View 98 Whippoorwill Cove Rd Winchester, TN MLS# 3145387
$0
3

Beds

4.0

Baths

3,258

Sq.Ft.

98 Whippoorwill Cove Rd

Winchester, TN

MiddleTennessee
View 102 Cannonball Ct Winchester, TN MLS# 3145506
  • Recently Listed
1 of 29
$559,900
2

Beds

2.1

Baths

1,425

Sq.Ft.

102 Cannonball Ct

Winchester, TN

MiddleTennessee
View 17 Cannonball Ct Winchester, TN MLS# 3145555
  • Recently Listed
1 of 81
$829,900
4

Beds

3.1

Baths

2,989

Sq.Ft.

17 Cannonball Ct

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 22 Driftwood Ct Winchester, TN MLS# 3145575
  • Recently Listed
1 of 36
$539,900
3

Beds

2.1

Baths

2,020

Sq.Ft.

22 Driftwood Ct

Winchester, TN

MiddleTennessee
View 120 Pontoon Pl Winchester, TN MLS# 3143137
  • Recently Listed
1 of 74
$649,900
3

Beds

2.1

Baths

2,317

Sq.Ft.

120 Pontoon Pl

Winchester, TN

MiddleTennessee
View 155 Cypress Point Dr Winchester, TN MLS# 3143288
  • Recently Listed
1 of 51
$869,900
3

Beds

2.1

Baths

2,236

Sq.Ft.

155 Cypress Point Dr

Winchester, TN

MiddleTennessee
View 1680 Bypass Rd Winchester, TN MLS# 3143338
  • Recently Listed
1 of 13
$0
3

Beds

2.0

Baths

1,400

Sq.Ft.

1680 Bypass Rd

Winchester, TN

MiddleTennessee
View 103 Anderton Dr Winchester, TN MLS# 3143442
  • Recently Listed
1 of 60
$496,800
5

Beds

3.0

Baths

2,160

Sq.Ft.

103 Anderton Dr

Winchester, TN

MiddleTennessee
View 287 Shasteen Bend Dr Winchester, TN MLS# 3138957
  • Recently Listed
1 of 78
$925,000
3

Beds

2.1

Baths

1,821

Sq.Ft.

287 Shasteen Bend Dr

Winchester, TN

MiddleTennessee
View 630 Shadowbrook Rd Winchester, TN MLS# 3139037
  • Recently Listed
1 of 78
$789,900
4

Beds

3.1

Baths

3,896

Sq.Ft.

630 Shadowbrook Rd

Winchester, TN

MiddleTennessee
View 121 N Cedar St Winchester, TN MLS# 3139451
  • Recently Listed
1 of 37
$384,900
5

Beds

3.0

Baths

3,343

Sq.Ft.

121 N Cedar St

Winchester, TN

MiddleTennessee
View 207 Franklin Park Winchester, TN MLS# 3138427
  • Recently Listed
1 of 37
$274,900
3

Beds

2.0

Baths

1,400

Sq.Ft.

207 Franklin Park

Winchester, TN

MiddleTennessee
View 119 Kenmore Ave Winchester, TN MLS# 3138643
  • Recently Listed
1 of 33
$245,000
3

Beds

2.0

Baths

1,276

Sq.Ft.

119 Kenmore Ave

Winchester, TN

MiddleTennessee
View 217 S Porter St Winchester, TN MLS# 3138749
  • Recently Listed
1 of 27
$299,999
3

Beds

2.1

Baths

1,575

Sq.Ft.

217 S Porter St

Winchester, TN

MiddleTennessee
View 215 S Porter St Winchester, TN MLS# 3138752
  • Recently Listed
1 of 27
$299,999
3

Beds

2.1

Baths

1,575

Sq.Ft.

215 S Porter St

Winchester, TN

MiddleTennessee
View 213 S Porter St Winchester, TN MLS# 3138753
  • Recently Listed
1 of 27
$299,999
3

Beds

2.1

Baths

1,575

Sq.Ft.

213 S Porter St

Winchester, TN

MiddleTennessee
View 201&203 3rd Ave NE Winchester, TN MLS# 242453
  • Recently Listed with Virtual Tour
1 of 36
$275,000
4

Beds

2.0

Baths

1,344

Sq.Ft.

201&203 3rd Ave NE

Winchester, TN

View 201&203 3rd Ave NE Winchester, TN MLS# 242455
  • Recently Listed with Virtual Tour
1 of 36
$275,000
4

Beds

2.0

Baths

1,344

Sq.Ft.

201&203 3rd Ave NE

Winchester, TN

View 0 Old Estill Springs Rd Winchester, TN MLS# 3137634
$199,900
Studio

Beds

0.0

Baths

0 Old Estill Springs Rd

Winchester, TN

MiddleTennessee
View 203 3rd Ave NE Winchester, TN MLS# 3137712
  • Recently Listed
1 of 37
$275,000
4

Beds

2.0

Baths

1,344

Sq.Ft.

203 3rd Ave NE

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

355

Estimated median home price

$299,999
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 - 100K76
$100K - 200K58
$200K - 300K50
$300K - 400K46
$400K - 500K30
$500K - 600K29
$600K - 700K17
$700K - 800K16
$800K - 900K7
$900K - 1M5
$1M - Max21

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family198
Townhouse10
Condo1
Commercial10
Rental13
Lots and Land129
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms4

(Data as of 3/15/2026)

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 3/16/2026.

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.