Upper Brookville Homes with Back Yard Lot features

Welcome to Upper Brookville, a hidden gem nestled in the picturesque landscapes of Nassau County, New York. Known for its serene ambiance and lush greenery, this charming village offers a perfect blend of suburban tranquility and urban convenience. With its tree-lined streets, elegant estates, and a strong sense of community, Upper Brookville is an ideal location for those seeking a peaceful retreat just a stone's throw away from the bustling heart of Long Island.

One of the standout features of homes in Upper Brookville is the generous backyard lots that many properties boast. These expansive outdoor spaces provide homeowners with the perfect canvas for creating their personal oasis. Imagine hosting summer barbecues, gardening, or simply enjoying a quiet evening under the stars in your own private sanctuary. The ample yard space not only enhances outdoor living but also allows for creative landscaping, play areas for children, and even the possibility of a pool or outdoor entertainment area.

Living in Upper Brookville means embracing a lifestyle of leisure and luxury. The village is home to several prestigious country clubs, parks, and recreational facilities, ensuring that residents have access to a variety of outdoor activities. With its close proximity to top-rated schools, shopping, and dining options, Upper Brookville strikes the perfect balance between peaceful living and modern conveniences.

Discover the charm of Upper Brookville, where spacious homes with beautiful backyard lots await to create lasting memories for you and your family. Experience the allure of this captivating village and make it your next home.

Newest Upper Brookville Homes with Back Yard Lot features

$8,995,000

5 Beds ⋅ 12 Baths ⋅ 1031340 MLS

A long driveway opens to a large courtyard with a classic fountain, revealing a magnificent Château-style Mansion on 2.03 acres of verdant property on a private cul-de-sac. Custom built for grand entertaining and everyday living, this incredible residence masterfully blends old-world European charm with modern luxury. A majestic 2-story entry foyer features a stunning domed-vaulted ceiling with a curved staircase, showcasing antiqued mirrored panels and an ornate wrought iron railing. Through a series of exquisite arches, the foyer leads to an expansive formal living room with a detailed ceiling and wall-to-wall windows as well as a palatial-sized dining room with a butler’s pantry that offers a wet bar and additional storage. The comfortable family room has a unique curved wall and a marble fireplace flanked by marble goddesses. Adjacent is a sitting room with a floor-to-ceiling built-in display wall and a cozy hexagonal built-in bay window seating area. Next door, an elegant study offers a productive place to work from home. A spectacular chef-inspired kitchen boasts a large breakfast area, dual islands, marble counters, a beautiful ILVE range with a show-stopping backsplash, Wolf, Miele and Sub-Zero appliances, plus an additional service kitchen to ensure effortless hosting. An opulent master suite retreat has a private sitting room with a fireplace, a convenient wet bar with refrigeration, 2 sets of French doors to front and rear balconies, and 2 walk-in closets – both with custom closet systems and one with a generous center island with storage – and features an incredible spa-like bath with a steam shower and a magnificent stand-alone soaking tub. All additional en-suite bedrooms are comfortable with ample walk-in closets and tastefully appointed baths with showers. The lower level is designed with a home gym, expansive recreation space, games area, raised stage, and handsome tufted leather doors leading to a state-of-the-art movie theater. An additional bonus space also offers a bedroom, closet, and a full bath with a shower. Flowing seamlessly outdoors, the lush, park-like property features an expansive bluestone terrace anchored by an outdoor fireplace and a gourmet summer kitchen equipped with a premium built-in grill, integrated refrigeration, and an artisanal pizza oven. Alongside the sparkling heated pool and large sun deck, a gorgeous cabana with a full bath and laundry provides an open yet covered space to relax, while dramatic torches illuminate the pool area at night, creating a resort-caliber experience. This exceptional smart home is complete with a Generac generator, central vacuum, Crestron security system, interior/exterior sound system, sprinkler system, radiant flooring, 3 fireplaces, fine millwork, and a 3-car garage. Just 27 miles from NYC, this French-inspired masterpiece of 5 bedrooms and 8 full baths/4 half baths, offers a tranquil retreat for the discerning buyer who appreciates a Gold Coast luxury lifestyle.

7 Covey Court, Upper Brookville

$3,500,000

5 Beds ⋅ 5 Baths ⋅ 1018330 MLS

Dream homes do exist. Perfectly situated on 2+ private, meticulously landscaped acres on a winding country lane, this charming 5-bedroom residence offers an unparalleled lifestyle. Every sun-drenched room provides stunning, expansive views of lush lawns, specimen trees, and vibrant perennial gardens. Exquisite Craftsmanship & Main Level Living. The main level showcases exceptional millwork, fine moldings, and rich hardwood flooring. A vaulted foyer welcomes you, leading to an elegant music room, a spacious living room, and a handsome cherry library with custom built-ins. The gourmet kitchen features premium appliances and custom Wood-Mode cabinetry, overlooking your private backyard oasis. A thoughtfully placed butler’s bar with a Sub-Zero wine cooler connects the kitchen to the formal dining room for seamless entertaining. A first-floor bedroom with a private en-suite bath is ideal for guests or multi-generational living. The second level hosts four additional bedrooms. The serene primary suite features a luxurious en-suite bath. Two additional bedrooms boast private en-suite baths, while the fourth bedroom enjoys access to a well-appointed hall bath. Step outside to your private resort, featuring an expansive deck that overlooks a heated, saltwater gunite pool. The entire property is fully fenced, private, and beautifully framed by mature landscaping. Car enthusiasts and organizers will love the two separate garages: a convenient main-level attached garage near the mudroom/kitchen, plus a second 2-car garage/storage area at the basement level. A massive, unfinished basement offers endless customization potential and features a direct walk-out entrance to the pool area. Enjoy the perfect balance of privacy and convenience. Located just moments from the village, this home offers an excellent commute while placing you in the highly coveted North Shore School District.

61 Linden Lane, Upper Brookville

$5,288,000

6 Beds ⋅ 7 Baths ⋅ 1010689 MLS

A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a two-story entryway, a luxurious primary suite on the main level, a free-form inground heated gunite pool with a waterfall, a covered outdoor kitchen, and a 3-car garage. Luxurious living with hidden privacy and easy access.

7 Fairway Court, Upper Brookville

$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

$4,000,000

4 Beds ⋅ 4 Baths ⋅ 955669 MLS

Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors that frame picturesque garden views and flood the interiors with natural light. The gracious living and dining areas are anchored by a striking double-sided stone fireplace, creating architectural interest and a warm, inviting ambiance. A sophisticated bar room with wine refrigeration and custom painted cabinetry enhances the cozy den, offering the perfect setting for entertaining. The expansive kitchen and family room serve as the heart of the home, featuring a dramatic double-height vaulted ceiling with loft above and seamless access to a side terrace ideal for outdoor dining and gatherings. Beautifully appointed with crisp white cabinetry, honed Absolute Black granite countertops, top-of-the-line appliances, and radiant heated floors, the kitchen flows effortlessly into the informal dining area and family room, complete with a raised-hearth stone fireplace. Additional highlights include pristine condition throughout, Newly painted and redone guest quarters, separate living and dining rooms, and a separate hot water heater., New generator, new gas line (2025), House newly painted and redecorated and grounds re landscaped. The Property in Spring is filled with an abundance of color with the Hellebores, Azaleas, Rhododendron. It is private and magical.

343 Chicken Valley Road, Upper Brookville

$3,499,999

6 Beds ⋅ 6 Baths ⋅ 986963 MLS

Welcome to this exceptional estate tucked away at the end of a long, winding driveway on just over two pristine acres in Upper Brookville. This stunning property offers the perfect blend of luxury, comfort, and versatility. The main residence features 5 bedrooms and 4.5 fully updated bathrooms across two thoughtfully designed levels. The expansive first floor hosts 4 bedrooms and 3.5 bathrooms, while the second floor offers a private bedroom with a full bath — all beneath dramatic double-height ceilings that flood every room with natural light. Sliding glass doors throughout all living areas seamlessly connect the indoors to the gorgeous grounds outside. The gourmet kitchen and all bathrooms have been meticulously updated with high-end finishes throughout. Radiant heated floors, four-zone AC and heat, integrated Sonos speakers, central vacuum, and a full-house generator ensure effortless comfort and year-round peace of mind. Outside, resort-style living awaits with a heated gunite pool featuring stunning waterfall and fountain elements, a outdoor barbecue, and beautifully manicured grounds. A separate one-bedroom guest cottage with a kitchenette, living room, and dining room provides ideal accommodations for guests or extended family. A three-car garage with its own basement completes this remarkable offering.

1095 Pine Valley Road, Upper Brookville

$8,995,000

6 Beds ⋅ 10 Baths ⋅ 970669 MLS

Maison Blanche: An Architectural Icon in Upper Brookville Experience the pinnacle of ultra-modern luxury at 31 Chestnut Hill Drive. Set on five flat, private acres at the crest of a premier cul-de-sac, this architectural sanctuary was originally designed by the renowned architect Gary Gallagher and redesigned by award-winning FAIA architect Stuart Narofsky, leading to an extensively renovated (2023–2026) masterpiece. The residence features six bedrooms with en-suite bathrooms, four additional half-baths, to include an expansive first-floor primary suite. Architectural highlights include two custom floating staircases with glass railings, porcelain and white oak floors, and frameless full-bodied Belldinni doors. The chef’s kitchens in the main and guest houses are equipped with Wi-Fi-controlled Thermador appliances and specialty quartz islands. Uniquely designed for wellness and entertainment, the second-floor features 3 bedrooms and a private gym and Finnish sauna, while the lower level boasts a Dolby-Atmos theater, wine tasting room, a yoga/massage spa, and a wet bar. Outside, a heated saline pool and spa are framed by a porcelain patio and an unobstructing glass railing, and an outdoor wet kitchen. App-controlled for the modern age, the estate features smart management of the custom steel entry gate, five-zone HVAC, motorized shades, security, and a whole-house generator. This is the new standard of Gold Coast living.

31 Chestnut Hill Drive, Upper Brookville

$2,895,000

4 Beds ⋅ 5 Baths ⋅ 967360 MLS

UPPER BROOKVILLE. Privately set behind sweeping lawns on over two acres in the Village of Upper Brookville, this elegant North Shore residence offers the privacy, scale, and timeless character synonymous with Gold Coast estate living. The home features 4 bedrooms, with primary suite on the main, and 3 full and 2 half baths, along with sun-filled living spaces, hardwood and tiled (radiant heated) floors, where seen, and classic architectural details throughout. A gracious entry leads to beautifully proportioned interiors designed for both everyday comfort and sophisticated entertaining. The formal living room with fireplace flows seamlessly into the dining room and adjoining sun room, creating an inviting setting for gatherings large or small. At the heart of the home, the chef’s kitchen features custom cabinetry, stone countertops, and a generous center island, opening naturally to the main living areas. The first-floor primary suite provides a private retreat complete with a walk in closet and a beautifully appointed bath with soaking tub and oversized shower. Additional bedroom/library on the first floor offers the perfect space for a home office or quiet relaxation. The second level includes additional bedrooms and bath, while the finished lower level offers exceptional entertaining amenities including a home theater, wine cellar, and bar/kitchenette. Outdoors, the property features expansive lawns and patios, mature landscaping, koi pond, fire pit, and an inground heated Gunite pool with detached guest/pool house (featuring full bath, kitchenette, living room with fireplace, and rec area), and 2 outdoor BBQ spaces, creating an ideal setting for summer entertaining and weekend gatherings. Conveniently located to world-class golf courses, equestrian estates, yacht clubs, and the charming villages of Locust Valley, Roslyn, and Manhasset, with Manhattan just a short commute away. A rare opportunity to enjoy refined estate living in the heart of Upper Brookville. Additional features: whole house generator, exterior lighting throughout, built in speakers throughout interior and exterior, 2 car attached heated garage, cul-de-sac location, and more.

1017 Friendly Road, Upper Brookville

Start Your Search

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.