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For sale
  • $1,498,888

    37-39 Main Street, Chester, NY 10918

    4beds
    7,308sqft
    Triplex, Multi Family
    Built in 1935
    -- sqft lot
    $-- Zestimate®
    $205/sqft
    $-- HOA

    What's special

    Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank Street Nestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades. The property features: • Fully Leased Commercial Space: Home to the popular Rustic Wheelhouse Restaurant, a well-established local favorite offering consistent foot traffic and long-term stability. • Three Leased Apartments: Spacious and updated residential units providing reliable rental income. • Bonus Rear Lot at 9 Bank Street: Included with the purchase, this additional parcel offers endless potential—ideal for building a garage, apartment, patio, or deck to further enhance the value and utility of the property. • Ample Municipal Parking: Convenient and plentiful public parking surrounds the property, ensuring ease of access for tenants, patrons, and guests. This historic gem is located on Main Street, within walking distance to shops, parks, and community amenities. Whether you’re seeking a turn-key investment or a hybrid commercial-residential property in a thriving village setting, 37-39 Main Street & 9 Bank Street deliver charm, income, and growth potential. Don’t miss your chance to own a piece of Chester’s history—fully updated and income-producing from day one.
    52 days
    |
    301
    |
    14
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    Zillow last checked: 8 hours ago

    Listing updated: October 28, 2025 at 11:11am

    Listing by:

    eXp Realty 888-276-0630,

    James Feldhaus 845-248-8008,

    Peter Panagiotis Kontrafouris 973-318-1484,

    eXp Realty

    Source: OneKey® MLS,MLS#: 873541MLS Logo

    Tour with a local agent

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 4
    • Full bathrooms: 4
    Heating
    • Has Heating (Unspecified Type)
    Cooling
    • Ductless
    Appliances
    • Laundry: Washer/Dryer Hookup, In Unit
    Features
    • Beamed Ceilings, Chefs Kitchen, Primary Bathroom, Open Floorplan
    • Flooring: Vinyl, Wood
    • Basement: Full
    • Attic: Finished
    Interior area
    • Total structure area: 7,308
    • Total interior livable area: 7,308 sqft

    Property

    Parking
    • Parking features: On Street
    • Has uncovered spaces: Yes
    Lot
    • Size: 2,394 Square Feet
    Details
    • Parcel number: 3322011020000001026.0000000
    • Special conditions: None

    Construction

    Type & style
    • Home type: MultiFamily
    • Property subtype: Triplex, Multi Family
    • Attached to another structure: Yes
    Condition
    • Year built: 1935

    Utilities & green energy

    • Gas: Separate Gas Meters: 4
    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: Natural Gas Available, Sewer Connected, Trash Collection Private, Water Available

    Community & HOA

    Location
    • Region: Chester

    Financial & listing details

    • Price per square foot: $205/sqft
    • Tax assessed value: $170,000
    • Annual tax amount: $12,067
    • Date on market: 6/5/2025
    • Cumulative days on market: 108 days
    • Listing agreement: Exclusive Right To Sell

    Estimated market value

    Not available

    Estimated sales range

    Not available

    Not available

    Price history

    Price history
    DateEventPrice
    10/22/2025Listed for sale$1,498,888-0.1%$205/sqft
    Source: OneKey® MLS #873541 Report a problem
    7/31/2025Listing removed$1,499,999$205/sqft
    Source: OneKey® MLS #873541 Report a problem
    6/5/2025Listed for sale$1,499,999$205/sqft
    Source: OneKey® MLS #873541 Report a problem

    Public tax history

    Public tax history
    Tax history is unavailable.

    BuyAbility℠ payment

    Estimated monthly payment
    All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
    HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
    Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
    See how much you could borrow to make a competitive offer.

    Boost your down payment with 6% savings match

    Earn up to a 6% match & get a competitive APY with a *. Zillow has partnered with to help get you home faster.

    Learn more*Terms apply. Match provided by Foyer. Account offered by Pacific West Bank, Member FDIC.

    Climate risks

    Neighborhood: 10918

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Chester Elementary School
    • Middle: Chester Academy-Middle/High School
    • High: Chester Academy-Middle/High School

    Source: OneKey® MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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