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$1,975,000
135 Days On Site

376 Windward Hill
Dorset, VT 05251

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
5,696
SqFt
$347
/SqFt
1965
Built
County:
VT-Bennington
Listing courtesy of Andrea C Kaplan of Four Seasons Sotheby's Int'l Realty
Call Now: 802-254-6400
Is this the listing for you? We can help make it yours.
802-254-6400
376 Windward Hill376 Windward Hill376 Windward Hill376 Windward Hill
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Monthly Payment (Est.)

$9,011
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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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Listing Snapshot
Price 
$1,975,000
Days On Site 
135 Days
Bedrooms 
4
Inside Area (SqFt) 
5,696 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
12.67 Acres
Year Built 
1965
MLS® Number 
5036105
Status 
Active
Property Tax 
$19,656.62
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
a month agoListing updated with changes from the MLS®
a month agoPrice changed to $1,975,000
4 months agoListing first seen on site
General Features
Acres 
12.67
Garage 
Yes
Garage Spaces 
3
Number Of Stories 
2
Parking 
GravelHeated GarageDrivewayAttached
Parking Spaces 
3
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Above 
5696
SqFt Total 
5696
Style 
Contemporary
Utilities 
Cable Available
Water Source 
WellPrivate
Zoning 
Residential
Interior Features
Appliances 
DishwasherDryerRefrigeratorMicrowaveWasher
Electric 
200+ Amp ServiceCircuit BreakersGenerator
Fireplace 
Yes
Fireplaces 
2
Flooring 
BrickCarpetCeramic Tile
Heating 
BaseboardForced AirRadiant
Interior 
Vaulted Ceiling(s)Walk-In Closet(s)High Speed Internet
Bedroom 2 
Bedroom 3 
Bedroom 4 
Dining Room 
Exercise Room 
Family Room 
Great Room 
Kitchen 
Office/Study 
Primary Bedroom 
Workshop 
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Exterior Features
Construction Details 
Wood Siding
Lot Features 
Rolling Slope
Other Structures 
Gazebo
Patio And Porch 
DeckScreened
Road Frontage 
Private Road
View 
Mountain(s)
Waterfront Features 
Pond
Waterview 
Mountain(s)
Community Features
School District 
Taconic and Green Regional
Schools
School District
Taconic and Green Regional
Elementary School
Dorset Elementary School
Middle School
The Dorset School
High School
Choice
Listing courtesy of Andrea C Kaplan of Four Seasons Sotheby's Int'l Realty



Copyright 2025, PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Last checked: 2025-08-28 09:40 AM UTC
Neighborhood & Commute
Source: Walkscore
Community information and market data Powered by ATTOM Data Solutions. Copyright ©2019 ATTOM Data Solutions. Information is deemed reliable but not guaranteed.
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