Upper Brookville NY Real Estate & Homes for Sale

A Legendary Estate with a Sports Sanctuary Step into a world where luxury meets athletic excellence at this exceptional Georgian Colonial estate in Upper Brookville. Set on over two acres along the most prestigious street in the area, this residence offers an unparalleled blend of history, elegance, and recreation. The centerpiece of this property is an oversized indoor sports sanctuary, designed for the ultimate sports professional or enthusiast. With a private tennis court, heated pool, and spa, this estate is built for year-round enjoyment. The expansive indoor court is adaptable for multiple sports, including hockey, basketball, badminton, and more perfect for training or leisure. The grand circa-1930 home, once owned by Josephine Hartford Douglas of the Great Atlantic & Pacific Tea Company legacy, exudes timeless sophistication. Inspired by her passion for sports, she constructed the original "Playhouse" after finding the renowned Piping Rock Club fully booked for a game of tennis. The recreation building originally housed a swimming pool, tennis court, music room, and drawing room echoing a heritage of grandeur and entertainment. Inside, the spacious residence boasts a beautifully updated kitchen, a luxurious master en-suite, and elegant living and dining spaces. Guest quarters provide comfort and privacy, while marble baths and exquisite architectural details enhance the home s superb appearance. This is more than a home it s a private sports retreat, a legacy property, and a rare opportunity to own a piece of history in an exclusive setting.

LOW TAXES!! Nestled in the prestigious village of Upper Brookville, this beautifully appointed 4-bedroom, 3.5-bathroom Colonial offers the perfect blend of timeless elegance and modern convenience. Set on 2 acres of serene, picturesque land, this home boasts a thoughtfully designed layout and an array of desirable features. The newly renovated kitchen serves as the heart of the home, featuring stainless steel appliances, a spacious island, and sleek finishes, making it a culinary enthusiast s dream. The open-concept first floor is designed for effortless entertaining, with a dining area complemented by a cozy fireplace, a bright and airy living room, a welcoming family room, and a convenient half bathroom. The second level is home to a private retreat: the primary suite with a walk-in closet and master bathroom. An additional bedroom with an en-suite bath ensures comfort for guests or extended family, while two more generously sized bedrooms offer flexibility, one of which includes walk-up stairs leading to a finished attic, ideal for use as an office, playroom, or additional storage. A partial basement expands the living space with a finished room and ample storage/utility areas. With its expansive property, modern amenities, and notably low taxes, this home presents an exceptional opportunity to enjoy luxury living in a prime location. Don t miss your chance to make this Upper Brookville gem your own!

Welcome to this exceptional 10,500 sq. ft. estate, located in the heart of Upper Brookville, New York. Fully redesigned in 2023, this custom Gold Coast residence showcases extraordinary craftsmanship and attention to detail throughout. Inside, you ll find thick-cut millwork, stained glass windows, round-top doors, coffered ceilings, and hand-carved staircases that highlight the home s unique character. With 7 bedrooms and 7.55 bathrooms, this estate features spacious formal entertaining areas, elegant stone gas fireplaces, and a sunlit eat-in kitchen. The kitchen boasts marble countertops, a Butler s Pantry, high-end Viking and True appliances, and a cozy round breakfast nook filled with natural light. The primary suite offers high ceilings, an expansive walk-in closet, and a luxurious marble en-suite bathroom with His & Her s vanities, a freestanding soaking tub, and a separate glass-enclosed shower. The exterior is a stunning example of North Shore architecture, constructed with brick, stone, slate, and cedar shake. Set on over 5 acres, the property features a private electric gate, Porte Cochere, a 4-car attached garage, and impeccably landscaped grounds. Outdoor amenities include a heated saltwater pool and spa, a built-in firepit, and a detached poolside cabana with a newly designed center-island kitchen. This estate blends timeless elegance with modern luxury, making it a truly distinctive offering in Upper Brookville.

Nestled in the cul-de-sac of Chestnut Hill Estates, one of Upper Brookville s most sought-after developments, this 15,000 sq. ft. estate redefines luxury living on over 5 acres of impeccably manicured grounds. A grand 30-foot marble-floored foyer with twin floating staircases makes an unforgettable first impression, highlighting masterful craftsmanship with intricate plaster moldings and marble flooring throughout. The first floor is designed for both grand entertaining and intimate gatherings, featuring a 65-ft formal living room, formal dining room, sitting room, and family room each with elegant marble fireplaces. The chef s kitchen is a masterpiece with radiant heat, a Sub-Zero refrigerator and freezer, 60 Viking range, three Bosch dishwashers, and a butler s pantry complete with a warming oven and additional dishwasher. A luxurious junior primary suite provides privacy and convenience, complemented by a full bath. Nearby, a dedicated spa area with a sauna offers the ultimate in relaxation. The second-floor primary suite is a private sanctuary with a fireplace, 14-ft coffered ceilings, a kitchenette, office, and his-and-hers walk-in closets. Four additional en-suite bedrooms, each with walk-in closets, complete the upper level. This estate s 20x50 indoor/outdoor pool with a retractable roof, jacuzzi, and spa is a standout feature, seamlessly merging indoor luxury with outdoor tranquility. A media room on the main level and a state-of-the-art fitness center add to the home s impressive amenities. The 6,500 sq. ft. finished lower level, with marble flooring, features three guest suites and expansive gathering areas. Outside, formal gardens in the rear of the property provide a serene escape, enhancing the estate s grandeur. Additional highlights include an elevator servicing all three levels, a 10-car garage, and a third-floor cupola with breathtaking 360° views. Located in one of Upper Brookville s premier enclaves, this estate offers a rare blend of timeless elegance and cutting-edge design.

Welcome to 279 Hillcrest Lane, an exquisite modified ranch nestled in the prestigious enclave of Upper Brookville, NY. This distinguished residence masterfully combines timeless charm with modern sophistication, all set on an expansive 87,133-square-foot lot graced by lush natural surroundings. Upon entry, you are greeted by a grand living room with soaring ceilings and a stately wood-burning fireplace, creating an inviting space for cozy evenings and intimate gatherings. The recently updated kitchen is a culinary delight, boasting all-new stainless steel appliances and seamlessly connecting to a dining area and a sunlit great room. Bathed in natural light, the great room offers a vibrant and welcoming atmosphere, ideal for entertaining and everyday living. A private office or den with its own wood-burning fireplace is conveniently located on the main floor, providing a peaceful retreat for work, study, or relaxation. The main floor also features a luxurious primary suite, thoughtfully designed with a tranquil sitting area overlooking the picturesque yard. The ensuite bathroom is a true sanctuary, complete with a double sink vanity and a walk-in shower, offering a spa-like escape within the comfort of home. The upper level is designed to accommodate family or guests, featuring three additional spacious bedrooms and a full bathroom. This layout ensures privacy and ample space for everyone in the household. The property includes a two-car attached garage, offering secure and convenient parking with direct access to the home. In addition to the garage, there is plenty of parking available on the driveway, making it perfect for hosting gatherings or accommodating guests. Outside, the property transforms into a serene oasis. A large, fenced yard encloses an expansive patio, perfect for alfresco dining and outdoor entertaining. The inground swimming pool beckons for relaxation, while the charming gazebo and a fully functioning garden add to the property s enchanting appeal. A rustic barn, thoughtfully situated near the garden, enhances the charm and provides versatile functionality. Combining elegance, comfort, and thoughtful design, this stunning property offers a refined lifestyle in one of Upper Brookville s most sought-after locations. Don t miss the opportunity to experience the beauty and sophistication of 279 Hillcrest Lane schedule your private tour today.

Nestled in the prestigious enclave of Upper Brookville, this magnificent all-brick residence at 21 Overbrooke Lane exudes timeless sophistication and modern comfort. The home spans an impressive 8,346 square feet (gross) of meticulously designed interior space, offering 6 graciously appointed bedrooms and 4.5 luxurious baths. The property is situated on a sprawling 2-acre lot, providing unparalleled privacy and a serene backdrop of a majestic pond for both relaxation and entertaining. Upon entering, you are greeted by a grand two-story foyer that sets the tone for the home's refined elegance. The expansive living room, warmed by a stately fireplace, flows seamlessly into the formal dining room. The inviting family room opens into a chef s eat-in kitchen, which features a substantial center island, ideal for both culinary pursuits and casual gatherings. A spacious three-car garage adds to the property s practicality while enhancing its grandeur. This is more than a home; it is a statement of elegance, an oasis of comfort, and an opportunity to experience Long Island living at its finest.

10 Colonial Drive is a stunning Georgian estate set on 5 impeccably landscaped acres in the prestigious Colonial Drive Estate of Upper Brookville. This 10,000 sq. ft. residence offers 6 bedrooms, 6 bathrooms, 4 fireplaces, a heated gunite pool, tennis court, and a 3-car garage. A Baccarat chandelier graces the double-height foyer, setting the tone for elegant living. The formal dining room flows seamlessly into a chef s kitchen, while a refined library with an ornate fireplace provides a serene retreat. The sun-drenched kitchen opens to an outdoor oasis, featuring beautifully landscaped gardens, a pool, and ample space for al fresco dining and entertaining. Upstairs, 4 spacious ensuite bedrooms, including a luxurious primary suite with a fireplace and spa-like bath, provide ultimate comfort. The finished basement offers endless possibilities. A private driveway and lush gardens complete this exceptional estate, offering unparalleled privacy and sophistication.

Situated in the prestigious Upper Brookville, this exquisite property offers a serene pond view with a charming fountain that enchants during the summer time. This stunning brick colonial home boasts six spacious bedrooms and four-and-a-half bathrooms. Completely renovated in 2019, this elegant residence combines classic charm with modern designs located in the highly sought-after North Shore School District, renowned as the top district in the area. This property offers an idyllic lifestyle in one of the most luxury and tranquility coveted neighborhoods., Additional information: Appearance:Immaculate,Separate Hotwater Heater:Y

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

The seller is willing to hold the mortgage to a qualified buyer. Located in a gated community in Upper Brookville, this 10,000-square-foot majestic Gold Coast estate welcomes you with a circular driveway, soaring ceilings, and a grand double staircase. This luxurious home boasts a balcony on the second floor, a raised panel mahogany ceiling, and built-in cabinets and bookcases. It contains a Chef's custom eat-in kitchen with double all Wolf appliances. This Estate features six fireplaces. All bedrooms enjoy en suite baths. The Main bedroom has four closets and an en suite bath with a fireplace, jacuzzi, and an enormous walk-in shower. The main house has seven elegant bedrooms, nine full baths, and two half baths. For the car lover, there is a three-car garage attached to the main house and a nine-car detached garage with heat and air conditioning. Over the detached garage, there is an elegant one-bedroom apartment. The basement contains a state-of-the-art media room, a 1200-bottle wine cellar, perfect for the collector or investor, a humidor for the cigar smoker, a game room, and a gym for those who enjoy staying fit at home. The full-house generator ensures uninterrupted power for this five-acre estate. For all those who appreciate nature, this home enjoys a garden that contains a variety of unique trees, vegetable gardens, and marvelous sprawling lawns. The Olympic pool is complemented by a pool house, a one-bedroom guest cottage, two outdoor kitchens, and a travertine patio for dining. Summer fun can be enjoyed by playing tennis and basketball, visiting nearby beaches, and enjoying North Shore luxury and amenities., Additional information: Appearance:Diamond,ExterioFeatures:Tennis,Interior Features:Guest Quarters,Separate Hotwater Heater:Y