90 Main ST new Save Request In-Person Tour Request Virtual Tour
Chester,NY 10918
Key Details
Property Type Single Family Home
Sub Type Single Family Residence
Listing Status Active
Purchase Type For Sale
Square Footage 3,955 sqft
Price per Sqft $328
MLS Listing ID 866395
Style Colonial,Mini Estate
Bedrooms 4
Full Baths 2
Half Baths 1
Year Built 1851
Annual Tax Amount $30,670
Lot Size 9.680 Acres
Property Sub-Type Single Family Residence
Property Description
"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.
Location
State NY
County Orange County
Interior
Heating Baseboard,Propane,Steam
Cooling None
Flooring Hardwood
Fireplaces Number 2
Exterior
Parking Features Driveway
Utilities Available Electricity Connected,Propane,Sewer Connected,Trash Collection Public,Water Connected
Building
Sewer Public Sewer
Water Public
Structure Type Brick
Schools
Elementary Schools Chester Elementary School
Middle Schools Chester Academy-Middle/High School
High Schools Chester Academy-Middle/High School
Others
Special Listing Condition None