$ 25,000,000
-
$25,000,000
Price -
13
Bed -
17
Bath -
22,429
SqFt
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About the Listing SHNT02 - 214893
Experience Applewood Estate — a generational North Shore compound where timeless architecture, historic provenance, and resort-caliber living unfold across more than 35 secluded acres in the esteemed Village of Upper Brookville. Once an operating apple orchard in the early 1900s and later owned by renowned American artist Montague Flagg, this extraordinary estate carries a legacy as rich as the land itself. Hidden behind a gated, tree-lined approach, the property reveals a breathtaking landscape of rolling lawns, mature specimen trees, formal gardens, peaceful water features, and open meadows designed to evoke the grandeur of Long Island’s historic Gold Coast estates. Inspired by Tudor Cotswold architecture, the compound is a masterclass in cohesive design, blending old-world craftsmanship with modern luxury across multiple residences and lifestyle amenities. The centerpiece is a magnificent custom-built Manor residence encompassing approximately 13,000 square feet of refined living space. Constructed in 2005 with slate, brick, and stone, the home showcases extraordinary craftsmanship through onyx marble accents, oversized parquet flooring, handcrafted iron fireplaces, detailed millwork, and dramatic entertaining spaces throughout. A grand foyer anchored by a sweeping staircase introduces interiors defined by warmth and scale, including a soaring ballroom with 23-foot coffered ceilings, an elegant library loft, meditation room, billiards lounge with wet bar, and a sun-filled eat-in kitchen with breakfast room overlooking the estate grounds. Designed as a true multi-structure compound, Applewood Estate includes several additional residences and guest accommodations, including a beautifully renovated barn residence with attached two-bedroom cottage, an additional two-bedroom cottage, a two-bedroom pool house, a one-bedroom studio, and a meticulously reconstructed circa-1914 stone barn now transformed into a luxurious retreat. Outdoor living is equally exceptional. The estate features a heated swimming pool and spa pavilion, built-in outdoor kitchen, resurfaced tennis court, separate sports court, expansive paddocks, and formal equestrian facilities complete with horse stables and a training ring. Additional highlights include a six-car detached garage, maintenance barn, commercial-grade 150kW generator, and secure gated entry, all thoughtfully integrated into the estate’s serene natural surroundings. Rarely does a property offer this level of acreage, architectural integrity, historical significance, and lifestyle versatility within one of the North Shore’s most coveted enclaves. Applewood Estate is not simply a home — it is a private world crafted for legacy living, grand entertaining, and timeless retreat.
Listing Highlights
Status
Active
Days on Site
6
Property Type
Residential
MLS ®
1001064
Year Built
2005
Total Square Footage
22,429
Lot/Acreage
35.47
County
Nassau County
School District
Locust Valley
Elementary School
Ann Macarthur Primary School
Middle School
Locust Valley Middle School
High School
Locust Valley High School
Interior Details
- Bedrooms: 13
- Bathrooms: 11 Full / 6 Half
- Appliances:
- Air Cond: Central Air
- Heating: Forced Air,Natural Gas,Radiant
- Fireplaces: 3
- Floor: Hardwood
- Above Ground Sq Ft:
- Below Ground Sq Ft: n/a
- Basement: Finished,Full
- Other: First Floor Bedroom,Cathedral Ceiling(s),Chandelier,Eat-in Kitchen,Entrance Foyer,Formal Dining,Granite Counters,Marble Counters,Pantry,Primary Bathroom,Master Downstairs,Sauna,Walk-In Closet(s),Wet Bar
- Water: Public
Exterior Details
- Lot Description: Back Yard,Cleared,Front Yard,Landscaped,Near Golf Course,Near Public Transit,Near School,Secluded,Sprinklers In Front,Sprinklers In Rear,No Waterfront
- Garage Capacity: 8 car
- Roof:
- Others: Balcony,Basketball Court,Garden,Lighting,Tennis Court(s)
- Sewer: Cesspool
- Parking Features: Driveway,Garage,Oversized,Private
Financial Details
- Tax Amount: $202,181
- Taxes w/Assessments: N/A
- Tax/Property ID: 2427-22-J-00-1141-0
- Tax Year: N/A
Payment Calculator
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Questions About..
1 Applewood Estate Upper Brookville, NY 11545
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