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$25,000,000
13 Beds ⋅ 17 Baths ⋅ 1001064 MLS
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.

1 Applewood Estate, Upper Brookville
$5,495,000
6 Beds ⋅ 8 Baths ⋅ 985121 MLS
An exceptional private brick estate compound set on approximately 7 meticulously manicured acres in Upper Brookville. This impressive residence offers grand scale, timeless elegance, luxurious landscaping, and a true lifestyle experience both inside and out. Filled with natural light, the home features vaulted ceilings, oversized windows, sweeping property views, 6 spacious bedrooms with en-suite baths, 7.5 baths, large eat-in kitchen with generous counter space and storage, and full finished basement. Designed for both daily living and elevated entertaining, every space offers comfort, presence, and functionality. The meticulously designed grounds create a resort style setting with a custom 22,000 gallon koi pond, custom lighting, newly resurfaced Har-Tru tennis court, heated gunite pool, 8-person hot tub, pool house with kitchenette, full bath and changing room, custom outdoor kitchen, and premium speaker system inside and out. Complete with space for 10-cars, car lifts, and carport, this rare Upper Brookville estate delivers privacy, scale, luxury, and an unmatched indoor and outdoor lifestyle. A rare opportunity to own a private Upper Brookville estate with exceptional amenities and beautifully maintained grounds.

45 Wolver Hollow Road, Upper Brookville
$5,585,000
9 Beds ⋅ 12 Baths ⋅ 885874 MLS
Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless elegance with modern comforts. A truly iconic Georgian estate nestled in the heart of Upper Brookville, this 17,587 square feet of total living space, this sprawling residence features 9 bedrooms, 9.555+ bathrooms, 10 wood-burning fireplaces, and exquisite architectural details, including vintage millwork, antique hand-painted wallpaper, and Samuel Yellin wrought-iron gates from the JP Morgan estate. Designed in 1924 by renowned architect James W. O’Connor and landscape architect Robert Ludlow Fowler, Gray Horse Farm is where classic architecture meets nearly 9 acres of pristine, equestrian-ready grounds. Perfectly suited for multigenerational living, the estate includes three separate guest/staff quarters (two 1-bedrooms and one 3-bedroom), offering privacy while staying connected. For those who love to entertain and enjoy the outdoors, the estate features a 20' x 55' heated saltwater pool with a pool house that's fully equipped, tennis and basketball courts, and a secret meditation garden you don't want to miss. For the car enthusiast there's a 7-car garage. Equestrian enthusiasts will appreciate the 3-stall stable, multiple paddocks, and run-in horse shed, all designed for top-tier country living. Additional highlights include a whole-house generator, —all just 27 miles from Manhattan. Whether you're seeking a premier equestrian retreat or an expansive generational compound, Gray Horse Farm delivers an unmatched lifestyle of luxury, privacy, and prestige. A rare offering close to top universities,marinas, beaches, golf, museums and americana shopping!

60 Piping Rock Road, Upper Brookville

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.