376 Windward Hill, Dorset, VT 05251
Local realty services provided by:ERA Key Realty Services



376 Windward Hill,Dorset, VT 05251
$1,975,000
- 4 Beds
- 5 Baths
- 5,696 sq. ft.
- Single family
- Active
Listed by:andrea kaplan
Office:four seasons sotheby's int'l realty
MLS#:5036105
Source:PrimeMLS
Price summary
- Price:$1,975,000
- Price per sq. ft.:$346.73
About this home
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.
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Home facts
- Year built:1965
- Listing Id #:5036105
- Added:122 day(s) ago
- Updated:August 01, 2025 at 10:17 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:5
- Full bathrooms:4
- Living area:5,696 sq. ft.
Heating and cooling
- Heating:Baseboard, Electric, Hot Air, Radiant Ceiling
Structure and exterior
- Roof:Standing Seam
- Year built:1965
- Building area:5,696 sq. ft.
- Lot area:12.67 Acres
Schools
- High school:Choice
- Middle school:The Dorset School
- Elementary school:Dorset Elementary School
Utilities
- Sewer:Concrete, Septic
Finances and disclosures
- Price:$1,975,000
- Price per sq. ft.:$346.73
- Tax amount:$19,656 (2025)
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