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 886 Hopkins Ln Winchester, TN MLS# 3137846
  • Recently Listed with Virtual Tour
1 of 49
$1,810,000
1

Beds

3.1

Baths

3,510

Sq.Ft.

886 Hopkins Ln

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 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# 3138149
  • Recently Listed
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
  • Virtual Tour
1 of 85
$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 696 Fanning Bend Dr Winchester, TN MLS# 3132898
  • Recently Listed
1 of 44
$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
$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 182 Loop Dr Winchester, TN MLS# 3136991
$1,200,000
5

Beds

3.0

Baths

3,640

Sq.Ft.

182 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 171 Cypress Point Dr Winchester, TN MLS# 3136803
  • Recently Listed
1 of 21
$1,168,000
5

Beds

4.1

Baths

3,191

Sq.Ft.

171 Cypress Point Dr

Winchester, TN

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

Beds

5.0

Baths

3,622

Sq.Ft.

11 Hammock Dr

Winchester, TN

MiddleTennessee
View 155 Hammock Dr Winchester, TN MLS# 3137098
  • Recently Listed
1 of 36
$1,095,000
4

Beds

4.1

Baths

3,365

Sq.Ft.

155 Hammock Dr

Winchester, TN

MiddleTennessee
View 185 Wakeboard Way Winchester, TN MLS# 3136186
  • Recently Listed with Virtual Tour
1 of 72
$1,039,990
6

Beds

4.1

Baths

3,811

Sq.Ft.

185 Wakeboard Way

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 2124 Boswell Rd Winchester, TN MLS# 2990003
$990,000
4

Beds

3.1

Baths

6,803

Sq.Ft.

2124 Boswell Rd

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

367

Estimated median home price

$240,000
Winchester TN Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Tennessee real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, TN.

Homes for Sale by Price in Winchester, TN

PriceCount
$0 - 100K105
$100K - 200K62
$200K - 300K44
$300K - 400K48
$400K - 500K25
$500K - 600K28
$600K - 700K16
$700K - 800K11
$800K - 900K4
$900K - 1M4
$1M - Max20

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family180
Townhouse5
Condo1
Commercial11
Rental18
Lots and Land163
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms3

(Data as of 3/3/2026)

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 3/3/2026.

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.