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$445,000

Listing Price

6beds

3baths

4,265sqft

19,166sqft lot

81 Main St, Chester, VT 05143

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  • Full foreclosure details

  • Home value, equity and ownership info

  • Find homes priced below market

  • Get full access with a FREE Account

Already a member?

For Sale

Off Market

Single Family

Home type

104.34

Price / sqft

1880

Year built

Home Details

Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont o

Interior Details

Square Feet
  • 4265

Bedrooms
  • 6

Bathrooms
  • 3

Heating
  • Has Heating:

    Yes

  • Heating Type:

    Forced Air With Air Conditioning

Cooling
  • Has Cooling:

    No

  • Cooling Type:

    N/A

Fuel
  • Has Fuel:

    No

  • Fuel Type:

    N/A

Basement
  • Has Basement:

    No

  • Basement Type:

    Basement (unspecified)

Flooring
  • Has Flooring:

    No

  • Flooring Type:

    N/A

Fireplace
  • Has Fireplace:

    Yes

  • Fireplace Type:

    N/A

Property Details

Lot Size
  • 19166

Water
  • No

Sewer
  • No

Parking
  • Type:

    N/A

  • Location:

    N/A

  • Status:

    N/A

  • Number of Spaces:

    N/A

Deck
  • N/A

Patio
  • N/A

Fence
  • N/A

Pool
  • N/A

Porch
  • N/A

Stoop
  • N/A

Breezeway
  • N/A

Construction Details

Number of Stories
  • 2

Style
  • N/A

Exterior
  • Wood Siding

Foundation
  • N/A

Roof
  • N/A

Roofing Material
  • Slate

Tax History

Year

Amount

Land

Improvement

Percent Change

Assessment

2019

$7,640

$77,600

$286,400

--%

$364,000

2018

$7,491

$77,600

$286,400

--%

$364,000

2017

$7,204

$77,600

$286,400

--%

$364,000

2016

$7,346

$77,600

$286,400

--%

$364,000

2015

$7,543

$77,600

$286,400

--%

$364,000

2011

$797

$77,600

$348,400

--%

$426,000

percent-home-icon

Average Home Price in 05143

Nearby Properties

Zip Code

Price

Bed

Bath

Sqft

Lot

Sold Date

$445,000

6 Beds

3 Baths

4,265 Sqft

19,166 Lot (sqft)

Sold 10/18/2026

percent-home-icon

Calculators

Mortgage

Mortgage Calculator

Calculate your monthly mortgage payments.
Household Income
70,000
$
Home price
445,000
$
Down payment
89,000
$
Mortgage Rate
6.5
%
Loan Term
Property Tax Rate
1.1
%
Homeowner's Insurance (Annual)
2,670
$
HOA (Monthly)
0
$
PMI
0
$
$2,881
Your Payment
Total Monthly Payment:$2,881
Percent of Income:49%
Affordable:No

Details for 81 MAIN ST

Property Debt

Foreclosure Contact Details

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