Property details
About 37-39 Main St
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.
Highlights
Summary
- Full Bathrooms: 4
- Basement: Yes
- Flooring Type: Vinyl, Wood
- Interior: Beamed Ceilings, Chefs Kitchen, High Ceilings, Primary Bathroom, Open Floorplan, Washer/Dryer Hookup
- Total Bedroom Count: 4
- Parking: On Street
- Architectural Style: Barndominium
- Heating: Natural Gas
- Cooling: Ductless
- List Price: $1,499,999
- Year Built: 1935
- Lot Size: 0.055 Acres
- MLS Number: 873541
- MLS Name: ONEKEY2
- Office Name: eXp Realty
- Office Phone: (888) 276-0630
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Price information
Property sales
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Tax history
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Nearby schools
3
Chester Elementary School
Public District KG-5
1.4 mi
•2 Herbert Dr
3
Goshen Intermediate School
Public District 3-5
4.8 mi
•13 McNally St
6
North Main Street School
Public District 2-5
4.8 mi
•212 N Main St
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $92,537. Typical income of Chester, NY residents is between $35k-100k annually. Residents typically live in single, no kids family. The most common level of education of people living in this area is post secondary degree.
How much money do the neighbors make?
What level of education do the neighbors have?
What types of families live nearby?
Are the neighbors home owners or renters?
How old are people in this area?
What do the neighbors do for fun?
NASCAR
Soccer
PGA/LPGA
Where do the neighbors shop?
Dick's Sporting Goods
Old Navy
Stein Mart
Where do the neighbors go to eat?
Arbys
Jimmy Johns
Cracker Barrel
What do the neighbors drive?
GMC
Lexus
Ram
What do the neighbors listen to?
Adult Hits
New Country
Oldies
Frequently asked questions
About 37-39 Main St
The listing price of 37-39 Main St property is $1,499,999.
The property 37-39 Main St is a multi located in Chester, New York, 10918.
Active Listing: 37-39 Main St is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 37-39 Main St are: Chester Elementary School (GreatSchools Rating 3/10), Goshen Intermediate School (GreatSchools Rating 3/10), North Main Street School (GreatSchools Rating 6/10), C J Hooker Middle School (GreatSchools Rating 4/10), Greenwood Lake Middle School (GreatSchools Rating 7/10), Washingtonville Middle School (GreatSchools Rating 4/10), Chester Academy (GreatSchools Rating 5/10), S S Seward Institute (GreatSchools Rating 5/10), Goshen Central High School (GreatSchools Rating 7/10).
The year of construction for 37-39 Main St is 1935.
This home is located at 37-39 Main St in Chester, NY and zip code 10918. Features: 4 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since June 5, 2025 and is currently priced at $1,499,999.
Over 3 listings were sold over their listed price in June 2025 in Chester, NY. In the same period over 3 listings were sold below the listed price and 2 listings were sold for the listed price. Between May and June 2025, Chester, NY real estate market has seen decrease in the number of listings by 7.5%. The median list price of listings available in June 2025 was $545,000, while the average time on the real estate market was 62 days.