37-39 Main Street Chester, NY $ 1,498,888
37-39 Main Street
$ 1,498,888
Share Save

37-39 Main Street

Chester, NY, 10918
$ 1,498,888
Bedrooms4 Baths4.0 Sq 7,308

Monthly Estimate*

$ 9,351

37-39 Main Street, Chester, NY 10918 - Image 1
37-39 Main Street, Chester, NY 10918 - Image 2
37-39 Main Street, Chester, NY 10918 - Image 3
37-39 Main Street, Chester, NY 10918 - Image 4
37-39 Main Street, Chester, NY 10918 - Image 5
37-39 Main Street, Chester, NY 10918 - Image 6
37-39 Main Street, Chester, NY 10918 - Image 7
37-39 Main Street, Chester, NY 10918 - Image 8
37-39 Main Street, Chester, NY 10918 - Image 9
37-39 Main Street, Chester, NY 10918 - Image 10
37-39 Main Street, Chester, NY 10918 - Image 11
37-39 Main Street, Chester, NY 10918 - Image 12
37-39 Main Street, Chester, NY 10918 - Image 13
37-39 Main Street, Chester, NY 10918 - Image 14
37-39 Main Street, Chester, NY 10918 - Image 15
37-39 Main Street, Chester, NY 10918 - Image 16
37-39 Main Street, Chester, NY 10918 - Image 17
37-39 Main Street, Chester, NY 10918 - Image 18
37-39 Main Street, Chester, NY 10918 - Image 19
37-39 Main Street, Chester, NY 10918 - Image 20
37-39 Main Street, Chester, NY 10918 - Image 21
37-39 Main Street, Chester, NY 10918 - Image 22
37-39 Main Street, Chester, NY 10918 - Image 23
37-39 Main Street, Chester, NY 10918 - Image 24
37-39 Main Street, Chester, NY 10918 - Image 25
37-39 Main Street, Chester, NY 10918 - Image 26
37-39 Main Street, Chester, NY 10918 - Image 27
37-39 Main Street, Chester, NY 10918 - Image 28

Multi-Family Home for sale in Chester, NY

for $1,498,888 with 4 bedrooms and 4 full baths. This 7,308 square foot home was built in 1935 on a lot size of 0.055.

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.

See more

Multi-Family Active

Price

$ 1,498,888

Bedrooms

4

Full Bath

4

Property Type

Multi-Family

Taxes

$ 12,067

Style

Barndominium

Lot Size

0.055

Year Built

1935

Town/City

Chester

County/Region

Orange

MLS | Web ID

873541

Features
Interior
Interior Amenities Beamed Ceilings Chefs Kitchen High Ceilings Primary Bathroom Open Floorplan Washer/Dryer Hookup
Basement Full
Flooring Vinyl Wood
Basement Features Full
Basement (Y/N) Y
Total Bedrooms 4
Total Baths 4
See more
General
Sewer Public Sewer
Heating Natural Gas
Cooling Ductless
Utilities Natural Gas Available Sewer Connected Trash Collection Private Water Available
Architectural Style Barndominium
Construction Materials Frame
Year Built 1935
Property Subtype Triplex
Tax Year 2024
Parcel Number 332201-102-000-0001-026.000-0000
Gross Income 111768
County Orange County
Operating Expense 11226
Insurance Expense 523
Property Type Residential Income
Garage Y/N N
Full Baths 4
High School Chester Academy-Middle/High School
City Chester Town
Senior Community Y/N N
High School District Chester
Number Of Units Total 4
Carport Y/N N
Elementary School Chester Elementary School
Property Attached Y/N Y
Tax Annual Amount 12067.42
Showing Instructions Please request 24/48 hours. Restaurant will be viewed first. Second look you can see each individual apartment.
Middle/Junior High School Chester Academy-Middle/High School
Trash Expense 153
Water Sewer Expense 125
Additional Parcels Y/N Y
Structure Type Barndominium
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Chester
Elementary School District Chester
Tax Assessed Value 170000
See more
Exterior
Parking Features On Street On Street
Water Source Public
Building Area Total 7308
Waterfront Y/N N
See more
Internal Only
Street Number 1 37
See more
* Excluded Features
List By
James Feldhaus

Listing Agent

Exp Realty

Broker

888-276-0630

Contact

Affordability Calculator

$10,357
Per Month
90%
10%
0%
Monthly Principal & Interest
$9,351
Monthly Property Taxes
$1,006
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
4100324 Elementary School
4100290 Middle School
Chester Academy-Middle/High School High School
Pricing History
DatePricePrice ChangeDescription
10/22/2025$1,498,888 -0.07% Price Down
6/5/2025$1,499,999 Listed Price

Map


See all

37-39 Main Street, Chester, NY, 10918 is a Multi-Family Home for sale at $1,498,888 with 7,308 sqft and a lot size of 0.055. 37-39 Main Street has 4 bedrooms, 4.0 baths, and was built in 1935. The property's zip code is 10918 which is in Chester, NY