For Sale

Listed by Steven Wrobel and Jake Garay

Source: OneKey #866395

90 Main Street, Chester, NY, 10918

$1,300,000

4
3
5526 sq. ft.
9.68 ac.

SingleFam

30+ days on the market

What's around 90 Main Street

About this property

"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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