View 97 Shady Cove Ln Winchester, TN MLS# 2969788
  • Virtual Tour
1 of 75
$2,100,000
2

Beds

3.1

Baths

3,410

Sq.Ft.

97 Shady Cove Ln

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 56
$1,579,900
4

Beds

4.0

Baths

3,720

Sq.Ft.

160 Wakeboard Way

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 208 Loop Dr Winchester, TN MLS# 3079800
  • Recently Listed
1 of 88
$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 2124 Boswell Rd Winchester, TN MLS# 2990003
$1,140,000
4

Beds

3.1

Baths

6,803

Sq.Ft.

2124 Boswell Rd

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 510 N Porter St Winchester, TN MLS# 3047314
  • Recently Listed
1 of 59
$999,999
3

Beds

2.1

Baths

2,677

Sq.Ft.

510 N Porter St

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
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
  • Recently Listed
1 of 87
$959,000
4

Beds

3.1

Baths

3,341

Sq.Ft.

279 Hammock Drive

Winchester, TN

MiddleTennessee
View 105 Cannonball Ct Winchester, TN MLS# 3067277
$949,900
5

Beds

5.0

Baths

4,748

Sq.Ft.

105 Cannonball Ct

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

341

Estimated median home price

$250,000
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 - 100K103
$100K - 200K46
$200K - 300K49
$300K - 400K40
$400K - 500K24
$500K - 600K22
$600K - 700K17
$700K - 800K14
$800K - 900K6
$900K - 1M6
$1M - Max14

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family174
Townhouse3
Condo0
Commercial11
Rental28
Lots and Land147
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms3

(Data as of 1/16/2026)

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 1/19/2026.

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.