372 total properties
View 205 Houghton Dr Winchester, TN MLS# 3099294
$389,500
4

Beds

3.0

Baths

2,640

Sq.Ft.

205 Houghton Dr

Winchester, TN

MiddleTennessee
View 295 Metcalf Rd Winchester, TN MLS# 3042339
$389,000
3

Beds

2.1

Baths

1,800

Sq.Ft.

295 Metcalf Rd

Winchester, TN

MiddleTennessee
View 204 8th Ave SE Winchester, TN MLS# 3111995
$388,204
3

Beds

3.0

Baths

2,476

Sq.Ft.

204 8th Ave SE

Winchester, TN

MiddleTennessee
The time to sell is now! THE TIME TO SELL IS NOW!
View 500 Golf Shores Dr Winchester, TN MLS# 2963154
  • Virtual Tour
1 of 55
$388,000
4

Beds

2.1

Baths

2,472

Sq.Ft.

500 Golf Shores Dr

Winchester, TN

MiddleTennessee
View 189 Pickney Rd Winchester, TN MLS# 3067416
$380,000
3

Beds

2.0

Baths

2,607

Sq.Ft.

189 Pickney Rd

Winchester, TN

MiddleTennessee
View 60 Sharp Cir Winchester, TN MLS# 2980827
$379,000
3

Beds

3.0

Baths

2,956

Sq.Ft.

60 Sharp Cir

Winchester, TN

MiddleTennessee
View 144 Wood Bluff Rd Winchester, TN MLS# 3131154
  • Recently Listed
1 of 64
$375,000
4

Beds

3.0

Baths

2,528

Sq.Ft.

144 Wood Bluff Rd

Winchester, TN

MiddleTennessee
View 401 E Petty Ln Winchester, TN MLS# 3134995
  • Recently Listed
1 of 59
$375,000
3

Beds

2.1

Baths

2,653

Sq.Ft.

401 E Petty Ln

Winchester, TN

MiddleTennessee
View 17 Favre Cir Winchester, TN MLS# 3051345
$374,900
3

Beds

2.0

Baths

1,615

Sq.Ft.

17 Favre Cir

Winchester, TN

MiddleTennessee
View 1718 Galloway Lane Winchester, TN MLS# 2967681
  • New Construction
1 of 52
$369,550
3

Beds

2.0

Baths

1,726

Sq.Ft.

1718 Galloway Lane

Winchester, TN

MiddleTennessee
View 26 Maple Bend Rd Winchester, TN MLS# 3131463
$365,000
3

Beds

2.0

Baths

1,487

Sq.Ft.

26 Maple Bend Rd

Winchester, TN

MiddleTennessee
View 305 Oak Leaf Cir Winchester, TN MLS# 3078671
    1 of 36
    OPEN HOUSE: Sunday 3/1 1:00 PM - 3:00 PM
    $364,000
    4

    Beds

    3.0

    Baths

    1,864

    Sq.Ft.

    305 Oak Leaf Cir

    Winchester, TN

    MiddleTennessee
    View 247 Golf Shores Dr Winchester, TN MLS# 3011800
    • Virtual Tour
    1 of 39
    $359,900
    3

    Beds

    2.0

    Baths

    1,518

    Sq.Ft.

    247 Golf Shores Dr

    Winchester, TN

    Courtesy of Tullahoma - WEICHERT, REALTORS® - Joe Orr & Associates
    View 442 Golf Shores Dr Winchester, TN MLS# 3098610
    $359,900
    3

    Beds

    2.0

    Baths

    1,668

    Sq.Ft.

    442 Golf Shores Dr

    Winchester, TN

    MiddleTennessee
    View 114 Chase Cir Winchester, TN MLS# 3130739
    • Recently Listed
    1 of 51
    $358,400
    2

    Beds

    2.0

    Baths

    1,782

    Sq.Ft.

    114 Chase Cir

    Winchester, TN

    MiddleTennessee
    View 362 Chase Cir Winchester, TN MLS# 2904382
    • Virtual Tour
    1 of 49
    $354,900
    2

    Beds

    2.0

    Baths

    1,701

    Sq.Ft.

    362 Chase Cir

    Winchester, TN

    MiddleTennessee
    View 543 Paynes Church Rd Winchester, TN MLS# 3018312
    • New Construction
    1 of 36
    $350,000
    3

    Beds

    2.0

    Baths

    1,508

    Sq.Ft.

    543 Paynes Church Rd

    Winchester, TN

    MiddleTennessee
    View 517 Paynes Church Rd Winchester, TN MLS# 3018326
    • New Construction
    1 of 36
    $350,000
    3

    Beds

    2.1

    Baths

    1,508

    Sq.Ft.

    517 Paynes Church Rd

    Winchester, TN

    MiddleTennessee
    View 563 Paynes Church Rd Winchester, TN MLS# 3031703
    • New Construction
    1 of 36
    $350,000
    3

    Beds

    2.0

    Baths

    1,508

    Sq.Ft.

    563 Paynes Church Rd

    Winchester, TN

    MiddleTennessee
    View 585 Paynes Church Rd Winchester, TN MLS# 3031708
    • New Construction
    1 of 36
    $350,000
    3

    Beds

    2.0

    Baths

    1,508

    Sq.Ft.

    585 Paynes Church Rd

    Winchester, TN

    MiddleTennessee

    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 2/27/2026.

    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.