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30 Upper Woods And Water Road, Winhall, VT 05340

$575,000
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New to the Market Active Under Contract
BEDS4 BATHS3 full SQUARE FEET2,400 MLS#5078937
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family SCHOOLBennington-Rutland

Listing Courtesy of: Winhall Real Estate
Agency Phone: 802-297-1550
Associate Name: Carrie Mathews
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Property Description

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.

30 Upper Woods And Water Road | MLS# 5078937

This single family home located at 30 Upper Woods And Water Road, Winhall, VT 05340 is currently listed for sale with an asking price of $575,000. This property was built in 1965 and has 4 bedrooms and 3 full baths with 2400 sq. ft. Upper Woods And Water Road is located within the Bennington-Rutland school district. Search Winhall real estate on brianaburke.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Interior Stairs
Cooling: Mini Split
Garage: 1
Heating: Propane, Baseboard, Multi Zone
Home Style: Chalet
Lot Size: 4.48 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $6,283
Year Built: 1965

Amenities

Cathedral Ceiling
Dining Area
Wood Fireplace
1 Fireplace
Hearth
Kitchen/Dining
Living/Dining
Primary BR w/ BA
Natural Light
Deck

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer
Baths 3/4: 2
Baths Full: 1
Construction: Stucco Exterior, Wood Exterior
Construction Status: Existing
Days on Site: 6
Driveway: Dirt, Gravel
Electric: Circuit Breaker(s)
Equipment: Smoke Detector
Exterior: Stucco Exterior, Wood Exterior
Flood Zone: No
Flooring: Bamboo, Laminate, Tile
Foundation: Concrete
Lot: Country Setting, Mountain View, Ski Area, Wooded, Adjoins St/Nat'l Forest, Near Skiing
Number of Rooms: 10
Parking: Carport
Road Frontage: 325
Roads: Cul-de-Sac, Dead End
Sewer: Septic
Sq. Ft. Above Grade Finished: 1200
Sq. Ft. Below Grade Finished: 1200
Sq. Ft. Total Finished: 2400
Total Stories: 2
Water: Drilled Well, Private
Zoning: Residential

Local Schools

High School: Choice
Middle School: Choice
Elementary School: Choice
School District: Bennington-Rutland

Listed By / Shown By

Listed By

Agency Name: Winhall Real Estate
Agency Phone: 802-297-1550
Agent Name: Carrie Mathews

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Shown By

Agent Name: Briana Burke
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 1,970.99 per month $1,279.70 Principal & Interest $523.58 Property Tax $167.71 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/17/2026. The listing information on this page last changed on 03/17/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 03/17/2026 12:00:06 AM EST) or MLSPIN MLS (last updated Mon 03/16/2026 11:38:19 PM EST) or Prime MLS (last updated Mon 03/16/2026 11:33:23 PM EST) or MREIS (last updated Mon 03/16/2026 11:55:19 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data Last Updated 2026-03-16 23:33:23

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