361 total properties
View 114 Chase Cir Winchester, TN MLS# 3130739
$358,400
2

Beds

2.0

Baths

1,782

Sq.Ft.

114 Chase Cir

Winchester, TN

MiddleTennessee
View 305 Oak Leaf Cir Winchester, TN MLS# 3078671
$357,900
4

Beds

3.0

Baths

1,864

Sq.Ft.

305 Oak Leaf Cir

Winchester, TN

MiddleTennessee
View 38 Murray Lake Dr Winchester, TN MLS# 3171352
$355,000
2

Beds

2.0

Baths

1,683

Sq.Ft.

38 Murray Lake Dr

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 1200 Little St Winchester, TN MLS# 3183263
  • Recently Listed
1 of 54
$350,000
5

Beds

2.0

Baths

1,600

Sq.Ft.

1200 Little St

Winchester, TN

MiddleTennessee
View 88 Meadow Ln Winchester, TN MLS# 3181717
  • Recently Listed
1 of 54
$349,900
3

Beds

2.0

Baths

1,708

Sq.Ft.

88 Meadow Ln

Winchester, TN

MiddleTennessee
View 442 Golf Shores Dr Winchester, TN MLS# 3098610
$339,900
3

Beds

2.0

Baths

1,668

Sq.Ft.

442 Golf Shores Dr

Winchester, TN

MiddleTennessee
View 6606 Old Tullahoma Rd Winchester, TN MLS# 3166640
$339,000
3

Beds

2.0

Baths

1,972

Sq.Ft.

6606 Old Tullahoma Rd

Winchester, TN

MiddleTennessee
View 1114 N High St Winchester, TN MLS# 3150020
$335,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

1114 N High St

Winchester, TN

Courtesy of Tullahoma - WEICHERT, REALTORS® - Joe Orr & Associates
View 387 Fairview Cir Winchester, TN MLS# 3160145
$334,500
3

Beds

2.0

Baths

1,439

Sq.Ft.

387 Fairview Cir

Winchester, TN

MiddleTennessee
View 101 Royal Oak Dr Winchester, TN MLS# 3150395
$330,000
3

Beds

2.0

Baths

1,510

Sq.Ft.

101 Royal Oak Dr

Winchester, TN

MiddleTennessee
View 101 Lisa Cir Winchester, TN MLS# 3152424
$329,999
3

Beds

2.0

Baths

1,540

Sq.Ft.

101 Lisa Cir

Winchester, TN

MiddleTennessee
View 0 Lynchburg Rd Winchester, TN MLS# 3173644
  • New Construction
1 of 35
$329,000
3

Beds

2.0

Baths

1,492

Sq.Ft.

0 Lynchburg Rd

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 1543 Paynes Church Rd Winchester, TN MLS# 3018312
  • New Construction
1 of 36
$325,000
3

Beds

2.0

Baths

1,508

Sq.Ft.

1543 Paynes Church Rd

Winchester, TN

MiddleTennessee
View 1517 Paynes Church Rd Winchester, TN MLS# 3018326
  • New Construction
1 of 36
$325,000
3

Beds

2.1

Baths

1,508

Sq.Ft.

1517 Paynes Church Rd

Winchester, TN

MiddleTennessee
View 1563 Paynes Church Rd Winchester, TN MLS# 3031703
  • New Construction
1 of 36
$325,000
3

Beds

2.0

Baths

1,508

Sq.Ft.

1563 Paynes Church Rd

Winchester, TN

MiddleTennessee
View 1585 Paynes Church Rd Winchester, TN MLS# 3031708
  • New Construction
1 of 36
$325,000
3

Beds

2.0

Baths

1,508

Sq.Ft.

1585 Paynes Church Rd

Winchester, TN

MiddleTennessee
View 1605 Paynes Church Rd Winchester, TN MLS# 3154737
  • New Construction
1 of 33
$325,000
3

Beds

2.0

Baths

1,508

Sq.Ft.

1605 Paynes Church Rd

Winchester, TN

MiddleTennessee
View 206 Homeward Ave Winchester, TN MLS# 3180120
  • Recently Listed
1 of 36
$325,000
3

Beds

2.0

Baths

1,999

Sq.Ft.

206 Homeward Ave

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 5/2/2026.

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.