19 Greentree Lane
Chester, NY, 10918 $ 3,400,000
Bedrooms4 Baths4.0 Sq 7,750 Monthly Estimate*
$ 20,934
for $3,400,000 with 4 bedrooms and 4 full baths. This 7,750 square foot home was built in 1986 on a lot size of 8.4.
Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that moment forward, every detail reinforces the same idea. This property was built intentionally, without compromise. Originally designed by renowned architect Paul Rudolph, the residence carries a level of architectural pedigree rarely available. Spanning over 7,750 square feet, the home blends that design legacy with modern performance, including radiant heated floors, geothermal systems, and thoughtfully curated living spaces that feel both refined and highly functional. What truly sets this property apart is the lifestyle it delivers. A private helipad offers direct access to Manhattan in approximately 14 minutes, redefining convenience at the highest level. The grounds unfold as a resort-caliber setting, anchored by a heated saltwater pool, three private cabanas, and a fully equipped outdoor kitchen with a dedicated dining space designed for effortless indoor outdoor living. A rare white sand beach introduces an unexpected element, creating a setting that feels more like a destination resort than a private residence. Inside, the home takes on a spa-like atmosphere, with wellness-driven features including a private sauna and spaces designed to restore and recharge. The primary suite is its own retreat, complete with a three-season room that extends the experience outdoors while maintaining complete privacy. A fully built-out home theater adds another layer to the lifestyle, bringing a true cinematic environment into the comfort of your own home. Beyond the property itself, the location adds another dimension. This is the perfect getaway for winter weekends, fall retreats, or summer escapes, surrounded by some of the Hudson Valley’s most sought-after destinations. Just minutes from LEGOLAND New York Resort, Woodbury Common Premium Outlets, Warwick Valley Winery & Distillery, local apple orchards throughout Warwick, Bear Mountain State Park for skiing and outdoor recreation, and the five-star Glenmere Mansion, the area offers a rare blend of recreation, luxury, and accessibility. Hiking, camping, fishing, skiing, biking, horseback riding, fine dining, and shopping are all within reach, creating a year-round lifestyle that is both active and refined. This is more than a residence. It is a fully realized compound, private, efficient, and architecturally significant, built for someone who values time, discretion, and a level of living that cannot be replicated.
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Single Family Coming Soon
FeaturesInteriorInterior Amenities Built-in Features Cathedral Ceiling(s) Chefs Kitchen Eat-in Kitchen Entertainment Cabinets Entrance Foyer Formal Dining High Speed Internet Kitchen Island Natural Woodwork Open Kitchen Original Detai
Flooring Hardwood Wood
Total Fireplaces 1
Fireplace Features Family Room Free Standing
Basement (Y/N) N
Half Baths 0
Total Bedrooms 4
Total Baths 4
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GeneralSewer Septic Tank
Heating Geothermal Radiant Floor
Cooling Central Air
Utilities Cable Connected Electricity Connected Phone Connected Propane Water Connected
Appliances Dishwasher Dryer Freezer Oven Range Refrigerator Washer Wine Refrigerator
Garage Spaces 2
Architectural Style Contemporary Estate
Construction Materials Wood Siding
Year Built 1986
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 332089-038-000-0001-066.100-0000
County Orange County
Property Type Residential
HOA N
Garage Y/N Y
Total Rooms 16
Full Baths 4
High School Chester Academy-Middle/High School
City Blooming Grove
Senior Community Y/N N
High School District Chester
Carport Y/N N
Elementary School Chester Elementary School
Property Attached Y/N N
Tax Annual Amount 30891.88
Middle/Junior High School Chester Academy-Middle/High School
Building Area Units Square Feet
Standard Status Coming Soon
Middle/Junior School District Chester
Elementary School District Chester
Tax Assessed Value 122900
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ExteriorParking Features Driveway Garage Off Street Private Driveway Garage Off Street Private
Water Source Well
Building Area Total 8200
Waterfront Y/N N
Horse Y/N N
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* Excluded FeaturesList Byjakegaray@serhant.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $20,934
- Monthly Property Taxes
- $2,574
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Chester, NY
Average List Price $862,656
Percent of Sale Price 75%
About Chester, NY 3,423 Population
-5% Since 2002
$ 54,539 Median Income
50.03 Median Age
26% Households with Children
Trends Information provided by ATTOM Data Solutions.
4100324 Elementary School
4100290 Middle School
Chester Academy-Middle/High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 4/23/2026 | $3,400,000 | | Listed Price |