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$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
$5,295,000
6 Beds ⋅ 9 Baths ⋅ 1021182 MLS
Imagine an exclusive lifestyle redefined within a private HOA gated community, where absolute security meets unparalleled luxury on a flat, beautifully landscaped 2.53-acre parcel. This masterfully constructed 7,000-square-foot estate—boasting an impressive six bedrooms and seven bathrooms, each with their own private balcony—is defined by ultra-high-quality finishes throughout, including radiant heated floors, a central vacuum system, and a private elevator servicing all levels. The crown jewel of the residence is a first floor year-round indoor wellness spa complete with a pristine indoor pool, relaxing sauna, and steam room facilities. Designed for flexible multi-generational living, the home features dual (2) primary suites with private balconies and jacuzzi baths, a media room for grand entertainment, a designer eat-in chef’s kitchen anchored by a massive island, and a beautifully finished walk-out lower level. Entertain brilliantly on the expansive rear patio with outdoor kitchen and covered pavilion. Conveniently located just 11 minutes to the Long Island Expressway, this luxury home seamlessly blends elite architecture with a truly exceptional compound experience.

5 Farmwoods 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
$2,988,000
6 Beds ⋅ 5 Baths ⋅ 1014387 MLS
Welcome to luxury living in Upper Brookville's most desirable location. This stunning furnished residence features 6 bedrooms, 5 bathrooms, an office, and a luxurious master suite with a steam shower, jacuzzi tub and a huge walk-in closet. Spread across beautifully landscaped grounds, enjoy amenities such as a Har-Tru tennis court, a heated Olympic-size pool with a spa, and a sun filled deck with an outdoor kitchen ideal for entertaining. The home boasts an integrated Sonos speaker system both indoors and outdoors, providing high-quality sound throughout. For fitness enthusiasts, there's an in-house gym, playground. The fenced property ensures privacy and security with gated access. Experience unparalleled comfort and elegance in this prestigious estate.

110 Linden 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
$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
$5,495,000
6 Beds ⋅ 8 Baths ⋅ 985121 MLS
An exceptional private brick estate compound set on approximately 7 meticulously manicured acres in Upper Brookville. This impressive residence offers grand scale, timeless elegance, luxurious landscaping, and a true lifestyle experience both inside and out. Filled with natural light, the home features vaulted ceilings, oversized windows, sweeping property views, 6 spacious bedrooms with en-suite baths, 7.5 baths, large eat-in kitchen with generous counter space and storage, and full finished basement. Designed for both daily living and elevated entertaining, every space offers comfort, presence, and functionality. The meticulously designed grounds create a resort style setting with a custom 22,000 gallon koi pond, custom lighting, newly resurfaced Har-Tru tennis court, heated gunite pool, 8-person hot tub, pool house with kitchenette, full bath and changing room, custom outdoor kitchen, and premium speaker system inside and out. Complete with space for 10-cars, car lifts, and carport, this rare Upper Brookville estate delivers privacy, scale, luxury, and an unmatched indoor and outdoor lifestyle. A rare opportunity to own a private Upper Brookville estate with exceptional amenities and beautifully maintained grounds.

45 Wolver Hollow 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
$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
$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
$3,500,000
6 Beds ⋅ 9 Baths ⋅ 906347 MLS
Elegance redefined in this stunning gem that blends an eclectic mix of mid-century modern design with a touch of contemporary sophistication, nestled on two lush, gated acres in Upper Brookville. From the moment you enter, the home captivates your imagination with its soaring 30-foot ceilings and dramatic windows and wood architectural elements. Clean lines, warm textures, and artful finishes create a sanctuary where luxury and tranquility meet. The expansive great room features floor-to-ceiling windows that flood the space with natural light, while rich wood accents and sculptural details evoke timeless mid-century character. Accents of bold color and modern materials add a sophisticated edge, striking the perfect balance between vintage charm and modern elegance. Stone fireplace soars through the expansive space, reminiscent of western grandeur. The design invites you to indulge in large-scale living without sacrificing comfort or intimacy. This home offers 6 bedrooms, 7 full baths plus 2 half baths, and a 3-car garage.Tennis court, Multiple heat and AC zones, electric Hunter Douglas window shades, full pool cabana with bath, and a fully gated property with separate entry and exit complete the offering. A true masterpiece, where the intersection of Zen design and glamour creates a lifestyle that embraces calm and beauty.

5 Carol Lane, Upper Brookville
$5,585,000
9 Beds ⋅ 12 Baths ⋅ 885874 MLS
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!

60 Piping Rock Road, 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.