Windham Vermont Homes for Sale

370 total properties
View 557 Trager Road Jamaica, VT MLS# 5076041
Save 557 Trager Road Jamaica, VT MLS# 5076041
1 of 60
$8,200,000
6

Beds

6.4

Baths

10,763

Sq.Ft.

557 Trager Road

Jamaica, VT

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Courtesy of WOHLER REALTY GROUP
View 464 Putney Road Brattleboro, VT MLS# 5067513
Save 464 Putney Road Brattleboro, VT MLS# 5067513
1 of 48
$5,500,000

464 Putney Road

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 454 Mountain Road Stratton, VT MLS# 5005058
  • Virtual Tour
Save 454 Mountain Road Stratton, VT MLS# 5005058
1 of 50
$4,999,000
6

Beds

7.1

Baths

8,720

Sq.Ft.

454 Mountain Road

Stratton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1950 Collins Road Halifax, VT MLS# 5062504
Save 1950 Collins Road Halifax, VT MLS# 5062504
1 of 60
$4,950,000
4

Beds

2.6

Baths

16,736

Sq.Ft.

1950 Collins Road

Halifax, VT

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Courtesy of WOHLER REALTY GROUP
View 1950 Collins Road Halifax, VT MLS# 5064468
Save 1950 Collins Road Halifax, VT MLS# 5064468
1 of 60
$4,950,000
24,148

Sq.Ft.

1950 Collins Road

Halifax, VT

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Courtesy of WOHLER REALTY GROUP
View 22 Stags Leap Lane Wilmington, VT MLS# 5079351
  • Recently Listed
Save 22 Stags Leap Lane Wilmington, VT MLS# 5079351
1 of 40
$4,087,000
6

Beds

5.2

Baths

7,090

Sq.Ft.

22 Stags Leap Lane

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 28 Spring Tree Road Brattleboro, VT MLS# 5067936
Save 28 Spring Tree Road Brattleboro, VT MLS# 5067936
1 of 44
$4,000,000
21,363

Sq.Ft.

28 Spring Tree Road

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 816 Black Bear Road Jamaica, VT MLS# 5030672
  • Virtual Tour
Save 816 Black Bear Road Jamaica, VT MLS# 5030672
1 of 60
$3,995,000
4

Beds

5.1

Baths

5,500

Sq.Ft.

816 Black Bear Road

Jamaica, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 168 Sunbowl Ridge Road # 168 AB Stratton, VT MLS# 5067327
Save 168 Sunbowl Ridge Road # 168 AB Stratton, VT MLS# 5067327
1 of 54
$3,750,000
6

Beds

6.1

Baths

5,660

Sq.Ft.

168 Sunbowl Ridge Road # 168 AB

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 1 Teddy Bear Lane Townshend, VT MLS# 5039407
Save 1 Teddy Bear Lane Townshend, VT MLS# 5039407
1 of 7
$3,640,000
54,759

Sq.Ft.

1 Teddy Bear Lane

Townshend, VT

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Courtesy of POMERLEAU REAL ESTATE
View 29 Mountain Ridge Drive Wilmington, VT MLS# 5068740
  • New Construction
Save 29 Mountain Ridge Drive Wilmington, VT MLS# 5068740
1 of 23
$3,500,000
5

Beds

4.1

Baths

7,000

Sq.Ft.

29 Mountain Ridge Drive

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 36 Woffenden Road Wilmington, VT MLS# 4971898
Save 36 Woffenden Road Wilmington, VT MLS# 4971898
1 of 41
$3,050,000
6

Beds

1.1

Baths

3,309

Sq.Ft.

36 Woffenden Road

Wilmington, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
View 4 Gold Medal Circle # 4 Stratton, VT MLS# 5059954
Save 4 Gold Medal Circle # 4 Stratton, VT MLS# 5059954
1 of 17
$2,495,000
Studio

Beds

0.0

Baths

4 Gold Medal Circle # 4

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 662 Howe Farm Road Jamaica, VT MLS# 4972272
  • Virtual Tour
Save 662 Howe Farm Road Jamaica, VT MLS# 4972272
1 of 35
$2,399,000
4

Beds

4.1

Baths

3,569

Sq.Ft.

662 Howe Farm Road

Jamaica, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 127 Fannie Hill Road Wilmington, VT MLS# 5054510
Save 127 Fannie Hill Road Wilmington, VT MLS# 5054510
1 of 59
$2,398,000
4

Beds

4.0

Baths

3,585

Sq.Ft.

127 Fannie Hill Road

Wilmington, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 32 Steep Hill Road Wilmington, VT MLS# 5056378
Save 32 Steep Hill Road Wilmington, VT MLS# 5056378
1 of 60
$2,195,000
5

Beds

4.1

Baths

4,200

Sq.Ft.

32 Steep Hill Road

Wilmington, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 95 Middletown Road Londonderry, VT MLS# 5064182
Save 95 Middletown Road Londonderry, VT MLS# 5064182
1 of 53
$2,150,000
7,564

Sq.Ft.

95 Middletown Road

Londonderry, VT

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Courtesy of NATHAN AUCTION & REAL ESTATE INC.
View 121 Fannie Hill Road Wilmington, VT MLS# 5069398
Save 121 Fannie Hill Road Wilmington, VT MLS# 5069398
1 of 32
$2,100,000
7

Beds

4.0

Baths

4,256

Sq.Ft.

121 Fannie Hill Road

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 97 North Brookwood Road Stratton, VT MLS# 5065289
Save 97 North Brookwood Road Stratton, VT MLS# 5065289
1 of 54
$2,050,000
4

Beds

4.1

Baths

2,486

Sq.Ft.

97 North Brookwood Road

Stratton, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 14 Tarheel Trail Wilmington, VT MLS# 5059352
Save 14 Tarheel Trail Wilmington, VT MLS# 5059352
1 of 35
$1,999,000
5

Beds

4.1

Baths

5,110

Sq.Ft.

14 Tarheel Trail

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER

Information deemed reliable but not guaranteed.

“Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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. Data last updated 3/23/2026”

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