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"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.
DAYS ON MARKET | 1 | LAST UPDATED | 5/23/2025 |
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YEAR BUILT | 1851 | COUNTY | Orange |
STATUS | Active | PROPERTY TYPE(S) | Single Family |
Elementary School | Chester Elementary School |
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Jr. High School | Chester Academy-Middle/High School |
High School | Chester Academy-Middle/High School |
ADDITIONAL DETAILS | |
AIR | None |
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APPLIANCES | Dishwasher, Gas Water Heater, Oven, Range, Refrigerator |
BARN/EQUESTRIAN | Yes |
BASEMENT | Full, Walk-Out Access |
CONSTRUCTION | Brick |
FIREPLACE | Yes |
HEAT | Baseboard, Propane, Steam |
INTERIOR | Built-in Features, Crown Molding, Entrance Foyer, High Ceilings |
LOT | 9.68 acre(s) |
PARKING | Driveway |
SEWER | Public Sewer |
STORIES | 3+ |
STYLE | Colonial, Mini Estate |
TAXES | 30670 |
UTILITIES | Electricity Connected, Propane, Sewer Connected, Water Connected |
WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with Serhant LLC

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Date Last Updated: 5/23/25 9:04 PM PDT
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