Windham Vermont Homes for Sale

498 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 24 Sawmill Road Stratton, VT MLS# 5095419
  • Recently Listed
Save 24 Sawmill Road Stratton, VT MLS# 5095419
1 of 53
$4,500,000
5

Beds

5.1

Baths

5,700

Sq.Ft.

24 Sawmill Road

Stratton, VT

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Courtesy of WINHALL REAL ESTATE
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# 5096846
  • Recently Listed
Save 816 Black Bear Road Jamaica, VT MLS# 5096846
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 1950 Collins Road Halifax, VT MLS# 5062504
Save 1950 Collins Road Halifax, VT MLS# 5062504
1 of 60
$3,800,000
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
$3,800,000
24,148

Sq.Ft.

1950 Collins Road

Halifax, VT

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Courtesy of WOHLER REALTY GROUP
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 238 Stowe Hill Road Wilmington, VT MLS# 5095093
  • Recently Listed with Virtual Tour
Save 238 Stowe Hill Road Wilmington, VT MLS# 5095093
1 of 59
$3,495,000
9

Beds

7.4

Baths

6,726

Sq.Ft.

238 Stowe Hill Road

Wilmington, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 14-15-17-21-25 Westminster Street # 150030018 Rockingham, VT MLS# 5085323
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
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 36 Woffenden Road Wilmington, VT MLS# 4971898
Save 36 Woffenden Road Wilmington, VT MLS# 4971898
1 of 41
$2,899,000
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 2060 Townshend Road Grafton, VT MLS# 5092853
Save 2060 Townshend Road Grafton, VT MLS# 5092853
1 of 60
$2,895,000
6

Beds

4.0

Baths

3,946

Sq.Ft.

2060 Townshend Road

Grafton, VT

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Courtesy of KW VERMONT
View 2060 Townshend Road Grafton, VT MLS# 5092854
Save 2060 Townshend Road Grafton, VT MLS# 5092854
1 of 60
$2,895,000
3,946

Sq.Ft.

2060 Townshend Road

Grafton, VT

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Courtesy of KW VERMONT
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 9 Mountain Reach Mews Road # 9 Stratton, VT MLS# 5094589
  • Recently Listed
Save 9 Mountain Reach Mews Road # 9 Stratton, VT MLS# 5094589
1 of 39
$2,250,000
3

Beds

3.1

Baths

2,824

Sq.Ft.

9 Mountain Reach Mews Road # 9

Stratton, VT

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Courtesy of WINHALL REAL ESTATE
View 392 Lake Raponda Road Wilmington, VT MLS# 5089881
Save 392 Lake Raponda Road Wilmington, VT MLS# 5089881
1 of 39
$2,195,000
4

Beds

4.0

Baths

3,524

Sq.Ft.

392 Lake Raponda Road

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 121 Fannie Hill Road Wilmington, VT MLS# 5095153
  • Recently Listed
Save 121 Fannie Hill Road Wilmington, VT MLS# 5095153
1 of 33
$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 74 North Brookwood Road Stratton, VT MLS# 5088735
Save 74 North Brookwood Road Stratton, VT MLS# 5088735
1 of 32
$1,975,000
4

Beds

3.0

Baths

3,212

Sq.Ft.

74 North Brookwood Road

Stratton, VT

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Courtesy of WWW.FLATFEEMLS4FREE.COM

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 6/30/2026”

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