Single Family Residence at 663 Depot Street, Chester

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51 photos

$390,000

Under contract

663 Depot Street

Chester, VT 05143

Listed by Betsy Adamovich · Real Broker LLC

Bedrooms

Bathrooms

N/A

Living area

N/A

Year built

1890

About this home

Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester’s Stone Village, the Grist Mill, and Smitty’s Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals.

Property details

MLS: Prime MLS
MLS #: 5086202
Property type: Single Family Residence
Subdivision: N/A
Status: Under contract
Days on market: 81
On market date: N/A
Stories: N/A
Total bathrooms: N/A
Garage spaces: 1
Parking spaces: N/A
Lot size: 1 acres

Location

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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary

Charlestown Primary School

9.01 mi away · Grades -1-5

Nearest school -- attendance-zone data not available here

5.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 217
Student:teacher ratio: 9.9:1
District: Fall Mountain Regional School District

Middle

Charlestown Middle School

8.8 mi away · Grades 6-8

Nearest school -- attendance-zone data not available here

5.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 146
Student:teacher ratio: 11.2:1
District: Fall Mountain Regional School District

High

None found nearby

Market position

How this listing compares to current activity in Chester, from live MLS data.

On the market 81 days -- 48 fewer days than Chester's current average of 129 days.

For reference, the median list price across 45 active listings in Chester right now is $270,000.

Mortgage calculator

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Home price

Down payment

Interest rate

Loan term

Adjust tax / insurance estimates

Property tax

% / yr

Home insurance

/mo

Est. monthly payment

$2,499/mo

$78,000 down

$312,000 loan

Principal & interest$2,024

Property tax (est.)$325

Home insurance (est.)$150

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Copyright 2026 PrimeMLS. 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 07/22/26.