Windsor Vermont Homes for Sale

581 total properties
View 650 Francis Road Barnard, VT MLS# 5066208
  • Virtual Tour
Save 650 Francis Road Barnard, VT MLS# 5066208
1 of 60
$39,000,000
2

Beds

4.3

Baths

9,950

Sq.Ft.

650 Francis Road

Barnard, VT

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Courtesy of BRAVYNIA
View 355 Greene Road Woodstock, VT MLS# 5066210
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Save 355 Greene Road Woodstock, VT MLS# 5066210
1 of 59
$18,000,000
7

Beds

7.3

Baths

12,520

Sq.Ft.

355 Greene Road

Woodstock, VT

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Courtesy of BRAVYNIA
View 115 Eastman Road Woodstock, VT MLS# 5039451
Save 115 Eastman Road Woodstock, VT MLS# 5039451
1 of 47
$8,000,000
3

Beds

3.1

Baths

5,384

Sq.Ft.

115 Eastman Road

Woodstock, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 412 Skyland Lane Woodstock, VT MLS# 5044620
  • New Construction with Virtual Tour
Save 412 Skyland Lane Woodstock, VT MLS# 5044620
1 of 48
$6,750,000
4

Beds

4.1

Baths

5,087

Sq.Ft.

412 Skyland Lane

Woodstock, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 3800 Weston Andover Road Andover, VT MLS# 5015743
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Save 3800 Weston Andover Road Andover, VT MLS# 5015743
1 of 41
$5,950,000
8

Beds

7.1

Baths

10,062

Sq.Ft.

3800 Weston Andover Road

Andover, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 476 Salt Ash Road Plymouth, VT MLS# 5047809
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Save 476 Salt Ash Road Plymouth, VT MLS# 5047809
1 of 60
$4,850,000
5

Beds

6.0

Baths

9,153

Sq.Ft.

476 Salt Ash Road

Plymouth, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 924 Okemo Ridge Road # S 11 Ludlow, VT MLS# 5076511
  • Recently Listed
Save 924 Okemo Ridge Road # S 11 Ludlow, VT MLS# 5076511
1 of 60
$4,775,000
7

Beds

6.1

Baths

6,624

Sq.Ft.

924 Okemo Ridge Road # S 11

Ludlow, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 85 Pallottas Hill Ludlow, VT MLS# 5063615
Save 85 Pallottas Hill Ludlow, VT MLS# 5063615
1 of 28
$4,500,000
Studio

Beds

0.0

Baths

85 Pallottas Hill

Ludlow, VT

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Courtesy of DIAMOND REALTY
View 85 Pallottas Hill Road Ludlow, VT MLS# 5063616
Save 85 Pallottas Hill Road Ludlow, VT MLS# 5063616
1 of 42
$4,500,000
4

Beds

2.0

Baths

3,150

Sq.Ft.

85 Pallottas Hill Road

Ludlow, VT

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Courtesy of DIAMOND REALTY
View 170 VT Route 100 Bridgewater, VT MLS# 5056089
Save 170 VT Route 100 Bridgewater, VT MLS# 5056089
1 of 39
$4,200,000
8,841

Sq.Ft.

170 VT Route 100

Bridgewater, VT

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Courtesy of KW VERMONT-KILLINGTON
View 5685 VT Route 12 Barnard, VT MLS# 5042800
Save 5685 VT Route 12 Barnard, VT MLS# 5042800
1 of 33
$3,945,000
5

Beds

5.1

Baths

8,122

Sq.Ft.

5685 VT Route 12

Barnard, VT

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Courtesy of SNYDER DONEGAN REAL ESTATE GROUP
View 348 Turtle Hill Road Ludlow, VT MLS# 5049540
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Save 348 Turtle Hill Road Ludlow, VT MLS# 5049540
1 of 60
$3,650,000
5

Beds

4.0

Baths

5,181

Sq.Ft.

348 Turtle Hill Road

Ludlow, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 657 Town Farm Road Ludlow, VT MLS# 5074911
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Save 657 Town Farm Road Ludlow, VT MLS# 5074911
1 of 60
$3,550,000
4

Beds

4.1

Baths

6,548

Sq.Ft.

657 Town Farm Road

Ludlow, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 61 Academy Circle Woodstock, VT MLS# 5002873
  • Virtual Tour
Save 61 Academy Circle Woodstock, VT MLS# 5002873
1 of 40
$3,500,000
6

Beds

4.2

Baths

5,433

Sq.Ft.

61 Academy Circle

Woodstock, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY
View 18 The Green Woodstock, VT MLS# 5056336
Save 18 The Green Woodstock, VT MLS# 5056336
1 of 42
$3,500,000
6

Beds

6.2

Baths

5,142

Sq.Ft.

18 The Green

Woodstock, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY
View 1726 Skitchewaug Trail Springfield, VT MLS# 5072374
Save 1726 Skitchewaug Trail Springfield, VT MLS# 5072374
1 of 58
$3,490,000
4

Beds

4.1

Baths

2,894

Sq.Ft.

1726 Skitchewaug Trail

Springfield, VT

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Courtesy of WETMORE REAL ESTATE
View 2769 Cloudland Road South Pomfret, VT MLS# 5064364
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Save 2769 Cloudland Road South Pomfret, VT MLS# 5064364
1 of 56
$3,400,000
4

Beds

3.1

Baths

3,485

Sq.Ft.

2769 Cloudland Road

South Pomfret, VT

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Courtesy of SNYDER DONEGAN REAL ESTATE GROUP
View 249 Sawyer Road Woodstock, VT MLS# 5072035
  • Virtual Tour
Save 249 Sawyer Road Woodstock, VT MLS# 5072035
1 of 26
$3,300,000
3

Beds

4.1

Baths

3,682

Sq.Ft.

249 Sawyer Road

Woodstock, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 191 Moon Shadow Drive # M19 Ludlow, VT MLS# 5077313
  • Recently Listed with Virtual Tour
Save 191 Moon Shadow Drive # M19 Ludlow, VT MLS# 5077313
1 of 60
$3,250,000
5

Beds

6.1

Baths

5,728

Sq.Ft.

191 Moon Shadow Drive # M19

Ludlow, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 00 Marsh Cross Road Andover, VT MLS# 5074909
  • Virtual Tour
Save 00 Marsh Cross Road Andover, VT MLS# 5074909
1 of 42
$3,150,000
Studio

Beds

0.0

Baths

00 Marsh Cross Road

Andover, VT

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Courtesy of LANDVEST, INC/WOODSTOCK

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 2/26/2026”

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