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$9,750,000
7 Beds ⋅ 14 Baths ⋅ 881369 MLS
Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a grand living room, banquet-sized dining room, inviting family room, and a serene primary suite with fireplace, sitting area, and generous mirrored closets. A spacious country eat-in kitchen and a lower entertainment level with bar and gym further enhance the home’s appeal. Outdoors, the estate opens to multi-tiered gardens, expansive terraces and patios, an in-ground pool, pool house with full kitchen, 2 full baths and guest quarters, tennis/sport court, golf hole with 3 tee boxes, apple orchard, trellis, and outdoor barbecuing area. A rare offering that captures the privacy, grace, and enduring appeal of the North Shore Gold Coast.

4 Red Fox Lane, Upper Brookville
$9,500,000
8 Beds ⋅ 9 Baths ⋅ 1038962 MLS
A Brilliant Architectural Harmony Defines This 7,100+ Square-Foot New-Construction Masterpiece, Where The Heritage Of A French Country Manor Meets The Sharp, Bespoke Elegance Of Modern Luxury. Approached Via A Sweeping Formal Motor Court, The Home Projects Enduring Permanence, Clad In Tailored, Limestone-Hued Ashlar Pierced By Expansive Black Steel-Framed Fenestration. Crossing The Threshold, The Arrival Gallery Establishes A Breathtaking Sense Of Scale. Anchored By A Honed, Dual-Tone Stone Floor Laid In A Classic Harlequin Motif, The Double-Height Foyer Draws The Eye Through Soaring, Light-Filled Living Spaces. The Culinary Quarters Redefine The Heart Of The Home, Featuring A Deep-Coffered Ceiling And Dual Monolithic Calacatta Gold Quartzite Islands. Concealing The Elite Professional Appliance Suite Is Custom White Oak Cabinetry, Supported By A Fully Equipped Scullery Designed For Flawless Entertaining And A Discreet Main-Level Guest Or Staff Bedroom Suite. Designed For Ultimate Privacy, The Main-Level Primary Suite Functions As A Secluded Retreat, Complete With A Glass-Enclosed Sunlit Conservatory, A Luxury Dressing Space, And A Spa-Inspired Bath With Radiant Heated Marble Floors. A Commercial-Grade Elevator Services All Three Levels, Ascending To An Open Architectural Loft And Four Graciously Scaled En-Suite Bedrooms. The Lower Level Serves As A Sweeping Recreation And Wellness Wing, Offering A Glass-Walled Fitness Center, Custom Wet Bar, Two Additional Bedrooms, And Endless Customization Potential. In Total, The Estate Boasts Eight Graciously Appointed Bedrooms, Seven Full Baths, And One Refined Powder Room. Outside, The Grounds Transition Seamlessly Into A Private Resort. A Custom Gunite Infinity-Edge Pool Is Framed By European Porcelain Pavers And A Fully Equipped Detached Pool House Featuring A Kitchen And Two Full Bathrooms. Engineered For Peak Performance And Effortless Living, The Estate’s Unseen Layers Are Just As Impressive, Featuring Whole-House Crestron Smart Automation, A Full-House Backup Generator, Multi-Zone Climate And Audio, And A Heated Three-Car Garage With Epoxy Flooring And Ev Charging. A True Sanctuary Built For The Legacy Portfolio.

25 Winding Lane, Upper Brookville
$2,295,000
4 Beds ⋅ 6 Baths ⋅ 1016394 MLS
Diamond in the Rough. Oversized cedar shake Cape Cod style home, offers 4453SF of living space on 2 flat acres in Upper Brookville. Traditional Colonial layout features a two-story entry foyer flanked by a formal living room with wood burning fireplace and formal dining rooms, both with large picture windows. An open concept kitchen/great room w/ fireplace is the heart of the home, with high ceilings, reclaimed wood beams, a wall of windows and sliding doors, a chef's kitchen with 48" Wolf cooking and SubZ refrigeration and a large island with seating. Off the kitchen is the mud room entry from the rear or 2-car attached garage, laundry room, bedroom and full bath. On the south side of the house, on the 1st level, the primary suite offers a tray ceiling, multiple walk-in closets, an ensuite marble bath with double sinks, shower, windowed tub and private water closet AND a private office/sitting room/library. Upstairs contains 2 huge bedrooms, each with walk-in closets and private bath, with a common area loft space. The basement is the full footprint of the house and is unfinished, housing utilities and storage. The 2.5 car detached carriage house offers room for additional vehicles and has an unfinished room above. Plenty of room for expansion; just your imagination is required to bring this beauty back to life.

7 Locust Lane, Upper Brookville
$1,980,000
4 Beds ⋅ 3 Baths ⋅ 1010311 MLS
Welcome to 279 Hillcrest Lane — A Rare Gold Coast Retreat on Over 2 Private Acres Nestled in the prestigious Village of Upper Brookville on New York's storied North Shore, 279 Hillcrest Lane is a beautifully updated modified ranch offering the perfect blend of timeless elegance, thoughtful modern upgrades, and exceptional outdoor living. Set on over 2 park-like acres (87,133 sq ft) of lush, professionally landscaped grounds, this distinctive residence delivers the privacy, scale, and lifestyle that define Gold Coast living at its finest. Turnkey Peace of Mind. Major capital improvements have been recently completed, including a brand-new GAF Timberline HDZ roof with ice-and-water shield, new synthetic felt underlayment, new pipe flanges, hips, ridge, and re-counterflashed chimneys — backed by a 10-year workmanship guarantee and 30-year material warranty. A new above-ground oil tank rounds out the mechanical upgrades, offering efficiency and long-term confidence for the discerning buyer. Sophisticated Interiors. A grand living room with soaring ceilings and a stately wood-burning fireplace sets an impressive tone upon entry. The renovated kitchen features brand-new stainless steel appliances and flows seamlessly into the dining area and a sun-drenched great room, where expansive windows frame serene views of the manicured grounds. A versatile home office or den — complete with its own fireplace — offers a refined space for focused work or quiet retreat. Effortless Main-Floor Living. The main-floor primary suite is a true sanctuary, featuring a peaceful sitting area and a thoughtfully appointed ensuite with a double vanity and walk-in shower. A second full bathroom and laundry are also conveniently located on the main level. Upstairs, three generously proportioned bedrooms and a full bath provide comfortable accommodations for family or guests. An Outdoor Oasis. Step outside to a fully fenced backyard designed for both relaxation and entertaining. An in-ground pool, charming gazebo, and spacious circular driveway with ample guest parking create the perfect backdrop for warm-weather gatherings. A working garden with a rustic barn adds a distinctive, pastoral character — ideal for storage, hobbies, or imaginative use. Location. Situated minutes from top-rated schools, premier equestrian facilities, world-class golf and country clubs, fine dining, boutique shopping, and convenient access to major transportation routes into Manhattan. This is North Shore living at its very best. A rare opportunity to own a turnkey estate in one of Long Island's most sought-after enclaves — where privacy, prestige, and natural beauty converge.

279 Hillcrest Lane, 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.