Chester, VT | 1397 Popple Dungeon Road

Christie's International Real Estate
$299,000
MLS#: 5073930
1,788
Sq Ft
3.3
Acres
2
Baths
3
Bedrooms
General Property Information
Property Status
Active Under Contract
Price
$299, 000
Property Type
Single Family
County
VT-Windsor
Agency / Brokerage
Daire Gibney
Barrett and Valley Associates Inc.
List Date
1/13/2026 7:00 PM
Acres
3.3
Year Built
1900
Bedrooms
3
Total Baths
2
Sq. Ft. (Total)
1,788
Tax Year
2025
Taxes
$6,786

Description

Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below, perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there’s room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery—rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont’s natural beauty. A property that offers privacy, water frontage, land, and mountain access—without giving up convenience.

Map

Interior Features
# Of Stories
2
Sq. Ft. (Total)
1,788
Sq. Ft. (Above Ground)
1,788
Sq. Ft. (Below Ground)
0
Sq. Ft. Unfinished
452
Rooms
7
Bedrooms
3
Baths
2
Heating
Oil
Basement Desc
Concrete, Concrete Floor, Unfinished, Interior Access

Town Market Snapshot

Source: Data provided by PrimeMLS, graph generated by Pall Spera Company

Exterior Features
Style of Residence
Cape
House Color
red
Time Share
No
Resort
No
Land Desc.
Country Setting
Roof Desc.
Asphalt Shingle
Driveway Desc.
Paved
Foundation Desc.
Concrete
Sewer Desc.
Private Available
Garage / Parking
Yes
Garage Spaces
1
Road Frontage
800
Zoning
Resiential
Elementary School
Chester-Andover Elementary
Middle School
Green Mountain UHSD #35
High School
Green Mountain UHSD #35

Affordability Estimate

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