Windham Vermont Homes for Sale

535 total properties
View Forrester Road Jamaica, VT MLS# 5082418
Save Forrester Road Jamaica, VT MLS# 5082418
1 of 27
$1,450,000
Studio

Beds

0.0

Baths

Forrester Road

Jamaica, VT

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Courtesy of LOWE'S REAL ESTATE, LLC
View 494-498 Goodaleville Road Jamaica, VT MLS# 5101688
Save 494-498 Goodaleville Road Jamaica, VT MLS# 5101688
1 of 47
$1,450,000
5

Beds

4.0

Baths

2,974

Sq.Ft.

494-498 Goodaleville Road

Jamaica, VT

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Courtesy of THE HAVEN GROUP
View 286 Coldbrook Road Wilmington, VT MLS# 5073006
Save 286 Coldbrook Road Wilmington, VT MLS# 5073006
1 of 15
$1,400,000
4

Beds

4.1

Baths

3,844

Sq.Ft.

286 Coldbrook Road

Wilmington, VT

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Courtesy of REAL BROKER LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 224 Cobble Ridge Road Londonderry, VT MLS# 5095311
Save 224 Cobble Ridge Road Londonderry, VT MLS# 5095311
1 of 43
$1,392,000
5

Beds

4.1

Baths

5,160

Sq.Ft.

224 Cobble Ridge Road

Londonderry, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 131,133,141 Green Street Brattleboro, VT MLS# 5093440
Save 131,133,141 Green Street Brattleboro, VT MLS# 5093440
1 of 26
$1,350,000
Studio

Beds

0.0

Baths

7,660

Sq.Ft.

131,133,141 Green Street

Brattleboro, VT

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Courtesy of BELLVILLE REALTY
View 23 Main Street Wardsboro, VT MLS# 5068110
Save 23 Main Street Wardsboro, VT MLS# 5068110
1 of 60
$1,300,000
7,633

Sq.Ft.

23 Main Street

Wardsboro, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 4427 West Hill Road South Jamaica, VT MLS# 5090616
Save 4427 West Hill Road South Jamaica, VT MLS# 5090616
1 of 36
$1,295,000
5

Beds

3.1

Baths

3,040

Sq.Ft.

4427 West Hill Road South

Jamaica, VT

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Courtesy of WINHALL REAL ESTATE
View 564 Goodaleville Road Jamaica, VT MLS# 5101689
Save 564 Goodaleville Road Jamaica, VT MLS# 5101689
1 of 38
$1,250,000
4

Beds

3.0

Baths

2,022

Sq.Ft.

564 Goodaleville Road

Jamaica, VT

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Courtesy of THE HAVEN GROUP
View 201 Chester Hill Road Grafton, VT MLS# 5097006
  • Virtual Tour
Save 201 Chester Hill Road Grafton, VT MLS# 5097006
1 of 54
$1,249,000
3

Beds

3.0

Baths

3,654

Sq.Ft.

201 Chester Hill Road

Grafton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 364 Houghtonville Road Grafton, VT MLS# 5095837
Save 364 Houghtonville Road Grafton, VT MLS# 5095837
1 of 50
$1,200,000
4

Beds

3.1

Baths

3,649

Sq.Ft.

364 Houghtonville Road

Grafton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 350 Sunset Lake Road Newfane, VT MLS# 5089719
Save 350 Sunset Lake Road Newfane, VT MLS# 5089719
1 of 60
$1,165,000
4

Beds

3.0

Baths

3,632

Sq.Ft.

350 Sunset Lake Road

Newfane, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1472 Carpenter Hill Road Guilford, VT MLS# 5104005
  • Recently Listed
Save 1472 Carpenter Hill Road Guilford, VT MLS# 5104005
1 of 45
$1,165,000
4

Beds

2.1

Baths

3,338

Sq.Ft.

1472 Carpenter Hill Road

Guilford, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 82 North Brookwood Road Stratton, VT MLS# 5086826
Save 82 North Brookwood Road Stratton, VT MLS# 5086826
1 of 60
$1,160,000
5

Beds

4.0

Baths

3,664

Sq.Ft.

82 North Brookwood Road

Stratton, VT

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Courtesy of WOHLER REALTY GROUP
View 2245 Burrington Hill Road Whitingham, VT MLS# 5090460
Save 2245 Burrington Hill Road Whitingham, VT MLS# 5090460
1 of 42
$1,150,000
4

Beds

1.0

Baths

1,972

Sq.Ft.

2245 Burrington Hill Road

Whitingham, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 43 Middle Ridge Road # 417 Stratton, VT MLS# 5097857
  • Virtual Tour
Save 43 Middle Ridge Road # 417 Stratton, VT MLS# 5097857
1 of 32
$1,150,000
3

Beds

3.1

Baths

1,775

Sq.Ft.

43 Middle Ridge Road # 417

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 70 Hunter Lane Jamaica, VT MLS# 5060615
Save 70 Hunter Lane Jamaica, VT MLS# 5060615
1 of 47
$1,140,000
4

Beds

3.0

Baths

4,193

Sq.Ft.

70 Hunter Lane

Jamaica, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 390 Pleasant Valley Road Brattleboro, VT MLS# 5088064
  • Virtual Tour
Save 390 Pleasant Valley Road Brattleboro, VT MLS# 5088064
1 of 55
$1,100,000
4

Beds

3.1

Baths

4,491

Sq.Ft.

390 Pleasant Valley Road

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 35 Theron Fisher Road Grafton, VT MLS# 5096455
  • Virtual Tour
Save 35 Theron Fisher Road Grafton, VT MLS# 5096455
1 of 48
$1,100,000
5

Beds

4.1

Baths

3,100

Sq.Ft.

35 Theron Fisher Road

Grafton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 778 Stratton Mountain Access Road # 2401 Stratton, VT MLS# 5099454
  • Virtual Tour
Save 778 Stratton Mountain Access Road # 2401 Stratton, VT MLS# 5099454
1 of 30
$1,060,000
3

Beds

3.0

Baths

1,587

Sq.Ft.

778 Stratton Mountain Access Road # 2401

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 1189 Cole Pond Road Jamaica, VT MLS# 5060071
Save 1189 Cole Pond Road Jamaica, VT MLS# 5060071
1 of 30
$1,040,000
5

Beds

4.1

Baths

3,363

Sq.Ft.

1189 Cole Pond Road

Jamaica, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L 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 8/20/2026”

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