$1,300,000

90 Main St Chester, NY 10918

Estimated payment $10,075/month

Total Views 6,505
4 Beds
2.5 Baths
3,955 Sq Ft
$329 Price per Sq Ft

Highlights

  • Guest House
  • 9.68 Acre Lot
  • Wood Flooring
  • Barn
  • Colonial Architecture
  • 2 Fireplaces

About This Home

"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 Agent

STEVEN WROBEL JR.

Serhant LLC License #10401339020 Listed on: 05/23/2025

Serhant LLC

Co-Listing Agent

Jake Garay

Serhant LLC License #10301216829

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $36,065

Year Built

  • Built in 1851

Parking

  • Driveway

Home Design

  • Mini Estate
  • Colonial Architecture
  • Brick Exterior Construction

Interior Spaces

  • 3,955 Sq Ft Home
  • 3-Story Property
  • Built-In Features
  • Crown Molding
  • High Ceiling
  • 2 Fireplaces
  • Entrance Foyer
  • Formal Dining Room
  • Wood Flooring

Kitchen

  • Oven
  • Range
  • Dishwasher

Bedrooms and Bathrooms

  • 4 Bedrooms

Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House

Outdoor Features

  • Covered Patio or Porch
  • Separate Outdoor Workshop
  • Outbuilding

Schools

  • Chester Elementary School
  • Chester Academy-Middle/High School

Utilities

  • No Cooling
  • Baseboard Heating
  • Heating System Uses Steam
  • Heating System Uses Propane

Additional Features

  • 9.68 Acre Lot
  • Guest House
  • Barn

Home Details

Home Type

Single Family

Est. Annual Taxes

$36,065

Year Built

Built in 1851

Lot Details

0

Listing Details

  • Property Type: Residential
  • Architectural Style: Colonial, Mini Estate
  • Property SubType: Single Family Residence
  • Levels: Three Or More
  • Year Built: 1851
  • Co List Office Mls Id: KEYSERHNT01
  • Co List Office Phone: 646-480-7665
  • Carport Y N: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Appliances: Dishwasher, Oven, Range, Refrigerator, Gas Water Heater
  • Interior Amenities: Built-in Features, Crown Molding, Entrance Foyer, Formal Dining, High Ceilings, Original Details
  • Fireplaces: 2
  • Flooring: Hardwood
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Basement: Full, Walk-Out Access
  • Total Bedrooms: 4
  • Fireplace: Yes
  • Living Area: 3955
  • Basement YN: Yes

Exterior Features

  • Other Structures: Barn(s), Garage(s), Guest House, Outbuilding, Workshop
  • Construction Materials: Brick
  • Patio and Porch Features: Covered, Porch
  • Waterfront: No

Garage/Parking

  • Garage: No
  • Parking Description: Driveway

Utilities

  • Cooling: None
  • Heating: Baseboard, Propane, Steam
  • Sewer: Public Sewer
  • Utilities: Electricity Connected, Propane, Sewer Connected, Trash Collection Public, Water Connected
  • Water Source: Public

Condo/Co-op/Association

  • Senior Community: No
  • Association: No

Schools

  • Middle School: Chester Academy-Middle/High School

Lot Info

  • Lot Size Acres: 9.68
  • Building Area Total: 5526
  • Property Attached: No

Rental Info

  • Lease Considered: No

Tax Info

  • Tax Annual Amount: 36065
  • Tax Year: 2025

MLS Schools

  • Elementary School: Chester Elementary School
  • High School: Chester Academy-Middle/High School
  • Middle School District: Chester

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

Date Event Price Change Sq Ft Price
05/23/2025 05/23/25 For Sale $1,300,000 -- $329 / Sq Ft
Source: OneKey® MLS

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Source: OneKey® MLS

MLS Number: 866395

OneKey® MLS
New York Orange County Chester 10918

90 Main St, Chester, NY

This home is located at 90 Main St, Chester, NY 10918 and is currently priced at $1,300,000, approximately $328 per square foot. This property was built in 1851. 90 Main St is a home located in Orange County with nearby schools including Chester Elementary School and Chester Academy - Middle/High School.

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Copyright 2025 OneKey® MLS. All rights reserved.

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STEVEN WROBEL JR.
Listing Agent
STEVEN WROBEL JR.
Section Image
Serhant LLC
(845) 552-9670