90 Main St

Chester, NY 10918
  • $1,300,000

    Price
  • 4

    Bed
  • 3

    Bath
  • 3,955

    SqFt

About the Listing SERHNT01 - 55072,33024

"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.

Listing Highlights for 90 Main St

Status Active
Days on Site 106
Property Type Residential
MLS ® 866395
Year Built 1851
Total Square Footage 3,955
Lot/Acreage 9.68

Interior Details

  • Bedrooms: 4
  • Bathrooms: 2 Full / 1 Half
  • Appliances: Dishwasher, Oven, Range, Refrigerator, Gas Water Heater
  • Air Cond:
  • Heating: Baseboard,Propane,Steam
  • Fireplaces: 2
  • Floor: Hardwood
  • Above Ground Sq Ft:
  • Below Ground Sq Ft: n/a
  • Basement: Full,Walk-Out Access
  • Other: Built-in Features,Crown Molding,Entrance Foyer,Formal Dining,High Ceilings,Original Details
  • Water: Public

Exterior Details

  • Lot Description: No Waterfront
  • Garage Capacity: N/A
  • Roof:
  • Others:
  • Sewer: Public Sewer
  • Parking Features: Driveway

Financial Details

  • Tax Amount: $36,065
  • Taxes w/Assessments: N/A
  • Tax/Property ID: N/A
  • Tax Year: N/A

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90 Main St Chester, NY 10918

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Originating MLS: onekey2

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