Listed by Gary Coger • Four Seasons Sotheby's Int'l Realty. Bought with Diamond Realty.
Off Market Apr 2024 for $416K
$602,026
Est. refi paymentEst. refi$2,673/mo
6
bd
•
3 ba
•
3,892
sq ft
595 Main St, Chester, VT 05143
About this home
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.
Multi-familyProperty Type
1988Year Built
1.51 acresLot Size
$155Est. Price/Sq.Ft.
Listed by Gary Coger• Four Seasons Sotheby's Int'l Realty
Enjoy privacy with this large two family that is within walking distance to downtown Chester! Possible retail opportunities with the barn near the street, this property has loads of potential. Live on one side, rent the other. Babbling brook to listen to off the back deck, peaceful and serene. Like to ski, Okemo and Stratton a stones throw away.
Public Records
Jun 3, 2004
Sold
$273,000
$70/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$4,952 (+4.8%)
$42,700 + $222,600
$265,300
2024
$4,726 (+12.2%)
$42,700 + $222,600
$265,300
2023
$4,212 (−34.2%)
$42,700 + $222,600
$265,300
2022
$6,405 (−2.8%)
$46,000 + $222,600
$268,600
2021
$6,591 (+4.0%)
$46,000 + $222,600
$268,600
2020
$6,335 (+13.2%)
$46,000 + $222,600
$268,600
2019
$5,598 (+2.0%)
$61,000 + $205,700
$266,700
2018
$5,489 (+2.0%)
$61,000 + $205,700
$266,700
2016
$5,383 (−2.6%)
$61,000 + $205,700
$266,700
2015
$5,526
$61,000 + $205,700
$266,700
2013
$121,900 + $353,200
$475,100
Tax history for 595 Main St
Year
Property tax
Land + Additions
Assessment*
2025
$4,952 (+4.8%)
$42,700 + $222,600
$265,300
2024
$4,726 (+12.2%)
$42,700 + $222,600
$265,300
2023
$4,212 (−34.2%)
$42,700 + $222,600
$265,300
2022
$6,405 (−2.8%)
$46,000 + $222,600
$268,600
2021
$6,591 (+4.0%)
$46,000 + $222,600
$268,600
2020
$6,335 (+13.2%)
$46,000 + $222,600
$268,600
2019
$5,598 (+2.0%)
$61,000 + $205,700
$266,700
2018
$5,489 (+2.0%)
$61,000 + $205,700
$266,700
2016
$5,383 (−2.6%)
$61,000 + $205,700
$266,700
2015
$5,526
$61,000 + $205,700
$266,700
2013
$121,900 + $353,200
$475,100
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
6
Baths
6
Stories
—
Lot width
—
Lot depth
—
Lot size
1.51 Acres
Year renovated
—
Sq. Ft.
3,892
Year built
1988
Style
Multi-Family (2-4 Unit)
County
Windsor County
APN
14404510877
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 2, 2026.
Property details
Interior
Basement Information
Basement: Yes
Basement Access: Interior
Equipment & Appliance Information
Appliances: Water Heater – Electric, Water Heater – Tank
Multi-Unit Information
Total Units: 2
# of 3+ Bedroom Units: 2
# of Baths (full): 3
Exterior Features: Deck, Gazebo, Outbuilding
Sewer: Public, Pump Up, Septic
Electric: 200 Amp
Foundation: Poured Concrete
Roof: Shingle - Asphalt
Driveway: Dirt
Heating: Electric, Gas Heater, Gas Heater - Vented, Hot Air, Wall Units