Windham Vermont Homes for Sale

562 total properties
View 26 Highlands Avenue # J2 Wilmington, VT MLS# 5107242
$949,000
4

Beds

4.0

Baths

3,494

Sq.Ft.

26 Highlands Avenue # J2

Wilmington, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 257 Dover Hill Road East Dover, VT MLS# 5107293
$895,000
3

Beds

4.0

Baths

3,981

Sq.Ft.

257 Dover Hill Road

East Dover, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
View 205 Wantastiquet Drive Brattleboro, VT MLS# 5106903
$525,000
3

Beds

2.1

Baths

2,330

Sq.Ft.

205 Wantastiquet Drive

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 171 Buttonwood Drive Brattleboro, VT MLS# 5106916
$499,000
2

Beds

2.0

Baths

1,775

Sq.Ft.

171 Buttonwood Drive

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 152 Main Street Grafton, VT MLS# 5106956
$489,999
4

Beds

2.0

Baths

2,400

Sq.Ft.

152 Main Street

Grafton, VT

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Courtesy of DEREK GREENE
View 19 Henry Street Rockingham, VT MLS# 5107035
$314,900
6

Beds

3.0

Baths

4,599

Sq.Ft.

19 Henry Street

Rockingham, VT

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Courtesy of TOWN AND COUNTRY REALTY
View 11 Crescent Drive Brattleboro, VT MLS# 5107263
$16,900
2

Beds

1.0

Baths

672

Sq.Ft.

11 Crescent Drive

Brattleboro, VT

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Courtesy of BHG MASIELLO BRATTLEBORO
View 632 Putney Road Brattleboro, VT MLS# 5106674
$600,000
480

Sq.Ft.

632 Putney Road

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 2855 Thompsonburg Road Londonderry, VT MLS# 5106736
1 of 58
OPEN HOUSE: Saturday 10/10 1:00 PM - 3:00 PM
$450,000
4

Beds

3.0

Baths

3,268

Sq.Ft.

2855 Thompsonburg Road

Londonderry, VT

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Courtesy of MARY MITCHELL MILLER REAL ESTATE
View 311 Dover Road Newfane, VT MLS# 5106777
$289,000
3

Beds

1.0

Baths

1,322

Sq.Ft.

311 Dover Road

Newfane, VT

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Courtesy of REAL BROKER LLC
View 639 Wilmington Cross Road Whitingham, VT MLS# 5106844
$309,000
3

Beds

1.0

Baths

1,200

Sq.Ft.

639 Wilmington Cross Road

Whitingham, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 3 Woodchuck Lane Wilmington, VT MLS# 5106862
$399,000
4

Beds

2.0

Baths

1,712

Sq.Ft.

3 Woodchuck Lane

Wilmington, VT

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Courtesy of BERKLEY & VELLER GREENWOOD/DOVER
View 77 Buttonwood Drive Brattleboro, VT MLS# 5106541
  • Adult Community
1 of 17
$439,000
2

Beds

2.0

Baths

1,550

Sq.Ft.

77 Buttonwood Drive

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 47 Upper Howes Road # A-23 Wilmington, VT MLS# 5106545
$449,000
3

Beds

2.0

Baths

1,200

Sq.Ft.

47 Upper Howes Road # A-23

Wilmington, VT

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Courtesy of CHIMNEY HILL REALTY
View 162 Buttonwood Drive Brattleboro, VT MLS# 5106580
$479,000
2

Beds

2.0

Baths

1,775

Sq.Ft.

162 Buttonwood Drive

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View Anderson Road Grafton, VT MLS# 5106592
$110,000
0.0

Baths

Anderson Road

Grafton, VT

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Courtesy of BARRETT & VALLEY ASSOC. INC
View 8 Penny Avenue Stratton, VT MLS# 5106381
$250,000
2

Beds

1.0

Baths

988

Sq.Ft.

8 Penny Avenue

Stratton, VT

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Courtesy of LOWE'S REAL ESTATE, LLC
View 619 Main Street Londonderry, VT MLS# 5106426
$489,000
4

Beds

2.1

Baths

2,100

Sq.Ft.

619 Main Street

Londonderry, VT

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Courtesy of CUMMINGS & CO
View 354 Orchard Street Brattleboro, VT MLS# 5106451
1 of 37
OPEN HOUSE: Saturday 10/10 11:00 AM - 1:00 PM
$585,000
4

Beds

2.1

Baths

2,212

Sq.Ft.

354 Orchard Street

Brattleboro, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 116 Teacher Road Jamaica, VT MLS# 5106080
$549,000
4

Beds

2.1

Baths

2,359

Sq.Ft.

116 Teacher Road

Jamaica, VT

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Courtesy of WINHALL REAL ESTATE

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 10/9/2026”

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