baths

6,176

Sq.Ft.

61 Joy Cir

Winchester, TN

MiddleTennessee
View 169 Joy Cir Winchester, TN MLS# 3013261
$1,350,000
3

Beds

3.1

Baths

3,183

Sq.Ft.

169 Joy Cir

Winchester, TN

MiddleTennessee
View 696 Fanning Bend Dr Winchester, TN MLS# 3132898
  • Recently Listed
1 of 24
OPEN HOUSE: Sunday 2/22 1:00 PM - 4:00 PM
$1,300,000
4

Beds

3.1

Baths

3,385

Sq.Ft.

696 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 712 Fanning Bend Dr Winchester, TN MLS# 3133386
  • Recently Listed
1 of 41
OPEN HOUSE: Sunday 2/22 1:00 PM - 4:00 PM
$1,275,000
4

Beds

4.1

Baths

3,492

Sq.Ft.

712 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 208 Loop Dr Winchester, TN MLS# 3079800
$1,229,900
4

Beds

3.1

Baths

2,906

Sq.Ft.

208 Loop Dr

Winchester, TN

MiddleTennessee
View 71 Fanning Bend Dr Winchester, TN MLS# 3046059
  • Virtual Tour
1 of 41
$1,175,000
4

Beds

3.0

Baths

2,583

Sq.Ft.

71 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 11 Hammock Dr Winchester, TN MLS# 3122192
  • Recently Listed with Virtual Tour
1 of 100
$1,100,000
4

Beds

5.0

Baths

3,622

Sq.Ft.

11 Hammock Dr

Winchester, TN

MiddleTennessee
View 211 Porter St S Winchester, TN MLS# 3110204
$1,099,000
Studio

Beds

0.0

Baths

6,300

Sq.Ft.

211 Porter St S

Winchester, TN

MiddleTennessee
View 0 Honey Ln Winchester, TN MLS# 2689137
$999,999
Studio

Beds

0.0

Baths

0 Honey Ln

Winchester, TN

MiddleTennessee
View 98 Whippoorwill Cove Rd Winchester, TN MLS# 2888152
  • New Construction
1 of 37
$995,900
3

Beds

4.0

Baths

3,258

Sq.Ft.

98 Whippoorwill Cove Rd

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 2/21/2026.

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.