View 801 S High St Winchester, TN MLS# 3097688
  • Recently Listed with Virtual Tour
1 of 49
$249,900
3

Beds

1.1

Baths

1,697

Sq.Ft.

801 S High St

Winchester, TN

MiddleTennessee
View 1019 Old Cowan Rd Winchester, TN MLS# 3097752
  • Recently Listed
1 of 23
$202,900
3

Beds

2.0

Baths

1,036

Sq.Ft.

1019 Old Cowan Rd

Winchester, TN

MiddleTennessee
View 80 Wiseman Lane Winchester, TN MLS# 3093345
  • Recently Listed
1 of 30
$454,900
4

Beds

2.0

Baths

2,216

Sq.Ft.

80 Wiseman Lane

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 52 Wiseman Lane Winchester, TN MLS# 3093348
  • Recently Listed
1 of 31
$429,900
5

Beds

2.0

Baths

2,094

Sq.Ft.

52 Wiseman Lane

Winchester, TN

MiddleTennessee
View 5257 Holders Cove Rd Winchester, TN MLS# 3093509
  • Recently Listed
1 of 12
$222,250
Studio

Beds

0.0

Baths

5257 Holders Cove Rd

Winchester, TN

MiddleTennessee
View 5257 Holders Cove Rd Winchester, TN MLS# 3093513
  • Recently Listed
1 of 12
$222,250
Studio

Beds

0.0

Baths

5257 Holders Cove Rd

Winchester, TN

MiddleTennessee
View 0 Old Tullahoma Rd Winchester, TN MLS# 3080240
  • Recently Listed
1 of 5
$249,999
Studio

Beds

0.0

Baths

0 Old Tullahoma Rd

Winchester, TN

MiddleTennessee
View 6421 Lynchburg Rd Winchester, TN MLS# 3080425
  • Recently Listed
1 of 25
$374,900
2

Beds

2.0

Baths

1,540

Sq.Ft.

6421 Lynchburg Rd

Winchester, TN

MiddleTennessee
View 400 Cessna Cir Winchester, TN MLS# 3080449
$315,000
5

Beds

3.0

Baths

2,240

Sq.Ft.

400 Cessna Cir

Winchester, TN

MiddleTennessee
View 0 Georgia Crossings Rd Winchester, TN MLS# 3083817
  • Recently Listed
1 of 12
$110,000
Studio

Beds

0.0

Baths

0 Georgia Crossings Rd

Winchester, TN

MiddleTennessee
View 638 Haddon Ln Winchester, TN MLS# 3079873
  • Recently Listed
1 of 12
$279,000
3

Beds

2.0

Baths

1,247

Sq.Ft.

638 Haddon Ln

Winchester, TN

MiddleTennessee
View 614 Haddon Ln Winchester, TN MLS# 3079877
  • Recently Listed
1 of 12
$279,000
3

Beds

2.0

Baths

1,247

Sq.Ft.

614 Haddon Ln

Winchester, TN

MiddleTennessee
View 1011 Massengill St Winchester, TN MLS# 3079950
  • Recently Listed
1 of 9
$199,900
3

Beds

2.0

Baths

1,672

Sq.Ft.

1011 Massengill St

Winchester, TN

MiddleTennessee
View 134 Kenmore Ave Winchester, TN MLS# 3080092
  • Recently Listed
1 of 20
$192,900
2

Beds

1.0

Baths

774

Sq.Ft.

134 Kenmore Ave

Winchester, TN

MiddleTennessee
View 101 N Shephard St Winchester, TN MLS# 3079702
  • Recently Listed
1 of 32
$332,900
3

Beds

2.1

Baths

1,358

Sq.Ft.

101 N Shephard St

Winchester, TN

MiddleTennessee
View 383 Strawberry Dr Winchester, TN MLS# 3079332
  • Recently Listed
1 of 20
$305,000
3

Beds

2.0

Baths

1,296

Sq.Ft.

383 Strawberry Dr

Winchester, TN

MiddleTennessee
View 286 Strawberry Dr Winchester, TN MLS# 3078933
  • Recently Listed
1 of 25
$269,900
3

Beds

2.0

Baths

1,150

Sq.Ft.

286 Strawberry Dr

Winchester, TN

MiddleTennessee
View 7010 Lynchburg Rd Winchester, TN MLS# 3073973
  • Recently Listed
1 of 22
$189,000
4

Beds

2.0

Baths

1,900

Sq.Ft.

7010 Lynchburg Rd

Winchester, TN

MiddleTennessee
View 0 Suntan Court Winchester, TN MLS# 3078602
  • Recently Listed
1 of 34
$140,000
Studio

Beds

0.0

Baths

0 Suntan Court

Winchester, TN

MiddleTennessee
View 305 Oak Leaf Cir Winchester, TN MLS# 3078671
  • Recently Listed
1 of 36
$374,900
4

Beds

3.0

Baths

1,864

Sq.Ft.

305 Oak Leaf Cir

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

339

Estimated median home price

$250,000
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 - 100K103
$100K - 200K46
$200K - 300K47
$300K - 400K41
$400K - 500K24
$500K - 600K21
$600K - 700K17
$700K - 800K14
$800K - 900K6
$900K - 1M6
$1M - Max14

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family172
Townhouse3
Condo0
Commercial11
Rental26
Lots and Land147
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms3

(Data as of 1/15/2026)

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 1/16/2026.

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.