Windham Vermont Homes for Sale

533 total properties
View 661 Wright Orchard Road Grafton, VT MLS# 5097782
Save 661 Wright Orchard Road Grafton, VT MLS# 5097782
1 of 13
$699,000
3

Beds

2.0

Baths

3,044

Sq.Ft.

661 Wright Orchard Road

Grafton, VT

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Courtesy of ENGEL & VOLKERS OKEMO
View 412 Hall Ranch Road Grafton, VT MLS# 5097786
Save 412 Hall Ranch Road Grafton, VT MLS# 5097786
1 of 48
$975,000
3

Beds

3.0

Baths

2,200

Sq.Ft.

412 Hall Ranch Road

Grafton, VT

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Courtesy of EXP REALTY
View 180 Debbie Higgins Lane Wardsboro, VT MLS# 5097788
Save 180 Debbie Higgins Lane Wardsboro, VT MLS# 5097788
1 of 21
$425,000
3

Beds

2.0

Baths

1,053

Sq.Ft.

180 Debbie Higgins Lane

Wardsboro, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 820 Western Avenue Brattleboro, VT MLS# 5097400
Save 820 Western Avenue Brattleboro, VT MLS# 5097400
1 of 12
$422,000
6

Beds

4.0

Baths

3,756

Sq.Ft.

820 Western Avenue

Brattleboro, VT

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Courtesy of NANCY JENKINS REAL ESTATE
View 28 Brook Street Brattleboro, VT MLS# 5097401
Save 28 Brook Street Brattleboro, VT MLS# 5097401
1 of 14
$465,500
8

Beds

4.0

Baths

3,364

Sq.Ft.

28 Brook Street

Brattleboro, VT

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Courtesy of NANCY JENKINS REAL ESTATE
View 145 Leon Stocker Drive Stratton, VT MLS# 5097239
  • Virtual Tour
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 1950 N. Main Street Londonderry, VT MLS# 5097168
Save 1950 N. Main Street Londonderry, VT MLS# 5097168
1 of 9
$350,000
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
Save 1950 North Main Street Londonderry, VT MLS# 5097171
1 of 25
$350,000
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
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 Westminster, VT MLS# 5097178
Save 1590 US Route 5 Westminster, VT MLS# 5097178
1 of 29
$275,000
3

Beds

1.0

Baths

1,668

Sq.Ft.

1590 US Route 5

Westminster, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
View 258 Chester Road Grafton, VT MLS# 5097081
  • 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
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
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
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
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
Save 120 Green Mountain Trail Londonderry, VT MLS# 5096890
1 of 17
$365,000
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 22 Valley Road Brattleboro, VT MLS# 5096935
Save 22 Valley Road Brattleboro, VT MLS# 5096935
1 of 34
$68,000
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
  • 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 176 Brophy Lane Londonderry, VT MLS# 5097037
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
Save 367 Stratton Gate Road Jamaica, VT MLS# 5097042
1 of 38
$495,000
4

Beds

3.0

Baths

2,115

Sq.Ft.

367 Stratton Gate Road

Jamaica, VT

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Courtesy of CUMMINGS & CO

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 8/23/2026”

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