376 Windward
Dorset, VT 05251
- 4 beds
- 5 baths
- 5,696 sqft
- ~13 acre lot
- $416 per sqft
- 1965 build
- – on site
Welcome to 376 Windward Hill, a stunning Southern Vermont estate with breathtaking views of the Taconic and Green Mountain Ranges. Spanning 12 acres, the property features a private trout pond and tranquil waterfall, creating a serene atmosphere. Inside, the home combines timeless elegance with modern comfort. Herringbone brick and hardwood floors lead to the expansive living room, highlighted by a two-story stone fireplace. This grand space flows seamlessly into the formal dining area, which opens to a screened porch and wrap-around deck, perfect for enjoying mountain vistas. The gourmet kitchen boasts a cozy bar, ample cabinetry, a butler's pantry, and top-of-the-line appliances. The primary suite offers sweeping views, deck access, and a spa-like bathroom with a jacuzzi tub and steam shower. The home includes three additional spacious bedrooms and a versatile office, plus a lower level with an exercise room, workshop, and family room for relaxation and productivity. Located minutes from Manchester and Dorset, 376 Windward Hill offers the perfect balance of privacy and convenience, making it an ideal retreat for both relaxation and entertaining.
Last checked:
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Last updated Apr 15, 2025
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MLS# 5036105 —
The Building
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Year Built:1965
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Pre-Construction:No
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Construction Status:Existing
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Construction Materials:Wood Frame, Wood Exterior
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Architectural Style:Contemporary
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Roof:Standing Seam
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Foundation:Concrete
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Equipment:Generator - Standby
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Total Stories:2
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Approx SqFt Total:5696
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Approx SqFt Total Finished:5,696 Sqft
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Approx SqFt Finished Above Grade:5,696 Sqft
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Approx SqFt Finished Below Grade:0 Sqft
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Approx SqFt Finished Above Grade Source:Public Records
Interior
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Total Rooms:12
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Features - Interior:Blinds, Fireplaces - 2, Living/Dining, Primary BR w/ BA, Natural Light, Vaulted Ceiling, Walk-in Closet
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Flooring:Brick, Carpet, Ceramic Tile, Wood
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Room 1 Level:2
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Room 2 Level:2
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Room 3 Level:2
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Room 4 Level:2
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Room 5 Level:2
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Room 6 Level:2
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Room 7 Level:2
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Room 8 Level:2
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Room 9 Level:1
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Room 10 Level:1
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Room 11 Level:1
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Room 1 Type:Great Room
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Room 2 Type:Dining Room
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Room 10 Type:Exercise Room
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Room 9 Type:Family Room
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Room 8 Type:Office/Study
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Room 7 Type:Bedroom
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Room 5 Type:Bedroom
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Room 4 Type:Primary BR Suite
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Room 3 Type:Kitchen
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Room 6 Type:Bedroom
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Room 11 Type:Workshop
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Rooms Level 1:Level 1: Exercise Room, Level 1: Family Room, Level 1: Workshop
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Rooms: Level 2Level 2: Bedroom, Level 2: Dining Room, Level 2: Great Room, Level 2: Kitchen, Level 2: Primary Bdm Ste, Level 2: Office/Study
Location
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Directions:From Route 30: Take Morse Hill Road for 1.2 miles. Take left onto Windward Hill. Follow for 700 feet, take slight right turn into drive. From Route 7A: Take Morse Hill Road for 2.4 miles. Take right onto Windward Hill. Follow for 700 feet, take slight right turn into drive.
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Latitude:43.222448000001002
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Longitude:-73.049068000000005
The Property
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Property Type:Single Family
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Property Class:Residential
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Seasonal:No
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Lot Features:Country Setting, Landscaped, Mountain View, Pond, Rolling
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Lot SqFt:551,905 Sqft
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Lot Acres:12 Sqft
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Zoning:Residential
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Exterior Features:Deck, Gazebo, Porch - Screened
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Driveway:Gravel
Listing Agent
- Contact info:
- Office phone:
- (802) 362-4551
Taxes
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Tax Year:2025
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Taxes TBD:No
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Tax - Gross Amount:$19,656.62
Beds
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Total Bedrooms:4
Baths
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Total Baths:5
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Full Baths:4
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Half Baths:1
The Listing
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Price Per SqFt:416.96
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Possession:At Closing
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Foreclosed/Bank-Owned/REO:No
Heating & Cooling
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Heating:Propane, Baseboard, Electric, Hot Air, Radiant Ceiling
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Cooling:Other
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Fuel Company:Dead River
Utilities
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Utilities:Cable - Available, Gas - LP/Bottle, Telephone Available
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Sewer:Concrete, Septic
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Electric:200 Amp, Circuit Breaker(s), Generator
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Water Source:Drilled Well
Appliances
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Appliances:Cooktop - Gas, Dishwasher, Dryer, Microwave, Oven - Double, Oven - Wall, Refrigerator, Washer, Water Heater - Owned
Schools
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Elementary School:Dorset Elementary School
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Middle Or Junior School:The Dorset School
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High School:Choice
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School District:Taconic and Green Regional
The Community
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Covenants:Yes
Parking
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Garage:Yes
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Garage Capacity:3
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Parking:Auto Open, Heated Garage, Driveway, Attached
Monthly cost estimate

Asking price
$2,375,000
Expense | Monthly cost |
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Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$12,717
|
Taxes | $1,638 |
Insurance | $653 |
Utilities | $379 See report |
Total | $15,387/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
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4/14/25
Apr 14, 2025
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Listed / Active | PRIME_MLS | $2,375,000 | |
9/22/24
Sep 22, 2024
|
Price Changed | PRIME_MLS | ||
7/31/24
Jul 31, 2024
|
Price Changed | PRIME_MLS |