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MLS ID KEY995223Last updated Oct 8, 2026

Single Family

4 Debbie Court

Pending · Chester Town · Orange County, NY 10918

Bedrooms
5 Beds
Bathrooms
6 Baths
Year built
1982
Est. monthly taxes
$1,745.47
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About this home

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.

Listing snapshot

Days on site
59 days
Listed on MLS
May 26, 2026
Full baths
5
Half baths
1
Annual property tax (MLS)
$20,945.59
Tax year
2024
Area source (MLS)
Public Records
Listing brokerage
Flag Realty Group
MLS ID
KEY995223
Last updated
Oct 8, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1982
Garage
Yes
Garage spaces
2
Parking
Attached
Water source
Well
Sewer
Septic Tank
Utilities
Electricity Available

Interior features

Basement
Finished, Full
Heating
Baseboard, Oil
Cooling
Central Air
Interior
First Floor Full Bath, Breakfast Bar, Chefs Kitchen, Eat-in Kitchen, Formal Dining, Granite Counters, Open Kitchen
Appliances
Dishwasher, Dryer, Freezer, Oven, Refrigerator, Stainless Steel Appliance(s)
Flooring
Hardwood

Exterior features

Architectural style
Colonial, Mini Estate
Construction materials
Frame
Private pool
No

Schools (MLS)

Elementary school
North Main Street
Elementary school district
Monroe-Woodbury
Middle school
Monroe-Woodbury Middle School
Middle school district
Monroe-Woodbury
High school
Monroe-Woodbury High School
High school district
Monroe-Woodbury

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. MLS status changed
  3. First seen on this site

Location

Chester Town · Orange County, NY 10918Show interactive map
4 Debbie Court

Chester Town · Orange County, NY 10918

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.