Upper Brookville Homes for Sale

Welcome to Upper Brookville, a hidden gem nestled in the heart of Nassau County, New York. This enchanting village, known for its lush landscapes and serene ambiance, offers a perfect blend of suburban tranquility and urban accessibility. With its picturesque tree-lined streets and sprawling estates, Upper Brookville is a haven for those seeking a peaceful retreat from the hustle and bustle of city life while remaining just a short drive away from the vibrant energy of New York City.

Upper Brookville boasts a rich history and a strong sense of community. Residents enjoy a lifestyle characterized by privacy, luxury, and a commitment to preserving the natural beauty of the area. The village is dotted with exquisite homes, many of which are set on expansive properties, providing ample space for outdoor activities and entertaining. The architectural styles range from classic colonial to modern masterpieces, ensuring that there is something for every discerning buyer.

For those looking to invest in real estate, Upper Brookville presents a unique opportunity. Homes for sale in this charming village offer not just a place to live, but a lifestyle steeped in elegance and comfort. With its top-rated schools, proximity to exquisite dining, and recreational amenities, Upper Brookville is an ideal choice for families and professionals alike.

Whether you’re searching for your dream home or a luxurious retreat, Upper Brookville invites you to explore its enchanting offerings. Discover the allure of this remarkable community and envision the possibilities that await you in your new home. Welcome to Upper Brookville, where your dream lifestyle awaits!

Newest Upper Brookville Homes for Sale

31 Chestnut Hill Drive, Upper Brookville

$7,850,000

6 Beds ⋅ 10 Baths ⋅ 1061123 MLS

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities. Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating staircases with glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island. The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space. Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining. Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

31 Chestnut Hill Drive, Upper Brookville

18 Chestnut Hill Drive, Upper Brookville

$4,980,000

7 Beds ⋅ 9 Baths ⋅ 1061600 MLS

Set on five magnificent acres of sprawling, level grounds along one of Long Island’s most coveted residential streets, this extraordinary contemporary estate, designed by acclaimed architectural firm Mojo Stumer, represents a sophisticated expression of modern luxury, architectural innovation, and resort-inspired living. Distinguished by dramatic proportions, soaring ceilings, expansive walls of glass, and a seamless connection between indoor and outdoor spaces, the residence offers an exceptional combination of architectural significance, privacy, and grand-scale entertaining. A grand entrance foyer introduces interiors defined by remarkable volume and natural light, leading to a breathtaking double-height great room anchored by a striking marble fireplace. Expansive windows frame picturesque views of the surrounding landscape, enhancing the home's connection to its private, park-like setting. The thoughtfully designed main level features an elegant formal dining room, spacious eat-in kitchen, inviting family room, and sophisticated lounge with a wet bar. A powder room and first-floor laundry provide additional convenience. Occupying a private wing of the main level, the luxurious first-floor primary suite offers an exceptional retreat, complete with a generous his and her walk-in closet and a beautifully appointed bathroom featuring a steam shower. An additional first-floor bedroom with a full bathroom provides ideal accommodations for guests or extended family. The second level features four generously proportioned guest bedrooms complemented by two full bathrooms. Additionally an expansive loft with its own balcony and full bathroom offers a versatile space ideally suited for a private office, additional lounge, or secluded retreat. Designed for recreation, wellness, and entertaining, the expansive lower level features a dramatic double-sided fireplace connecting the game room and entertainment spaces. A spacious recreation area with a wet bar provides the perfect setting for gatherings, while a substantial private gym with its own full bathroom creates a dedicated fitness retreat. Additional accommodations include a staff or guest bedroom and another full bathroom. Beyond the residence sits a remarkable private resort featuring a swimming pool, hot tub, and tennis court. A substantial poolside cabana offers a full indoor kitchen, outdoor wet bar, comfortable lounge, full bathroom, and dedicated laundry facilities. A built-in outdoor grill completes the exceptional entertaining amenities, providing an effortless transition between indoor luxury and outdoor leisure. A four-car garage further complements the estate, providing generous space for automobiles and storage. The property presents a remarkable opportunity to experience architectural distinction, privacy, and an uncompromising lifestyle.

18 Chestnut Hill Drive, Upper Brookville

39 Chestnut Hill Drive, Upper Brookville

$12,750,000

8 Beds ⋅ 12 Baths ⋅ 1056809 MLS

Built in 2001 and privately set on five pristine acres, this extraordinary estate is a residence of rare character and enduring elegance, blending old-world craftsmanship, architectural drama, and gracious modern living. From richly detailed formal rooms to expansive spaces designed for entertaining, every level reveals another layer of thoughtful design. The home makes an immediate impression with a distinguished foyer featuring classic checkered flooring, where graceful archways establish a sense of symmetry and sophistication. Beyond, the formal living room is beautifully appointed with intricate hardwood floors, a marble fireplace and mantel, and French doors opening directly to the terrace, creating an effortless connection between the interiors and gardens. A formal office boasts distinguished rich hardwood paneling, an intricately finished plaster ceiling, and its own wood-burning fireplace. The formal dining room is equally refined, framed by substantial moldings and anchored by another fireplace—an elegant setting for both intimate dinners and grand-scale entertaining. One of the home's most memorable architectural moments is a discreet curved staircase leading to the dramatic family room. Here, soaring vaulted ceilings, exposed wood beams, and a monumental stone fireplace create a remarkable sense of scale. A concealed door reveals a private wet bar, adding an unexpected and sophisticated element for entertaining. The kitchen and service areas have been conceived with both beauty and function in mind. A handsome butler's pantry features a hand-painted tile backsplash, marble countertops, and abundant preparation space. The expansive farmhouse-inspired eat-in kitchen is finished with warm terracotta floors, two porcelain farmhouse sinks, oversized chef's appliances, a substantial center island, and a sun-filled breakfast area overlooking the grounds. A pantry and discreetly positioned powder room are located just off the kitchen, while a circular rear staircase provides convenient access between levels. A separate side entrance opens to a practical mudroom with an additional service pantry, complete with sink and refrigerator. Ascending to the second floor, an oval wood architectural ceiling crowns a gracious landing overlooking the level below, creating a striking transition to the private bedroom quarters. The secondary accommodations include four generously proportioned bedrooms, one with its own loft space, each appointed with a marble en-suite bath. Near the rear-stair landing, a convenient preparation or household station with sink adds functionality, while a private office provides a dedicated workspace. The primary suite is an extraordinary private retreat. Generous in scale and beautifully secluded, it offers separate dressing rooms and walk-in closets, along with a spa-inspired bath featuring a jetted soaking tub and oversized walk-in shower. An adjoining sitting room creates a quiet sanctuary, with access to a walk-up attic offering additional possibilities. The lower level rivals the principal entertaining spaces in both scale and amenities. Remarkably high ceilings enhance an expansive den and recreation area, complemented by a powder room, full bar, billiards and game room, wine cellar, professionally matted gym, and an impressive 15-seat private theater. Two additional staff or guest rooms, supported by two full baths, complete this exceptionally versatile level. Across the estate's five pristine acres, the grounds unfold as a private resort. Expansive slate and brick terraces provide multiple settings for dining and entertaining, while covered patios framed by graceful archways offer shaded retreats overlooking the property. Beyond, a swimming pool and spa form the centerpiece of the property's recreational amenities, accompanied by a substantial, one-of-a-kind pool house that further elevates the estate's resort-like appeal.

39 Chestnut Hill Drive, Upper Brookville

$4,200,000

6 Beds ⋅ 8 Baths ⋅ 1043804 MLS

Welcome to 10 Laurel Woods Drive, an expansive 8,000+ square-foot residence privately situated on 5.45 park-like acres in Upper Brookville. Set behind wrought iron gates at the end of a quiet, tree-lined cul-de-sac, this impressive expanded ranch offers exceptional scale, privacy, and a true estate-like setting. The home features six bedrooms and eight bathrooms, including a spacious first-floor primary suite. Generously proportioned interiors are designed for both everyday living and large-scale entertaining, with formal living and dining rooms, a sitting room, and an expansive great room, all enhanced by new flooring. A newly renovated, state-of-the-art chef’s kitchen serves as the heart of the home, thoughtfully equipped with both gas and electric cooking stations. Just beyond, a dedicated mudroom provides direct access to the four-car garage, offering exceptional space for car enthusiasts, collectors, or additional storage. The fully finished lower level provides extensive additional living and entertaining space, complete with a dedicated theater room, wet bar, gym, and ample room for recreation, gatherings, and flexible use. Outside, the property unfolds as a private retreat. A newly repaved tennis court, updated gunite swimming pool with new equipment, and dedicated pool house are surrounded by sweeping lawns and mature landscaping. Meandering walking paths extend throughout the grounds, complemented by a fire pit and garden, creating numerous spaces to relax, entertain, and enjoy the remarkable natural setting. Offering substantial interior space, extensive amenities, and more than five acres of beautifully established grounds, 10 Laurel Woods Drive presents a rare opportunity to enjoy estate living in one of the North Shore’s most desirable villages

10 Laurel Woods Drive, Upper Brookville

$3,999,000

6 Beds ⋅ 9 Baths ⋅ 1045340 MLS

Perfect Generational Compound with Multiple Guest Suites plus Master Suites on 1st and 2nd floor. Elegance redefined. This fully gated extraordinary Upper Brookville estate seamlessly blends mid-century modern design with contemporary sophistication, set on two lush, gated acres. Soaring 30-foot ceilings, dramatic windows, rich wood architectural elements, clean lines, and sculptural details create a striking sense of tranquility. Palatial in scale yet thoughtfully designed for comfortable living and entertaining, this residence offers remarkable versatility with resort-style amenities. A true architectural masterpiece where Zen-inspired design meets glamour and beauty, creating a luxurious lifestyle. The expansive great room features floor-to-ceiling windows, warm wood accents, and a dramatic stone fireplace soaring through the space, evoking a sense of Western grandeur. Bold color and modern materials add a sophisticated edge, balancing timeless mid-century character with contemporary elegance. The over 1,000-square-foot first-floor primary suite is exquisitely designed and decorated as a private retreat. The expansive floor plan offers six bedrooms, seven full baths, and two half baths, along with multiple separate guest suites with private entrances. One additional space can easily be converted to a private music studio or creative space, providing exceptional flexibility for a variety of living arrangements. Over $500,000 in recent renovations and improvements include the renovated kitchen and bathrooms, upgraded flooring, and enhancements to the outdoor pool and pool deck. Additional amenities include a private tennis court (TLC), multiple heating and air-conditioning zones, luxury window coverings, a full pool cabana with bath, and a three-car garage.

5 Carol Lane, Upper Brookville

$3,480,000

6 Beds ⋅ 5 Baths ⋅ 1033074 MLS

Step away from the everyday and into this gracious, light-filled ranch, where every room feels like an invitation to relax. Sun-drenched and spacious, the interconnected living areas create an effortless flow — warm, welcoming, and made for both quiet mornings and lively gatherings. Built for entertaining, the home features a gourmet kitchen ready for your next dinner party, a formal dining room anchored by a cozy fireplace, a comfortable den, and an oversized living room with sweeping views of the beautifully landscaped grounds. The private wing offers four bedrooms — two with en-suite baths — plus a shared full bathroom and a relaxed, informal den for everyday living. On the opposite side of the home, two additional bedrooms and a full bath offer flexibility and privacy for guests, family, or a home office setup. Outside, the property is nothing short of breathtaking. A long, winding driveway sets the tone, leading past a charming gazebo, rolling lawns, and a private Gunite pool complete with a tranquil koi pond and cascading waterfall. The pool house rounds it all out with showers, a full bathroom, and a recreation room — perfect for summer days that never have to end. This is more than a home — it's a lifestyle.

24 Winding Lane, Upper Brookville

$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

$4,998,000

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

343 Chicken Valley Road, Upper Brookville

$3,700,000

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

$3,795,000

6 Beds ⋅ 6 Baths ⋅ 996646 MLS

Framed by sweeping pond views and set on over 2 private acres spanning both Old Brookville and Upper Brookville, this beautifully renovated brick estate offers an exceptional blend of luxury, privacy, and convenience. Tucked away on a quiet cul-de-sac yet just minutes from shopping, dining, and major highways, the home features 6 bedrooms, 5.5 baths, a bright open layout, and hardwood floors throughout. The custom gourmet kitchen overlooks the scenic backyard and pond, while the first-floor primary suite provides a private retreat. Every bedroom offers direct bathroom access through either an en-suite or Jack-and-Jill layout. Additional highlights include spacious entertaining areas, a full finished basement, guest accommodations, a full-house natural gas generator, and a 3-car attached garage. Outside, beautifully landscaped grounds, stone patio, create a resort-like setting overlooking the ponds picturesque year-round views.

23 Overbrook Lane, Upper Brookville

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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.