1 Applewood Estate Upper Brookville, NY 11545 New

UPDATED: 05/26/2026 09:01 AM ON MARKET: 8 days on market

$25,000,000

13 Beds17 Baths22,429 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 22,429 sqft

Price per Sqft $1,114

MLS Listing ID 1001064

Style Estate

Bedrooms 13

Full Baths 11

Half Baths 6

HOA Y/N No

Rental Info No

Year Built 2005

Annual Tax Amount $202,181

Lot Size 35.470 Acres

Acres 35.47

Property Sub-Type Single Family Residence

Source onekey2

Location

State NY

County Nassau County

Rooms

Basement Finished,Full

Interior

Interior Features 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

Heating Forced Air,Natural Gas,Radiant

Cooling Central Air

Flooring Hardwood

Fireplaces Number 3

Fireplace Yes

Appliance Other

Exterior

Exterior Feature Balcony,Basketball Court,Garden,Lighting,Tennis Court(s)

Parking Features Driveway,Garage,Oversized,Private

Garage Spaces 8.0

Fence Partial

Utilities Available Electricity Connected,Natural Gas Connected,Water Connected

View Open,Panoramic

Garage true

Private Pool Yes

Building

Lot Description Back Yard,Cleared,Front Yard,Landscaped,Near Golf Course,Near Public Transit,Near School,Secluded,Sprinklers In Front,Sprinklers In Rear

Sewer Cesspool

Water Public

Structure Type Brick,Stone

Schools

Elementary Schools Ann Macarthur Primary School

Middle Schools Locust Valley Middle School

High Schools Locust Valley

School District Locust Valley

Others

Senior Community No

Special Listing Condition None

Property Description

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.

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