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 141 Whippoorwill Cove Rd Winchester, TN MLS# 3178272
$1,900,000
3

Beds

3.0

Baths

2,451

Sq.Ft.

141 Whippoorwill Cove Rd

Winchester, TN

MiddleTennessee
View 912 Dinah Shore Blvd Winchester, TN MLS# 3179543
  • Recently Listed
1 of 94
$1,900,000
33,200

Sq.Ft.

912 Dinah Shore Blvd

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 3819 Tullahoma Hwy Winchester, TN MLS# 3000595
$1,800,000
Studio

Beds

0.0

Baths

3819 Tullahoma Hwy

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 644 Fanning Bend Dr Winchester, TN MLS# 3156440
$1,525,000
4

Beds

3.1

Baths

3,922

Sq.Ft.

644 Fanning Bend Dr

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 71 Slalom Cir Winchester, TN MLS# 3112698
  • Virtual Tour
1 of 85
$1,495,000
4

Beds

4.0

Baths

4,500

Sq.Ft.

71 Slalom Cir

Winchester, TN

MiddleTennessee
View 160 Wakeboard Way Winchester, TN MLS# 3138149
$1,495,000
4

Beds

4.0

Baths

3,720

Sq.Ft.

160 Wakeboard Way

Winchester, TN

MiddleTennessee
View 86 Simmons Cir Winchester, TN MLS# 3169835
  • Recently Listed
1 of 67
$1,475,000
4

Beds

4.2

Baths

4,080

Sq.Ft.

86 Simmons Cir

Winchester, TN

MiddleTennessee
View 0 Cowan Highway Winchester, TN MLS# 2795751
$1,450,000
999,999

Sq.Ft.

0 Cowan Highway

Winchester, TN

MiddleTennessee
View 61 Joy Cir Winchester, TN MLS# 3046246
$1,449,500
6

Beds

5.1

Baths

6,176

Sq.Ft.

61 Joy Cir

Winchester, TN

MiddleTennessee
View 696 Fanning Bend Dr Winchester, TN MLS# 3132898
  • New Construction
1 of 44
$1,300,000
4

Beds

3.1

Baths

3,385

Sq.Ft.

696 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 645 Wildwood Trce Winchester, TN MLS# 3167457
  • Recently Listed with Virtual Tour
1 of 49
$1,275,000
2

Beds

3.0

Baths

2,460

Sq.Ft.

645 Wildwood Trce

Winchester, TN

MiddleTennessee
View 712 Fanning Bend Dr Winchester, TN MLS# 3169834
  • Recently Listed
1 of 57
$1,275,000
4

Beds

4.1

Baths

3,492

Sq.Ft.

712 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 100 Barefoot Way Winchester, TN MLS# 3177964
$1,249,900
4

Beds

4.1

Baths

2,800

Sq.Ft.

100 Barefoot Way

Winchester, TN

MiddleTennessee
View 914 N Jefferson St Winchester, TN MLS# 3163497
  • Virtual Tour
1 of 99
$1,199,900
4

Beds

3.0

Baths

2,714

Sq.Ft.

914 N Jefferson St

Winchester, TN

MiddleTennessee
View 71 Fanning Bend Dr Winchester, TN MLS# 3046059
  • Virtual Tour
1 of 39
$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
$1,168,000
5

Beds

4.1

Baths

3,191

Sq.Ft.

171 Cypress Point Dr

Winchester, TN

MiddleTennessee
View 208 Loop Dr Winchester, TN MLS# 3173240
  • Recently Listed
1 of 89
$1,150,000
4

Beds

3.1

Baths

2,906

Sq.Ft.

208 Loop Dr

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

369

Estimated median home price

$325,000
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 - 100K65
$100K - 200K69
$200K - 300K42
$300K - 400K42
$400K - 500K31
$500K - 600K33
$600K - 700K24
$700K - 800K17
$800K - 900K10
$900K - 1M7
$1M - Max29

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family210
Townhouse9
Condo1
Commercial13
Rental13
Lots and Land129
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms4

(Data as of 4/23/2026)

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 4/23/2026.

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.