05301 Homes for Sale

89 total properties
View 16 Willow Street Brattleboro, VT MLS# 5084386
Save 16 Willow Street Brattleboro, VT MLS# 5084386
1 of 39
$399,900
3

Beds

1.1

Baths

1,339

Sq.Ft.

16 Willow Street

Brattleboro, VT

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Courtesy of BHG MASIELLO KEENE
View 176 High Street Brattleboro, VT MLS# 5075240
Save 176 High Street Brattleboro, VT MLS# 5075240
1 of 34
$459,900
5

Beds

4.0

Baths

3,064

Sq.Ft.

176 High Street

Brattleboro, VT

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Courtesy of HOFFMAN REAL ESTATE
View 77 Buttonwood Drive Brattleboro, VT MLS# 5081478
  • Adult Community
Save 77 Buttonwood Drive Brattleboro, VT MLS# 5081478
1 of 32
$469,000
2

Beds

2.0

Baths

1,550

Sq.Ft.

77 Buttonwood Drive

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
The time to sell is now! THE TIME TO SELL IS NOW!
View 81 Chapin Street Brattleboro, VT MLS# 5082621
Save 81 Chapin Street Brattleboro, VT MLS# 5082621
1 of 27
$475,000
3

Beds

3.0

Baths

1,246

Sq.Ft.

81 Chapin Street

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 30 Chapin Street Brattleboro, VT MLS# 5089156
  • Recently Listed
Save 30 Chapin Street Brattleboro, VT MLS# 5089156
1 of 31
$475,000
3

Beds

2.1

Baths

2,400

Sq.Ft.

30 Chapin Street

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 49 Oles Drive Guilford, VT MLS# 5087831
  • Virtual Tour
Save 49 Oles Drive Guilford, VT MLS# 5087831
1 of 51
$489,000
3

Beds

2.0

Baths

1,716

Sq.Ft.

49 Oles Drive

Guilford, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 214 Putney Road Brattleboro, VT MLS# 5076579
Save 214 Putney Road Brattleboro, VT MLS# 5076579
1 of 46
$495,000
4

Beds

2.1

Baths

2,756

Sq.Ft.

214 Putney Road

Brattleboro, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 41 Chapin Street Brattleboro, VT MLS# 5087925
  • Recently Listed with Virtual Tour
Save 41 Chapin Street Brattleboro, VT MLS# 5087925
1 of 51
$499,000
4

Beds

2.1

Baths

2,874

Sq.Ft.

41 Chapin Street

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 33 Oak Street Brattleboro, VT MLS# 5086282
  • Recently Listed
Save 33 Oak Street Brattleboro, VT MLS# 5086282
1 of 24
$535,000
Studio

Beds

0.0

Baths

4,116

Sq.Ft.

33 Oak Street

Brattleboro, VT

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Courtesy of EXP REALTY
View 72 Landmark Hill Drive Brattleboro, VT MLS# 5076290
Save 72 Landmark Hill Drive Brattleboro, VT MLS# 5076290
1 of 26
$550,000
6,466

Sq.Ft.

72 Landmark Hill Drive

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 72 Landmark Hill Drive Brattleboro, VT MLS# 5076291
Save 72 Landmark Hill Drive Brattleboro, VT MLS# 5076291
1 of 26
$550,000
8

Beds

4.0

Baths

6,466

Sq.Ft.

72 Landmark Hill Drive

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 932 Middle Road Dummerston, VT MLS# 5056932
Save 932 Middle Road Dummerston, VT MLS# 5056932
1 of 39
$585,000
Studio

Beds

0.0

Baths

932 Middle Road

Dummerston, VT

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Courtesy of ACORN REAL ESTATE GROUP LLC
View 171 Green Meadow Brattleboro, VT MLS# 5086904
  • Recently Listed
Save 171 Green Meadow Brattleboro, VT MLS# 5086904
1 of 37
$595,000
3

Beds

3.0

Baths

2,172

Sq.Ft.

171 Green Meadow

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 143 Hillwinds Road Brattleboro, VT MLS# 5082786
Save 143 Hillwinds Road Brattleboro, VT MLS# 5082786
1 of 46
$625,000
5

Beds

3.1

Baths

2,520

Sq.Ft.

143 Hillwinds Road

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 11 Strawberry Hill Brattleboro, VT MLS# 5082239
  • Virtual Tour
Save 11 Strawberry Hill Brattleboro, VT MLS# 5082239
1 of 37
$639,000
4

Beds

2.1

Baths

2,573

Sq.Ft.

11 Strawberry Hill

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 299 Sunset Lake Road Brattleboro, VT MLS# 5074103
Save 299 Sunset Lake Road Brattleboro, VT MLS# 5074103
1 of 42
$650,000
3

Beds

2.1

Baths

1,995

Sq.Ft.

299 Sunset Lake Road

Brattleboro, VT

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Courtesy of ACORN REAL ESTATE GROUP LLC
View 47 Oak Hill Drive Dummerston, VT MLS# 5083747
Save 47 Oak Hill Drive Dummerston, VT MLS# 5083747
1 of 40
$675,000
3

Beds

2.0

Baths

2,100

Sq.Ft.

47 Oak Hill Drive

Dummerston, VT

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Courtesy of ACORN REAL ESTATE GROUP LLC
View 423 and 435 Marlboro Road Brattleboro, VT MLS# 5086506
  • Recently Listed
Save 423 and 435 Marlboro Road Brattleboro, VT MLS# 5086506
1 of 27
$695,000
10,888

Sq.Ft.

423 and 435 Marlboro Road

Brattleboro, VT

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Courtesy of RE/MAX TOWN & COUNTRY
View 5 Hillwinds North Brattleboro, VT MLS# 5081610
Save 5 Hillwinds North Brattleboro, VT MLS# 5081610
1 of 37
$795,000
4

Beds

2.2

Baths

3,600

Sq.Ft.

5 Hillwinds North

Brattleboro, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 104 Juniper Ridge Road Brattleboro, VT MLS# 5082195
Save 104 Juniper Ridge Road Brattleboro, VT MLS# 5082195
1 of 60
$795,000
4

Beds

3.1

Baths

3,212

Sq.Ft.

104 Juniper Ridge Road

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA 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 5/18/2026”

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