Windham Vermont Homes for Sale

372 total properties
View 29 Pikes Falls Road Jamaica, VT MLS# 5078084
Save 29 Pikes Falls Road Jamaica, VT MLS# 5078084
1 of 33
OPEN HOUSE: Sunday 3/29 11:00 AM - 1:00 PM
$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
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 23 Deepwood Park Brattleboro, VT MLS# 5077950
Save 23 Deepwood Park Brattleboro, VT MLS# 5077950
1 of 18
$49,000
3

Beds

1.0

Baths

924

Sq.Ft.

23 Deepwood Park

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 761 Stratton Mountain Access Road # 322 Stratton, VT MLS# 5078472
Save 761 Stratton Mountain Access Road # 322 Stratton, VT MLS# 5078472
1 of 24
$680,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

761 Stratton Mountain Access Road # 322

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 23 Wilsons Woods Road Brattleboro, VT MLS# 5077786
Save 23 Wilsons Woods Road Brattleboro, VT MLS# 5077786
1 of 60
$499,000
4

Beds

3.1

Baths

2,312

Sq.Ft.

23 Wilsons Woods Road

Brattleboro, VT

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Courtesy of EXP REALTY
View 22 High Point Drive # 511 Stratton, VT MLS# 5077795
Save 22 High Point Drive # 511 Stratton, VT MLS# 5077795
1 of 37
$850,000
4

Beds

3.1

Baths

1,993

Sq.Ft.

22 High Point Drive # 511

Stratton, VT

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Courtesy of STRATTON REAL ESTATE
View 169 Sun and Ski Road Wilmington, VT MLS# 5077813
Save 169 Sun and Ski Road Wilmington, VT MLS# 5077813
1 of 34
$95,000
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 29
$699,995
4

Beds

2.0

Baths

2,000

Sq.Ft.

152 Main Street

Grafton, VT

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Courtesy of DEREK GREENE
View 4138 West Hill Road S Jamaica, VT MLS# 5077783
  • Virtual Tour
Save 4138 West Hill Road S Jamaica, VT MLS# 5077783
1 of 35
$559,000
3

Beds

3.0

Baths

2,704

Sq.Ft.

4138 West Hill Road S

Jamaica, VT

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Courtesy of SKIHOME REALTY
View 0 Ellen Ware Road Townshend, VT MLS# 5077624
Save 0 Ellen Ware Road Townshend, VT MLS# 5077624
1 of 13
$298,000
Studio

Beds

0.0

Baths

0 Ellen Ware Road

Townshend, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 752 Rte 9 East Wilmington, VT MLS# 5077558
Save 752 Rte 9 East Wilmington, VT MLS# 5077558
1 of 24
$329,000
4

Beds

1.1

Baths

1,088

Sq.Ft.

752 Rte 9 East

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 175 Sak Road Vernon, VT MLS# 5077474
Save 175 Sak Road Vernon, VT MLS# 5077474
1 of 20
$400,000
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
$1,750,000
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 34 Binney Brook Road Wilmington, VT MLS# 5077341
Save 34 Binney Brook Road Wilmington, VT MLS# 5077341
1 of 37
$675,000
4

Beds

3.0

Baths

2,516

Sq.Ft.

34 Binney Brook Road

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 00 Turkey Mountain Road Jamaica, VT MLS# 5077252
Save 00 Turkey Mountain Road Jamaica, VT MLS# 5077252
1 of 26
$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 30
$289,000
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
  • Virtual Tour
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 16 Robin Way Brattleboro, VT MLS# 5076950
Save 16 Robin Way Brattleboro, VT MLS# 5076950
1 of 17
$245,000
3

Beds

2.1

Baths

1,680

Sq.Ft.

16 Robin Way

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY

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 3/26/2026”

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