View 1657 Boswell Rd Winchester, TN MLS# 2746411
$3,800,000
6

Beds

6.2

Baths

8,002

Sq.Ft.

1657 Boswell Rd

Winchester, TN

MiddleTennessee
View 901 Wildwood Trce Winchester, TN MLS# 2994915
$2,850,000
3

Beds

3.2

Baths

4,880

Sq.Ft.

901 Wildwood Trce

Winchester, TN

MiddleTennessee
View 7542 Chestnut Ridge Rd Winchester, TN MLS# 3058553
  • Recently Listed
1 of 40
$2,000,000
Studio

Beds

0.0

Baths

7542 Chestnut Ridge Rd

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 740 Bluff Dr Winchester, TN MLS# 3030443
$1,849,000
4

Beds

3.0

Baths

2,800

Sq.Ft.

740 Bluff Dr

Winchester, TN

MiddleTennessee
View 3819 Tullahoma Hwy Winchester, TN MLS# 3000595
$1,800,000
Studio

Beds

0.0

Baths

3819 Tullahoma Hwy

Winchester, TN

MiddleTennessee
View 959 Fanning Bend Dr Winchester, TN MLS# 3051974
  • Recently Listed
1 of 52
$1,750,000
6

Beds

6.2

Baths

4,778

Sq.Ft.

959 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 410 Dinah Shore Blvd Winchester, TN MLS# 2901941
$1,600,000
11,588

Sq.Ft.

410 Dinah Shore Blvd

Winchester, TN

MiddleTennessee
View 1000 N Vine St Winchester, TN MLS# 3015965
$1,600,000
4

Beds

2.0

Baths

2,164

Sq.Ft.

1000 N Vine St

Winchester, TN

MiddleTennessee
View 1750 Awalt Dr Winchester, TN MLS# 2868246
$1,599,000
5

Beds

4.1

Baths

3,797

Sq.Ft.

1750 Awalt Dr

Winchester, TN

MiddleTennessee
View 86 Simmons Circle Winchester, TN MLS# 3038884
  • New Construction
1 of 29
$1,550,000
4

Beds

4.2

Baths

4,080

Sq.Ft.

86 Simmons Circle

Winchester, TN

MiddleTennessee
View 0 Cowan Highway Winchester, TN MLS# 2795751
$1,500,000
999,999

Sq.Ft.

0 Cowan Highway

Winchester, TN

MiddleTennessee
View 405 Sharp Springs Rd Winchester, TN MLS# 3056561
  • Recently Listed
1 of 8
$1,500,000
Studio

Beds

0.0

Baths

405 Sharp Springs Rd

Winchester, TN

MiddleTennessee
View 61 Joy Cir Winchester, TN MLS# 3046246
$1,499,500
6

Beds

5.1

Baths

6,176

Sq.Ft.

61 Joy Cir

Winchester, TN

MiddleTennessee
View 169 Joy Cir Winchester, TN MLS# 3013261
$1,350,000
3

Beds

3.1

Baths

3,183

Sq.Ft.

169 Joy Cir

Winchester, TN

MiddleTennessee
View 712 Fanning Bend Dr Winchester, TN MLS# 3051965
  • Recently Listed
1 of 31
$1,329,000
4

Beds

4.1

Baths

3,492

Sq.Ft.

712 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 2124 Boswell Rd Winchester, TN MLS# 2990003
$1,250,000
4

Beds

3.1

Baths

6,803

Sq.Ft.

2124 Boswell Rd

Winchester, TN

MiddleTennessee
View 208 Loop Dr Winchester, TN MLS# 2929213
$1,239,900
4

Beds

3.1

Baths

2,906

Sq.Ft.

208 Loop Dr

Winchester, TN

MiddleTennessee
View 71 Fanning Bend Dr Winchester, TN MLS# 3046059
  • Virtual Tour
1 of 41
$1,175,000
4

Beds

3.0

Baths

2,583

Sq.Ft.

71 Fanning Bend Dr

Winchester, TN

MiddleTennessee
View 45 Hammock Dr Winchester, TN MLS# 3046079
    1 of 73
    OPEN HOUSE: Sunday 12/14 12:00 PM - 2:00 PM
    $1,150,000
    5

    Beds

    4.1

    Baths

    3,596

    Sq.Ft.

    45 Hammock Dr

    Winchester, TN

    MiddleTennessee
    View 0 Honey Ln Winchester, TN MLS# 2689137
    $999,999
    Studio

    Beds

    0.0

    Baths

    0 Honey Ln

    Winchester, TN

    MiddleTennessee

    About Winchester

    Listings in Winchester, TN

    354

    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 - 100K105
    $100K - 200K54
    $200K - 300K51
    $300K - 400K42
    $400K - 500K25
    $500K - 600K14
    $600K - 700K18
    $700K - 800K14
    $800K - 900K7
    $900K - 1M5
    $1M - Max19

    Homes for Sale by Type in Winchester, TN

    Property TypeCount
    Single Family171
    Townhouse6
    Condo0
    Commercial11
    Rental16
    Lots and Land162
    Condo/Town/CoOp0
    CoOp0
    Multi Family2
    Mobile Home1
    Farms1

    (Data as of 12/13/2025)

    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 12/14/2025.

    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.