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.
Active
Listed by:
Daire Gibney,
Barrett and Valley Associates Inc. 802-875-2323
Price cut: $50K (1/30)
$399,000
1397 Popple Dungeon Road, Chester, VT 05143
3beds
1,788sqft
Est.:
Single Family Residence
Built in 1900
3.3 Acres Lot
$381,000 Zestimate®
$223/sqft
$-- HOA
What's special
- 25 days |
- 4,476 |
- 186 |
Zillow last checked: 8 hours ago
Listing updated: January 30, 2026 at 06:08am
Listed by:
Daire Gibney,
Barrett and Valley Associates Inc. 802-875-2323
Source: PrimeMLS,MLS#: 5073930
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 3/4 bathrooms: 1
Heating
- Oil
Cooling
- None
Features
- Basement: Concrete,Concrete Floor,Unfinished,Interior Access,Interior Entry
Interior area
- Total structure area: 2,240
- Total interior livable area: 1,788 sqft
- Finished area above ground: 1,788
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Paved
- Garage spaces: 1
Features
- Levels: Two
- Stories: 2
- Waterfront features: River Front
- Frontage length: Road frontage: 800
Lot
- Size: 3.3 Acres
- Features: Country Setting
Details
- Parcel number: 14404511573
- Zoning description: Resiential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape
- Property subtype: Single Family Residence
Materials
- Wood Frame
- Foundation: Concrete
- Roof: Asphalt Shingle
Condition
- New construction: No
- Year built: 1900
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Private Available
- Utilities for property: Phone Available
Community & HOA
Location
- Region: Chester
Financial & listing details
- Price per square foot: $223/sqft
- Tax assessed value: $232,900
- Annual tax amount: $6,786
- Date on market: 1/14/2026
- Road surface type: Paved
Estimated market value
$381,000
$362,000 - $400,000
$3,082/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/30/2026 | Price change | $399,000-11.1%$223/sqft |
Source: | ||
| 1/14/2026 | Listed for sale | $449,000+277.3%$251/sqft |
Source: | ||
| 8/24/2001 | Sold | $119,000$67/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $232,900 |
| 2023 | -- | $232,900 |
| 2022 | -- | $232,900 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,345/mo
Principal & interest
$1547
Property taxes
$658
Home insurance
$140
Climate risks
Neighborhood: 05143
Nearby schools
GreatSchools rating
- 5/10Chester-Andover Usd #29Grades: PK-6Distance: 2.3 mi
- 7/10Green Mountain Uhsd #35Grades: 7-12Distance: 2.6 mi
Schools provided by the listing agent
- Elementary: Chester-Andover Elementary
- Middle: Green Mountain UHSD #35
- High: Green Mountain UHSD #35
- District: Two Rivers Supervisory Union
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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