2769 Cloudland Rd

Woodstock, VT 05091

$3,300,000
Last Sold Price
4
Beds
3,485 Sq. Ft.
$947 / Sq. Ft.
3,485
Sq. Ft.
$947
per Sq. Ft.
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Closed 4/15/26Virtual Tour
Closed 4/15/26Virtual Tour

Description

Breathtaking long range views of Killington Peak and Saskadena 6 greet you as you wind your way up to your private slice of Heaven. Situated on nearly 91 acres, this spectacular property offers everything, from the views and open fields to the saltwater pool tucked nicely into the hillside to the trails running throughout the woods and a lovely stone patio aligned perfectly for evening sunsets. Inside, nearly every aspect of the house has been updated. There are four bedrooms including a primary...Breathtaking long range views of Killington Peak and Saskadena 6 greet you as you wind your way up to your private slice of Heaven. Situated on nearly 91 acres, this spectacular property offers everything, from the views and open fields to the saltwater pool tucked nicely into the hillside to the trails running throughout the woods and a lovely stone patio aligned perfectly for evening sunsets. Inside, nearly every aspect of the house has been updated. There are four bedrooms including a primary with ensuite bath and two additional full baths. The fully renovated kitchen is open to the dining area which leads to the living room with new floor to ceiling windows overlooking the Pomfret hills and mountains beyond. A stone fireplace anchors the living room, complete with a new insert and chimney liner. Between mini splits in all rooms and radiant floor heat in select areas, this house is fossil fuel free and derives most of its power from 61 onsite solar panels. Two Tesla power walls provide backup in the event of a grid outage. Separate from the main house is a two room cottage that was completely redone and currently set up as a guest bedroom and office, with a half bath inside and a seasonal outdoor shower on the deck. A short trek up through the woods takes you to an open meadow with a small cabin awaiting some finishing touches. Located privately atop the coveted Cloudland neighborhood just minutes from downtown Woodstock and Saskadena 6, this is a must see property.
  1. Listed by Dan Noble • Snyder Donegan Real Estate Group • Cell: 802-356-6044

Sold By Coldwell Banker LIFESTYLES - Hanover

Property Details for 2769 Cloudland Road

Zoning
RR
LISTING UPDATED: 04/15/2026 04:13 PM

Property Details for 2769 Cloudland Road

StatusClosed
MLS #5064364
Days on Market25
Taxes$13,423 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1927
Lot Size90.80 AC / 3,955,248 SF
CountyWindsor County
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Location

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Building Information for 2769 Cloudland Road

Stories1Year Built1927Building Size-Lot Size90.80 AC / 3,955,248 SF

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$17,736 per month

30 year fixed, 6.46% Interest

Principal and Interest

$16,617

Property Taxes

$1,119

HOA Dues

$0

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Property Information for 2769 Cloudland Road

Summary
Location and General Information
  • City: Pomfret
  • County: VT-Windsor
  • Directions: From Woodstock, take Rte. 12 to Pomfret Rd. Bear right on Pomfret Rd. to Barber Hill. Take a right and go all the way to the end of the road. Go left on Cloudland Rd. and go .4 miles to driveway on the right. Go up the driveway past the first house on the left all the way to the top.
  • Latitude: 43.667249785912894
  • Longitude: -72.501346005278961
  • Road Frontage: No
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05067
Taxes and HOA Information
  • SPAN Number: 489-154-10398
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 1.00
  • Driveway: Dirt, Gravel, Paved
Property
Lot Information
  • Lot Features: Country Setting, Field/Pasture, Hilly, Landscaped, Mountain View, Open, Recreational, Secluded, Sloping, Timber, Trail/Near Trail, View, Wooded, Near Skiing, Near Snowmobile Trails
  • Lot Size Acres: 90.8
  • Total Finished Area: 3485.0
  • Above Grade Finished Area: 3485.0
  • Above Grade Finished Area Source: Measured
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 0.0
  • Lot Size Square Feet: 3955248.0
  • Total Area: 3485.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Yes
  • Year Built: 1927
  • School District: Mountain Views Supervisory Union
  • High School: Woodstock Senior UHSD #4
  • Middle/Jr School: Woodstock Union Middle Sch
  • Elementary School: Woodstock Elementary School
Utilities
  • Electric: 200+ Amp Service, Circuit Breaker(s), Energy Storage Device, On-Site
  • Sewer: Leach Field, On-Site Septic Exists, Private, Septic
  • Water Source: Drilled Well
  • Utilities: Phone
  • Internet: Fiber Optic Internet, High Speed Intrnt at Site
Interior and Exterior Features
Exterior Features
  • Construction Materials: Log Home, Masonry, Wood Frame, Clapboard Exterior, Stone Exterior, Wood Exterior, Wood Siding, Spray Foam Insulation
  • Roof: Metal, Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Water Heater
  • Basement: No
  • Basement Description: Crawl Space
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Full Bathroom, Level 1: 1/2 Bathroom, Level 1: 3/4 Bathroom, Level 1: Dining Room, Level 1: Family Room, Level 1: Foyer, Level 1: Kitchen, Level 1: Living Room, Level 1: Primary Bdm Ste, Level 1: Mudroom, Level 1: Office/Study
  • Rooms: Level 2: Level 2: Bonus Room
  • Flooring: Slate/Stone, Wood
  • Heating: Solar, Radiant Floor, Wood Stove, Mini Split
  • Cooling: Mini Split
  • Total Stories: 1
  • Rooms Total: 12
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 1
  • Bedrooms Total: 4
  • Bathrooms Total: 4
Room Information
Room 1
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Level: 1
  • Room Type: Primary BR Suite
Room 5
  • Room Level: 1
  • Room Type: Bathroom Full
Room 6
  • Room Level: 1
  • Room Type: Bedroom
Room 7
  • Room Level: 1
  • Room Type: Bedroom
Room 8
  • Room Level: 1
  • Room Type: Bathroom Full
Room 9
  • Room Level: 1
  • Room Type: Family Room
Room 10
  • Room Level: 1
  • Room Type: Bathroom Three Quarter
Room 11
  • Room Level: 1
  • Room Type: Foyer
Room 12
  • Room Level: 1
  • Room Type: Mudroom
Room 13
  • Room Level: 2
  • Room Type: Bonus Room
Room 14
  • Room Level: 1
  • Room Type: Bedroom
Room 15
  • Room Level: 1
  • Room Type: Office/Study
Room 16
  • Room Level: 1
  • Room Type: Bathroom Half

Property History for 2769 Cloudland Road

DateEvent & SourcePriceAppreciation
Apr 15, 2026

Sold

New England Real Estate Network #5064364

$3,300,000—
Apr 15, 2026

Pending

New England Real Estate Network #5064364

—
Oct 29, 2025

Active Under Contract

New England Real Estate Network #5064364

—
Oct 4, 2025

Listed (Active)

New England Real Estate Network #5064364

$3,400,000—
Dec 11, 2020

Sold

New England Real Estate Network #4808114

$750,000—
Sep 30, 2020

Pending

New England Real Estate Network #4808114

—
May 30, 2020

Listed (Active)

New England Real Estate Network #4808114

$875,000—
DateEvent & SourcePrice
04/15/2026

Sold

New England Real Estate Network #5064364

$3,300,000
04/15/2026

Pending

New England Real Estate Network #5064364

—
10/29/2025

Active Under Contract

New England Real Estate Network #5064364

—
10/04/2025

Listed (Active)

New England Real Estate Network #5064364

$3,400,000
12/11/2020

Sold

New England Real Estate Network #4808114

$750,000
09/30/2020

Pending

New England Real Estate Network #4808114

—
05/30/2020

Listed (Active)

New England Real Estate Network #4808114

$875,000

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

Schools near 2769 Cloudland Road

This home is within Windsor Central Unified Union School District.
Rating
School
Type
Grades
Distance
The Prosper Valley School
Public - 5 to 6
Woodstock Senior Uhsd #4
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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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

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 04/20/2026 07:08 PM