1397 Popple Dungeon Road Chester, VT $ 399,000
1397 Popple Dungeon Road
$ 399,000
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1397 Popple Dungeon Road

Chester, VT, 05143
$ 399,000
Bedrooms3 Baths2.0 Sq 1,788

Monthly Estimate*

$ 2,457

Listed by Daire Gibney, Barrett and Valley Associates Inc., 802-380-5464, dgibney.bva@gmail.com
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Single Family Home for sale in Chester, VT

for $399,000 with 3 bedrooms and 2 full baths. This 1,788 square foot home was built in 1900 on a lot size of 3.3.

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.

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Single Family Active

Price

$ 399,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 0

Style

Cape

Lot Size

3.3

Year Built

1900

Town/City

Chester

County/Region

Windsor

MLS | Web ID

5073930

Features
Interior
Basement Description Concrete Concrete Floor Unfinished Interior Access
Basement Yes
Beds 3
Total Rooms 7
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General
Road Frontage Yes
Sewer Private Available
Heating Oil
Cooling None
Utilities Telephone Available
Roof Asphalt Shingle
Garage Yes
current use No
Flood Zone Unknown
Zoning Resiential
3/4 Baths 1
Full Baths 1
Half Baths 0
Bathrooms 2
Year Built 1900
Electric Circuit Breaker(s)
Style Cape
Stories Count 2
Construction Status Existing
Type Single Family
Auction No
Tax Year 2025
Status Detail 0
Covenants Unknown
Construction Materials Wood Frame
High School Green Mountain UHSD #35
City Chester
School District Two Rivers Supervisory Union
Seasonal No
Elementary School Chester-Andover Elementary
Middle School Green Mountain UHSD #35
DOM 17
Price Per Sq Ft Total AG 223.15
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Exterior
Lot Features Country Setting River Frontage
Driveway Paved
Lot Size Area 3.3
Water Source Drilled Well
Garage Capacity 1
Foundation Concrete
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* Excluded Features
List By
Daire Gibney

Listing Agent

Barrett And Valley Associates Inc.

Broker

(802) 380-5464

Phone

dgibney.bva@gmail.com

Email

Affordability Calculator

$2,457
Per Month
100%
0%
0%
Monthly Principal & Interest
$2,457
Monthly Property Taxes
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Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
1784476 Elementary School
1009082 Middle School
Green Mountain UHSD #35 High School High School
Pricing History
DatePricePrice ChangeDescription
1/30/2026$399,000 -11.14% Price Down
1/14/2026$449,000 Listed Price

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1397 Popple Dungeon Road, Chester, VT, 05143 is a Single Family Home for sale at $399,000 with 1,788 sqft and a lot size of 3.3. 1397 Popple Dungeon Road has 3 bedrooms, 2.0 baths, and was built in 1900. The property's zip code is 05143 which is in Chester, VT