Leave a Message

Thank you for your message. We will be in touch with you shortly.

90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
90 Main Street
VIEW PHOTOS
$1,300,000

90 Main Street

4 Beds 3 Baths 3,955 Sq.Ft.

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.

Share Property

Location

90 Main Street, Chester, NY 10918

Status

For Sale
image

Schedule a Showing

I would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Schedule a Showing

I would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.
Thank you for your interest in 90 Main Street, Chester, NY 10918. We are reviewing your request and will be in touch shortly!
Steven Wrobel Jr.

Steven Wrobel Jr.

TITLE

Licensed Real Estate Salesperson

Jake Garay

Jake Garay

TITLE

Team Lead, Associate Real Estate Broker

Property Amenities

Interior
Appliances Dishwasher, Oven, Range, Refrigerator, Gas Water Heater
Flooring Hardwood
Total Bedrooms: 4
Half Bathrooms: 1
Full Bathrooms: 2
Other Interior Features Built-in Features, Crown Molding, Entrance Foyer, Formal Dining, High Ceilings, Original Details
Area & Lot
Lot Area 9.68 Acres
Living area 3,955 Sq.Ft.
MLS® ID 866395
Year Built 1851
School District Chester
High School Chester Academy-Middle/High School
Middle School Chester Academy-Middle/High School
Elementary School Chester Elementary School
Architecture Styles Colonial, Mini Estate
Type Residential
Status For Sale
Exterior
Stories 3
Air conditioning None
Heat type Baseboard, Propane, Steam
Water Source Public
Sewer Public Sewer
Parking Driveway
Utilities Electricity Connected, Propane, Sewer Connected, Trash Collection Public, Water Connected
Finance
Sales Price $1,300,000
Real Estate Tax $36,065 yearly

Mortgage Calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.
$0,000 Your Payment 20 15 65
$0,000 Your Payment

Work With Me

To me, every relationship means so much more than a transaction. That's why I strive to build strong, lasting relationships with each and every client that goes beyond business. I understand what is at stake when finding your dream home, which is why we work closely with you every step of the way--making the otherwise overwhelming process completely stress-free.

Follow Us on Instagram