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
View 959 Fanning Bend Dr Winchester, TN MLS# 3051974
  • New Construction
1 of 52
$1,750,000
6

Beds

6.2

Baths

4,778

Sq.Ft.

959 Fanning Bend Dr

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 86 Simmons Circle Winchester, TN MLS# 3038884
  • New Construction
1 of 29
$1,550,000
4

Beds

4.2

Baths

4,080

Sq.Ft.

86 Simmons Circle

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 712 Fanning Bend Dr Winchester, TN MLS# 3051965
  • New Construction
1 of 31
$1,329,000
4

Beds

4.1

Baths

3,492

Sq.Ft.

712 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 208 Loop Dr Winchester, TN MLS# 2929213
$1,239,900
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 995 Dripping Springs Rd Winchester, TN MLS# 3044907
$999,900
3

Beds

2.1

Baths

2,256

Sq.Ft.

995 Dripping Springs Rd

Winchester, TN

MiddleTennessee
View 98 Whippoorwill Cove Rd Winchester, TN MLS# 2888152
  • New Construction
1 of 37
$998,000
3

Beds

4.0

Baths

3,258

Sq.Ft.

98 Whippoorwill Cove Rd

Winchester, TN

MiddleTennessee
View 138 Kayak Way Winchester, TN MLS# 3012603
  • New Construction with Virtual Tour
1 of 66
$949,900
4

Beds

4.1

Baths

3,040

Sq.Ft.

138 Kayak Way

Winchester, TN

MiddleTennessee
View 105 Cannonball Ct Winchester, TN MLS# 3067277
  • Recently Listed
1 of 36
$949,900
5

Beds

5.0

Baths

4,748

Sq.Ft.

105 Cannonball Ct

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

345

Estimated median home price

$242,000
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 - 100K108
$100K - 200K53
$200K - 300K47
$300K - 400K41
$400K - 500K23
$500K - 600K17
$600K - 700K16
$700K - 800K12
$800K - 900K7
$900K - 1M6
$1M - Max15

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family161
Townhouse6
Condo0
Commercial12
Rental24
Lots and Land162
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms1

(Data as of 12/27/2025)

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 12/28/2025.

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.