Windham Vermont Homes for Sale

408 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 38
$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 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 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
$2,999,000
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 14-15-17-21-25 Westminster Street # 150030018 Rockingham, VT MLS# 5085323
  • Recently Listed
Save 14-15-17-21-25 Westminster Street # 150030018 Rockingham, VT MLS# 5085323
1 of 38
$2,900,000
34,419

Sq.Ft.

14-15-17-21-25 Westminster Street # 150030018

Rockingham, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 14-15-17-21-25- Westminster Street Rockingham, VT MLS# 5085325
  • Recently Listed
Save 14-15-17-21-25- Westminster Street Rockingham, VT MLS# 5085325
1 of 39
$2,900,000
Studio

Beds

0.0

Baths

34,419

Sq.Ft.

14-15-17-21-25- Westminster Street

Rockingham, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
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 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
View 74 N Brookwood Road Stratton, VT MLS# 5088735
  • Recently Listed
Save 74 N Brookwood Road Stratton, VT MLS# 5088735
1 of 32
$1,975,000
4

Beds

3.0

Baths

3,212

Sq.Ft.

74 N Brookwood Road

Stratton, VT

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Courtesy of WWW.FLATFEEMLS4FREE.COM
View 95 Middletown Road Londonderry, VT MLS# 5064182
Save 95 Middletown Road Londonderry, VT MLS# 5064182
1 of 53
$1,800,000
7,564

Sq.Ft.

95 Middletown Road

Londonderry, VT

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Courtesy of NATHAN AUCTION & REAL ESTATE INC.
View 95 Middletown Road Londonderry, VT MLS# 5087347
  • Recently Listed
Save 95 Middletown Road Londonderry, VT MLS# 5087347
1 of 50
$1,800,000
4

Beds

3.2

Baths

4,853

Sq.Ft.

95 Middletown Road

Londonderry, VT

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Courtesy of NATHAN AUCTION & REAL ESTATE INC.
View 89A Sun Bowl Ridge Road # 89A Stratton, VT MLS# 5071361
  • Virtual Tour
Save 89A Sun Bowl Ridge Road # 89A Stratton, VT MLS# 5071361
1 of 33
$1,760,000
4

Beds

3.1

Baths

2,698

Sq.Ft.

89A Sun Bowl Ridge Road # 89A

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 148B Sun Bowl Ridge Road # 148B Stratton, VT MLS# 5012015
Save 148B Sun Bowl Ridge Road # 148B Stratton, VT MLS# 5012015
1 of 31
$1,750,000
4

Beds

3.1

Baths

2,698

Sq.Ft.

148B Sun Bowl Ridge Road # 148B

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 197 Lake Raponda Road Wilmington, VT MLS# 5072561
Save 197 Lake Raponda Road Wilmington, VT MLS# 5072561
1 of 32
$1,697,000
4

Beds

3.0

Baths

2,420

Sq.Ft.

197 Lake Raponda Road

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 5/14/2026”

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