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.
For sale
Price cut: $14K (6/4)
$785,000
4 Debbie Court, Chester, NY 10918
5beds
5,403sqft
Single Family Residence, Residential
Built in 1982
5.4 Acres Lot
$-- Zestimate®
$145/sqft
$-- HOA
What's special
- 58 days |
- 3,680 |
- 314 |
Zillow last checked:
Listing updated:
Listed by:
Flag Realty Group 845-205-0089,
Joseph Rosenfeld 845-205-0089
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 995223
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Heating
- Baseboard, Oil
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Freezer, Oven, Refrigerator, Stainless Steel Appliance(s)
Features
- First Floor Full Bath, Breakfast Bar, Chefs Kitchen, Eat-in Kitchen, Formal Dining, Granite Counters, Open Kitchen
- Flooring: Hardwood
- Basement: Finished,Full
- Attic: Full
Interior area
- Total structure area: 5,403
- Total interior livable area: 5,403 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Garage spaces: 2
Lot
- Size: 5.4 Acres
Details
- Parcel number: 3322890070000001067.0000000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Mini Estate
- Property subtype: Single Family Residence, Residential
Materials
- Frame
Condition
- Year built: 1982
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Electricity Available
Community & HOA
HOA
- Has HOA: No
Location
- Region: Chester
Financial & listing details
- Price per square foot: $145/sqft
- Tax assessed value: $318,150
- Annual tax amount: $20,945
- Date on market: 5/26/2026
- Cumulative days on market: 160 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/4/2026 | Price change | $785,000-1.8%$145/sqft |
Source: | ||
| 5/26/2026 | Listed for sale | $799,000$148/sqft |
Source: | ||
| 5/4/2026 | Listing removed | $799,000$148/sqft |
Source: | ||
| 4/23/2026 | Price change | $799,000-4.9%$148/sqft |
Source: | ||
| 4/12/2026 | Price change | $840,000-1.2%$155/sqft |
Source: | ||
| 2/18/2026 | Listed for sale | $849,999+0.1%$157/sqft |
Source: | ||
| 1/26/2026 | Listing removed | $849,000$157/sqft |
Source: | ||
| 12/22/2025 | Price change | $849,000-0.1%$157/sqft |
Source: | ||
| 12/16/2025 | Listed for sale | $850,000+59.5%$157/sqft |
Source: | ||
| 8/21/2025 | Sold | $533,000-23.7%$99/sqft |
Source: Public Record Report a problem | ||
| 6/29/2025 | Price change | $699,000-0.1%$129/sqft |
Source: | ||
| 6/27/2025 | Price change | $699,999-12.5%$130/sqft |
Source: | ||
| 6/24/2025 | Listed for sale | $799,999+2185.7%$148/sqft |
Source: | ||
| 8/21/2019 | Sold | $35,000-89.8%$6/sqft |
Source: Public Record Report a problem | ||
| 12/5/2016 | Sold | $341,900-11.2%$63/sqft |
Source: | ||
| 10/25/2016 | Price change | $385,000-8.1%$71/sqft |
Source: HomeSmart Homes and Estates #4609008 Report a problem | ||
| 10/21/2016 | Pending sale | $419,000$78/sqft |
Source: HomeSmart Homes and Estates #4609008 Report a problem | ||
| 6/6/2016 | Price change | $419,000-1.4%$78/sqft |
Source: HomeSmart Homes and Estates #4609008 Report a problem | ||
| 5/28/2016 | Price change | $425,000-5.6%$79/sqft |
Source: HomeSmart Homes and Estates #4609008 Report a problem | ||
| 4/26/2016 | Price change | $450,000-4.1%$83/sqft |
Source: HomeSmart Homes and Estates #4609008 Report a problem | ||
| 4/5/2016 | Price change | $469,000-1.3%$87/sqft |
Source: HomeSmart Homes and Estates #4609008 Report a problem | ||
| 3/10/2016 | Listed for sale | $475,000-1%$88/sqft |
Source: HomeSmart Homes and Estates #4609008 Report a problem | ||
| 7/31/2015 | Listing removed | $479,900$89/sqft |
Source: RE/MAX Homes And Estates-Commercial Division #4514820 Report a problem | ||
| 6/14/2015 | Price change | $479,900-4%$89/sqft |
Source: RE/MAX Homes And Estates-Commercial Division #4514820 Report a problem | ||
| 4/15/2015 | Price change | $500,000-10.7%$93/sqft |
Source: RE/MAX Homes And Estates #4514820 Report a problem | ||
| 3/10/2015 | Listed for sale | $559,900+22.5%$104/sqft |
Source: Regal Homes & Properties Inc #4421841 Report a problem | ||
| 9/2/2003 | Sold | $457,000$85/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $314,200 -1.2% |
| 2024 | -- | $318,150 |
| 2023 | -- | $318,150 |
| 2022 | -- | $318,150 |
| 2021 | -- | $318,150 |
| 2020 | -- | $318,150 |
| 2019 | -- | $318,150 |
| 2018 | -- | $318,150 |
| 2017 | $18,658 | $318,150 |
| 2016 | -- | $318,150 -19.5% |
| 2015 | -- | $395,000 |
| 2014 | -- | $395,000 |
| 2013 | -- | $395,000 |
| 2012 | -- | $395,000 |
| 2011 | -- | $395,000 |
| 2010 | -- | $395,000 |
| 2009 | -- | $395,000 |
| 2007 | -- | $395,000 |
| 2006 | -- | $395,000 |
| 2005 | -- | $395,000 +59.3% |
| 2004 | -- | $248,000 |
| 2002 | -- | $248,000 |
| 2001 | -- | $248,000 |
| 2000 | -- | $248,000 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 10918
Getting around
0 / 100
Car-DependentNearby schools
GreatSchools rating
- 5/10North Main Street SchoolGrades: 2-5Distance: 4 mi
- 4/10Monroe Woodbury Middle SchoolGrades: 6-8Distance: 6.3 mi
- 7/10Monroe Woodbury High SchoolGrades: 9-12Distance: 6.5 mi
Schools provided by the listing agent
- Elementary: North Main Street
- Middle: Monroe-Woodbury Middle School
- High: Monroe-Woodbury High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Orange County
- Chester
- 10918
- 4 Debbie Court






