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
The time to sell is now! THE TIME TO SELL IS NOW!
View 279 Hammock Drive Winchester, TN MLS# 2800415
  • New Construction
1 of 87
$949,000
4

Beds

3.1

Baths

3,341

Sq.Ft.

279 Hammock Drive

Winchester, TN

MiddleTennessee
View 101 Cypress Point Dr Winchester, TN MLS# 3045267
$899,900
4

Beds

3.1

Baths

3,738

Sq.Ft.

101 Cypress Point Dr

Winchester, TN

MiddleTennessee
View 494 Cascade Dr Winchester, TN MLS# 2993628
$899,000
4

Beds

3.1

Baths

3,361

Sq.Ft.

494 Cascade Dr

Winchester, TN

MiddleTennessee
View 155 Cypress Point Dr Winchester, TN MLS# 2979931
$869,900
3

Beds

2.1

Baths

2,236

Sq.Ft.

155 Cypress Point Dr

Winchester, TN

MiddleTennessee
View 7 S College St Winchester, TN MLS# 2812486
$850,000
9,970

Sq.Ft.

7 S College St

Winchester, TN

MiddleTennessee
View 133 Wakeboard Way Winchester, TN MLS# 2696011
  • Virtual Tour
1 of 55
$849,900
4

Beds

4.0

Baths

3,101

Sq.Ft.

133 Wakeboard Way

Winchester, TN

MiddleTennessee
View 74 Summerlake Ct Winchester, TN MLS# 2944564
  • New Construction
1 of 38
$825,000
3

Beds

3.1

Baths

2,504

Sq.Ft.

74 Summerlake Ct

Winchester, TN

MiddleTennessee
View 347 Campfire Court Winchester, TN MLS# 3037409
$819,999
4

Beds

3.0

Baths

2,930

Sq.Ft.

347 Campfire Court

Winchester, TN

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

0 College St

Winchester, TN

MiddleTennessee
View 630 Shadowbrook Rd Winchester, TN MLS# 2985394
$799,900
3

Beds

3.1

Baths

3,896

Sq.Ft.

630 Shadowbrook Rd

Winchester, TN

MiddleTennessee
View 309 Campfire Ct Winchester, TN MLS# 3033823
  • Virtual Tour
1 of 55
$799,900
4

Beds

3.1

Baths

2,886

Sq.Ft.

309 Campfire Ct

Winchester, TN

MiddleTennessee
View 397 Campfire Ct Winchester, TN MLS# 3059004
  • Recently Listed
1 of 92
$799,900
5

Beds

3.1

Baths

2,805

Sq.Ft.

397 Campfire Ct

Winchester, TN

MiddleTennessee
View 585 Deep Hollow Ln Winchester, TN MLS# 3007546
$799,000
Studio

Beds

0.0

Baths

585 Deep Hollow Ln

Winchester, TN

MiddleTennessee
View 16 Blairmont Ct Winchester, TN MLS# 3034533
  • New Construction
1 of 71
$792,900
4

Beds

3.1

Baths

4,109

Sq.Ft.

16 Blairmont Ct

Winchester, TN

MiddleTennessee
View 82 Hammock Dr Winchester, TN MLS# 3048125
$785,000
4

Beds

3.1

Baths

3,118

Sq.Ft.

82 Hammock Dr

Winchester, TN

MiddleTennessee
View 71 Windjammer Ct Winchester, TN MLS# 2914485
$775,000
4

Beds

3.1

Baths

3,017

Sq.Ft.

71 Windjammer Ct

Winchester, TN

MiddleTennessee
View 102 Summer Lake Ct Winchester, TN MLS# 2979668
  • New Construction
1 of 35
$775,000
4

Beds

3.1

Baths

2,688

Sq.Ft.

102 Summer Lake Ct

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

354

Estimated median home price

$249,900
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 - 100K105
$100K - 200K54
$200K - 300K51
$300K - 400K42
$400K - 500K25
$500K - 600K14
$600K - 700K18
$700K - 800K14
$800K - 900K7
$900K - 1M5
$1M - Max19

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family171
Townhouse6
Condo0
Commercial11
Rental16
Lots and Land162
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms1

(Data as of 12/13/2025)

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 12/15/2025.

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.