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.
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
- 52 days |
- 301 |
- 14 |
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#: 873541
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
| Date | Event | Price |
|---|---|---|
| 10/22/2025 | Listed for sale | $1,498,888-0.1%$205/sqft |
Source: | ||
| 7/31/2025 | Listing removed | $1,499,999$205/sqft |
Source: | ||
| 6/5/2025 | Listed for sale | $1,499,999$205/sqft |
Source: | ||
Public tax history
Public tax history
Tax history is unavailable.BuyAbility℠ payment
Estimated monthly payment
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Neighborhood: 10918
Nearby schools
GreatSchools rating
- 3/10Chester Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 4/10Chester Academy Middle High SchoolGrades: 6-12Distance: 0.5 mi
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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