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Photo of 19 Greentree Lane, Chester NY
19 Greentree Lane
Chester, NY 10918
Bedrooms
4
Full Baths
4
Partial Baths
0
Acres
8.40
Interior Sqft
365,904
Age
40
Heating
N/A
Fireplaces
1
Cooling
Central Air
Water
Well
Sewer
Private
Garages
2
Taxes
$30,892
Parking
Driveway
Additional Details Below

Description

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.nnA 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.nnOriginally 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.nnWhat truly sets this property apart is the lifestyle it delivers.nnA 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.nnInside, 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.nnBeyond 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.nnThis 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.

Schools

Chester Elementary School

Chester Academy-middle/high School Middle School

Chester Academy-middle/high School

See More Homes in Chester School District

Location

Listing Details

Summary
Design Type

Wood Siding

Architectural Type

Contemporary, Estate

Parking

Driveway, Garage, Off Street, Private

Interior Features
Flooring

Hardwood, Wood

Fireplace(s)

Family Room, Free Sta

Interior Features

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 Details, Pantry, Primary Bathroom

Appliances

Dishwasher, Dryer, Freezer, Oven, Range, Refrigerator, Washer, Wine Refrigerator

Utilities
Cooling

Central Air

Heating

Geothermal, Radiant Floor

Sewer

Septic Tank

Water

Well

Miscellaneous

Assessment : 122,900
Zoning:
Lattitude : 41.38937
Longitude : -74.2505
MLS# : KEY988789
Views : 123
Listing Courtesy: Jake Garay of Serhant LLC

Notes

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The data relating to real estate for sale or lease on this web site comes in part from OneKey™ MLS. Real estate listings held by brokerage firms are marked with the OneKey™ MLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. Copyright 2026 OneKey™ MLS. All rights reserved.

Presentation: © 2026 EveryHome, Realtors, All Rights Reserved. EveryHome is licensed by the New York Real Estate Commission - License 103112063

Real estate listings held by brokerage firms other than EveryHome are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.

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