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$575,000
New Listing

30 Upper Woods and Water Road
Winhall, VT 05340

For Sale|Single Family Residence|Active
4
Beds
3
Total Baths
1
Full Bath
2
Partial Baths
2,400
SqFt
$240
/SqFt
1965
Built
County:
VT-Bennington
Listing courtesy of Carrie Mathews of Winhall Real Estate
Call Now: 802-254-6400
Is this the listing for you? We can help make it yours.
802-254-6400
30 Upper Woods and Water Road30 Upper Woods and Water Road30 Upper Woods and Water Road30 Upper Woods and Water Road
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Monthly Payment (Est.)

$2,623
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Perched to capture breathtaking long-range views, this striking ski home offers an unforgettable vantage point of Magic Mountain and Stratton, with Bromley visible to the northwest—a daily reminder that some of Southern Vermont’s best skiing and outdoor adventure are just minutes away. With its cool, modern vibe and classic alpine character, the home perfectly blends style, comfort, and mountain living. The main living area is designed to showcase the spectacular scenery, with large windows that frame the surrounding mountains and fill the space with natural light. A wood-burning fireplace anchors the living room, creating the perfect spot to gather after a day on the slopes. Clean architectural lines, warm materials, and thoughtful updates give the home a contemporary yet welcoming feel throughout. Several upgrades and renovations provide comfort and efficiency for years to come. The property also includes a carport, providing convenient covered parking so you won’t have to clear snow off your car after a Vermont snowfall, along with space for skis and all the gear that comes with an active mountain lifestyle. Perfectly located just minutes from Bromley Mountain and a short drive to Stratton Resort, this home is ideally positioned for year-round recreation—from skiing and snowboarding in winter to hiking, biking, and golf in the warmer months. An added benefit of this property, if you opt to join, is that a Bromley Bond is available, providing driveway plowing, and garbage pickup services. Whether you are seeking a full-time residence or a retreat, this unique mountain home offers style, views, and an unbeatable Southern Vermont location. Closing to occur on or after June 15. The buyer may elect to close earlier and allow the seller to rent the property back until June 15. This property will transfer unfurnished.

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Listing Snapshot
Price 
$575,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
2,400 sqft
Total Baths 
3
Full Baths 
1
Partial Baths 
2
Lot Size 
4.48 Acres
Year Built 
1965
MLS® Number 
5078937
Status 
Active
Property Tax 
$6,283.54
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
3 hours agoListing updated with changes from the MLS®
4 hours agoListing first seen on site
General Features
Acres 
4.48
Garage 
Yes
Garage Spaces 
1
Number Of Stories 
2
Parking 
GravelCarport
Parking Spaces 
1
Property Sub Type 
Single Family Residence
Security 
Smoke Detector(s)
Sewer 
Septic Tank
SqFt Above 
1200
SqFt Below 
1200
SqFt Total 
2400
Style 
Chalet
Utilities 
Cable Available
Water Source 
PrivateWell
Zoning 
Residential
Interior Features
Appliances 
DryerRefrigeratorWasherDishwasherElectric Range
Basement 
Full
Cooling 
Wall Unit(s)
Electric 
Circuit Breakers
Fireplace 
Yes
Fireplace Features 
Wood Burning
Fireplaces 
1
Flooring 
BambooLaminateTile
Heating 
ZonedPropaneBaseboard
Interior 
Cathedral Ceiling(s)High Speed Internet
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Exterior Features
Construction Details 
StuccoWood Siding
Frontage 
325
Lot Features 
WoodedCul-De-Sac
Patio And Porch 
Deck
Roof 
Shingle
View 
Mountain(s)
Waterview 
Mountain(s)
Community Features
School District 
Bennington/Rutland
Schools
School District
Bennington/Rutland
Elementary School
Choice
Middle School
Choice
High School
Choice
Listing courtesy of Carrie Mathews of Winhall Real Estate



Copyright 2026, 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: 2026-03-11 08:48 PM UTC
Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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