1397 Popple Dungeon Road

Active Under Contract

$299,000

3 beds2 baths1,788 sqft$167/sqft

1397 Popple Dungeon Rd, Chester, VT 05143

Est: $2,085/moGet pre-approved

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.

LISTING UPDATED: 08/10/2026 07:15 PM

Listed by Daire Gibney • Barrett and Valley Associates Inc.

Property Details for 1397 Popple Dungeon Road

Status

Active Under Contract

MLS #

5073930

Days on Market

195

Taxes

$6,786 / year

HOA Fees

Condo/Co-op Fees

Property Type

Single Family

MLS Type

Residential / Single Family

Year Built

1900

Lot Size

3.30 AC / 143,748 SF

County

Windsor County

Waterfront Property

Zoning

Resiential

Location

Homepage
VT
Windsor County
Chester
05143
1397 Popple Dungeon Rd

Listing Courtesy of Barrett and Valley Associates Inc.

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Building Information for 1397 Popple Dungeon Road

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

Payment Calculator

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$2,085 per month

30 year fixed, 6.55% Interest

Principal and Interest

$1,520

Property Taxes

$566

HOA Dues

The Payment Calculator is for illustrative purposes only.

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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

Virtual Tour

Property Panorama Virtual Tour: https://tour.neren.com/1397-Popple-Dungeon-Road-Chester-VT-05143/unbranded

Property

Lot Information

Lot Features: Country Setting
Lot Size Acres: 3.3

Road Frontage Length: 800.0
Total Finished Area: 1788.0
Above Grade Finished Area: 1788.0
Above Grade Finished Area Source: Public Records
Above Grade Unfinished Area: 0.0
AboveGradeUnfinishedAreaSource: Public Records
Below Grade Finished Area: 0.0
Below Grade Finished Area Source: Public Records
Below Grade Unfinished Area: 452.0
BelowGradeUnfinishedAreaSource: Public Records
Lot Size Square Feet: 143748.0
Total Area: 2240.0

Property and Assessments

Property Class: Residential
Property Type: Single Family

Flood Zone: Unknown
PreConstruction: No
Resort: No
Surveyed: No
Year Built: 1900
School District: Two Rivers Supervisory Union
High School: Green Mountain UHSD #35
Middle/Jr School: Green Mountain UHSD #35
Elementary School: Chester-Andover Elementary

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
Rooms Total: 7
Bathrooms Full: 1
Bathrooms Half: 0
Bathrooms One Quarter: 0
Bathrooms Three Quarter: 1
Bedrooms Total: 3
Bathrooms Total: 2

Property History for 1397 Popple Dungeon Road

Date	Event & Source	Price	Appreciation
Aug 8, 2026	Active Under Contract New England Real Estate Network #5073930		—
Jan 14, 2026	Temporarily Off Market New England Real Estate Network #5073930		—
Jan 14, 2026	Listed (Active) New England Real Estate Network #5073930	$449,000	—

Date	Event & Source	Price
08/08/2026	Active Under Contract New England Real Estate Network #5073930	—
01/14/2026	Temporarily Off Market New England Real Estate Network #5073930	—
01/14/2026	Listed (Active) New England Real Estate Network #5073930	$449,000

For completeness, we 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 SqFtUnfinished Basement SqFt452 SqFtLot Size143,748 SqFtStyleSingle Family ResidenceYear Built1900Year Renovated1900CountyWINDSORAPN(045) 412022

Schools near 1397 Popple Dungeon Road

This home is within Green Mountain Unified School District.


Rating	School	Type	Grades	Distance
6/10	Chester-Andover Usd #29	Public - Serves this home	PK to 6	2.3 mi
7/10	Green Mountain Uhsd #35	Public - Serves this home	7 to 12	2.6 mi


Rating	School	Distance
6/10	Chester-Andover Usd #29 PublicPK to 6 Serves this home	2.3 mi
7/10	Green Mountain Uhsd #35 Public7 to 12 Serves this home	2.6 mi

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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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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 08/19/2026 12:13 PM

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