Listed by Tyleen Murray • Kelley Real Estate, Inc.
For sale
$399,000
Est. $2,449/mo —
7
bd
•
2 ba
•
2,496
sq ft
2055 & 2071 Main & 28 Pleasant St, Cavendish, VT 05142
About this home
Three properties are being sold together with some owner terms possible. Investors, Dreamers, Skiers, Business Owners. .. Many possibilities and much potential. Bring your ideas. Weddings in the barn? Indoor growing? A ski house? A cafe or store? Lots of flexibility with no zoning. Renovations can continue or property can be sold as it is. In the past, the Okemo Shuttle has stopped across the street at Mill Street. It is a quick drive to Proctorsville - bakery, brewery, restaurant, store. 2071 Main Street could be used as a single family or two units. The town currently lists 7 bedrooms. The upper level is almost renovated with still a few things to do and the prep work has begun in the lower level. Live in the upper unit and have your business in the lower unit or have another income-producing unit or make into one amazing single-family home. Even the attic was once used as living space perhaps as part of a third unit. The chimney flashing has been addressed, slate work done, a membrane roof over the bay window area installed, some support work and vapor barrier added in basement, many windows reglazed, soffit and fascia painted, etc. The cosmetic work in the upper unit is done with the bathroom in progress. The barn that is on 2071 Main Street has had work done to the roof (sheathing boards, slate, and ridge cap). The upper level is an impressive open space. The lower workshop area of the barn needs flooring work. 2055 Main Street was once a large building built around 1880 and was the Fletcher Library. It was most recently a 4-unit apartment building with office space on the lower level. After a fire, the newer concrete foundation at the back of the structure was capped and covered for a future use. This property also has a large barn which has had work done to the roof. 28 Pleasant Street is behind the Main Street properties and has a separate access off Pleasant Street. Schedule your tour today! One of the owners is a licensed real estate broker.
Sale and tax history for 2055 & 2071 Main & 28 Pleasant St
Sale History
Tax History
Date
Event
Price
PrimeMLS #5102974
Sep 4, 2026
Price Changed
$399,000
$160/sq ft
Aug 1, 2026
Listed
$439,000
$176/sq ft
PrimeMLS #5100125
Sep 4, 2026
Price Changed
$399,000
$160/sq ft
Jul 19, 2026
Listed
$439,000
$176/sq ft
Jul 15, 2026
Coming Soon
$439,000
$176/sq ft
+35
Three properties are being sold together with some owner terms possible. Investors, Dreamers, Skiers, Business Owners. .. Many possibilities and much potential. Bring your ideas. Weddings in the barn? Indoor growing? A ski house? A cafe or store? Lots of flexibility with no zoning. Renovations can continue or property can be sold as it is. In the past, the Okemo Shuttle has stopped across the road at Mill Street. It is a quick drive to Proctorsville - bakery, brewery, restaurant, store. 2071 Main Street has two units in the house with a total of 7 bedrooms. The upper leve is almost renovated with still a few things to do and the prep work has begun in the lower level. Live in the upper unit and have your business in the lower unit or have another income-producing unit. Perhaps make this home into one amazing single-family home. Even the attic was once used as living space perhaps as part of a third unit. The chimney flashing has been addressed, slate work done, a membrane roof over the bay window area installed, some support work and vapor barrier added in basement, many windows reglazed, soffit and fascia painted, etc. The cosmetic work in the upper unit is done with the bathroom in progress. The barn that is on 2071 Main Street has had work done to the roof (sheathing boards, slate, and ridge cap). The upper level is an impressive open space. The lower workshop area of the barn needs flooring work. 2055 Main Street was once a large building built around 1880 and was the Fletcher Library. It was most recently a 4-unit apartment building with office space on the lower level. After a fire, the newer concrete foundation at the back of the structure was capped and covered for a future use. This property also has a large barn which has had work done to the roof. 28 Pleasant Street is behind the Main Street properties and has a separate access off Pleasant Street. Showings start on 7/19/2026. Schedule your tour today! One of the owners is a licensed real estate broker.
As the MLS and public records start to fill up, we'll list the details here.
Public record
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
—
Year renovated
—
Finished Sq. Ft.
—
Unfinished Sq. Ft.
—
Total Sq. Ft.
—
Year built
—
Style
Multi-Family (2-4 Unit)
County
Windsor County
APN
132-041-11077
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 15, 2026.
Historical weather
Cavendish, VT • 05142
Average low and high temperatures (°F)
26
14
30
14
45
27
57
36
65
47
77
58
82
63
78
57
73
52
60
41
45
32
31
18
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
73/ 100
Good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9 hrs
3.9 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 2055 & 2071 Main & 28 Pleasant St
$381,618
$17K under list price of $399K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $315K to $615K.