View 155 Hammock Dr Winchester, TN MLS# 3137098
  • Recently Listed
1 of 52
$1,095,000
4

Beds

4.1

Baths

3,365

Sq.Ft.

155 Hammock Dr

Winchester, TN

MiddleTennessee
View 185 Wakeboard Way Winchester, TN MLS# 3136186
  • Recently Listed with Virtual Tour
1 of 72
$1,039,990
6

Beds

4.1

Baths

3,811

Sq.Ft.

185 Wakeboard Way

Winchester, TN

MiddleTennessee
View 0 Honey Ln Winchester, TN MLS# 2689137
$999,999
Studio

Beds

0.0

Baths

0 Honey Ln

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 2124 Boswell Rd Winchester, TN MLS# 2990003
$990,000
4

Beds

3.1

Baths

6,803

Sq.Ft.

2124 Boswell 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 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 279 Hammock Drive Winchester, TN MLS# 3079153
  • New Construction
1 of 89
$899,995
4

Beds

3.1

Baths

3,341

Sq.Ft.

279 Hammock Drive

Winchester, TN

MiddleTennessee
View 73 Cypress Point Dr Winchester, TN MLS# 3118220
$899,000
4

Beds

3.1

Baths

2,684

Sq.Ft.

73 Cypress Point Dr

Winchester, TN

MiddleTennessee
View 53 River Watch Way Winchester, TN MLS# 3146597
  • Recently Listed
1 of 75
$879,900
5

Beds

4.1

Baths

3,095

Sq.Ft.

53 River Watch Way

Winchester, TN

MiddleTennessee
View 494 Cascade Dr Winchester, TN MLS# 2993628
$879,000
4

Beds

3.1

Baths

3,361

Sq.Ft.

494 Cascade Dr

Winchester, TN

MiddleTennessee
View 282 Owl Hollow Ln Winchester, TN MLS# 3123764
$877,000
4

Beds

3.0

Baths

3,484

Sq.Ft.

282 Owl Hollow Ln

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 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
View 0 College St Winchester, TN MLS# 2975107
$800,000

0 College St

Winchester, TN

MiddleTennessee
View 364 Blair Pond Rd Winchester, TN MLS# 3133833
$800,000
2,306

Sq.Ft.

364 Blair Pond Rd

Winchester, TN

MiddleTennessee
View 20 Windjammer Ct Winchester, TN MLS# 3078990
$799,900
4

Beds

3.0

Baths

3,032

Sq.Ft.

20 Windjammer Ct

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 16 Blairmont Ct Winchester, TN MLS# 3128456
  • New Construction
1 of 71
$780,900
4

Beds

3.1

Baths

4,109

Sq.Ft.

16 Blairmont Ct

Winchester, TN

MiddleTennessee
View 347 Campfire Court Winchester, TN MLS# 3037409
$779,900
4

Beds

3.0

Baths

2,930

Sq.Ft.

347 Campfire Court

Winchester, TN

MiddleTennessee
View 74 Summerlake Ct Winchester, TN MLS# 2944564
  • New Construction
1 of 38
$775,000
3

Beds

3.1

Baths

2,504

Sq.Ft.

74 Summerlake Ct

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 - 500K31
$500K - 600K29
$600K - 700K17
$700K - 800K16
$800K - 900K6
$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 3/16/2026)

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 3/18/2026.

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.