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
OPEN HOUSE: Sunday 1/11 1:00 PM - 3:00 PM
$269,900
3

Beds

2.0

Baths

1,150

Sq.Ft.

286 Strawberry Dr

Winchester, TN

MiddleTennessee
View 105 Shephard St N Winchester, TN MLS# 3072082
  • Recently Listed
1 of 24
$332,900
3

Beds

2.1

Baths

1,358

Sq.Ft.

105 Shephard St N

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
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
$299,900
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 418 Woods Edge Rd Winchester, TN MLS# 3048816
$299,900
4

Beds

2.1

Baths

1,236

Sq.Ft.

418 Woods Edge Rd

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 132 Highland Dr Winchester, TN MLS# 3034778
$279,900
3

Beds

2.0

Baths

1,466

Sq.Ft.

132 Highland Dr

Winchester, TN

MiddleTennessee
View 25 Glasner Ln Winchester, TN MLS# 3030995
  • New Construction
1 of 32
$335,000
3

Beds

2.0

Baths

1,500

Sq.Ft.

25 Glasner Ln

Winchester, TN

MiddleTennessee
View 0 Kayak Way Winchester, TN MLS# 3018220
$245,000
Studio

Beds

0.0

Baths

0 Kayak Way

Winchester, TN

MiddleTennessee
View 620 Maple Bend Rd Winchester, TN MLS# 3017138
$260,000
3

Beds

2.0

Baths

1,632

Sq.Ft.

620 Maple Bend Rd

Winchester, TN

MiddleTennessee
View 115 Heath Lane Winchester, TN MLS# 3017022
  • New Construction
1 of 5
$289,900
3

Beds

2.0

Baths

1,311

Sq.Ft.

115 Heath Lane

Winchester, TN

MiddleTennessee
View 70 Woods Edge Rd Winchester, TN MLS# 3015014
$249,900
3

Beds

2.0

Baths

1,352

Sq.Ft.

70 Woods Edge Rd

Winchester, TN

MiddleTennessee
View 4025 David Crockett Pkwy W Winchester, TN MLS# 3013903
$289,900
4

Beds

2.0

Baths

2,560

Sq.Ft.

4025 David Crockett Pkwy W

Winchester, TN

MiddleTennessee
View 206 Homeward Ave Winchester, TN MLS# 3014079
$279,900
3

Beds

2.0

Baths

1,999

Sq.Ft.

206 Homeward Ave

Winchester, TN

MiddleTennessee

About Winchester

Listings in Winchester, TN

332

Estimated median home price

$247,000
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 - 100K107
$100K - 200K46
$200K - 300K44
$300K - 400K38
$400K - 500K22
$500K - 600K18
$600K - 700K16
$700K - 800K13
$800K - 900K6
$900K - 1M6
$1M - Max16

Homes for Sale by Type in Winchester, TN

Property TypeCount
Single Family162
Townhouse3
Condo0
Commercial13
Rental24
Lots and Land151
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms1

(Data as of 1/9/2026)

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 1/10/2026.

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.