Upper Brookville NY Real Estate & Homes for Sale

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!

Welcome to Lions Gate A Private North Shore Estate of Distinction nestled in the heart of Long Island's Gold Coast; Lions Gate is a grand and secluded country estate offering an unparalleled lifestyle of elegance and comfort. Located within the esteemed Locust Valley School District - home to the prestigious International Baccalaureate program, this magnificent residence blends refined architectural detail with the serenity of resort-style living, all set on five spectacular acres directly abutting the protected Hope Goddard Iselin Preserve, offering acres of unspoiled natural beauty and tranquil hiking trails. Approached through an impressive automatic brick and wrought-iron gate, a sweeping, tree-lined drive meanders to a stately motor court and elegant front courtyard. A separate rear service drive discreetly accesses a four-car garage and additional parking down a private drive-an extension of the side yard ensuring both privacy and practicality. The estate offers approximately 8,500 square feet of luxurious interior living space, with twelve spacious rooms including seven bedrooms, six full baths, and two elegant powder rooms. First floor primary bedroom. The interior reveals an artful blend of grandeur and warmth. Expansive principal rooms flow seamlessly from one to the next, highlighted by custom millwork, oversized windows, and thoughtful built-ins. The formal great room is anchored by a wood-burning fireplace and French doors opening to a grand rear patio. A sophisticated wet bar connects to an expansive den with a second fireplace, while the formal dining room also opens to the outdoor terrace, creating a harmonious indoor-outdoor entertaining experience. The chef's kitchen, bathed in natural light from front-to-back exposures and skylights, is designed to serve as the heart of the home. New top-of-the-line windows, doors, and roof enhance the home's overall appeal, blending luxury with lasting quality. The lower level has been fully designed for year-round recreation and entertainment. A custom-built bar and billiards room set the stage for lively gatherings, while a state-of-the-art home theater, dedicated gaming room, and a fully equipped summer kitchen provide every imaginable amenity. A private home gym, oversized laundry room, utility rooms, and several generous walk-in cedar closets offer practicality with luxurious flair. Extensive custom storage, multiple walk-ins, and direct access to the four-car garage add to the home's thoughtful functionality. Outside, the estate transforms into a private resort. An expansive, heated in-ground pool is accompanied by a charming cabana with two changing rooms and a covered sitting area for relaxing in shade or sun. A professional-grade tennis court, oversized lawn chess set, and formal gardens designed with curated specimen plantings offer year-round visual interest and endless enjoyment. Just minutes from exclusive North Shore country clubs, fine dining, equestrian centers, and the Town of Oyster Bay's beaches, boating, and nature preserves, Lions Gate is more than a home - it is a legacy property designed for those who value privacy, grandeur, and effortless luxury. View 3D tour and floor plan.

La Isabella A Gracious 2 Acre Estate In Prestigious Upper Brookville Offering Timeless Colonial Architecture With Modern Luxury. Set Behind A Sweeping Drive And Surrounded By Mature Magnolia, Dogwood, And Maple Trees, This Home Is Crafted For Multigenerational Living With Privacy And Sophistication. Inside, A Dramatic Double-Height Foyer And Sweeping Staircase Welcome You To Spacious Sunlit Rooms Perfect For Entertaining And Everyday Life. The Formal Living And Dining Rooms Provide Elegant Settings, While The Expansive Kitchen Features Stainless Steel Appliances, A Large Island With Seating, Walk-In Pantry, And Eat-In Area Opening To A Stone Patio. The Family Room Includes A Gas Fireplace, Custom Built-Ins, And Wet Bar With Wine Cooler. Main-Level In-Law Suite With Full Bath Offers Flexibility And Privacy. Upstairs, The Luxurious Primary Suite Has A Private Terrace, Electric Fireplace, And Space For A Spa Bath. A Second En Suite Bedroom, Third Bedroom, And Bonus Room Complete The Upper Level. Outdoors, Unwind By A Stunning Pool Accented With A Natural Stone Waterfall, Expansive Lawns, And A Three-Season Room. The Lower Level Offers Storage And Potential For A Gym Or Media Room. Near Top Golf, Schools, And New York City.

Tucked away on a fully fenced, over two-acre, park-like, electronic-gated property, stands a sprawling Farm Rach expanded and remodeled in 2007. This 5,400-square-foot mini estate of your dreams is located in the scenic Upper Brookville village. With rolling wooded open spaces rife with wildlife and dotted with grand and historic estates, you will be close to boating, golf, equestrian facilities, quaint village shopping, museums, and Long Island Railroad with about a 40-minute commute to Manhattan. Within about a mile radius of your home you will find four golf courses, a produce farm, a nursery (both with stores), and mansion museums and preserves. Oyster Bay, Locust Valley, and East Norwich villages are just a little farther away. Surrounded by sprawling, level lawns bounded by rows of evergreens and split-rail fences, the main building wraps around a delightful outdoor entertainment complex with large Gunite, saltwater pool, with hot tub and water feature, expansive bluestone patios, and a large, covered cooking pavilion with ample bar seating. Think of the fabulous summer parties you can enjoy in this inviting setting. At the end of the pool, a garden offers colorful plantings, fruit frees and a privacy wall of evergreens. On the east side of the pool, a free-standing, legal guest cottage may invite its guest to an early morning dip, and on the west side, a large recreation room, with full bath, walk-in closet, a large pub-like wet bar with wine cooler, a game area, and a home theater, can serve as a great cabana party room. A bookcase-lined hall leads from the pool party room into the sitting room of a large in-law suite that includes a summer kitchen, laundry room, luxury full bath, and bedroom. A hall opens from the apartment into the main house where a banquet-sized dining room creates a Tuscan atmosphere with a stone fireplace and open-beam ceiling. The spacious eat-in kitchen has similar open-beam ceiling and rustic lighting. It offers extensive cherry cabinetry, granite counters, several windows overlooking the front courtyard, a huge center island with wine cooler, a walk-in pantry, and high-end stainless-steel appliances, including a double wall oven with convection, and a six-burner glass cooktop beneath a custom copper exhaust hood. The spacious, sunny, two-story entrance foyer, with powder room, features a staircase, with ornate iron balustrade, ascending to a second-floor balcony. The adjoining, spacious and welcoming living room provides sunny views through huge front and rear windows, a closet, and access to the attached two-car garage. Two steps down from the foyer and kitchen, an immense, sun-drenched four-season room features stone floors, huge windows overlooking the pool and patio, access area the pool, and a stone corner wall housing an arched wood-burning oven/fireplace; perfect for pizza parties. On the second floor, a balcony with study area leads down a hall to two bedrooms, a hall bath, and the primary bedroom wing. This private retreat offers a spacious bedroom with ample windows, two walk-in closets, and a luxury marble bath with walk-in shower, twin vanities, and whirlpool tub. Accessed from the entrance foyer, the partial basement has a spacious gym area, a laundry area, and room for ample storage. Additional features include: central vacuum; two fireplaces; electronic gate; smart thermostat; fully-fenced property, second fence around pool area; whole-house entertainment system with speakers; Energy Star appliances; hardwood floors where seen; and fruit trees (apple, pear, peach). Offering so many possibilities for the various areas of this expansive home and on such a beautiful level property, with sweeping lawns and shady tree areas, this amazing mini-estate is ready for you to move in and start living the life your dreams. View 3D tour & floor plan.

Behold Applewood Estate, an expansive 35+ acre serene property nestled within the prestigious Village of Upper Brookville. This unmatched North Shore architectural masterpiece with 6+ dwellings, offers both grandeur and elegance. The unrivaled property was meticulously designed with professional landscaping, decorated with mature privacy hedges, formal gardens with water features and rolling green lawn space. Rooted in history, this magnificent estate was once an Apple Orchard Farm back in the early 1900's and was also formerly owned by the celebrated 19th-century American Artist Montague Flagg. The bespoke Main Residence encompasses an impressive 13,000 Sq.Ft. of living space, was custom built with Slate, Brick and Stone in 2005 and is a testament to high-end design and luxury living. Designer details include Onyx Marble installations, spacious primary rooms, oversized parquet wood floors, handmade iron fireplaces, thick-cut millwork and more. A grand Foyer with a winding staircase, a Great Room with intricate coffered 23 foot ceilings and a magnificent Library loft and a handcrafted Meditation Room, a Billiards/Game room with a Wet-Bar and a Eat-In-Kitchen with a Breakfast Room overlooking the peaceful backyard are just a few of the interior highlights that make this home truly special. Additionally, this unrivaled estate features several detached houses including a 2 Bedroom Colonial Residence and a meticulously reconstructed circa 1914 Stone Barn, now serving as a guest retreat. This distinguished horse-property includes a newly resurfaced tennis court, a separate sports court, a 6-door detached garage, a commercial-grade 150kW generator, a long tree-lined driveway and a secure gated entrance, ensuring peace, beauty and privacy. Equestrian enthusiasts will appreciate the formal horse stables complete with a training ring. The property further boasts a heated in-ground pool pavilion with a jetted jacuzzi spa and a built-in outdoor kitchen, as well as a 1 bedroom Pool House and numerous other refined amenities, making it a Gold Coast sanctuary of relaxation and sophistication.

Rare Opportunity on Private Gated Upper Brookville Lane. Only 11 Homes Built & Seldom Offered For Sale. Pride of Ownership throughout This Turn Key Brick Colonial on Quiet Interior 2A+ Site. Attention to Detail, Functional Floor Plan for Contemporary Living & Entertaining Indoors and Outdoors. Magnificent Landscaped Grounds Complete with Outdoor Kitchen, Oversized Patio, Gunite Pool with Waterfall, Gazebo, Koa Pond, Bocce Court & Generator. A Must See, Additional information: Appearance:Pristine,Interior Features:Guest Quarters,Marble Bath,Separate Hotwater Heater:Yes