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$2,961/mo
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Market trends in 05091, VT
Last updated August 2026
Buyer's Market
Seller's Market
Buyer's market
Sale-to-List Price
94.8%
0.7% MoM
Median sale price
$750K
$120K MoM
Avg. days on market
68d
30 days MoM
Recently sold homes
9
8 MoM
Provided by Redfin
Sale history for 3429 Cloudland Rd
Date
Event
Price
PrimeMLS #4924249
Aug 5, 2022
Listed
$4,250,000
PrimeMLS #4779987
Sep 11, 2020
Sold
$2,200,000
Jul 31, 2020
Contingent
—
Jun 10, 2020
Price Changed
$2,580,000
Oct 5, 2019
Listed
$3,100,000
+34
One of the most iconic properties in Vermont - Farm is located on desirable Cloudland Road, just 10 minutes from Woodstock village. The incredibly picturesque, pastoral land component comprises 115 acres of fields, gardens, woods, trails, and two ponds. The property is conserved both in the Vermont Current Use program and by the Vermont Land Trust. Next to the large second pond is a small cabin complete with bunk beds and a wood stove - perfect when you want to go “off-grid” and camp out on your own property. The original farmhouse c. 1790 - has been updated and expanded and now connects via a radiant-heated brick passageway to a newer, fabulous barn complete with 6 horse stalls, tack room, and a large finished wood-paneled recreation room upstairs. Two other large barns with workshops and garages and for storage- are nearby. The property comes with an array of motorized vehicles and equipment including a tractor, UTV and ATVs w wheels and tracks, two dirt bike motorcycles and a diesel-powered snowcat groomer. The property also includes a separate historic 1-room schoolhouse up on Cloudland Road, that was converted into a 1 bedroom apartment perfect for guests, kids or caretakers, with some of the best views in the area - and looks down over the Sleepy Hollow Farm itself.
PrimeMLS #149724
Nov 4, 2004
Sold
$2,150,000
Oct 19, 2004
Delisted
—
May 24, 2004
Listed
$2,475,000
SLEEPY HOLLOW FARM INCLUDES A GUEST HOUSE WHICH IS THE OLD CLOUDLAND SCHOOLHOUSE, AND A LOG CABIN. THE MAIN HOUSE IS A 1790 CENTER CHIMNEY ANTIQUE CAPE. THE PROPERTY IS CONSERVED IN THE VLT AND ENROLLED IN THE VERMONT CURRENT USE PROGRAM
As the MLS and public records start to fill up, we'll list the details here.
Public record
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Lot size
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Year renovated
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Sq. Ft.
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Year built
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Style
Single Family Residential
County
Windsor County
APN
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Accessible
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HOA Dues
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Last updated by owner on May 8, 2023.
Property details
Public facts
Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Windsor County
APN: —
Home facts updated by county records on May 8, 2023
Around this home
Schools
The Prosper Valley School
Public 5-6 • Assigned • 1.1mi
9/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
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
1/10 Heat Factor
6 days above 91° expected this year, 14 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
Pomfret, VT • 05067
Average low and high temperatures (°F)
27
11
30
11
44
24
56
34
64
45
77
54
82
60
79
53
74
49
61
38
45
30
31
15
Jan
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Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.4 hours in
June and 3.3 hours in December, placing it below the
U.S. average for solar exposure.
8.4 hrs
3.3 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$3.51M – $4.24M
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