81 Windward Hl

Dorset, VT 05251

$875,000
Last Sold Price
4
Beds
4,650 Sq. Ft.
$188 / Sq. Ft.
4,650
Sq. Ft.
$188
per Sq. Ft.
Closed 12/19/25
Closed 12/19/25

Description

Set on a quiet private road in the heart of Dorset, Vermont, this distinguished four bedroom Colonial blends classic New England architecture with modern comfort. Framed by mountain views and surrounded by natural beauty, the property offers the perfect balance of privacy, charm, and convenience. Inside, you’ll find inviting spaces designed for both everyday living and gracious entertaining. Three fireplaces provide warmth and character throughout the home, creating cozy gathering spots in every...Set on a quiet private road in the heart of Dorset, Vermont, this distinguished four bedroom Colonial blends classic New England architecture with modern comfort. Framed by mountain views and surrounded by natural beauty, the property offers the perfect balance of privacy, charm, and convenience. Inside, you’ll find inviting spaces designed for both everyday living and gracious entertaining. Three fireplaces provide warmth and character throughout the home, creating cozy gathering spots in every season. The finished walkout basement extends the living space, ideal for a family room, home office, or guest suite. Outdoors, the property continues to impress. A dedicated garden space invites you to cultivate your own vegetables, herbs, or flowers, while the mountain backdrop offers year-round beauty. The private setting allows you to enjoy peaceful mornings on the porch or evenings by the fire, all just minutes from Dorset village amenities.
  1. Listed by Adrienne Sherwood • Four Seasons Sotheby's Int'l Realty

Sold By Four Seasons Sotheby's Int'l Realty

Property Details for 81 Windward Hill

Zoning
Residential
LISTING UPDATED: 12/19/2025 06:35 PM

Property Details for 81 Windward Hill

StatusClosed
MLS #5061525
Days on Market59
Taxes$11,748 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1981
Lot Size5.80 AC / 252,648 SF
CountyBennington County

Location

Add your commute

Building Information for 81 Windward Hill

Stories2Year Built1981Building Size-Lot Size5.80 AC / 252,648 SF

Payment Calculator

$5,244 per month

30 year fixed, 6.15% Interest

Principal and Interest

$4,265

Property Taxes

$979

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 81 Windward Hill

Summary
Location and General Information
  • City: Dorset
  • County: VT-Bennington
  • Directions: From VT Rte 30 to Morse Hill Rd, left onto Windward Hill Rd, 1st house on left
  • Latitude: 43.219670510127585
  • Longitude: -73.051074884933485
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Hill
  • Zip Code: 05251
Taxes and HOA Information
  • SPAN Number: 180-057-10929
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Paved
Virtual Tour
Property
Lot Information
  • Lot Features: Country Setting, Landscaped, Mountain View, View
  • Lot Size Acres: 5.8
  • Road Frontage Length: 564.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Easements: Yes
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1981
Utilities
  • Electric: 200+ Amp Service
  • Sewer: Private, Septic
  • Water Source: Drilled Well
  • Utilities: Cable Available, Telephone Available
  • Internet: Fiber Optic Internt Avail, High Speed Intrnt Avail, DSL Available
Interior and Exterior Features
Exterior Features
  • Color: blue
  • Construction Materials: Wood Frame
  • Roof: Asphalt Shingle
Interior Features
  • Appliances: Dishwasher, Dryer, Range Hood, Microwave, Electric Range, Refrigerator, Washer, Owned Water Heater, Exhaust Fan
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Climate Controlled, Concrete, Daylight, Finished, Full, Insulated, Interior Stairs, Storage Space, Walkout, Exterior Access, Basement Stairs
  • Rooms: Level 1: Level 1: Den, Level 1: Dining Room, Level 1: Kitchen, Level 1: Laundry Room, Level 1: Living Room, Level 1: Mudroom, Level 1: Rec Room
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Primary Bdm Ste
  • Rooms: Level B: Level B: Family Room
  • Flooring: Carpet, Ceramic Tile, Hardwood, Laminate, Manufactured, Tile, Wood, Vinyl Plank
  • Heating: Wood, Baseboard, Hot Water, Multi Zone
  • Cooling: Wall AC Units, Whole House Fan
  • Total Stories: 2.5
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: Den
Room 4
  • Room Level: 1
  • Room Type: Living Room
Room 5
  • Room Level: 1
  • Room Type: Laundry Room
Room 6
  • Room Level: 1
  • Room Type: Mudroom
Room 7
  • Room Level: Basement
  • Room Type: Family Room
Room 8
  • Room Level: 1
  • Room Type: Rec Room
Room 9
  • Room Level: 2
  • Room Type: Primary BR Suite
Room 10
  • Room Level: 2
  • Room Type: Bedroom
Room 11
  • Room Level: 2
  • Room Type: Bedroom
Room 12
  • Room Level: 2
  • Room Type: Bedroom

Property History for 81 Windward Hill

DateEvent & SourcePriceAppreciation
Dec 19, 2025

Sold

New England Real Estate Network #5061525

$875,000—
Dec 7, 2025

Pending

New England Real Estate Network #5061525

—
Nov 14, 2025

Active Under Contract

New England Real Estate Network #5061525

—
Sep 16, 2025

Listed (Active)

New England Real Estate Network #5061525

$975,000—
May 27, 2021

Sold

New England Real Estate Network #4853063

$579,000—
May 27, 2021

Pending

New England Real Estate Network #4853063

—
Mar 30, 2021

Listed (Active)

New England Real Estate Network #4853063

$579,000—
Jun 2, 2015

Expired

New England Real Estate Network #4397607

—
Dec 29, 2014

Listed (Active)

New England Real Estate Network #4397607

$598,000—
DateEvent & SourcePrice
12/19/2025

Sold

New England Real Estate Network #5061525

$875,000
12/07/2025

Pending

New England Real Estate Network #5061525

—
11/14/2025

Active Under Contract

New England Real Estate Network #5061525

—
09/16/2025

Listed (Active)

New England Real Estate Network #5061525

$975,000
05/27/2021

Sold

New England Real Estate Network #4853063

$579,000
05/27/2021

Pending

New England Real Estate Network #4853063

—
03/30/2021

Listed (Active)

New England Real Estate Network #4853063

$579,000
06/02/2015

Expired

New England Real Estate Network #4397607

—
12/29/2014

Listed (Active)

New England Real Estate Network #4397607

$598,000

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

Schools near 81 Windward Hill

This home is within Taconic and Green Regional School District.
Rating
School
Type
Grades
Distance
Dorset Elementary School
Public - PK to 8
Rating
School
Distance
Dorset Elementary School
PublicPK to 8

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 Four Seasons Sotheby's Int'l Realty

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 02/02/2026 06:36 PM