373 total properties
View 120 1st Ave NW NW Winchester, TN MLS# 2970577
$459,000
1,982

Sq.Ft.

120 1st Ave NW NW

Winchester, TN

MiddleTennessee
View 300 Old Clark Rd Winchester, TN MLS# 3080461
$459,000
3

Beds

2.0

Baths

1,840

Sq.Ft.

300 Old Clark Rd

Winchester, TN

MiddleTennessee
View 0 Lookout Drive Winchester, TN MLS# 3015909
  • New Construction
1 of 11
$454,900
4

Beds

2.0

Baths

1,890

Sq.Ft.

0 Lookout Drive

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 80 Wiseman Lane Winchester, TN MLS# 3093345
  • New Construction
1 of 30
$454,900
4

Beds

2.0

Baths

2,216

Sq.Ft.

80 Wiseman Lane

Winchester, TN

MiddleTennessee
View 246 Lookout Dr Winchester, TN MLS# 3134022
  • Recently Listed
1 of 32
$449,900
4

Beds

2.0

Baths

2,044

Sq.Ft.

246 Lookout Dr

Winchester, TN

MiddleTennessee
View 0 Rowe Gap Rd Winchester, TN MLS# 3050490
$447,750
Studio

Beds

0.0

Baths

0 Rowe Gap Rd

Winchester, TN

MiddleTennessee
View 148 Anderton Dr Winchester, TN MLS# 3098443
$435,000
4

Beds

3.0

Baths

1,943

Sq.Ft.

148 Anderton Dr

Winchester, TN

MiddleTennessee
View 160 Anderton Dr Winchester, TN MLS# 2927606
$429,900
4

Beds

2.0

Baths

1,900

Sq.Ft.

160 Anderton Dr

Winchester, TN

MiddleTennessee
View 495 Favre Cir Winchester, TN MLS# 3050407
$429,900
3

Beds

2.0

Baths

2,246

Sq.Ft.

495 Favre Cir

Winchester, TN

MiddleTennessee
View 52 Wiseman Lane Winchester, TN MLS# 3093348
  • New Construction
1 of 31
$429,900
4

Beds

2.0

Baths

2,094

Sq.Ft.

52 Wiseman Lane

Winchester, TN

MiddleTennessee
View 225 Crimson Dr Winchester, TN MLS# 3131145
  • Recently Listed with Virtual Tour
1 of 72
$429,900
3

Beds

2.1

Baths

2,485

Sq.Ft.

225 Crimson Dr

Winchester, TN

MiddleTennessee
View 25 Billy Goat Hill Rd Winchester, TN MLS# 3119009
$419,999
3

Beds

2.0

Baths

1,803

Sq.Ft.

25 Billy Goat Hill Rd

Winchester, TN

MiddleTennessee
View 135 Carter Rd Winchester, TN MLS# 3070138
  • Virtual Tour
1 of 52
OPEN HOUSE: Saturday 2/28 11:00 AM - 1:00 PM
$415,000
4

Beds

3.1

Baths

2,884

Sq.Ft.

135 Carter Rd

Winchester, TN

MiddleTennessee
View 74 Freedom Ln Winchester, TN MLS# 3058554
$399,999
2

Beds

2.0

Baths

2,244

Sq.Ft.

74 Freedom Ln

Winchester, TN

MiddleTennessee
View 44 Houghton Dr Winchester, TN MLS# 3042360
$399,900
4

Beds

2.2

Baths

2,197

Sq.Ft.

44 Houghton Dr

Winchester, TN

MiddleTennessee
View 44 Rocky Hollow Dr Winchester, TN MLS# 3119275
  • Virtual Tour
1 of 39
$399,900
3

Beds

3.0

Baths

2,208

Sq.Ft.

44 Rocky Hollow Dr

Winchester, TN

MiddleTennessee
View 219 Old Mill Rd Winchester, TN MLS# 3067446
$399,000
3,050

Sq.Ft.

219 Old Mill Rd

Winchester, TN

MiddleTennessee
View 219 Old Mill Rd Winchester, TN MLS# 3067448
$399,000
3

Beds

2.0

Baths

3,050

Sq.Ft.

219 Old Mill Rd

Winchester, TN

MiddleTennessee
View 1111 Holders Cove Rd Winchester, TN MLS# 2946840
$395,000
3

Beds

1.1

Baths

1,508

Sq.Ft.

1111 Holders Cove Rd

Winchester, TN

MiddleTennessee
View 232 Favre Cir Winchester, TN MLS# 3122648
$395,000
3

Beds

2.0

Baths

1,938

Sq.Ft.

232 Favre Cir

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 2/26/2026.

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.