Sold
Last Sold Price
6 beds3,892 sqft$107/sqft
595 Main St, Chester, VT 05143
Multi FamilyProperty Type
1.51 acresLot Size
1988Year Built
$107/sq ftPrice per sq ft

Description

Exciting Investment Opportunity! Discover this expansive 2-unit side-by-side duplex conveniently nestled on Main Street, yet cleverly set back for peaceful seclusion and views of the tranquil Williams River. Each generously sized unit spans 1,900 square feet and boasts three inviting bedrooms, each accompanied by its own ensuite bathroom—a luxurious touch ensuring comfort and privacy for all residents. Step inside to find spacious, light-filled interiors characterized by airy open floor plans, lofty...Exciting Investment Opportunity! Discover this expansive 2-unit side-by-side duplex conveniently nestled on Main Street, yet cleverly set back for peaceful seclusion and views of the tranquil Williams River. Each generously sized unit spans 1,900 square feet and boasts three inviting bedrooms, each accompanied by its own ensuite bathroom—a luxurious touch ensuring comfort and privacy for all residents. Step inside to find spacious, light-filled interiors characterized by airy open floor plans, lofty ceilings, and rustic exposed beams, creating an atmosphere of warmth and charm. The heart of each unit features a well-appointed kitchen, perfect for entertaining, while convenient in-unit laundry facilities add an extra layer of convenience to daily living. Embrace the serene outdoors from the expansive decks, offering ample space for dining, relaxation, and enjoying the soothing sounds of the river. This property presents an excellent opportunity for savvy investors or homeowners seeking supplemental income. Consider residing in one unit while leasing the other—a smart financial move that could offset your mortgage and expenses. Location-wise, you'll find yourself ideally situated within easy reach of the vibrant town green, with local amenities and Okemo and Stratton Mountain just a short drive away, outdoor adventure and recreation are always within reach. While the units could benefit from some cosmetic updates they are structurally sound and poised for the next chapter.

    Sold By Diamond Realty

    • Listed by: Gary Coger • Four Seasons Sotheby's Int'l Realty
    Listing closed: 04/15/2024 12:00 AM • Source: New England Real Estate Network, MLS#: 4985574

    Location

    Add your commute

    Payment Calculator

    $2,672 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $2,114

    Property Taxes

    $557

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

    Know your buying power with a preapproval and custom rate in minutes

    Rocket Mortgage1

    Property Information for 595 Main Street

    Property Details
    • Taxes: $6,685 / year
    • MLS Type: Multi Family
    • Zoning: res
    Building Information
    • Stories: 2
    • Residences: 2
    • Year Built: 1988
    • Lot Size: 1.51 AC / 65,775 SF
    Summary
    Location and General Information
    • City: Chester
    • County: VT-Windsor
    • Latitude: 43.265518500683065
    • Longitude: -72.606397169311506
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Street
    • Zip Code: 05143
    Taxes and HOA Information
    • SPAN Number: 144-045-10877
    • Tax - Gross Amount: $6,684.77
    • Tax Year: 2023
    • Taxes TBD: No
    School Information
    • School - High: Green Mountain UHSD #35
    • School - District: Chester School District
    • School - Elementary: Chester-Andover Elementary
    • School - Middle/Jr: Green Mountain UHSD #35
    Parking
    • Garage: No
    • Driveway: Dirt
    Property
    Lot Information
    • Lot - Sqft: 65776.0
    • Lot Features: Country Setting, Level, Major Road Frontage, River, River Frontage
    • Lot Size Acres: 1.51
    • Road Frontage Length: 130.0
    • Square Feet Apx Finished Above Grade: 3892.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Total: 5792.0
    • Square Feet Apx Total Finished: 3892.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 1900.0
    • Square Feet Apx Unfinished BG Source: Estimated
    Property and Assessments
    • Property Class: Multi-Family
    • Easements: No
    • Flood Zone: Unknown
    • Foundation: Poured Concrete
    • PreConstruction: No
    • Surveyed: No
    • Year Built: 1988
    Utilities
    • Electric: 200 Amp
    • Sewer: Public, Pump Up, Septic
    • Water Source: Public
    • Utilities: Cable - Available, Gas - LP/Bottle
    • Separate Utilities: Yes
    • Internet: Fiber Optic Internt Avail, High Speed Intrnt -Avail, Internet - Fiber Optic
    Interior and Exterior Features
    Exterior Features
    • Construction Materials: Wood Frame, Wood Siding
    • Features - Exterior: Deck, Gazebo, Outbuilding
    • Roads: Paved, Public
    • Roof: Shingle - Asphalt
    Interior Features
    • Appliances: Water Heater – Electric, Water Heater – Tank
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Crawl Space, Dirt, Unfinished
    • Total Full Baths: 3
    • Flooring: Carpet, Hardwood, Laminate, Manufactured
    • Heat Fuel: Electric, Gas - LP/Bottle
    • Heating: Electric, Gas Heater, Gas Heater - Vented, Hot Air, Wall Units
    • Cooling: None
    • Total Rooms Above Ground: 14
    • Total Stories: 2
    Multi Family
    Multi-Family Information
    • Total Units: 2
    • Total 1 BR Units: 0
    • Total 2 BR Units: 0
    • Total 3+ BR Units: 2
    Unit Information
    Unit 1
    • Unit 1 Style: 2 level duplex
    • Unit 1 Baths: 3
    • Unit 1 Bedrooms: 3
    • Unit 1 Apx Sqft: 1900.0
    • Unit 1 Rooms: 7
    • Unit 1 Info: Appliances Included, Ceiling Fan, Deck, Den, Dishwasher, Dryer, Electric, Fireplace - Wood, Heat - Gas, Primary BR w/ BA, Mudroom, Range - Electric, Refrigerator, Skylight, Washer, Water Heater
    Unit 2
    • Unit 2 Style: 2 level duplex
    • Unit 2 Baths: 3
    • Unit 2 Rooms: 7
    • Unit 2 Apx Sqft: 1900.0
    • Unit 2 Bedrooms: 3
    • Unit 2 Info: Appliances Included, Ceiling Fan, Deck, Den, Dishwasher, Dryer, Electric, Fireplace - Gas, Heat, Heat - Gas, Loft, Primary BR w/ BA, Range - Gas, Refrigerator, Skylight, Washer, Water Heater

    Property History for 595 Main Street

    DateEvent & SourcePriceAppreciation
    Apr 15, 2024

    Sold (Public Record)

    Public Record #1531139983

    $416,000

    +10.1% / yr

    Apr 15, 2024

    Sold

    New England Real Estate Network #4985574

    $416,000
    Apr 15, 2024

    Expired

    New England Real Estate Network #4985576

    DateEvent & SourcePrice
    04/15/2024

    Sold (Public Record)

    Public Record #1531139983

    $416,000

    +10.1% / yr

    04/15/2024

    Sold

    New England Real Estate Network #4985574

    $416,000
    04/15/2024

    Expired

    New England Real Estate Network #4985576

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

    Public Records for 595 Main Street

    Taxable ValueLand$42,700Additions$222,600Total$265,300
    Tax Record2025$4,952 ($413 / month)
    Home Facts
    Baths6Total Finished SqFt3,892 SqFtAbove Grade Finished SqFt3,892 SqFtLot Size65,776 SqFtStyleDuplexYear Built1988Year Renovated1988CountyWINDSORAPN(045) 565041.200

    Schools near 595 Main Street

    This home is within Green Mountain Unified School District.
    Rating
    School
    Type
    Grades
    Distance
    Public - PK to 6
    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.

    Similar Homes

    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. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

    Listing Courtesy of Four Seasons Sotheby's Int'l Realty

    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 09/01/2026 06:32 PM