Windsor Vermont Homes for Sale

646 total properties
View 51 East Ash Road Plymouth, VT MLS# 5025237
Save 51 East Ash Road Plymouth, VT MLS# 5025237
1 of 60
OPEN HOUSE: Saturday 12/20 10:00 AM - 1:00 PM
$2,950,000
7

Beds

7.3

Baths

13,410

Sq.Ft.

51 East Ash Road

Plymouth, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 240 Piper Hill Road Weston, VT MLS# 5064867
  • Virtual Tour
Save 240 Piper Hill Road Weston, VT MLS# 5064867
1 of 60
$2,950,000
5

Beds

6.1

Baths

8,056

Sq.Ft.

240 Piper Hill Road

Weston, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 340 North Hartland Road Hartford, VT MLS# 5026321
Save 340 North Hartland Road Hartford, VT MLS# 5026321
1 of 16
$2,900,000
13,144

Sq.Ft.

340 North Hartland Road

Hartford, VT

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Courtesy of THE CLERKIN AGENCY, P.C.
The time to sell is now! THE TIME TO SELL IS NOW!
View 1497 Bowman Road Barnard, VT MLS# 5071203
  • Recently Listed
Save 1497 Bowman Road Barnard, VT MLS# 5071203
1 of 60
$2,895,000
5

Beds

5.4

Baths

8,249

Sq.Ft.

1497 Bowman Road

Barnard, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY
View 113 North Village Road Ludlow, VT MLS# 5012032
Save 113 North Village Road Ludlow, VT MLS# 5012032
1 of 38
$2,650,000
5

Beds

5.1

Baths

6,188

Sq.Ft.

113 North Village Road

Ludlow, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 41 Pleasant Street Woodstock, VT MLS# 5056243
Save 41 Pleasant Street Woodstock, VT MLS# 5056243
1 of 54
$2,599,000
5,993

Sq.Ft.

41 Pleasant Street

Woodstock, VT

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Courtesy of KW VERMONT WOODSTOCK
View 41 Pleasant Street Woodstock, VT MLS# 5062350
Save 41 Pleasant Street Woodstock, VT MLS# 5062350
1 of 54
$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 2677 Hartford Avenue Hartford, VT MLS# 5063389
Save 2677 Hartford Avenue Hartford, VT MLS# 5063389
1 of 24
$2,499,999
19,673

Sq.Ft.

2677 Hartford Avenue

Hartford, VT

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Courtesy of THE CLERKIN AGENCY, P.C.
View 254 Town Line Road Plymouth, VT MLS# 5057998
Save 254 Town Line Road Plymouth, VT MLS# 5057998
1 of 60
$2,499,000
4

Beds

3.1

Baths

5,079

Sq.Ft.

254 Town Line Road

Plymouth, VT

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Courtesy of KW VERMONT-KILLINGTON
View 46 Partridge Road Ludlow, VT MLS# 5064278
  • Virtual Tour
Save 46 Partridge Road Ludlow, VT MLS# 5064278
1 of 57
$2,499,000
5

Beds

3.2

Baths

5,305

Sq.Ft.

46 Partridge Road

Ludlow, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 248 Gird Lot Road Weathersfield, VT MLS# 5044086
  • Virtual Tour
Save 248 Gird Lot Road Weathersfield, VT MLS# 5044086
1 of 59
$2,495,000
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 719 Walker Hill Road Barnard, VT MLS# 5047791
Save 719 Walker Hill Road Barnard, VT MLS# 5047791
1 of 59
$2,395,000
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 1362 Barnard Road Woodstock, VT MLS# 5066205
  • Virtual Tour
Save 1362 Barnard Road Woodstock, VT MLS# 5066205
1 of 60
$2,395,000
4

Beds

2.0

Baths

3,000

Sq.Ft.

1362 Barnard Road

Woodstock, VT

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Courtesy of BRAVYNIA
View 134 Chester Arthur Road Hartford, VT MLS# 5053412
Save 134 Chester Arthur Road Hartford, VT MLS# 5053412
1 of 32
$2,300,000
4

Beds

4.1

Baths

3,524

Sq.Ft.

134 Chester Arthur Road

Hartford, VT

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Courtesy of WETMORE REAL ESTATE
View 5518 VT Route 12 Barnard, VT MLS# 4882232
Save 5518 VT Route 12 Barnard, VT MLS# 4882232
1 of 40
$2,299,000
8,363

Sq.Ft.

5518 VT Route 12

Barnard, VT

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Courtesy of WETMORE REAL ESTATE
View 5518 VT Route 12 Barnard, VT MLS# 4882340
  • Virtual Tour
Save 5518 VT Route 12 Barnard, VT MLS# 4882340
1 of 40
$2,299,000
6

Beds

3.1

Baths

7,619

Sq.Ft.

5518 VT Route 12

Barnard, VT

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Courtesy of WETMORE REAL ESTATE
View 3 Elm Street Woodstock, VT MLS# 5045785
Save 3 Elm Street Woodstock, VT MLS# 5045785
1 of 8
$2,200,000
14,205

Sq.Ft.

3 Elm Street

Woodstock, VT

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Courtesy of WETMORE REAL ESTATE
View 199 & 207 Main Street Ludlow, VT MLS# 5057892
Save 199 & 207 Main Street Ludlow, VT MLS# 5057892
1 of 49
$2,200,000
9,307

Sq.Ft.

199 & 207 Main Street

Ludlow, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 0 Mountain Road Ludlow, VT MLS# 5069010
Save 0 Mountain Road Ludlow, VT MLS# 5069010
1 of 18
$2,200,000
Studio

Beds

0.0

Baths

0 Mountain Road

Ludlow, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 0 VT Route 106 Reading, VT MLS# 5071026
  • Recently Listed
Save 0 VT Route 106 Reading, VT MLS# 5071026
1 of 11
$2,200,000
Studio

Beds

0.0

Baths

0 VT Route 106

Reading, VT

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Courtesy of WILLIAMSON GROUP SOTHEBYS INTL. REALTY

Information deemed reliable but not guaranteed.

“Copyright 2025 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 12/15/2025”

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