View 657 Pickney Rd Winchester, TN MLS# 3080347
  • Recently Listed
1 of 66
$600,000
3

Beds

2.1

Baths

2,782

Sq.Ft.

657 Pickney Rd

Winchester, TN

MiddleTennessee
View 250 Awalt Dr Winchester, TN MLS# 3013399
$599,999
4

Beds

2.0

Baths

3,068

Sq.Ft.

250 Awalt Dr

Winchester, TN

MiddleTennessee
View 101 Westmeade Dr Winchester, TN MLS# 3030695
$599,900
5

Beds

4.1

Baths

3,510

Sq.Ft.

101 Westmeade Dr

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 50 Pontoon Place Winchester, TN MLS# 3093533
  • Recently Listed
1 of 57
$599,900
4

Beds

3.1

Baths

2,497

Sq.Ft.

50 Pontoon Place

Winchester, TN

MiddleTennessee
View 891 Hopkins Ln Winchester, TN MLS# 3002197
$599,000
3

Beds

2.2

Baths

3,534

Sq.Ft.

891 Hopkins Ln

Winchester, TN

MiddleTennessee
View 46 Willow Dr Winchester, TN MLS# 3013369
$599,000
3

Beds

2.1

Baths

2,920

Sq.Ft.

46 Willow Dr

Winchester, TN

MiddleTennessee
View 267 Golf Course Ln Winchester, TN MLS# 3015616
  • Virtual Tour
1 of 90
$599,000
5

Beds

2.3

Baths

3,755

Sq.Ft.

267 Golf Course Ln

Winchester, TN

MiddleTennessee
View 1000 Dinah Shore Blvd Winchester, TN MLS# 3046818
$595,000
6,984

Sq.Ft.

1000 Dinah Shore Blvd

Winchester, TN

MiddleTennessee
View 319 Campfire Ct Winchester, TN MLS# 3051467
$595,000
3

Beds

3.1

Baths

2,579

Sq.Ft.

319 Campfire Ct

Winchester, TN

MiddleTennessee
View 656 SHADOWBROOK RD Winchester, TN MLS# 3078727
  • Recently Listed
1 of 82
OPEN HOUSE: Sunday 1/18 1:00 PM - 3:00 PM
$589,000
3

Beds

2.1

Baths

2,946

Sq.Ft.

656 SHADOWBROOK RD

Winchester, TN

MiddleTennessee
View 18 Shady Cove Ln Winchester, TN MLS# 3080250
  • Recently Listed
1 of 40
OPEN HOUSE: Sunday 1/18 2:00 PM - 4:00 PM
$589,000
3

Beds

2.0

Baths

1,788

Sq.Ft.

18 Shady Cove Ln

Winchester, TN

MiddleTennessee
View 54 Foyer Dr Winchester, TN MLS# 2944542
$575,000
4

Beds

2.2

Baths

2,749

Sq.Ft.

54 Foyer Dr

Winchester, TN

MiddleTennessee
View 261 Franklin Heights Dr Winchester, TN MLS# 2968341
$575,000
3

Beds

3.0

Baths

3,523

Sq.Ft.

261 Franklin Heights Dr

Winchester, TN

MiddleTennessee
View 44 Hammock Dr Winchester, TN MLS# 3068567
  • Virtual Tour
1 of 46
$575,000
3

Beds

2.1

Baths

2,296

Sq.Ft.

44 Hammock Dr

Winchester, TN

MiddleTennessee
View 249 Lookout Dr Winchester, TN MLS# 2980753
  • New Construction
1 of 63
$559,900
3

Beds

2.1

Baths

2,973

Sq.Ft.

249 Lookout Dr

Winchester, TN

MiddleTennessee
View 102 Cannonball Ct Winchester, TN MLS# 3061734
$559,900
2

Beds

2.1

Baths

1,425

Sq.Ft.

102 Cannonball Ct

Winchester, TN

MiddleTennessee
View 0 DECHERD BLVD Winchester, TN MLS# 3071515
  • Recently Listed with Virtual Tour
1 of 9
$550,000

0 DECHERD BLVD

Winchester, TN

Courtesy of Tullahoma - WEICHERT, REALTORS® - Joe Orr & Associates
View 974 Lynchburg Rd Winchester, TN MLS# 2650363
$549,900
6

Beds

4.0

Baths

8,508

Sq.Ft.

974 Lynchburg Rd

Winchester, TN

MiddleTennessee
View 109 Carter Farris Ln Winchester, TN MLS# 2981370
$549,900
6

Beds

4.0

Baths

3,158

Sq.Ft.

109 Carter Farris Ln

Winchester, TN

MiddleTennessee
View 290 Maple Bend Rd Winchester, TN MLS# 3093643
  • Recently Listed with Virtual Tour
1 of 68
$543,900
4

Beds

2.0

Baths

1,925

Sq.Ft.

290 Maple Bend Rd

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 1/18/2026.

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.