View 1011 Massengill St Winchester, TN MLS# 3149814
$199,900
3

Beds

2.0

Baths

1,672

Sq.Ft.

1011 Massengill St

Winchester, TN

MiddleTennessee
View 106 Wiseman Ln Winchester, TN MLS# 3150005
  • Recently Listed
1 of 15
$429,900
4

Beds

2.0

Baths

2,089

Sq.Ft.

106 Wiseman Ln

Winchester, TN

MiddleTennessee
View 1114 N High St Winchester, TN MLS# 3150020
  • Recently Listed
1 of 46
$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
The time to sell is now! THE TIME TO SELL IS NOW!
View 124 Lookout Drive Winchester, TN MLS# 3149648
  • Recently Listed
1 of 54
$454,900
4

Beds

2.0

Baths

1,890

Sq.Ft.

124 Lookout Drive

Winchester, TN

MiddleTennessee
View 0 Michelle Lane Winchester, TN MLS# 3148531
$99,900
Studio

Beds

0.0

Baths

0 Michelle Lane

Winchester, TN

MiddleTennessee
View 142 Hammock Drive Winchester, TN MLS# 3148575
  • New Construction
1 of 33
OPEN HOUSE: Sunday 3/29 12:00 PM - 4:00 PM
$744,900
4

Beds

3.1

Baths

3,034

Sq.Ft.

142 Hammock Drive

Winchester, TN

MiddleTennessee
View 52 Island Way Winchester, TN MLS# 3148713
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Sunday 3/29 12:00 PM - 4:00 PM
$364,900
2

Beds

2.0

Baths

1,339

Sq.Ft.

52 Island Way

Winchester, TN

MiddleTennessee
View 1110 Hunt St Winchester, TN MLS# 3149095
  • Recently Listed
1 of 23
$219,900
3

Beds

2.0

Baths

2,040

Sq.Ft.

1110 Hunt St

Winchester, TN

MiddleTennessee
View 110 Dotson Ln Winchester, TN MLS# 3149143
  • Recently Listed
1 of 30
$225,000
3

Beds

2.0

Baths

1,380

Sq.Ft.

110 Dotson Ln

Winchester, TN

MiddleTennessee
View 232 Loop Dr Winchester, TN MLS# 3147892
  • Recently Listed
1 of 41
$1,249,000
5

Beds

4.1

Baths

3,670

Sq.Ft.

232 Loop Dr

Winchester, TN

MiddleTennessee
View 134 Wiseman Ln Winchester, TN MLS# 3148314
  • New Construction
1 of 18
$464,900
4

Beds

2.0

Baths

2,274

Sq.Ft.

134 Wiseman Ln

Winchester, TN

MiddleTennessee
View 96 Maple Dr Winchester, TN MLS# 3148318
$425,000
4

Beds

4.0

Baths

2,003

Sq.Ft.

96 Maple Dr

Winchester, TN

MiddleTennessee
View 260 Lookout Dr Winchester, TN MLS# 3147516
  • Recently Listed with Virtual Tour
1 of 45
$699,000
3

Beds

2.1

Baths

3,115

Sq.Ft.

260 Lookout Dr

Winchester, TN

MiddleTennessee
View 0 River Watch Way Winchester, TN MLS# 3147762
  • Recently Listed
1 of 15
$139,900
Studio

Beds

0.0

Baths

0 River Watch Way

Winchester, TN

MiddleTennessee
View 3754 Aedc Rd Winchester, TN MLS# 3146742
$449,000
2

Beds

1.0

Baths

3,560

Sq.Ft.

3754 Aedc Rd

Winchester, TN

MiddleTennessee
View 517 Bluff Dr Winchester, TN MLS# 3146900
$1,195,000
2

Beds

2.2

Baths

3,384

Sq.Ft.

517 Bluff Dr

Winchester, TN

MiddleTennessee
View 211 S Porter St Winchester, TN MLS# 3146939
  • Recently Listed
1 of 27
$299,999
3

Beds

2.1

Baths

1,575

Sq.Ft.

211 S Porter St

Winchester, TN

MiddleTennessee
View 102 Edgewater Dr Winchester, TN MLS# 3146994
  • Recently Listed
1 of 61
$242,900
3

Beds

1.0

Baths

1,076

Sq.Ft.

102 Edgewater Dr

Winchester, TN

MiddleTennessee
View 1584 Liberty Rd Winchester, TN MLS# 3146250
  • Recently Listed
1 of 28
$0
Studio

Beds

0.0

Baths

1584 Liberty Rd

Winchester, TN

MiddleTennessee
View 203 Campfire Ct Winchester, TN MLS# 3146348
  • Recently Listed
1 of 84
$450,000
4

Beds

2.1

Baths

2,141

Sq.Ft.

203 Campfire Ct

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

356

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 - 100K79
$100K - 200K61
$200K - 300K48
$300K - 400K39
$400K - 500K31
$500K - 600K29
$600K - 700K16
$700K - 800K17
$800K - 900K8
$900K - 1M5
$1M - Max23

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family196
Townhouse9
Condo1
Commercial10
Rental11
Lots and Land133
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home1
Farms3

(Data as of 3/24/2026)

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 3/24/2026.

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.