Windham Vermont Homes for Sale

404 total properties
View 7 Grassy Brook Road Brookline, VT MLS# 5077982
Save 7 Grassy Brook Road Brookline, VT MLS# 5077982
1 of 58
$525,000
3

Beds

2.1

Baths

2,772

Sq.Ft.

7 Grassy Brook Road

Brookline, VT

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Courtesy of FLEX REALTY
View 300 Route 121 Grafton, VT MLS# 5078071
  • Virtual Tour
Save 300 Route 121 Grafton, VT MLS# 5078071
1 of 55
$699,900
3

Beds

2.0

Baths

2,450

Sq.Ft.

300 Route 121

Grafton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 29 Pikes Falls Road Jamaica, VT MLS# 5078084
Save 29 Pikes Falls Road Jamaica, VT MLS# 5078084
1 of 33
$349,000
4

Beds

2.0

Baths

2,520

Sq.Ft.

29 Pikes Falls Road

Jamaica, VT

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Courtesy of WINHALL REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 135 Country Hill Brattleboro, VT MLS# 5077870
Save 135 Country Hill Brattleboro, VT MLS# 5077870
1 of 26
$395,000
3

Beds

2.1

Baths

2,128

Sq.Ft.

135 Country Hill

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 169 Sun and Ski Road Wilmington, VT MLS# 5077813
Save 169 Sun and Ski Road Wilmington, VT MLS# 5077813
1 of 30
$89,000
Studio

Beds

0.0

Baths

169 Sun and Ski Road

Wilmington, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
View 6795 VT Route 100 Londonderry, VT MLS# 5077737
Save 6795 VT Route 100 Londonderry, VT MLS# 5077737
1 of 35
$350,000
4

Beds

1.2

Baths

2,460

Sq.Ft.

6795 VT Route 100

Londonderry, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 152 Main Street Grafton, VT MLS# 5077738
Save 152 Main Street Grafton, VT MLS# 5077738
1 of 30
$599,995
4

Beds

2.0

Baths

2,700

Sq.Ft.

152 Main Street

Grafton, VT

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Courtesy of DEREK GREENE
View 175 Sak Road Vernon, VT MLS# 5077474
Save 175 Sak Road Vernon, VT MLS# 5077474
1 of 27
$369,900
3

Beds

2.0

Baths

1,599

Sq.Ft.

175 Sak Road

Vernon, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 792 Stratton Mtn Access Road # 4310 Stratton, VT MLS# 5077320
  • Virtual Tour
Save 792 Stratton Mtn Access Road # 4310 Stratton, VT MLS# 5077320
1 of 14
$649,000
2

Beds

2.0

Baths

1,148

Sq.Ft.

792 Stratton Mtn Access Road # 4310

Stratton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 4669 Vermont Rte 100 Londonderry, VT MLS# 5077331
  • Virtual Tour
Save 4669 Vermont Rte 100 Londonderry, VT MLS# 5077331
1 of 39
$1,600,000
7

Beds

5.0

Baths

4,649

Sq.Ft.

4669 Vermont Rte 100

Londonderry, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 00 Turkey Mountain Road Jamaica, VT MLS# 5077252
Save 00 Turkey Mountain Road Jamaica, VT MLS# 5077252
1 of 49
$500,000
Studio

Beds

0.0

Baths

00 Turkey Mountain Road

Jamaica, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 116 Birge Street # 3 Brattleboro, VT MLS# 5077121
Save 116 Birge Street # 3 Brattleboro, VT MLS# 5077121
1 of 36
$269,000
1

Beds

1.0

Baths

2,000

Sq.Ft.

116 Birge Street # 3

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 16 Rock Split Way Wilmington, VT MLS# 5077016
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Save 16 Rock Split Way Wilmington, VT MLS# 5077016
1 of 60
$749,000
4

Beds

4.0

Baths

2,964

Sq.Ft.

16 Rock Split Way

Wilmington, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 34 Main Street Wardsboro, VT MLS# 5076783
Save 34 Main Street Wardsboro, VT MLS# 5076783
1 of 27
$349,000
3

Beds

3.0

Baths

1,750

Sq.Ft.

34 Main Street

Wardsboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 11 Hassey Bend # 9 Wilmington, VT MLS# 5076844
Save 11 Hassey Bend # 9 Wilmington, VT MLS# 5076844
1 of 32
$239,000
2

Beds

1.1

Baths

1,160

Sq.Ft.

11 Hassey Bend # 9

Wilmington, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 8559 VT Route 30 # Lots 2 & 3 Jamaica, VT MLS# 5076767
Save 8559 VT Route 30 # Lots 2 & 3 Jamaica, VT MLS# 5076767
1 of 13
$120,000
Studio

Beds

0.0

Baths

8559 VT Route 30 # Lots 2 & 3

Jamaica, VT

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Courtesy of WINHALL REAL ESTATE
View 214 Putney Road Brattleboro, VT MLS# 5076579
Save 214 Putney Road Brattleboro, VT MLS# 5076579
1 of 46
$495,000
4

Beds

2.1

Baths

2,756

Sq.Ft.

214 Putney Road

Brattleboro, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3996 Route 30 Jamaica, VT MLS# 5076624
Save 3996 Route 30 Jamaica, VT MLS# 5076624
1 of 34
$539,000
4

Beds

3.0

Baths

3,081

Sq.Ft.

3996 Route 30

Jamaica, VT

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Courtesy of WINHALL REAL ESTATE
View 56 Whitetail Drive Vernon, VT MLS# 5076475
  • Virtual Tour
Save 56 Whitetail Drive Vernon, VT MLS# 5076475
1 of 60
$674,950
3

Beds

2.1

Baths

2,386

Sq.Ft.

56 Whitetail Drive

Vernon, VT

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Courtesy of RE/MAX HERITAGE
View 72 Landmark Hill Drive Brattleboro, VT MLS# 5076290
Save 72 Landmark Hill Drive Brattleboro, VT MLS# 5076290
1 of 26
$550,000
6,466

Sq.Ft.

72 Landmark Hill Drive

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY

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 5/17/2026”

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