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Residential Land with Home for Sale in Chester, Vermont

1397 Popple Dungeon Rd, Chester, VT 05143

$449,000
3.3 acres
Active
ago
Est $2,765/mo

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.

1,788
Sq feet
3
Beds
1
Full bath
1
3/4 bath
1900
Built

Location

Street address
1397 Popple Dungeon Rd
School district
Two Rivers Supervisory Union
Elevation
983 feet
Coordinates
43.2446, -72.6311

Property details

Acreage
3.3 acres
Zoning
Resiential
MLS #
NNEREN 5073930
Posted

Property taxes

2025
$6,786

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Exterior

Parking Spaces
1
Parking
Garage, Paved or Surfaced

Structure

Stories
2
Heating
Oil
Roof
Asphalt, Shingle

Interior

Room Count
7
Rooms
Basement, Bathroom x 2, Bedroom x 3

Nearby schools

NameLevelDistrictDescription
Chester-Andover ElementaryElementaryTwo Rivers Supervisory Union
Green Mountain UHSD #35MiddleTwo Rivers Supervisory Union
Green Mountain UHSD #35HighTwo Rivers Supervisory Union

Listing history

DateEventPriceChangeSource
Jan 14, 2026New listing$449,000NNEREN
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This 3.3-acre property is located at 1397 Popple Dungeon Rd in Chester, VT 05143. The property is available for sale for $449,000. It has a 1,788 sq ft 3 bedroom, 1 bath house built in 1900.

Checked 2 hours ago — Updated

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