- 4 beds
- 3 baths
- 3,955 sqft
- ~10 acre lot
- $328 per sqft
- 1851 build
- – on site
"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.
Last checked:
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Checking…
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Last updated Jun 8, 2025
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MLS# 866395 —
The Building
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Year Built:1851
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Basement:true
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Architectural Style:Colonial, Mini Estate
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Construction Materials:Brick
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Patio And Porch Features:Covered, Porch
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Building Area Units:Square Feet
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Building Area Total:5526
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Building Area Source:Public Records
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Attic:Partial,Partially Finished,Walkup
Interior
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Levels:Three Or More
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Living Area:3955
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Total Rooms:15
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Interior Features:Built-in Features, Crown Molding, Entrance Foyer, Formal Dining, High Ceilings, Original Details
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Fireplaces Total:2
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Fireplace:true
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Flooring:Hardwood
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Living Area Source:Public Records
Financial & Terms
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Lease Considered:false
The Property
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Lot Size Acres:9.68
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Property Type:Residential
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Property Subtype:Single Family Residence
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Property Attached:false
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Waterfront:false
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Water Access:No
Listing Agent
- Contact info:
- Agent phone:
- (845) 489-1544
- Office phone:
- (646) 480-7665
Taxes
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Tax Year:2025
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Tax Source:Municipality
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Tax Annual Amount:36065
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Included In Taxes:Trash
Beds
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Total Bedrooms:4
Baths
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Full Baths:2
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Half Baths:1
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Total Baths:3
The Listing
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Special Listing Conditions:None
Heating & Cooling
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Heating:Baseboard, Propane, Steam
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Cooling:None
Utilities
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Sewer:Public Sewer
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Utilities:Electricity Connected, Propane, Sewer Connected, Trash Collection Public, Water Connected
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Water Source:Public
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Electric Company:Orange & Rockland
Appliances
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Appliances:Dishwasher, Oven, Range, Refrigerator, Gas Water Heater
Schools
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High School:Chester Academy Middle/High School
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Elementary School:Chester Elementary School
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High School District:Chester
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Middle School:Chester Academy-Middle/High School
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Elementary School District:Chester
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Middle School District:Chester
The Community
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Association:false
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Senior Community:false
Parking
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Parking Features:Driveway
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Garage:false
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Carport:false
Extra Units
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Other Structures:Barn(s), Garage(s), Guest House, Outbuilding, Workshop
Monthly cost estimate

Asking price
$1,300,000
Expense | Monthly cost |
---|---|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$6,961
|
Taxes | $3,005 |
Insurance | $357 |
Utilities | $382 See report |
Total | $10,705/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
---|---|---|---|---|
5/23/25
May 23, 2025
|
Listed / Active | ONEKEY | $1,300,000 |