90 Main ST, Chester, NY 10918 - MLS#866395 - Anthony Crews

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Anthony Crews

anthony@atcrewsnyc.com +1(917) 702-1951

$1,300,000

Est. payment - /mo

4 Beds

3 Baths

3,955 SqFt

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UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 3,955 sqft

Price per Sqft $328

MLS Listing ID 866395

Style Colonial,Mini Estate

Bedrooms 4

Full Baths 2

Half Baths 1

HOA Y/N No

Rental Info No

Year Built 1851

Annual Tax Amount $30,670

Lot Size 9.680 Acres

Acres 9.68

Property Sub-Type Single Family Residence

Source onekey2

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.

Location

State NY

County Orange County

Rooms

Basement Full, Walk-Out Access

Interior

Interior Features Built-in Features, Crown Molding, Entrance Foyer, Formal Dining, High Ceilings, Original Details

Heating Baseboard, Propane, Steam

Cooling None

Flooring Hardwood

Fireplaces Number 2

Fireplace Yes

Appliance Dishwasher, Oven, Range, Refrigerator, Gas Water Heater

Exterior

Parking Features Driveway

Utilities Available Electricity Connected, Propane, Sewer Connected, Trash Collection Public, Water Connected

Garage false

Building

Sewer Public Sewer

Water Public

Level or Stories Three Or More

Structure Type Brick

Schools

Elementary Schools Chester Elementary School

Middle Schools Chester Academy-Middle/High School

High Schools Chester Academy-Middle/High School

Others

Senior Community No

Special Listing Condition None

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Listed by Serhant LLC

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Anthony Crews

+1(917) 702-1951

Broker

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90 Main ST Chester, NY 10918

Anthony Crews

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

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