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$1,300,000
5 Beds 4 Baths 1048006 MLS
Waterview Inspired Elegance on Mill Neck Creek Perched majestically just a block from the sparkling waters of Mill Neck Creek, this enchanting 1939 classic blends timeless architectural grace with modern warmth. Set on an elevated vantage point that captures sweeping, shimmering water views and gentle breezes, 10 Holden Lane is a rare coastal haven offering an idyllic lifestyle. A long, verdant driveway lined with lush evergreens and mature plantings welcomes you home, setting a private and serene tone. Step up to the inviting spacious porch, the ultimate spot to unwind with your morning coffee while taking in the active, picturesque water views right outside your door. Property Highlights Main Residence: A thoughtfully curated 1939 layout featuring a spacious formal living room and dining room, a sun-drenched sunroom flanked by two fireplaces (one on each side), and rich character throughout. Flexible Accommodation: Includes a convenient first-floor bedroom and full bathroom, three well-proportioned bedrooms on the second level, and an additional bedroom and bath on the lower level. Detached Cottage: Exceptionally spacious, featuring a grand bedroom with high ceilings, a full bath, a full kitchen, and an open-concept living area,ideal for guests, extended family, or a private home office. Prime Waterfront Proximity: The property extends all the way down to the street just steps from Mill Neck Creek, placing the water practically in your front yard.

10 Holden Lane, Bayville

$5,299,000
6 Beds 7 Baths 1044684 MLS
Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale rooms ideal for both everyday living and entertaining. A grand foyer introduces the home’s elegant flow. The formal living room includes a fully equipped custom marble wet bar, while the open-concept den is framed by floor-to-ceiling windows overlooking the backyard and anchored by a marble fireplace.The custom kitchen opens seamlessly to the formal dining room and is complimented by thoughtful storage cabinetry, a large center island, Gaggenau gas appliances, double Bosch dishwashers, and a Sub-Zero refrigerator/freezer. Upstairs, all five bedrooms are en suite, offering privacy and comfort for guests alike. The extra-large primary suite serves as a private retreat, featuring dual outfitted custom walk-in closets and a luxurious marble bath with a steam shower, soaking tub, and two vanities. A spacious laundry room is conveniently located on this level. A well-designed service area beyond the kitchen includes a mudroom, a walk-in pantry, a full bath, and convenient access to the three-car garage, back staircase, and steps leading to the basement. The main level also features a generously sized bedroom, ideal for guests or extended stays. Radiant heated floors are featured in all bathrooms and the mudroom. The outdoor space is equally impressive, featuring a heated 40' x 20' Gunite saltwater pool, paver patio, and outdoor kitchen—perfect for entertaining or enjoying the serene, private grounds.

63 Fruitledge Road, Brookville

$3,999,000
6 Beds 9 Baths 1045340 MLS
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

$5,950,000
6 Beds 5 Baths 1036864 MLS
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.

898 Chicken Valley Road, Matinecock

$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

$3,799,000
5 Beds 5 Baths 1027379 MLS
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 thoughtfully updated living space throughout. 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.

15 Dogwood Hill, Brookville

$1,200,000
2 Beds 3 Baths 1026338 MLS
Welcome to your dream coastal retreat! This custom built 2 bedroom , 3 bath contemporary home offers the perfect blend of modern luxury and effortless Long Island Sound side beach living. With private beach rights through the Pine-Howard Civic Association just steps from your front door you'll enjoy breathtaking views. Recent 2023 construction meticulously designed also includes a Fuji clean outside treatment system and is fully elevated to FEMA compliant standards for ultimate peace of mind. Walking distance to charming local shops, seaside dining & vibrant community spots. Step inside to an open concept layout designed to impress. Sleek living space with dramatic high beamed ceilings create an airy spacious feel. A cozy electric fireplace serves as the living areas stunning focal point. A gourmet kitchen beautifully appointed with custom cabinetry and stainless steel appliances. A luxurious spa inspired primary suite bathroom complete with whirlpool walk-in deep soaking tub. Private deck perfectly situated for hosting family gatherings and enjoying morning coffee.

6 Howard Road, Bayville

$3,195,000
5 Beds 5 Baths 1020514 MLS
Down a long, private driveway canopied by mature trees, 17 Danton Lane is a modern 5-bedroom, 4.5-bath home that spans approximately 7,000 square feet on over 4 acres, in one of Locust Valley's most coveted beach enclaves, just a stroll from a private beach. A striking 2 story atrium foyer welcomes you in, with glass doors beckoning straight out to the backyard. The kitchen, redesigned in 2019, features large countertops, custom cabinetry, and Viking appliances, while a newly finished basement offers a full bathroom, gym and recreational space. On the main floor, the impressively large great room is designed for entertaining with oversized windows and elegant fireplace. On the other side of the house, the two-story primary suite includes a soaking tub, walk-in closets, and an upstairs office/den. The grounds, designed by Dubner, offer layered points of interest throughout, from a sparkling gunite pool with jacuzzi to a serene koi pond, creating a series of destinations to discover rather than a single view. Clean, contemporary design meets total privacy, lush surroundings, and private beach access on over 4 acres at 17 Danton Lane.

17 Danton Lane N, Locust Valley

$5,888,000
6 Beds 6 Baths 1001932 MLS
Discover unparalleled luxury in the heart of Muttontown at 2 Chelmsford Drive, a striking post-modern custom-designed new construction set on a breathtaking 2-acre country club setting. Surrounded by specimen plantings and professionally curated landscaping, this extraordinary estate offers exceptional craftsmanship, sophisticated design, and resort-style amenities throughout. A dramatic custom pivot front door opens to a grand paneled foyer with soaring ceilings ranging from 14 to 20 feet, creating an impressive first impression. Wide-plank white oak floors and custom Pella windows enhance the home's warm, contemporary elegance. The state-of-the-art chef’s kitchen is a true showpiece, featuring rich walnut cabinetry, stunning black quartzite countertops, and a full suite of premium Wolf appliances, including double ovens, a six-burner cook top with griddle, microwave, built-in coffee system, separate ice maker, beverage refrigerator drawers and subzero refrigerator. The formal dining room offers soaring ceilings and walls of glass that open to an outdoor entertaining terrace complete with a full kitchen, pizza oven, and fireplace. The spectacular living room features a double-sided gas fireplace and a custom plaster ceiling. The luxurious primary suite boasts a dramatic 20-foot ceiling, built-in designer headboard feature wall, private deck overlooking the expansive grounds, two custom walk-in closets, and a designer spa bath. Three additional bedrooms are conveniently located on the main level. A stunning illuminated floating staircase leads to the lower level, where you will find additional guest bedrooms, a private gym with adjoining sauna and bath, a large movie theater, and an oversized recreation room with wet bar and glass doors opening directly to the backyard oasis. Designed for ultimate outdoor enjoyment, the country club-inspired grounds feature an oversized heated saltwater Gunite pool with spa, an elegant cabana with outdoor kitchen, and a separate pool house for storage. Automobile enthusiasts will appreciate the extraordinary garage capacity for up to 10 vehicles, including two car lifts, along with a circular paved driveway that completes this one-of-a-kind estate. 2 Chelmsford Drive is a masterfully designed residence that seamlessly blends architectural excellence, luxury amenities, and unparalleled lifestyle living.

2 Chelmsford Drive, Muttontown

$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

$924,000
4 Beds 2 Baths 1001116 MLS
Welcome to 28 Satinwood Road, a spacious and thoughtfully updated four-bedroom, two-bath home in the beautiful village of Bayville, offering more than 2,200 square feet of flexible living space in an established non-flood zone neighborhood that offers access to private village beaches, docks, pickleball, tennis courts and mooring rights. Locust Valley School District. Plenty of restaurants, activities with close proximity to shopping-everything that makes Bayville village living special. Move-in ready and filled with natural light, this home combines a thoughtfully updated interior with the space, storage and practical features that are hard to find—including a two-car garage, flexible lower-level living space, a generator with automatic transfer switch and a double gate at the side yard offers dedicated space for additional cars, a boat, trailer or RV. For added convenience, washer and gas dryer hookups are located on both levels, eliminating the need to carry laundry between floors and adding even greater flexibility to the home’s two- level layout. The main level welcomes you with freshly painted walls, gleaming hardwood floors and large windows with plenty of natural light. The completely remodeled kitchen features high ceilings, solid-surface countertops, a deep stainless-steel farmhouse sink, newer appliances, soft-close cabinetry, abundant storage and gas cooking. Sliding glass doors open directly to the large deck, creating an easy flow for outdoor dining and entertaining. The adjoining living and dining rooms feature hardwood floors, crown molding and oversized windows, providing a bright, comfortable gathering space. Throughout the home, thoughtful upgrades include wood-paneled doors, custom blinds, updated lighting and Elfa closet systems. Just down the gallery style hall you’ll find three of the four bedrooms. The spacious primary bedroom with deep double-door closets and windows on multiple walls for wonderful natural light. Two additional bedrooms comfortably accommodate queen-size beds and include custom closet systems. The main-level full bath offers a large vanity with storage, tub/shower combination and ceramic tile flooring. The lower level adds exceptional flexibility for today’s lifestyles. A fourth bedroom with a custom closet system sits alongside a beautifully remodeled bath that feels like a spa retreat with stone pebble floor shower and custom tilework. Combined with a spacious den/flex area, separate laundry and sliding doors leading to a large sunny backyard, this level is ideal for multigenerational living, extended-stay guests, a home office, fitness area or additional Rec space. The two-car garage provides additional storage and workshop space. The attic, accessed by newer pull-down stairs, provides even more storage. Major improvements add comfort and peace of mind, including newer central air, updated electrical, newer hot water heater and a generator with automatic transfer switch. Move in, unpack and start enjoying life in Bayville.

28 Satinwood Road, Bayville

$2,749,000
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

$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.