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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.
"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.
Overview
Property Type
Residential
Location
90 Main Street, Chester, NY 10918
MLS ID
866395
Listing Last Updated
5/23/2025 4:13 PM
Property Features & Amenities
Interior
Total Bedrooms
4
Full Bathrooms
2
Half Bathrooms
1
Flooring
Hardwood
Appliances
Dishwasher, Oven, Range, Refrigerator, Gas Water Heater
Other Interior Features
Built-in Features, Crown Molding, Entrance Foyer, Formal Dining, High Ceilings, Original Details
Exterior
Stories
3
Water Source
Public
Utilites
Electricity Connected, Propane, Sewer Connected, Trash Collection Public, Water Connected
Parking
Driveway
Heat Type
Baseboard, Propane, Steam
Air Conditioning
None
Sewer
Public Sewer
Details
Architecture Styles
Colonial, Mini Estate
Financial
Price
$1,300,000
Real Estate Tax
$36,065/yr
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