List Price: $299,000 | $167 per sq.ft. | 3 Bedroom | 2 Bathroom | 2 Story Single Family Home
Price Change! Reduced by $150,000 down 50% on July 29th 2026

Listed Wednesday Jan 14, 2026 | MLS# 5073930
1397 Popple Dungeon Road Chester VT
Listed by Daire Gibney Barrett and Valley Associates Inc.
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.

Heating: Oil
Total Rooms: 7
Total Baths: 2
Full Baths: 1
3/4 Baths: 1
Total Bedrooms: 3

Building Info
Year Built: 1900
Type: Wood Frame
Total Structure SqFt.: 2240
Finished Sqft. Above Ground: 1788
Apx Below Grade Unfinished SqFt.: 452
Basement: Concrete | Concrete Floor | Unfinished | Interior Access

Exterior Info
Style: Cape
Exterior Color red
Roof: Asphalt Shingle

Utilities
Electric: Circuit Breaker(s)
Water: Drilled Well
Sewer: Private Available

Land Description:
Country Setting | River Frontage
Lot size: 3.3 acres
Zoned: Resiential
Surveyed: No
Flood Zone: Unknown
Seasonal: No
Road Frontage: 800
Driveway: Paved



Taxes $6,786
Assesed Value Not Reported
Schools
School District: Two Rivers Supervisory Union
Elementary School: Chester-Andover Elementary
Middle School: Green Mountain UHSD #35
High School: Green Mountain UHSD #35

© 2000-2026 Clerkin Agency Real Estate
NEREN Logo
565 Maple Street, White River Junction, Vermont. 05001 802-295-1355
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 August 1st, 2026

PLEASE NOTE: Both New Hampshire and Vermont law require brokers and agents to disclose at the “time of first business meeting, prior to any discussion of confidential information”, in New Hampshire’s case, and “first reasonable opportunity”, in Vermont’s case, the nature of the relationships brokers have or may have with customers and clients. Each state requires that a disclosure form be presented to consumers for their review and acknowledgment at the appropriate time. These forms can be accessed here:
VT: VERMONT REAL ESTATE COMMISSION MANDATORY CONSUMER DISCLOSURE FORM
NH: NEW HAMPSHIRE REAL ESTATE COMMISSION BROKERAGE RELATIONSHIP DISCLOSURE FORM