3429 Cloudland Rd

5,134 Sq. Ft.
$429 / Sq. Ft.
5,134
Sq. Ft.
$429
per Sq. Ft.

Description

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...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.
  1. Listed by John Snyder • Snyder Donegan Real Estate Group

Sold By Snyder Donegan Real Estate Group

Property Details for 3429 Cloudland Road

Parking
Parking Spaces 5
Zoning
Res
LISTING UPDATED: 05/08/2023 04:56 PM

Property Details for 3429 Cloudland Road

StatusClosed
MLS #4779987
Days on Market300
Taxes$39,630 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1790
Lot Size115.79 AC / 5,043,812 SF
CountyWindsor County
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Building Information for 3429 Cloudland Road

Stories2Year Built1790Building Size-Lot Size115.79 AC / 5,043,812 SF

Payment Calculator

$14,381 per month

30 year fixed, 6.46% Interest

Principal and Interest

$11,078

Property Taxes

$3,303

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 3429 Cloudland Road

Summary
Location and General Information
  • City: Pomfret
  • County: VT-Windsor
  • Latitude: 43.658013311855335
  • Longitude: -72.507270893859868
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05067
Taxes and HOA Information
  • SPAN Number: 48915410610
  • Tax - Gross Amount: $39,630.00
  • Tax Year: 2019
  • Taxes TBD: No
School Information
  • School - High: Woodstock Senior UHSD #4
  • School - District: Windsor Central
  • School - Elementary: Woodstock Elementary School
  • School - Middle/Jr: Woodstock Union Middle Sch
Parking
  • Garage: Yes
  • Garage Capacity: 4.00
  • Driveway: Gravel
Property
Lot Information
  • Lot - Sqft: 5043812.0
  • Lot Size Acres: 115.79
  • Road Frontage Length: 1052.0
  • Square Feet Apx Finished Above Grade: 5134.0
  • Square Feet Apx Finished AG Source: Other
  • Square Feet Apx Finished Below Grade: 0.0
  • Square Feet Apx Finished BG Source: Other
  • Square Feet Apx Total: 5134.0
  • Square Feet Apx Total Finished: 5134.0
  • Square Feet Apx Unfinished Above Grade: 0.0
  • Square Feet Apx Unfinished AG Source: Other
  • Square Feet Apx Unfinished Below Grade: 0.0
  • Square Feet Apx Unfinished BG Source: Other
Property and Assessments
  • Current Use: Yes
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Easements: Yes
  • Flood Zone: No
  • Foundation: Concrete, Stone
  • PreConstruction: No
  • Surveyed: Yes
  • Year Built: 1790
Utilities
  • Cable Company: EC Fiber is at road
  • Electric: 200 Amp, Circuit Breaker(s)
  • Sewer: 1000 Gallon, Leach Field - On-Site, Private
  • Utilities: DSL, Internet - Cable, Multi Phone Lines, Underground Utilities
Interior and Exterior Features
Exterior Features
  • Color: Red
  • Features - Exterior: Barn, Fence - Partial, Guest House, Outbuilding, Patio, Shed
  • Roads: Gravel, Public
  • Roof: Shingle - Asphalt, Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Range Hood, Freezer, Microwave, Range - Gas, Refrigerator, Trash Compactor, Washer
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Bulkhead, Concrete, Crawl Space, Dirt, Stairs - Exterior, Unfinished
  • Baths - Total: 5
  • Baths - Full: 2
  • Half Baths: 2
  • One Quarter Baths: 0
  • Three Quarter Bath: 1
  • Rooms - Total: 13
  • Rooms: Level 1: Level 1: Breezeway, Level 1: Dining Room, Level 1: Family Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Primary Bedroom, Level 1: Office/Study, Level 1: Other
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Rec Room
  • Bedrooms - Total: 4
  • Equipment: Air Conditioner, CO Detector, Security System, Smoke Detector
  • Features - Interior: Blinds, Cedar Closet, Dining Area, Draperies, Fireplace - Gas, Fireplace - Wood, Fireplaces - 3+, Hearth, Kitchen/Family, Primary BR w/ BA, Vaulted Ceiling, Walk-in Closet, Walk-in Pantry, Window Treatment, Laundry - 1st Floor
  • Flooring: Brick, Slate/Stone, Wood
  • Heat Fuel: Gas - LP/Bottle, Oil
  • Heating: Baseboard, Hot Air, Hot Water, Multi Zone, Stove - Wood
  • Cooling: Central AC, Multi Zone
  • Total Stories: 2
Room Information
Room 1
  • Room Dimensions: 12 x 14
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Dimensions: 13.5 x 13.5
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Dimensions: 27.5 x 14.5
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Dimensions: 23 x 16
  • Room Level: 1
  • Room Type: Family Room
Room 5
  • Room Dimensions: 13.5 x 13.5
  • Room Level: 1
  • Room Type: Office/Study
Room 6
  • Room Dimensions: 36 x 27
  • Room Level: 2
  • Room Type: Rec Room
Room 7
  • Room Dimensions: 16 x 19
  • Room Level: 1
  • Room Type: Primary Bedroom
Room 8
  • Room Dimensions: 10.5 x 13
  • Room Level: 2
  • Room Type: Bedroom
Room 9
  • Room Dimensions: 12.5 x 12
  • Room Level: 2
  • Room Type: Bedroom
Room 10
  • Room Dimensions: 13.5 x 11.5
  • Room Level: 2
  • Room Type: Bedroom
Room 11
  • Room Dimensions: 14.5 x 8
  • Room Level: 1
  • Room Type: Other
Room 12
  • Room Dimensions: 10 x 22
  • Room Level: 1
  • Room Type: Breezeway

Property History for 3429 Cloudland Road

DateEvent & SourcePriceAppreciation
Aug 5, 2022

Sold

New England Real Estate Network #4924249

$4,250,000
Aug 5, 2022

Pending

New England Real Estate Network #4924249

Aug 5, 2022

Listed (Active)

New England Real Estate Network #4924249

$4,250,000
Sep 16, 2020

Sold (Public Record)

Public Record #677524968

$2,200,000
Sep 11, 2020

Sold

New England Real Estate Network #4779987

$2,200,000
Sep 11, 2020

Pending

New England Real Estate Network #4779987

Oct 5, 2019

Price Change

New England Real Estate Network #4779987

$3,100,000
Oct 5, 2019

Listed (Active)

New England Real Estate Network #4779987

$2,580,000
Jun 1, 2016

Expired

New England Real Estate Network #4439660

Jul 22, 2015

Listed (Active)

New England Real Estate Network #4439660

$3,150,000
Apr 13, 2015

Expired

New England Real Estate Network #4412286

Apr 9, 2015

Listed (Active)

New England Real Estate Network #4412286

$2,970,000
Mar 17, 2014

Expired

New England Real Estate Network #4192518

Oct 16, 2012

Listed (Active)

New England Real Estate Network #4192518

$3,300,000
Sep 2, 2008

Expired

New England Real Estate Network #2679396

Sep 15, 2007

Listed (Active)

New England Real Estate Network #2679396

$3,950,000
Nov 4, 2004

Sold

New England Real Estate Network #149724

$2,150,000
Oct 19, 2004

Pending

New England Real Estate Network #149724

May 24, 2004

Price Change

New England Real Estate Network #149724

$2,750,000
May 24, 2004

Listed (Active)

New England Real Estate Network #149724

$2,475,000
DateEvent & SourcePrice
08/05/2022

Sold

New England Real Estate Network #4924249

$4,250,000
08/05/2022

Pending

New England Real Estate Network #4924249

08/05/2022

Listed (Active)

New England Real Estate Network #4924249

$4,250,000
09/16/2020

Sold (Public Record)

Public Record #677524968

$2,200,000
09/11/2020

Sold

New England Real Estate Network #4779987

$2,200,000
09/11/2020

Pending

New England Real Estate Network #4779987

10/05/2019

Price Change

New England Real Estate Network #4779987

$3,100,000
10/05/2019

Listed (Active)

New England Real Estate Network #4779987

$2,580,000
06/01/2016

Expired

New England Real Estate Network #4439660

07/22/2015

Listed (Active)

New England Real Estate Network #4439660

$3,150,000
04/13/2015

Expired

New England Real Estate Network #4412286

04/09/2015

Listed (Active)

New England Real Estate Network #4412286

$2,970,000
03/17/2014

Expired

New England Real Estate Network #4192518

10/16/2012

Listed (Active)

New England Real Estate Network #4192518

$3,300,000
09/02/2008

Expired

New England Real Estate Network #2679396

09/15/2007

Listed (Active)

New England Real Estate Network #2679396

$3,950,000
11/04/2004

Sold

New England Real Estate Network #149724

$2,150,000
10/19/2004

Pending

New England Real Estate Network #149724

05/24/2004

Price Change

New England Real Estate Network #149724

$2,750,000
05/24/2004

Listed (Active)

New England Real Estate Network #149724

$2,475,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 3429 Cloudland Road

Taxable ValueLand-Additions-Total-
Home Facts
Beds0Lot Size5,043,813 SqFtStyleResidentialCountyWINDSORAPN(154) 0515-

Schools near 3429 Cloudland Road

This home is within Windsor Central Unified Union School District.
Rating
School
Type
Grades
Distance
Public - 5 to 6
Public - 7 to 12
Rating
School
Distance
The Prosper Valley School
Public5 to 6

Woodstock Senior Uhsd #4
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of Snyder Donegan Real Estate Group

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 04/05/2026 04:53 PM