Windham Vermont Homes for Sale

498 total properties
View 3333 West River Road Dummerston, VT MLS# 5097216
  • Recently Listed
Save 3333 West River Road Dummerston, VT MLS# 5097216
1 of 51
$525,000
4

Beds

3.0

Baths

2,240

Sq.Ft.

3333 West River Road

Dummerston, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 145 Leon Stocker Drive Stratton, VT MLS# 5097239
  • Recently Listed
Save 145 Leon Stocker Drive Stratton, VT MLS# 5097239
1 of 40
$785,000
3

Beds

4.0

Baths

3,086

Sq.Ft.

145 Leon Stocker Drive

Stratton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 78 Middle Ridge Road # 307 Stratton, VT MLS# 5097284
Save 78 Middle Ridge Road # 307 Stratton, VT MLS# 5097284
1 of 1
$1,250,000
3

Beds

3.0

Baths

1,586

Sq.Ft.

78 Middle Ridge Road # 307

Stratton, VT

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Courtesy of WINHALL REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 1950 N. Main Street Londonderry, VT MLS# 5097168
  • Recently Listed
Save 1950 N. Main Street Londonderry, VT MLS# 5097168
1 of 9
$385,000
7

Beds

4.0

Baths

3,551

Sq.Ft.

1950 N. Main Street

Londonderry, VT

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Courtesy of TPW REAL ESTATE
View 1950 North Main Street Londonderry, VT MLS# 5097171
  • Recently Listed
Save 1950 North Main Street Londonderry, VT MLS# 5097171
1 of 25
$385,000
7

Beds

4.0

Baths

3,551

Sq.Ft.

1950 North Main Street

Londonderry, VT

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Courtesy of TPW REAL ESTATE
View 0 Happy Haven Road # Lot 45 Wilmington, VT MLS# 5097175
  • Recently Listed
Save 0 Happy Haven Road # Lot 45 Wilmington, VT MLS# 5097175
1 of 29
$115,000
Studio

Beds

0.0

Baths

0 Happy Haven Road # Lot 45

Wilmington, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 1590 US Route 5 Route Westminster, VT MLS# 5097178
  • Recently Listed
Save 1590 US Route 5 Route Westminster, VT MLS# 5097178
1 of 29
$275,000
3

Beds

1.0

Baths

1,668

Sq.Ft.

1590 US Route 5 Route

Westminster, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
View 258 Chester Road Grafton, VT MLS# 5097081
  • Recently Listed with Virtual Tour
Save 258 Chester Road Grafton, VT MLS# 5097081
1 of 46
$734,000
3

Beds

3.2

Baths

4,285

Sq.Ft.

258 Chester Road

Grafton, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 2074 Vt Rt 30 Jamaica, VT MLS# 5097088
  • Recently Listed
Save 2074 Vt Rt 30 Jamaica, VT MLS# 5097088
1 of 27
$140,000
1

Beds

1.0

Baths

400

Sq.Ft.

2074 Vt Rt 30

Jamaica, VT

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Courtesy of MICHAEL ENGLAND REAL ESTATE
View 2977 Vermont Route 100 Whitingham, VT MLS# 5097108
  • Recently Listed
Save 2977 Vermont Route 100 Whitingham, VT MLS# 5097108
1 of 28
$995,000
12,802

Sq.Ft.

2977 Vermont Route 100

Whitingham, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
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 8 Beech Tree Lane Newfane, VT MLS# 5096860
  • Recently Listed
Save 8 Beech Tree Lane Newfane, VT MLS# 5096860
1 of 33
$339,000
2

Beds

1.0

Baths

1,056

Sq.Ft.

8 Beech Tree Lane

Newfane, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 120 Green Mountain Trail Londonderry, VT MLS# 5096890
  • Recently Listed
Save 120 Green Mountain Trail Londonderry, VT MLS# 5096890
1 of 16
$390,000
4

Beds

2.0

Baths

1,536

Sq.Ft.

120 Green Mountain Trail

Londonderry, VT

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Courtesy of TPW REAL ESTATE
View 160 Akley Road Brattleboro, VT MLS# 5096932
  • Recently Listed
Save 160 Akley Road Brattleboro, VT MLS# 5096932
1 of 40
$490,000
3

Beds

2.1

Baths

2,182

Sq.Ft.

160 Akley Road

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 22 Valley Road Brattleboro, VT MLS# 5096935
  • Recently Listed
Save 22 Valley Road Brattleboro, VT MLS# 5096935
1 of 34
$78,000
2

Beds

1.0

Baths

552

Sq.Ft.

22 Valley Road

Brattleboro, VT

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Courtesy of FLEX REALTY
View 201 Chester Hill Road Grafton, VT MLS# 5097006
  • Recently Listed with 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 88 Happy Haven Road Wilmington, VT MLS# 5097015
  • Recently Listed
Save 88 Happy Haven Road Wilmington, VT MLS# 5097015
1 of 25
$389,900
5

Beds

2.0

Baths

2,168

Sq.Ft.

88 Happy Haven Road

Wilmington, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 176 Brophy Lane Londonderry, VT MLS# 5097037
  • Recently Listed
Save 176 Brophy Lane Londonderry, VT MLS# 5097037
1 of 43
$535,000
4

Beds

2.0

Baths

1,816

Sq.Ft.

176 Brophy Lane

Londonderry, VT

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Courtesy of CUMMINGS & CO
View 367 Stratton Gate Road Jamaica, VT MLS# 5097042
  • Recently Listed
Save 367 Stratton Gate Road Jamaica, VT MLS# 5097042
1 of 38
$515,000
4

Beds

3.0

Baths

2,115

Sq.Ft.

367 Stratton Gate Road

Jamaica, VT

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Courtesy of CUMMINGS & CO
View 0 Pine Banks Road Westminster, VT MLS# 5096685
  • Recently Listed
Save 0 Pine Banks Road Westminster, VT MLS# 5096685
1 of 11
$585,000
Studio

Beds

0.0

Baths

0 Pine Banks Road

Westminster, VT

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Courtesy of BHG MASIELLO BRATTLEBORO

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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