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.
Active
Listed by:
Andrea Kaplan,
Four Seasons Sotheby's Int'l Realty 802-362-4551
$2,375,000
376 Windward Hill, Dorset, VT 05251
4beds
5,696sqft
Est.:
Single Family Residence
Built in 1965
12.67 Acres Lot
$-- Zestimate®
$417/sqft
$-- HOA
What's special
Two-story stone fireplacePrivate trout pondFormal dining areaTimeless eleganceTranquil waterfallMountain vistasScreened porch
- 12 days
- on Zillow |
- 955 |
- 32 |
Zillow last checked: 7 hours ago
Listing updated: April 15, 2025 at 09:29am
Listed by:
Andrea Kaplan,
Four Seasons Sotheby's Int'l Realty 802-362-4551
Source: PrimeMLS,MLS#: 5036105

Travel times
Tour with a buyer’s agent
Tour with a buyer’s agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Heating
- Propane, Baseboard, Electric, Hot Air, Radiant Ceiling
Cooling
- Other
Appliances
- Included: Gas Cooktop, Dishwasher, Dryer, Microwave, Double Oven, Oven - Wall, Refrigerator, Washer, Water Heater - Owned
Features
- Living/Dining, Primary BR w/ BA, Natural Light, Vaulted Ceiling(s), Walk-In Closet(s)
- Flooring: Brick, Carpet, Ceramic Tile, Wood
- Windows: Blinds
- Has basement: No
- Number of fireplaces: 2
- Fireplace features: Fireplaces - 2
Interior area
- Total structure area: 5,696
- Total interior livable area: 5,696 sqft
- Finished area above ground: 5,696
Property
Parking
- Total spaces: 3
- Parking features: Gravel, Auto Open, Heated Garage, Driveway, Attached
- Garage spaces: 3
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Porch - Screened
- Has view: Yes
- View description: Mountain(s)
- Waterfront features: Pond
Lot
- Size: 12.67 Acres
- Features: Country Setting, Landscaped, Rolling Slope
Details
- Additional structures: Gazebo
- Parcel number: 18005710652
- Zoning description: Residential
- Other equipment: Generator - Standby
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Frame, Wood Exterior
- Foundation: Concrete
- Roof: Standing Seam
Condition
- New construction: No
- Year built: 1965
Utilities & green energy
- Electric: 200+ Amp Service, Circuit Breakers, Generator
- Sewer: Concrete, Septic Tank
- Utilities for property: Cable Available, Gas - LP/Bottle, Phone Available, High Speed Intrnt -Avail
Community & HOA
Location
- Region: Dorset
Financial & listing details
- Price per square foot: $417/sqft
- Tax assessed value: $842,800
- Annual tax amount: $19,656
- Date on market: 4/14/2025
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