REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your agent will contact you to discuss available opportunities.

In-PersonVirtual Tour

Fri

Jul

Sat

Jul

Sun

Jul

Nikki Douglass

nikkidouglass@kw.com +1(603) 557-0834

Listed by Andrea C Kaplan • Four Seasons Sotheby's Int'l Realty

$ 1,975,000

Est. payment -/mo

Save

Price Dropped by $400K

376 Windward HL Dorset, VT 05251

4 Beds

5 Baths

5,696 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family

Listing Status Active

Purchase Type For Sale

Square Footage 5,696 sqft

Price per Sqft $346

MLS Listing ID 5036105

Bedrooms 4

Full Baths 4

Half Baths 1

Construction Status Existing

Year Built 1965

Annual Tax Amount $19,656

Tax Year 2025

Lot Size 12.670 Acres

Acres 12.67

Property Sub-Type Single Family

Property Description

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.

Location

State VT

County Vt-bennington

Area Vt-Bennington

Zoning Residential

Interior

Cooling Other

Flooring Brick, Carpet, Ceramic Tile, Wood

Exterior

Garage Spaces 3.0

Utilities Available Cable Available, Propane, Telephone Available

Roof Type Standing Seam

Building

Story 2

Sewer Concrete, Septic

Architectural Style Contemporary

Construction Status Existing

Schools

Elementary Schools Dorset Elementary School

Middle Schools The Dorset School

High Schools Choice

School District Taconic And Green Regional

Nikki Douglass

Lead Agent/CEO | License ID: 059216

+1(603) 557-0834

Nikki Douglass

376 Windward HL Dorset, VT 05251

Key Details

Location

Interior

Exterior

Building

Schools

GET MORE INFORMATION

Go tour this home

376 Windward HL