Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
Listing photo for 37-39 Main Street, Chester, NY
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37-39 Main Street,

Chester, NY

$1,498,888

4 Beds
4 Baths
7,308 Sqft
0.06 Acres

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.

Facts & Features
MLS® # 873541
Price $1,498,888
Bedrooms 4
Bathrooms 4.00
Full Baths 4
Square Footage 7,308
Acres 0.06
Year Built 1935
Type Residential Income
Sub-Type Triplex
Style Barndominium
Status Active
MLS hgmls
Community Information
Address 37-39 Main Street
City Chester
County Orange
State NY
Zip Code 10918
Amenities
Utilities Natural Gas Available, Sewer Connected, Trash Collection Private, Water Available
Parking On Street
Is Waterfront No
Has Pool No
Interior
Interior Vinyl, Wood
Interior Features Beamed Ceilings, Chefs Kitchen, High Ceilings, Primary Bathroom, Open Floorplan, Washer/Dryer Hookup
Heating Natural Gas
Cooling Ductless
Has Basement Yes
Basement Full
Fireplace No
Exterior
Construction Frame
School Information
District Chester
Elementary Chester Elementary School
Middle Chester Academy-Middle/High School
High Chester Academy-Middle/High School
Additional Information
Date Listed June 5th, 2025
Days on Market 186
Short Sale No
RE / Bank Owned No
Listing Details
Listing Courtesy of eXp Realty
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Listing information last updated on December 8th, 2025 at 8:50pm EST.