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Land with Home for Sale in Chester, New York

19 Greentree Ln, Chester, NY 10918

$3,400,000
8.4 acres
Active sale
ago
Est $18,882/mo

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.

7,750
Sq feet
4
Beds
4
Full baths
1986
Built

Location

Street address
19 Greentree Ln
School district
Chester
Elevation
455 feet
Coordinates
41.3894, -74.2501

Property details

Acreage
8.4 acres
MLS #
MLSLI 988789
Posted

Property taxes

2025
$30,892

Parcels

  • 332089-038-000-0001-066.100-0000

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Franchise
None

Exterior

Parking
Driveway, Garage, Off Street
Pool
Private

Structure

Style
Contemporary
Stories
3
Water
Well
Sewer
Septic Tank
Heating
Geothermal, Radiant, Radiant Floor
Cooling
Central Air
Materials
Wood Siding

Interior

Room Count
16
Rooms
Bathroom x 4, Bedroom x 4, Dining Room
Flooring
Hardwood, Wood
Fireplaces
Yes
Appliances
Dishwasher, Dryer, Freezer, Oven, Range, Refrigerator, Washer, Wine Refrigerator
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, Quartz/Quartzite Counters, Recessed Lighting, Walk-In Closet(s), Washer/Dryer Hookup

Property utilities

CategoryTypeStatus
GasPropaneConnected

Nearby schools

NameTypeDistrict
Chester Elementary SchoolElementaryChester
Chester Academy-Middle/High SchoolMiddleChester
Chester Academy-Middle/High SchoolHighChester

Listing history

DateEventPriceChangeSource
Apr 29, 2026New listing$3,400,000MLSLI
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This 8.4-acre property is located at 19 Greentree Ln in Chester, NY 10918. The property is available for sale for $3,400,000. It has a 7,750 sq ft 4 bedroom, 4 bath house built in 1986.

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