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luxury houses for sale Upper Brookville, United States

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30

House with pool and garden Upper Brookville (United States)

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.nnHidden 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 Islands 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.nnThe 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.nnDesigned 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.nnOutdoor 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 estates serene natural surroundings.nnRarely does a property offer this level of acreage, architectural integrity, historical significance, and lifestyle versatility within one of the North Shores most coveted enclaves. Applewood Estate is not simply a home it is a private world crafted for legacy living, grand entertaining, and timeless retreat.

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$25,000,000
2,084
13bedrooms
11bathrooms

By Annonceur International

50

Property Upper Brookville (United States)

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.

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$8,995,000
5bedrooms
12bathrooms
land 8,256

By Daniel Gale Sotheby's International Realty

32

Property with pool Upper Brookville (United States)

Set on five flat, impeccably landscaped acres at the end of a quiet cul-de-sac, this stately Georgian brick estate represents one of the most private and desirable settings within Upper Brookville’s prestigious gated Colonial Drive enclave. Positioned on a private road of distinguished luxury estates and further enhanced by its own secondary gated entrance, the property offers a rare double gated level of security and exclusivity. A grand double height foyer welcomes you, anchored by a magnificent Baccarat chandelier, immediately setting a tone of timeless elegance. The home is thoughtfully designed for both grand scale entertaining and comfortable everyday living, featuring 4 fireplaces, a formal living room, elegant dining room, refined library, and a luxury bar area. The main level includes two bedrooms with two full bathrooms nearby, ideal for guests or extended living, along with a fully equipped laundry room. At the heart of the home, the sun-drenched chef’s kitchen is enhanced by skylights and oversized custom windows, creating a bright and inviting atmosphere. Completed with premium appliances including a double wall Wolf oven, Wolf gas cooktop, and two Bosch dishwashers, breakfast nook and two pantries. The space seamlessly connects to the main living areas and opens to the patio, where retractable awnings provide effortless indoor to outdoor living. Upstairs, four spacious en-suite bedrooms include a luxurious primary suite featuring its own fireplace and a spa-inspired bath, offering a true private retreat. A Juliet balcony giving a view of serene front outdoor space. A finished attic adds a versatile open space suitable for a variety of lifestyle needs. The outdoor grounds are equally exceptional, showcasing expansive flat land, a heated gunite pool, tennis court, and multiple areas for entertaining and al fresco dining, all set within one of the most picturesque locations on Colonial Drive. Additional highlights include a finished basement with extra high ceilings, a whole house surround sound system, a recently updated roof (approximately 4 years old), and newer windows (approximately 1 year old). Updated Kitchen and bathrooms. Custom-made furnishings imported from Italy are included, further elevating the home’s refined aesthetic. This extraordinary estate seamlessly blends classic Georgian architecture with modern upgrades, offering unparalleled privacy, scale, and sophistication in one of the North Shore’s most coveted locations.

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$6,475,000
6bedrooms
6bathrooms
land 2ha

By Daniel Gale Sotheby's International Realty

45

Property with pool Upper Brookville (United States)

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.

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$3,500,000
5bedrooms
5bathrooms
land 8,256

By Daniel Gale Sotheby's International Realty

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27

House Upper Brookville (United States)

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.

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$3,700,000
4bedrooms
4bathrooms
land 2.2ha

By Daniel Gale Sotheby's International Realty

Contract pending
38

House Upper Brookville (United States)

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.

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$1,980,000
4bedrooms
3bathrooms
land 8,094

By Daniel Gale Sotheby's International Realty

Contract pending
28

House Upper Brookville (United States)

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.

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$9,750,000
7bedrooms
14bathrooms
land 4.1ha

By Daniel Gale Sotheby's International Realty

624 listings near Upper Brookville

Nearby
47

Property Muttontown (United States)

Set on two flat, quiet and bucolic acres surrounded by beautiful park-like plantings, mature specimen trees and colorful perennials, this renovated four-bedroom Center Hall Colonial offers serene country setting with exceptional convenience for commuting. A dramatic and elegant entry hall welcomes you with marble flooring and a striking staircase with decorative wrought-iron banister. Just off the foyer is a beautifully appointed full bath featuring custom, high-end porcelain and marble finishes. At the heart of the home is the sleek and stunning eat-in kitchen, thoughtfully designed with two sinks, two dishwashers and a quartzite waterfall center island with seating. GE Café appliances, a French oven and porcelain farmhouse sink complete the sophisticated space. Recessed ceiling lighting and motion-activated floor lighting provide both ambiance and effortless nighttime navigation. Radiant heat adds an additional level of comfort. The spacious formal living room features a wood-burning fireplace with marble surround and an abundance of natural light fro a wall of windows and French doors opening to the bluestone rear patio-ideal for seamless indoor-outdoor entertaining. The sunny formal living room showcases beautiful new wood floors and flows into a private office/den with French doors opening to a covered concrete patio. Upstairs are four bright bedrooms, including a spacious primary en-suite. All bathrooms have been custom designed with luxurious European finishes, including Grohe fixtures, heated towel bars and radiant heat. Outside, the spectacular, level property creates a truly dreamy setting. Expansive lawns, established perrenials and magnificent mature specimen trees surround a fenced, heated Gunite in-ground pool, offering exceptional privacy and a resort-like atmosphere. Numerous recent improvements include new Pella windows throughout, an updated cesspool, roof and plumbing, a new boiler and a full-house generator. Smart-home features allow heating, cooling, washer and dryer functions to be conveniently controlled from your phone. A beautifully renovated home combining timeless elegance, modern amenities and magnificent grounds in an exceptionally peaceful setting.

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$2,480,000
4bedrooms
3bathrooms
land 8,094

By Daniel Gale Sotheby's International Realty

Nearby
30

House with pool and garden Glen Head (United States)

Introducing An Unparalleled Masterpiece Of Luxury Living On Estate Suited For A Celebrity. This Prestigious And Exclusive Private Brick Compound Situated On 7 Acres Of Lush, Sprawling Grounds In Upper Brookville Offers A Lifestyle That Seamlessly Combines Timeless Elegance With Modern Luxury. Vaulted Ceilings, Creating A Sense Of Openness. Oversized Windows With An Abundance Of Natural Light & Panoramic Views Of The Property. 6 Oversized Bedrooms W/En-Suite Baths, 7 1/2 baths, Large EIK With Generous Counter Space & Storage. For The Car Lover Enthusiast W/10 Car Garage, Top-Of-The-Line Car Lifts & Car Port. Entertainers Exclusive Front & Backyard. Custom-Designed 22,000 Gallon Koi Pond With Thoughtfully Placed Stone Work, Fountains & Lighting. Newly Resurfaced Har-Tru Tennis Court, Gunite Heated Pool, 8 Person Hot Tub, Pool House W/Kitchenette, Full Bath & Changing Room. Custom Outdoor Kitchen, Premium Speaker System Both Inside & Out. Embrace A Lifestyle In Your Private Sanctuary! Google Maps, Waze

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$5,895,000
790
6bedrooms
7bathrooms

By Annonceur International

Nearby
30

House with pool Glen Head (United States)

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!

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$5,585,000
1,634
9bedrooms
12bathrooms
land 3.6ha

By Annonceur International

Nearby
30

House Oyster Bay (United States)

Maison Blanche: An Architectural Icon in Upper BrookvillenExperience 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 (20232026) masterpiece.nnThe 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 chefs kitchens in the main and guest houses are equipped with Wi-Fi-controlled Thermador appliances and specialty quartz islands.nnUniquely 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.nnApp-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. GPS. Off of Chicken Valley Rd.

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$8,995,000
939
6bedrooms
6bathrooms

By Annonceur International

Nearby
45

Property with pool Matinecock (United States)

Set amid mature, beautifully landscaped grounds in the coveted Village of Matinecock, this distinguished brick North Shore residence, built in 2006, offers an exceptional combination of scale, craftsmanship, privacy, and resort-inspired living. Rich hardwood floors, substantial millwork, designer wallcoverings, and thoughtfully updated interiors create a home that is at once impressive and inviting. A dramatic, columned double-height foyer with graceful bridal staircases sets an elegant tone upon arrival. The formal dining room is distinguished by a coffered ceiling, while a handsome wood-burning fireplace anchors the spacious den. French doors extend the living spaces to an expansive slate-and-brick terrace overlooking the lush grounds. Designed for both everyday living and effortless entertaining, the eat-in chef’s kitchen features custom cabinetry extending to the ceiling, marble countertops, an oversized center island, generous pantry storage, wine refrigeration, and professional-grade Thermador stainless steel appliances. The first floor primary suite is a private retreat, entered through double doors and appointed with a fireplace, sitting den, two closets, substantial moldings, and an en-suite bath. A formal living room, sunroom with terracotta floors, beautifully appointed laundry room with abundant storage, an elegant powder room, and a bedroom with an attached full bath complete the first floor. Outdoors, the residence unfolds as a private North Shore oasis. The fully fenced 2.06-acre property is framed by mature landscaping and enhanced by multiple fountains and water features. An inviting saltwater swimming pool with an electric cover is framed by handsome slate terraces, while a built-in spa with a cascading waterfall flowing into the pool enhances the resort-like setting. A beautifully designed teak outdoor shower and playset complete an environment equally suited to sophisticated entertaining and leisurely summer days. For the automobile enthusiast or collector, an extraordinary combination of attached and detached garaging accommodates up to eight vehicles - a rare and remarkably versatile offering. Additional amenities include radiant heat beneath tiled areas, central vacuum, whole-house water filtration, natural gas, a generator, integrated audio, Lutron lighting system, seamless speaker systems, and an electric privacy gate at the entrance to the property. The expansive unfinished lower level, with tall ceilings and concrete floors, includes a matted fitness area, provides direct access to the attached garage, and offers substantial storage along with exciting potential for future recreation, wine, or entertainment spaces. Private yet welcoming, refined yet eminently livable, this exceptional Matinecock residence captures the enduring appeal of North Shore estate living, with gracious interiors, expansive grounds, resort-like amenities, and an extraordinary setting designed to be enjoyed in every season. Located within the esteemed Locust Valley Central School District.

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$5,950,000
6bedrooms
5bathrooms
land 8,094

By Daniel Gale Sotheby's International Realty

Nearby
30

House with pool East Norwich (United States)

Tucked behind a private gated drive and set across over eight pristine acres, this iconic 1916 manor estate has been comprehensively restored and strategically enhanced to meet the expectations of today’s most discerning buyer. Historic architecture remains intact, while modern systems, technology, and amenities have been elevated to a truly exceptional level. Grand formal living and dining rooms feature museum-quality moldings and millwork, offering a refined backdrop for both intimate gatherings and large-scale entertaining. The gourmet kitchen is designed for serious cooking and seamless hosting, flowing naturally into the home’s main living spaces. A striking paneled library with wood-burning fireplace provides a moody, private retreat, while the showstopping 23’ x 44’ great room by Smiros & Smiros commands attention with 16-foot ceilings and a dramatic stone fireplace—engineered for memorable entertaining. The primary suite functions as a true private residence within the home, complete with a separate sitting room, coffee bar, and half bath, a spa-caliber marble bathroom with radiant heated floors, and dual dressing rooms. Five additional en-suite bedrooms, including a fully ADA-accessible suite, along with an office overlooking the gardens, complete the second level. Amenities rival those of a private resort, including a paneled elevator, indoor endless lap pool, catering kitchen, dog spa, a fully refreshed gym, and a discreet panic room / walk-in vault offering an elevated level of security. For the automotive collector, the estate delivers rare flexibility: a heated three-car garage with soaring ceiling heights designed to accommodate lifts for up to six vehicles, complemented by two additional single-car garages. The grounds are equally intentional. A new slate roof, heated gunite pool, Har-Tru tennis court with lighting (recently resurfaced and fenced), putting green, English gardens, playhouse, and curated outdoor lighting create a private, park-like setting designed for year-round enjoyment. Extensive masonry restoration, irrigation repair, landscape clearing, and exterior upgrades have been executed at scale. Behind the scenes, the home has undergone substantial systems modernization, including new and serviced HVAC, complete attic insulation, comprehensive electrical upgrades, restored fireplaces, upgraded pool infrastructure, a fully serviced gate and telecom system, and enterprise-grade security with AI-enabled cameras and property-wide WiFi coverage. The interior has been fully refreshed with newly painted finishes, refinished hardwood floors, custom window screens throughout, and exterior trim replaced with durable Azek for longevity. This is not simply a restored estate—it is a fully realized modern compound, where legacy architecture meets forward-thinking execution

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$10,750,000
1,213
9bedrooms
12bathrooms

By Annonceur International

Nearby
11

House with garden Matinecock (United States)

660 Chicken Valley Road , Locust Valley, Long Island Gold Coast Positioned within the most coveted enclave of Locust Valley on Long Island’s historic Gold Coast, 660 Chicken Valley Road is not merely a residence—it is a private estate of enduring significance, designed for a highly discerning buyer who values legacy, discretion, and uncompromising quality. Set across approximately 5.33 acres of secluded, manicured grounds and encompassing nearly 16,500 square feet of interior living space, the estate embodies a rare combination of architectural integrity, refined craftsmanship, and long-term asset strength—an offering seldom available in today’s market. Architectural Integrity & Engineering Excellence The residence far exceeds conventional residential standards, delivering exceptional structural durability and long-term stability. Every element—from roofing systems to drainage engineering, from acoustic insulation to thermal efficiency—has been executed to a near commercial-grade level, ensuring the property performs as beautifully as it presents over time. A fully integrated geothermal heating system, paired with advanced climate and humidity control, provides year-round comfort while preserving fine art, furnishings, and materials at an optimal level. Smart home integration allows full remote operation globally, supported by central vacuum, multi-zone climate control, and a whole-house generator—ensuring seamless living without compromise. Security and privacy are paramount, with dual gated access, an extended private drive, and discreet contingency features that elevate the estate to a level of true residential security. Interiors , Bespoke Craft, Quiet Luxury The interior experience is defined not by excess, but by precision. From hand-finished hardwood floors to finely executed crown moldings, each detail reflects a commitment to craftsmanship that is increasingly rare. The kitchen and service areas are appointed with best-in-class appliances—including Wolf, Sub-Zero, and Miele—integrated with custom millwork and carefully selected stone surfaces. These spaces function equally as a private culinary environment and a sophisticated setting for entertaining. The primary suite is conceived as a private retreat, featuring a fireplace, a fully appointed dressing room, and a spa-caliber bathroom with radiant heated floors, a freestanding soaking tub, and a multi-function shower system—delivering a daily experience of understated indulgence. Technology is seamlessly embedded throughout the home, integrating lighting, climate, and security into a unified system that supports effortless, modern living while preserving warmth and timeless character. Grounds , A Private Landscape of Distinction The estate grounds offer a level of scale and privacy rarely achieved. A defining feature is the approximately 2,000-foot cherry blossom-lined drive, creating a seasonal spectacle that transforms the approach into an experience of quiet grandeur—both cinematic and deeply personal. The landscape unfolds with expansive lawns, mature trees, and curated outdoor environments designed for both solitude and large-scale entertaining. Recreational amenities further enhance the lifestyle offering, positioning the estate as a true private resort. Location & Investment Perspective Locust Valley remains one of the most tightly held and supply-constrained markets on the Gold Coast. Properties of this caliber—combining land scale, construction quality, and privacy—are increasingly rare. This offering represents not only a primary or secondary residence, but a strategic long-term asset with strong preservation of value and generational appeal. 660 Chicken Valley Road is not defined by square footage alone, but by what it represents. It is a residence for those who understand that true luxury is not declared—it is recognized. Here, ownership is not simply acquired. It is inherited forward.

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$8,937,200
6bedrooms
12bathrooms
land 2.2ha

By Daniel Gale Sotheby's International Realty

Nearby
12

House Locust Valley (United States)

Enter the wrought iron gates and along a private drive, Rolling Meadows reveals itself with the quiet authority of architecture built without haste — a classic brick Georgian residence with stately columns and a slate roof, set amid nine-plus acres of gracious formal gardens and mature specimen trees. Inside, wide plank oak floors create genuine character. A sweeping staircase rises from the entry foyer; the living room and imported Filipino mahogany-paneled library each offer wood-burning marble fireplaces; the formal dining room features a distinct china showcase; and the chef’s kitchen — with its substantial center island and adjoining breakfast room — is designed for both daily living and entertaining. The principal suite is positioned on the main floor, offering exceptional privacy, generous dressing, and a unique ensuite bath. A first-floor guest suite, three additional second floor bedrooms, a substantial bonus room and a three-car attached garage complete the residence. The grounds are as fully realized as the interiors. An Innocenti and Webel pool and dedicated pool house provide an effortless setting for outdoor entertaining. The equestrian facility comprises a seven-stall barn, multiple paddocks and on-site staff quarters. The serious equestrian infrastructure is complemented by a three-car attached garage. There are two additional outdoor garages on the estate. Rolling Meadows is that increasingly rare proposition: a fully equipped country estate where architectural pedigree, equestrian infrastructure, and the warmth of a well-appointed home meet without compromise. A property of this character is best understood in person.

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$4,500,000
6bedrooms
4bathrooms
land 3.9ha

By Daniel Gale Sotheby's International Realty

Nearby
50

Property Brookville (United States)

Set on two flat, beautifully landscaped acres along a low-traffic street in Brookville, yet just minutes from major highways and shopping, this classic Colonial built in 1964 offers 3,838 square feet of thoughtfully updated living space. An extensive renovation touched nearly every corner of the home, from all new Marvin windows and doors to central air, updated heating, and a full repaint inside and out. The kitchen underwent its own complete transformation, emerging with high end appliances, a center island, and gas cooking, ideal for anyone who loves to cook and entertain. Three fireplaces warm the home throughout, found in the den, the living room, and the sunroom, where a new gas fireplace adds year round comfort. Upstairs, five bedrooms include a primary suite with a walk-in closet and an en suite bath featuring a soaking tub, stall shower, and double vanity, while a sixth bedroom was converted into a convenient laundry room. Three full baths and two half baths serve the home's living spaces, and a full unfinished basement offers ample storage or future potential. The three car garage, expanded from its original two car footprint, sits above with a second story that shares a wall with the primary suite. Comfort continues with three zone heating and air conditioning, a 400 amp electrical service, an automatic propane generator, and a Control4 smart home system managing sound, lighting, and video throughout. Outside, mature landscaping surrounds a brand new in-ground pool, a pergola, and an outdoor kitchen with a gas BBQ, perfect for warm weather gatherings. A new thirty year asphalt roof, new driveway, and updated sprinkler system round out a home where every major system and finish has been thoughtfully addressed. Colonial in style and scaled for gracious living, 15 Dogwood Hill offers a rare combination of space, setting, and easy access to everything Long Island's North Shore has to offer.

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$3,799,000
5bedrooms
5bathrooms
land 8,094

By Daniel Gale Sotheby's International Realty

Nearby
Contract pending
44

House Matinecock (United States)

Set behind gated access on over 10 breathtaking acres, this extraordinary estate embodies timeless luxury, exceptional craftsmanship, and effortless livability. A sweeping drive, interlocking stone walkway, and stately covered entrance create an impressive arrival, while beautifully appointed interiors offer warmth, sophistication, and abundant natural light. Designed with both grand-scale entertaining and comfortable everyday living in mind, the residence features 8 bedrooms, 6 full baths, and 3 half baths, including a thoughtfully positioned first-floor guest wing offering privacy and convenience. Rich wood detailing, custom built-ins, marble finishes, and expansive windows are found throughout. A handsome wood-paneled library and bespoke study evoke classic old-world elegance, while gracious entertaining spaces flow seamlessly from one to the next. The beautifully appointed dining room is highlighted by a dramatic floor-to-ceiling bowed window that fills the space with an abundance of natural light. An adjoining wet bar leads seamlessly to the chefs's kitchen, where an oversized center island, breakfast bar, state-of-the-art appliances, and extensive prep areas create an exceptional setting for everything from intimate gatherings to large-scale entertaining. An impressive array of lifestyle amenities includes a custom dance and ballet studio, expansive fitness space, resurfaced tennis court, and spectacular in-ground Gunite pool surrounded by mature trees and private lounging areas. A raised stone patio provides an elegant setting for outdoor dining and entertaining, while an attached pool cabana room with its own bathroom offers exceptional convenience and a seamless connection to the pool and outdoor living areas. From spa-inspired baths and sun-filled sitting rooms to multiple garages and extensive parking, every detail of the remarkable estate has been thoughtfully considered. Sophisticated without feeling formal, the property offers exceptional privacy, gracious proportions, and resort-style amenities in a truly magnificent setting.

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$6,680,000
8bedrooms
9bathrooms
land 4.4ha

By Daniel Gale Sotheby's International Realty

Nearby
35

House with pool Brookville (United States)

Welcome to this commanding five-bedroom contemporary residence, a spectacular home where soaring architecture, abundant natural light, and resort-style amenities combine to create an extraordinary living experience. From the moment you enter the dramatic two-story foyer, you are captivated by three magnificent floor-to-ceiling Palladian windows that frame breathtaking views of the terraced, verdant grounds beyond. The home's impressive two-story ceilings, rich hardwood floors, four fireplaces, and generously proportioned principal rooms create an atmosphere that is both grand and inviting, while seamlessly blending the beauty of the outdoors with every interior space. Designed for both everyday living and elegant entertaining, the home features a stunning culinary kitchen appointed with lacquered cabinetry, dual center islands, and an extraordinary Redwood Triple Glass Conservatory that bathes the space in natural sunlight. After dining in the elegant dinig room enhanced by a fireplace, a comfortable den provides the perfect place to unwind, while a private home office offers an ideal remote work environment. The main-level primary suite serves as a luxurious retreat, complete with a sitting room, spa-inspired bath, and custom-fitted closets. Upstairs, three additional bedrooms are complemented by a welcoming loft with a fireplace—a wonderful gathering space for relaxation and recreation. The home's most exceptional feature awaits on the walk-out lower level: a meticulously maintained heated indoor swimming pool that can be enjoyed year-round, creating a private resort within your own home. Outside, the beautifully terraced landscape is anchored by impressive natural boulders that enhance the property's architectural beauty and park-like setting. A serene, Zen-inspired brook gently winds through the grounds, creating a soothing sense of tranquility, while expansive bluestone patios, an outdoor kitchen, and lush lawns provide the perfect setting for entertaining, recreation, and peaceful reflection. This is a rare opportunity to experience luxury living at its finest. Generator and Level 3EV Charging

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$3,900,000
5bedrooms
7bathrooms
land 8,134

By Daniel Gale Sotheby's International Realty

Nearby
19

House Brookville (United States)

Experience pristine living in this exquisite diamond Brookville home, offering unsurpassed value in a highly coveted location. The prestigious approach features a long circular driveway, welcoming you to a serene retreat. The exterior boasts mature specimen plantings and estate fencing encircling a country club style yard with a Gunite inground gas heated pool. The flat entertaining backyard and brick patio, provides ample space to add tennis, pickleball or sport court. This serene oasis is perfect for relaxation and entertainment. Inside the kitchen features hardwood cabinets, complimented by gleaming hardwood flooring throughout the home. The architectural roof adds to the home's timeless elegance. First floor bedroom with en-suite bath and his and hers walk in closets, laundry, and a versatile bedroom/office with a walkout to the fabulous yard. There is so much more to this exceptional property that must be seen to be fully appreciated. Don't miss this rare opportunity to own a true retreat in a serene oasis.

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$2,599,888
7bedrooms
5bathrooms
land 8,134

By Daniel Gale Sotheby's International Realty

Nearby
6

House Oyster Bay (United States)

Experience timeless elegance and grand-scale living in this extraordinary residence offering over 13,000 square feet of luxurious living space, perfectly set on more than 5 acres of manicured grounds. Enter through the impressive dual staircase foyer that sets the tone for this stately home, featuring 9 bedrooms and 9 bathrooms designed for comfort and sophistication. The main level boasts exquisite wood flooring throughout, detailed crown molding, and a seamless flow between the formal dining room, great room, and family room - perfect for both intimate gatherings and large-scale entertaining. The chef's mahogany kitchen is a masterpiece, showcasing a granite center island, Viking appliances, and a butler's pantry for effortless hosting. A private office, recreation rooms, and a fully equipped gym add to the home's unmatched amenities. Retreat to the expansive primary suite, featuring dual walk-in closets, his-and-her spa-inspired baths, and a private balcony overlooking the resort-style pool and outdoor kitchen area. The partially finished basement with 10-foot ceilings offers endless possibilities for customization. Outside, a sparkling in-ground pool, outdoor entertaining space, and lush landscaping create your own private oasis. A three-car attached garage and a grand circular driveway accommodating 30+ vehicles complete this rare offering. Located in the prestigious Matinecock Village of Oyster Bay, this remarkable estate combines classic craftsmanship with modern luxury - the perfect place to call home.

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$5,995,000
1,078
6bedrooms
6bathrooms

By Annonceur International

Nearby
36
Video

Property Old Brookville (United States)

Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Step outside to your own private resort, where multiple stone patios, a fully equipped outdoor kitchen, sparkling in-ground pool, and beautifully appointed pool house provide the ultimate setting for entertaining or quiet relaxation, all surrounded by meticulously landscaped grounds and unmatched privacy. The luxurious primary suite serves as a private retreat, complete with a large dressing room and a spa-inspired bath featuring a soaking tub, oversized shower, and refined finishes. Five additional spacious bedrooms, along with seven full bathrooms and three half bathrooms, provide exceptional accommodations. The finished lower level is designed for both recreation and relaxation, offering a custom wine cellar, state-of-the-art home theater, fitness center, expansive recreation room, and abundant storage. Perfectly blending timeless design with modern luxury, this remarkable estate offers an unparalleled lifestyle in one of Old Brookville’s most sought-after locations, where privacy, sophistication, and exceptional entertaining come together in a truly extraordinary setting.

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$5,250,000
6bedrooms
10bathrooms
land 1.6ha

By Daniel Gale Sotheby's International Realty

Nearby
38

House Brookville (United States)

‘Haut Bois’ is a refined brick-and-stucco French chateau nestled in the heart of Brookville, New York. Inspired by the Louis XIV hunting lodge that later became the Palace of Versailles, this extraordinary 18-room estate is steeped in history, elegance, and timeless beauty. Originally built in 1916 by renowned architect Ogden Codman Jr. and meticulously restored in the late 20th century, this one-of-a-kind masterpiece sits at the end of a private road on eight pristine acres. Beyond its wrought-iron gates, a long, tree-lined stone driveway leads to the stately residence, where every detail reflects exceptional craftsmanship and sophistication - from antique stone fireplace mantels and hand-painted wallpaper to crystal chandeliers and bespoke finishes throughout. A grand entrance hall with a sweeping marble staircase welcomes you to the main level. The formal living and dining rooms, each adorned with French doors, open seamlessly to the outdoor entertaining terraces and overlook the breathtaking formal gardens. The chef’s eat-in kitchen features a spacious center island, custom cabinetry, a La Cornue range with matching hood, premium appliances, and granite countertops. Completing the main level are a wet bar, library, den, powder room, and a private guest bedroom with an en-suite bath. Upstairs, the luxurious primary suite offers separate dressing rooms, multiple walk-in closets, and two exquisite marble bathrooms. Three additional generously sized bedrooms, two full baths, and elevator access complete the upper level. The lower level is thoughtfully designed for both recreation and comfort, featuring separate guest quarters, a billiards room, playroom, laundry room, fitness area, spa, and sauna. The basement level includes abundant storage, a temperature-controlled wine cellar, and access to the attached four-car garage. Originally landscaped by famed French architect Jacques Gréber, the grounds are nothing short of spectacular. Highlights include a stunning step-down courtyard, irrigated vegetable garden, gated tennis court, in-ground pool with pool house, chipping and putting green, and an outdoor fireplace and grilling area. Cloaked in ivy and grandeur, and tucked away along Long Island’s storied Gold Coast, ‘Haut Bois’ stands as one of the last remaining architectural treasures of its era.

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$14,900,000
7bedrooms
9bathrooms
land 3.2ha

By Daniel Gale Sotheby's International Realty

Nearby
32

Property Muttontown (United States)

Steeped in architectural pedigree and timeless elegance, this extraordinary Muttontown estate, on 3.84 bucolic acres, was designed by renowned architect Marion Sims Wyeth, celebrated for his iconic work on Mar-a-Lago in Palm Beach. Privately tucked behind an impeccably landscaped half mile-long drive off Route 106, the property unfolds as a secluded North Shore sanctuary of exceptional beauty and distinction. Set amidst sweeping lawns, manicured gardens, and picturesque equestrian grounds, the stately brick residence, crowned with a slate roof and introduced by a charming courtyard entry, exudes enduring sophistication. Inside, grand formal entertaining rooms showcase exquisite millwork, original hardwood floors, dramatic wrought-iron railings, and an abundance of French doors that flood the interiors with natural light while seamlessly connecting the home to its breathtaking surroundings. Offering five bedrooms and five-and-a-half baths, the home masterfully balances grandeur with comfort. The formal living room, complete with a fireplace and built-in wet bar, creates an inviting setting for entertaining, while the sunlit breakfast turret and updated chef’s kitchen, appointed with premium professional-grade appliances, provide effortless everyday functionality. A spacious family room and elegant powder room complete the main living spaces. The first-floor primary suite serves as a luxurious private retreat, featuring dual full baths, a fireplace, expansive walk-in closets, and an intimate sitting room. The upper level offers two generously proportioned bedrooms and a beautifully appointed full bath with a thoughtfully separated vanity and shower area. Completing the space is an expansive unfinished attic, presenting exceptional potential for storage or future customization. Additional highlights include a walk-out finished lower level with laundry, bedroom with full bathroom and direct access to the attached two-car garage. Designed for both gracious living and sophisticated entertaining, the residence boasts expansive slate terraces spanning the length of the home, overlooking the stone courtyard driveway, private gardens, charming pergola, and in-ground gunite pool - evoking the romance and refinement of a storybook North Shore estate. A true horse property, the fully fenced equestrian amenities are equally exceptional, featuring a pristine multi-stall barn built-by Morton, thoughtfully designed grazing paddocks, and scenic walking trails woven throughout the grounds. A truly rare offering, this remarkable estate presents an unparalleled opportunity to own a significant piece of Long Island history, all within the esteemed Syosset Central School District.

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$3,995,000
5bedrooms
6bathrooms
land 1.6ha

By Daniel Gale Sotheby's International Realty

Nearby
Contract pending
24

House with terrace East Norwich (United States)

Welcome to 43 Highwood Road! A warm and welcoming 4 Bedroom, 4 Bath home, situated in the heart of East Norwich. This residence has been meticulously cared for with thoughtful improvements. In addition to an exceptional primary bedroom with ensuite and an expansive walk in closet, there are 3 generous sized bedrooms. The house highlights soaring vaulted ceilings and skylights, enhancing the open floor layout. The L-shaped living room and dining room features an inviting wood burning fireplace. The kitchen, complete with stainless steel appliances, boasts custom cabinetry and beautiful granite counters and backsplash. The inviting family room offers a wet bar for entertaining and sliders to the outdoor patio. The outdoor space is a tranquil retreat to take in the picturesque golf course views. Additional features include an attached one car garage, new driveway with ample parking, and a 4 zone in ground sprinkler system. Ideally located near historic Oyster Bay, boutiques, dining, beaches, park, and LIRR.

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$1,159,000
4bedrooms
4bathrooms
land 931

By Daniel Gale Sotheby's International Realty

Nearby
32
Video

Property Old Brookville (United States)

Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private resort: a sparkling pool glistening in the sun, a full tennis court for a quick match, and beautifully landscaped gardens that feel like your own private park. Whether you’re entertaining on a grand scale or enjoying quiet evenings under the stars, this property delivers it all.

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$5,490,000
6bedrooms
6bathrooms
land 1.5ha

By Daniel Gale Sotheby's International Realty

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