372 total properties
View 311 N Jefferson St Winchester, TN MLS# 3034046
$349,900
4

Beds

2.0

Baths

3,888

Sq.Ft.

311 N Jefferson St

Winchester, TN

MiddleTennessee
View 305 Duncan Ln Winchester, TN MLS# 3041331
$349,900
3

Beds

2.1

Baths

1,692

Sq.Ft.

305 Duncan Ln

Winchester, TN

MiddleTennessee
View 605 Strawberry Dr Winchester, TN MLS# 2992033
$344,900
3

Beds

2.0

Baths

1,632

Sq.Ft.

605 Strawberry Dr

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 170 Brandi Cir Winchester, TN MLS# 3117028
$344,900
3

Beds

2.0

Baths

1,663

Sq.Ft.

170 Brandi Cir

Winchester, TN

MiddleTennessee
View 240 Myers Rd Winchester, TN MLS# 3014240
$338,000
4

Beds

3.0

Baths

1,960

Sq.Ft.

240 Myers Rd

Winchester, TN

MiddleTennessee
View 103 Lisa Cir Winchester, TN MLS# 2995865
$330,000
3

Beds

2.0

Baths

1,570

Sq.Ft.

103 Lisa Cir

Winchester, TN

MiddleTennessee
View 204 Orchard Ln Winchester, TN MLS# 3046743
$329,900
3

Beds

2.0

Baths

1,680

Sq.Ft.

204 Orchard Ln

Winchester, TN

MiddleTennessee
View 105 Shephard St N Winchester, TN MLS# 3072082
$327,900
3

Beds

2.1

Baths

1,358

Sq.Ft.

105 Shephard St N

Winchester, TN

MiddleTennessee
View 101 N Shephard St Winchester, TN MLS# 3079702
$327,900
3

Beds

2.1

Baths

1,358

Sq.Ft.

101 N Shephard St

Winchester, TN

MiddleTennessee
View 116 Elkins Street Winchester, TN MLS# 1517337
$325,000
3

Beds

2.0

Baths

312

Sq.Ft.

116 Elkins Street

Winchester, TN

Chattanooga
Courtesy of SWAFFORDS PROPERTY SHOP
View 116 Elkins Street Winchester, TN MLS# 2968291
$325,000
3

Beds

2.0

Baths

312

Sq.Ft.

116 Elkins Street

Winchester, TN

MiddleTennessee
View 25 Glasner Ln Winchester, TN MLS# 3030995
  • New Construction
1 of 32
$325,000
3

Beds

2.0

Baths

1,500

Sq.Ft.

25 Glasner Ln

Winchester, TN

MiddleTennessee
View 209 Franklin Park Winchester, TN MLS# 3118292
$325,000
3

Beds

2.0

Baths

2,053

Sq.Ft.

209 Franklin Park

Winchester, TN

MiddleTennessee
View 667 Maple Bend Rd Winchester, TN MLS# 2992113
$320,000
2

Beds

1.1

Baths

1,200

Sq.Ft.

667 Maple Bend Rd

Winchester, TN

MiddleTennessee
View 109 Shephard St N Winchester, TN MLS# 2752494
$319,999
3

Beds

2.1

Baths

1,358

Sq.Ft.

109 Shephard St N

Winchester, TN

MiddleTennessee
View 400 Cessna Cir Winchester, TN MLS# 3080449
  • Virtual Tour
1 of 24
$314,000
5

Beds

3.0

Baths

2,218

Sq.Ft.

400 Cessna Cir

Winchester, TN

MiddleTennessee
View 103 N Shephard St Winchester, TN MLS# 3042038
$309,900
3

Beds

2.0

Baths

1,213

Sq.Ft.

103 N Shephard St

Winchester, TN

MiddleTennessee
View 99 N Shephard St Winchester, TN MLS# 3059253
  • New Construction
1 of 22
$309,900
3

Beds

2.0

Baths

1,213

Sq.Ft.

99 N Shephard St

Winchester, TN

MiddleTennessee
View 383 Strawberry Dr Winchester, TN MLS# 3079332
$305,000
3

Beds

2.0

Baths

1,296

Sq.Ft.

383 Strawberry Dr

Winchester, TN

MiddleTennessee
View 111 Dogwood Ln Winchester, TN MLS# 3098815
$300,000
3

Beds

1.0

Baths

1,822

Sq.Ft.

111 Dogwood Ln

Winchester, TN

MiddleTennessee

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 2/27/2026.

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.