View 119 Highland Dr Winchester, TN MLS# 3112733
  • Recently Listed
1 of 18
$254,900
3

Beds

1.0

Baths

1,433

Sq.Ft.

119 Highland Dr

Winchester, TN

MiddleTennessee
View 1102 N High St Winchester, TN MLS# 3112949
  • Recently Listed
1 of 27
$259,900
3

Beds

2.0

Baths

1,353

Sq.Ft.

1102 N High St

Winchester, TN

MiddleTennessee
View 111 Dogwood Ln Winchester, TN MLS# 3098815
  • Recently Listed
1 of 26
$305,000
3

Beds

1.0

Baths

1,822

Sq.Ft.

111 Dogwood Ln

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
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 0 Holders Cove Rd Winchester, TN MLS# 3093513
$240,000
Studio

Beds

0.0

Baths

0 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 400 Cessna Cir Winchester, TN MLS# 3080449
  • Recently Listed with Virtual Tour
1 of 25
$315,000
5

Beds

3.0

Baths

2,218

Sq.Ft.

400 Cessna Cir

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 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 286 Strawberry Dr Winchester, TN MLS# 3078933
$259,900
3

Beds

2.0

Baths

1,150

Sq.Ft.

286 Strawberry Dr

Winchester, TN

MiddleTennessee
View 0 Long View Dr Winchester, TN MLS# 3060534
$250,000
Studio

Beds

0.0

Baths

0 Long View Dr

Winchester, TN

MiddleTennessee
View 43 Liberty Rd Winchester, TN MLS# 3059571
$319,000
3

Beds

2.0

Baths

1,525

Sq.Ft.

43 Liberty Rd

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 14 Hazelwood Ln Winchester, TN MLS# 3054444
  • Virtual Tour
1 of 34
$289,900
3

Beds

2.0

Baths

1,552

Sq.Ft.

14 Hazelwood Ln

Winchester, TN

MiddleTennessee
View 41 Cheyenne Ave Winchester, TN MLS# 3051344
$279,900
3

Beds

2.0

Baths

1,563

Sq.Ft.

41 Cheyenne Ave

Winchester, TN

MiddleTennessee
View 96 Liberty Rd Winchester, TN MLS# 3046899
$290,900
3

Beds

2.0

Baths

1,224

Sq.Ft.

96 Liberty Rd

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 159 Apple Dr Winchester, TN MLS# 3039115
$249,900
3

Beds

2.0

Baths

1,248

Sq.Ft.

159 Apple Dr

Winchester, TN

MiddleTennessee
View 210 E Petty Ln Winchester, TN MLS# 3039433
$239,000
3

Beds

1.1

Baths

1,250

Sq.Ft.

210 E Petty Ln

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

326

Estimated median home price

$249,900
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 - 100K107
$100K - 200K42
$200K - 300K39
$300K - 400K45
$400K - 500K20
$500K - 600K21
$600K - 700K16
$700K - 800K12
$800K - 900K4
$900K - 1M5
$1M - Max15

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family160
Townhouse3
Condo0
Commercial12
Rental24
Lots and Land144
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms3

(Data as of 2/1/2026)

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 2/1/2026.

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.