90 Main Street, Chester, NY 10918
Local realty services provided by:Better Homes and Gardens Real Estate Shore & Country Properties



90 Main Street,Chester, NY 10918
$1,300,000
- 4 Beds
- 3 Baths
- 3,955 sq. ft.
- Single family
- Active
Listed by:steven wrobel jr
Office:serhant llc.
MLS#:866395
Source:One Key MLS
Price summary
- Price:$1,300,000
- Price per sq. ft.:$235.25
About this home
"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.
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Home facts
- Year built:1851
- Listing Id #:866395
- Added:82 day(s) ago
- Updated:July 20, 2025 at 03:10 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:3
- Full bathrooms:2
- Half bathrooms:1
- Living area:3,955 sq. ft.
Heating and cooling
- Heating:Baseboard, Propane, Steam
Structure and exterior
- Year built:1851
- Building area:3,955 sq. ft.
- Lot area:9.68 Acres
Schools
- High school:Chester Academy-Middle/High School
- Middle school:Chester Academy-Middle/High School
- Elementary school:Chester Elementary School
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$1,300,000
- Price per sq. ft.:$235.25
- Tax amount:$36,065 (2025)
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