1397 Popple Dungeon Rd

Chester, VT 05143

$449,000
Price
3
Beds
1,788 Sq. Ft.
$251 / Sq. Ft.
1,788
Sq. Ft.
$251
per Sq. Ft.

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...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. Listed by Daire Gibney • Barrett and Valley Associates Inc.

Property Details for 1397 Popple Dungeon Road

Zoning
Resiential
LISTING UPDATED: 01/14/2026 08:41 PM

Property Details for 1397 Popple Dungeon Road

StatusActive
MLS #5073930
Days on Market8
Taxes$6,786 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1900
Lot Size3.30 AC / 143,748 SF
CountyWindsor County

Location

Listing Courtesy of Barrett and Valley Associates Inc.
Add your commute

Building Information for 1397 Popple Dungeon Road

Stories2Year Built1900Building Size-Lot Size3.30 AC / 143,748 SF

Payment Calculator

$2,754 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,188

Property Taxes

$566

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 1397 Popple Dungeon Road

Summary
Location and General Information
  • City: Chester
  • County: VT-Windsor
  • Latitude: 43.244674000000998
  • Longitude: -72.631264999999999
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05143
Taxes and HOA Information
  • SPAN Number: 144-045-11573
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 1.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Country Setting, River Frontage
  • Lot Size Acres: 3.3
  • Road Frontage Length: 800.0
Property and Assessments
  • Current Use: No
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: Unknown
  • PreConstruction: No
  • Resort: No
  • Surveyed: No
  • Year Built: 1900
Utilities
  • Electric: Circuit Breaker(s)
  • Sewer: Private Available
  • Water Source: Drilled Well
  • Utilities: Telephone Available
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Color: red
  • Construction Materials: Wood Frame
  • Roof: Asphalt Shingle
Interior Features
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Concrete, Concrete Floor, Unfinished, Interior Access
  • Heating: Oil
  • Cooling: None
  • Total Stories: 2

Property History for 1397 Popple Dungeon Road

DateEvent & SourcePriceAppreciation
Jan 14, 2026

Listed (Active)

New England Real Estate Network #5073930

$449,000—
DateEvent & SourcePrice
01/14/2026

Listed (Active)

New England Real Estate Network #5073930

$449,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1397 Popple Dungeon Road

Taxable ValueLand$46,600Additions$186,300Total$232,900
Tax Record2024$6,461 ($538 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,788 SqFtAbove Grade Finished SqFt1,788 SqFtLot Size143,748 SqFtStyleSingle Family ResidenceYear Built1900CountyWINDSORAPN(045) 412022Fireplace TypeHas Fireplace

Schools near 1397 Popple Dungeon Road

This home is within Green Mountain Unified School District.
Rating
School
Type
Grades
Distance
Chester-Andover Usd #29
Public - PK to 6
Green Mountain Uhsd #35
Public - 7 to 12
Rating
School
Distance
Chester-Andover Usd #29
PublicPK to 6

Green Mountain Uhsd #35
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1397 Popple Dungeon Road, Chester, VT 05143

1397 Popple Dungeon Road is a single family home for sale in Chester, VT 05143. This property was listed for sale on January 14, 2026 by Barrett and Valley Associates Inc., it's currently listed at $449,000. This listing's school district is Green Mountain Unified School District. Nearby schools include Chester-Andover Usd #29 and Green Mountain Uhsd #35. 1397 Popple Dungeon Road is a 3-bed, 2-bath, 1,788 sqft single family home built in 1900.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Barrett and Valley Associates Inc.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 01/22/2026 06:41 AM