Presented by CS Realty Request Showing Print Listing

Mortgage Calculator

Down Payment
Length (years)
Rate (percent)
Single Family House in Orange County
MLS Number866395
Address90 Main Street, Chester, NY 10918 show map
Price$1,300,000 show mortgage calculator
Acres0
Bedrooms4
Bathrooms2 / 1
Year Built1851
Est. Sq. Footage3955
Elementary SchoolChester Elementary School
Jr High-Middle SchoolChester Academy-Middle/High School
High SchoolChester Academy-Middle/High School
Estimated Taxes$36,065
HOA Fees
Level 1
Level 2
Level 3
Remarks

"The House on the Hill" Proudly offered for the first time in over 70 years. This expansive and character-rich home overlooks the heart of the village while offering nearly 10 acres of space, privacy, and endless potential. Set across three separate parcels totaling 9.68 acres, the property features a main house with approximately 4,000 sq ft, a charming 2-bedroom guest cottage, a large dairy barn, and multiple additional outbuildings—perfect for storage, hobbies, or future repurposing. The main residence is a classic 4-bedroom, 2.5-bath old-style home, full of original details and thoughtful design. From the moment you step onto the covered front porch, you’re greeted with panoramic views and a sense of timeless charm. Inside, the first floor offers high ceilings, hardwood floors, a wood-burning fireplace, multiple living rooms, and an eat-in kitchen with space to gather. Two separate staircases lead upstairs to four bedrooms and two full bathrooms, along with a bonus space. A walk-up third floor includes two additional rooms that can serve as offices, playrooms, or guest quarters. The walk-out basement features a second fireplace, a built-in bar, and direct access to a sunken courtyard—a unique and private setting for entertaining or relaxing outdoors. The guest cottage is ideal for extended family, visitors, or rental income, offering 2 bedrooms, 1 full bath, and its own private space away from the main home. Outside, the sprawling front lawn, mature trees, and open acreage provide both seclusion and a sense of grandeur. Whether you're dreaming of a small farm, multigenerational living, or simply a private escape with room to grow, this property is a rare find with deep roots and lasting appeal. Conveniently located just minutes from shops, schools, parks, and major commuter routes, this is an incredible opportunity to own a storied piece of Chester history—with the space and structure to shape your future.

Amenities

Porch

This listing is Courtesy of Serhant LLC ().

Request a Showing - Make an Appointment - More Information
(917) 921-4934

Please use the form below to contact us. Thank you - CS Realty & Relocation Services. "Brokers of Better Rentals & Residences since 1986."

Subject
Your Name
Email Address
Phone Number--
Preferred Showing Time
Preferred Showing Date
Question or Comment
You will be contacted by a buyer's agent who will represent you on this listing.