Listed by Danny Kogut • Williamson Group Sothebys Intl. Realty (Cell: 802-952-8588).
For sale
$1,350,000
Est. $8,683/mo —
4
bd
•
3.5 ba
•
2,650
sq ft
33 Highfield Dr, Windsor, VT 05089
About this home
An exceptional 13.1-acre equestrian property with direct access to the GMHA trail system in sought-after West Windsor. This Lindal Cedar home features expansive windows, vaulted ceilings, and wide decks overlooking grassy pastures and distant views of Mt. Ascutney. The newly designed kitchen includes Crown Point cabinetry, granite countertops, and stainless-steel appliances. Upstairs, the primary bedroom has a wood-burning fireplace, while the ensuite bathroom offers a soaking tub and tiled shower. Two additional bedrooms on the main level each with a bathroom. First-floor laundry / powder room. Mudroom with custom cabinetry and direct access to a 2-car garage. Automatic generator. The stone patio includes a fire pit, and the property has electric dog fencing. A custom two-story barn offers five stalls with direct access, heated tack room, automatic heated waterers, large, fenced grass paddocks, an oversized riding ring and round pen, All-season recreational opportunities with easy access to VAST snowmobile trails. Hike and cycle on the dirt road system. 15 minutes to GMHA, 20 minutes to Woodstock. 30 minutes to Hanover, NH, 2.25 hours to Boston.
Single-familyProperty Type
1988Year Built
13.01 acresLot Size
$509Price/Sq.Ft.
2 car garageParking
Listed by Danny Kogut• Williamson Group Sothebys Intl. Realty
Listed by Scott Monahan• Williamson Group Sothebys Intl. Realty
HORSE LOVERS TAKE NOTE! WONDERFUL LINDAL CEDAR HOME ON 13 ACRES OF OPEN MEADOW PASTURE RIGHT IN THE MIDDLE OF GMHA COUNTRY. GENTLY ROLLING LAND, VIEW OF ASCUTNEY. SUNNY, PASSIVE-SOLAR HOME W/ OPEN FLOOR PLAN, 2 STONE FIREPLACES-1 IN MASTER BEDROOM SUITE
Year
Property tax
Land + Additions
Assessment*
2025
$10,027 (+0.3%)
$321,000 + $558,100
$879,100
2024
$9,996 (+9.1%)
$321,000 + $551,000
$872,000
2023
$9,160 (−14.3%)
$172,900 + $376,200
$549,100
2022
$10,684 (−11.1%)
$172,900 + $376,200
$549,100
2021
$12,018 (+1.5%)
$172,900 + $376,200
$549,100
2020
$11,844 (−2.6%)
$172,900 + $376,200
$549,100
2019
$12,159 (+9.5%)
$172,900 + $376,200
$549,100
2018
$11,108 (+6.1%)
$172,900 + $376,200
$549,100
2016
$10,468 (+1.0%)
$172,900 + $376,200
$549,100
2015
$10,363 (−4.0%)
$172,900 + $376,200
$549,100
2014
$10,790
$172,900 + $376,200
$549,100
Public record
Beds
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Lot size
13.1 Acres
Year renovated
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Finished Sq. Ft.
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Unfinished Sq. Ft.
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Total Sq. Ft.
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Year built
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Style
Other
County
Windsor County
APN
73823510203
Parking Spaces
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Basement
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Accessible
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HOA Dues
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Features
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Last updated by owner on Sep 2, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
2/10 Heat Factor
7 days above 91° expected this year, 16 days in 30 years
3/10 Wind Factor
5% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Windsor, VT • 05089
Average low and high temperatures (°F)
27
13
31
13
46
26
57
36
65
47
77
57
82
61
79
56
74
50
61
40
46
31
32
17
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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Oct
Nov
Dec
Sun exposure
Try the sun simulator tool to see how light moves across the property at different times of day and year.
Provided by Shadowmap
Redfin Estimate for 33 Highfield Dr
$1,339,502
$10K under list price of $1.35M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $548K to $2.0M.