Windham Vermont Homes for Sale

535 total properties
View 1018 South Hill Road Jamaica, VT MLS# 5102407
Save 1018 South Hill Road Jamaica, VT MLS# 5102407
1 of 24
$189,500
2

Beds

1.0

Baths

893

Sq.Ft.

1018 South Hill Road

Jamaica, VT

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Courtesy of REAL BROKER LLC
View 1372 Vtrt 100 S Jamaica, VT MLS# 5101991
Save 1372 Vtrt 100 S Jamaica, VT MLS# 5101991
1 of 21
$175,000
3

Beds

2.0

Baths

1,576

Sq.Ft.

1372 Vtrt 100 S

Jamaica, VT

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Courtesy of MICHAEL ENGLAND REAL ESTATE
View 15 Skyline Drive Vernon, VT MLS# 5102083
Save 15 Skyline Drive Vernon, VT MLS# 5102083
1 of 37
$679,000
3

Beds

3.1

Baths

2,476

Sq.Ft.

15 Skyline Drive

Vernon, VT

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Courtesy of BHG MASIELLO BRATTLEBORO
The time to sell is now! THE TIME TO SELL IS NOW!
View 54 Linden Street Brattleboro, VT MLS# 5102098
Save 54 Linden Street Brattleboro, VT MLS# 5102098
1 of 26
$489,000
3,202

Sq.Ft.

54 Linden Street

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 50 Terrace Street Brattleboro, VT MLS# 5102102
Save 50 Terrace Street Brattleboro, VT MLS# 5102102
1 of 14
$680,000
7

Beds

7.0

Baths

5,540

Sq.Ft.

50 Terrace Street

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 0 Stickney Brook Road Dummerston, VT MLS# 5101849
Save 0 Stickney Brook Road Dummerston, VT MLS# 5101849
1 of 14
$249,999
Studio

Beds

0.0

Baths

0 Stickney Brook Road

Dummerston, VT

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Courtesy of GREENWALD REALTY GROUP
View 15 Sawmill Road Stratton, VT MLS# 5101885
Save 15 Sawmill Road Stratton, VT MLS# 5101885
1 of 51
$5,100,000
10

Beds

9.1

Baths

6,648

Sq.Ft.

15 Sawmill Road

Stratton, VT

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Courtesy of WOHLER REALTY GROUP
View 00 Kidder Hill Road Grafton, VT MLS# 5101930
Save 00 Kidder Hill Road Grafton, VT MLS# 5101930
1 of 4
$45,000
Studio

Beds

0.0

Baths

00 Kidder Hill Road

Grafton, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 3 Eldredge Road Rockingham, VT MLS# 5101931
  • Virtual Tour
Save 3 Eldredge Road Rockingham, VT MLS# 5101931
1 of 60
$1,600,000
5

Beds

5.0

Baths

6,118

Sq.Ft.

3 Eldredge Road

Rockingham, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View Worden Road Jamaica, VT MLS# 5101763
Save Worden Road Jamaica, VT MLS# 5101763
1 of 13
$99,000
Studio

Beds

0.0

Baths

Worden Road

Jamaica, VT

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Courtesy of WINHALL REAL ESTATE
View 56 Park Laughton Road Dummerston, VT MLS# 5101601
Save 56 Park Laughton Road Dummerston, VT MLS# 5101601
1 of 27
$519,000
3

Beds

2.1

Baths

1,784

Sq.Ft.

56 Park Laughton Road

Dummerston, VT

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Courtesy of DEREK GREENE
View 8 Two Brook Road Wilmington, VT MLS# 5101723
Save 8 Two Brook Road Wilmington, VT MLS# 5101723
1 of 4
$28,000
Studio

Beds

0.0

Baths

8 Two Brook Road

Wilmington, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 57 Castle Hill Road Wilmington, VT MLS# 5101430
  • Virtual Tour
Save 57 Castle Hill Road Wilmington, VT MLS# 5101430
1 of 60
$690,000
5

Beds

4.0

Baths

2,642

Sq.Ft.

57 Castle Hill Road

Wilmington, VT

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Courtesy of SKIHOME REALTY
View 23 Main Street Rockingham, VT MLS# 5101445
Save 23 Main Street Rockingham, VT MLS# 5101445
1 of 40
$200,000
4

Beds

4.0

Baths

5,340

Sq.Ft.

23 Main Street

Rockingham, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 2022 Route 9 Marlboro, VT MLS# 5101448
Save 2022 Route 9 Marlboro, VT MLS# 5101448
1 of 40
$235,000
3

Beds

2.0

Baths

1,410

Sq.Ft.

2022 Route 9

Marlboro, VT

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Courtesy of FLEX REALTY
View 7 Underhill Avenue Rockingham, VT MLS# 5101481
Save 7 Underhill Avenue Rockingham, VT MLS# 5101481
1 of 22
$209,900
3

Beds

2.0

Baths

1,374

Sq.Ft.

7 Underhill Avenue

Rockingham, VT

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Courtesy of BHHS VERANI UPPER VALLEY
View 182 Partridge Lane Jamaica, VT MLS# 5101508
Save 182 Partridge Lane Jamaica, VT MLS# 5101508
1 of 44
$136,000
Studio

Beds

0.0

Baths

182 Partridge Lane

Jamaica, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
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 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 36 Paul's Road # 6-259 Guilford, VT MLS# 5101085
Save 36 Paul's Road # 6-259 Guilford, VT MLS# 5101085
1 of 26
$330,000
4

Beds

1.0

Baths

2,189

Sq.Ft.

36 Paul's Road # 6-259

Guilford, 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 8/21/2026”

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