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4 Debbie Court, Chester, NY 10918

Orange County

Key Facts

5Beds
6Baths
5,403Sq Ft
1982Year Built
5.40Lot (acres)
2Garage

Description

Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the expansive setting, inviting curb appeal, and peaceful surroundings that make this property truly special. Inside, the home features bright sun-filled living spaces, spacious entertaining areas, hardwood flooring, and a beautifully designed kitchen with abundant cabinetry, generous counter space, and an ideal layout for both everyday living and hosting guests. The warm and inviting family room with fireplace creates the perfect gathering space, while multiple spacious bedrooms and well-appointed baths provide comfort and flexibility for today’s lifestyle. Unique rustic-inspired bonus spaces add warmth, charm, and character throughout the home. Step outside to your own private outdoor oasis featuring expansive lawn space, pool area, multiple entertaining spaces, and scenic wooded surroundings offering year-round enjoyment and tranquility. A rare opportunity to own a property that offers privacy, character, and endless possibilities in one of the area’s most desirable locations. See it today and experience everything this exceptional home has to offer.

Property Information

Property Type

Residential

Sub-Type

Single Family Residence

Style

Colonial / Mini Estate

Year Built

1982

Living Area

5,403 sq ft

Lot Size

5.40 acres

Garage Spaces

2

Days on Market

42

MLS® Listing#

995223

Property Features

Interior

Breakfast BarEat-in KitchenGranite Counters

Appliances

DishwasherDryerFreezerOvenRefrigeratorStainless Steel Appliance(s)

Cooling

Central Air

Heating

BaseboardOil

Flooring

Hardwood

Basement

FinishedFull

Parking

Attached

Construction

Frame

Utilities

Electricity Available

Sewer

Septic Tank

Water Source

PrivateWell

Schools

Elementary:
North Main Street
Middle:
Monroe-Woodbury Middle School
High:
Monroe-Woodbury High School

Financial Details

Annual Taxes

$20,946

Assessed Value

$318,150

Parcel Number

332289-007-000-0001-067.000-0000

Affordability Calculator

$157,000

Estimated monthly payment

$4,178/mo

Principal $628,000 · Est. interest $876,116 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Chester, NY

$680,952
Median Listing Price
53
Median Days on Market
2,316
Median Sq Ft
$266
Median Price / Sq Ft
89
Active Listings
  • This home’s price is 15% above the area median.
  • Its price per sq ft is 45% below the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Chester, NY.

Location

Map showing the location of 4 Debbie Court, Chester, NY 10918

Points of Interest in Chester, NY

Showing the Chester area map.

Nearby Schools

  • Chester High School

    Secondary · 3.1 mi away

  • Monroe Woodbury Central School-Bus Transportation

    School · 3.3 mi away

  • Greenwood Lake Middle School

    Secondary · 3.3 mi away

  • Inspire

    School · 3.8 mi away

  • Gan Shalom Nursery School

    Elementary · 3.8 mi away

  • Creative Children Christian Preschool

    School · 3.8 mi away

  • Chester Academy

    School · 3.8 mi away

  • North Main Street School

    Elementary · 3.9 mi away

  • Chester Elementary School

    Elementary · 4.1 mi away

  • Sacred Heart School

    School · 4.1 mi away

  • Pine Tree Elementary School

    Elementary · 4.3 mi away

  • Kings Elementary School

    Elementary · 4.5 mi away

  • Sapphire Elementary School

    Elementary · 4.9 mi away

  • Joel Kiryas School District

    School · 5.2 mi away

  • Bais Rochel School

    School · 5.2 mi away

  • Florida Union Free School District

    School · 5.3 mi away

  • S S Seward Institute

    Secondary · 5.3 mi away

  • Kiryas Joel Village School

    Elementary · 5.3 mi away

  • Golden Hill Elementary School

    Elementary · 5.9 mi away

  • Orange-Ulster Boces

    School · 6.1 mi away

Commute Calculator

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Nearby Homes

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Similar Home Values

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Moving Cost Estimate

EXIT Agents in Chester

Listing Courtesy: Flag Realty Group - 8452050089

Presented by: Joseph Rosenfeld

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' 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 deemed reliable but not guaranteed. Copyright ©2026 OneKey MLS. All Rights Reserved
Fair Housing Notice

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by HGAR. MLS® Listing#995223. © 2026EXIT Realty®. All rights reserved.