Windsor Vermont Homes for Sale

703 total properties
View 5798 South Road Woodstock, VT MLS# 5094600
$2,950,000
8

Beds

5.3

Baths

6,200

Sq.Ft.

5798 South Road

Woodstock, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY
View 2687 Garvin Hill Road Woodstock, VT MLS# 5112419
  • Virtual Tour
1 of 47
$2,600,000
5

Beds

4.1

Baths

4,328

Sq.Ft.

2687 Garvin Hill Road

Woodstock, VT

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Courtesy of SNYDER DONEGAN REAL ESTATE GROUP
View 41 Pleasant Street Woodstock, VT MLS# 5056243
$2,599,000
5,993

Sq.Ft.

41 Pleasant Street

Woodstock, VT

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Courtesy of KW VERMONT WOODSTOCK
The time to sell is now! THE TIME TO SELL IS NOW!
View 41 Pleasant Street Woodstock, VT MLS# 5062350
$2,599,000
9

Beds

11.0

Baths

5,993

Sq.Ft.

41 Pleasant Street

Woodstock, VT

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Courtesy of KW VERMONT WOODSTOCK
View 114 Oak Ridge Way Woodstock, VT MLS# 5087228
  • Virtual Tour
1 of 60
$2,500,000
4

Beds

3.1

Baths

5,127

Sq.Ft.

114 Oak Ridge Way

Woodstock, VT

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Courtesy of SNYDER DONEGAN REAL ESTATE GROUP
View 2677 Hartford Avenue Hartford, VT MLS# 5063389
$2,499,999
19,673

Sq.Ft.

2677 Hartford Avenue

Hartford, VT

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Courtesy of THE CLERKIN AGENCY, P.C.
View 3398 Jericho Road Hartford, VT MLS# 5108462
$2,499,000
5

Beds

5.0

Baths

4,462

Sq.Ft.

3398 Jericho Road

Hartford, VT

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Courtesy of KW VERMONT WOODSTOCK
View 420 Quechee Road Hartland, VT MLS# 5115420
  • Virtual Tour
1 of 60
$2,499,000
5

Beds

4.0

Baths

4,562

Sq.Ft.

420 Quechee Road

Hartland, VT

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Courtesy of KW COASTAL AND LAKES & MOUNTAINS REALTY/HANOVER
View 232 Town Farm Hill Road Hartland, VT MLS# 5108362
  • Virtual Tour
1 of 60
$2,495,000
3

Beds

1.1

Baths

2,476

Sq.Ft.

232 Town Farm Hill Road

Hartland, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY
View 1726 Skitchewaug Trail Springfield, VT MLS# 5098535
$2,450,000
4

Beds

4.1

Baths

2,894

Sq.Ft.

1726 Skitchewaug Trail

Springfield, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY
View 340 North Hartland Road Hartford, VT MLS# 5026321
$2,400,000
13,144

Sq.Ft.

340 North Hartland Road

Hartford, VT

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Courtesy of THE CLERKIN AGENCY, P.C.
View 2 Dublin Road Plymouth, VT MLS# 5082041
$2,400,000

2 Dublin Road

Plymouth, VT

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Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
View 2709 W Woodstock Road Woodstock, VT MLS# 5117895
  • Recently Listed
1 of 52
$2,400,000
7,769

Sq.Ft.

2709 W Woodstock Road

Woodstock, VT

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Courtesy of COLDWELL BANKER HOMES UNLIMITED
View 55 Cherry Hill Springfield, VT MLS# 5090495
$2,300,000
6

Beds

4.0

Baths

8,656

Sq.Ft.

55 Cherry Hill

Springfield, VT

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Courtesy of WINHALL REAL ESTATE
View 14 Olcott Road Norwich, VT MLS# 5110640
  • Virtual Tour
1 of 57
$2,300,000
4

Beds

4.1

Baths

4,832

Sq.Ft.

14 Olcott Road

Norwich, VT

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Courtesy of SNYDER DONEGAN REAL ESTATE GROUP
View 248 Gird Lot Road Weathersfield, VT MLS# 5044086
  • Virtual Tour
1 of 50
$2,295,000
5

Beds

4.1

Baths

4,800

Sq.Ft.

248 Gird Lot Road

Weathersfield, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 254 Town Line Road Plymouth, VT MLS# 5095474
$2,250,000
4

Beds

3.1

Baths

5,079

Sq.Ft.

254 Town Line Road

Plymouth, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 9671 VT Route 12 Barnard, VT MLS# 5086468
$2,195,000
3

Beds

3.0

Baths

2,997

Sq.Ft.

9671 VT Route 12

Barnard, VT

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Courtesy of SNYDER DONEGAN REAL ESTATE GROUP
View 719 Walker Hill Road Barnard, VT MLS# 5088843
$2,195,000
3

Beds

3.2

Baths

4,329

Sq.Ft.

719 Walker Hill Road

Barnard, VT

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Courtesy of SNYDER DONEGAN REAL ESTATE GROUP
View 1702 North Puckerbrush Road Reading, VT MLS# 5090750
$2,195,000
5

Beds

3.2

Baths

7,374

Sq.Ft.

1702 North Puckerbrush Road

Reading, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. 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 11/15/2026”

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