ML# :3584301 Welcome to 16 Cherrywood, a light-filled oasis nestled in one of Locust Valley’s most sought-after small neighborhoods. This exquisite 4, 500 square-foot residence boasts an elegant open floor plan that seamlessly blends spacious living with intimate gathering spaces, perfect for entertaining guests or enjoying quiet moments. Featuring four generously-sized bedrooms and 5-1/2 luxurious bathrooms, this home showcases numerous architectural details, including tray ceilings, wood-burning fireplaces, a paneled library, wet bar, and a harmonious mix of brick, hardwood, and tile floors throughout. Step outside to discover your private paradise which overlooks a breathtaking 7+ acre protected sanctuary. The beautifully landscaped grounds are adorned with huge mature trees, manicured gardens, and a secluded rose and peony garden area, providing a serene backdrop for outdoor living. Multiple sliding glass doors invite the outdoors in, leading you to lovely awninged bluestone terraces with a heated swimming pool, perfect for alfresco dining and relaxation. A full house generator, security system, CAC, sprinkler system, radiant and gas heat, complete this residence. HOA $7, 500 annually. Don’t miss the chance to own this remarkable home that combines elegance, comfort, and unparalleled natural beauty. Schedule your private showing today and experience the lifestyle that awaits at 16 Cherrywood!
16 Cherrywood Rd, Oyster Bay, NY, 11560
ML# :3583291 Experience world-class resort living at Legends Yacht & Beach Club, an exclusive gated community set on 46 verdant waterfront acres along the North Shore of Long Island. With only 47 private residences, this community offers unparalleled amenities, including a private beach, marina, heated pool, elegant clubhouse, and indoor clay tennis courts-all maintained to perfection for stress-free living. This elegant home offers the perfect blend of luxury, comfort and a boat slip. The formal living room and dining room are ideal for entertaining, while the bright eat-in kitchen and cozy den with a gas fireplace provide everyday comfort. A dedicated office adds functionality. The grand primary bedroom is a private oasis with a spa like ensuite, while two additional bedrooms feature their own ensuites for guest privacy. The expansive finished basement includes a gym area, bar, media room, and a bonus room with a full bath.
5 Pembroke Drive, Oyster Bay, NY, 11542
ML# :3582290 Waterfront luxury awaits at this stunning four-bedroom, four-bath home in the exclusive Oak Point community of Bayville on Long Island’s North Shore. Blending contemporary elegance with beach town charm, this home offers expansive, unobstructed views of the Long Island Sound, just 30 miles from Manhattan and halfway to the Hamptons. Rarely will you find a home with such a perfect combination of panoramic water views nestled on a cul-de-sac within a private community complete with private beach access. Bayville’s tranquil coastal setting offers a perfect balance of serenity and accessibility, with a small-town feel, sandy beaches, and the convenience of nearby upscale dining and boutique shopping. Some of the homes features include radiant heated floors, a generator, a heated driveway, designer Italian tiles, quartz countertops and quartz fireplaces, and custom glasswork throughout to maximize the breathtaking water views. Two primary suites, each with a custom-built walk-in closet and spa-like bath, provide ultimate luxury, while natural light and water views pour in from oversized windows. Ideal for entertaining, the home boasts three fireplaces, an all-season room, a deck with a pergola, and an in-ground heated pool, all of which come together for seamless indoor-outdoor living. This is more than a home-it’s a chance to experience a lifestyle of privacy, luxury, and waterfront tranquility in one of Long Island’s most desirable communities. This home has everything anyone could possibly want whether as a summer getaway or a primary residence. Claim this extraordinary property and make it your own personal sanctuary. This home is NOT in a flood zone.
15 Oak Point Drive N, Oyster Bay, NY, 11709
ML# :3579507 Presenting an unrivaled 26-acre waterfront estate known as MiddleSea, recently transformed by a meticulous multimillion-dollar renovation with unparalleled luxury. Showcasing spectacular panoramic views, this exceptional property features over 2, 000 feet of Sandy Beach, ensuring complete privacy. This world-class estate has 4 distinct homes: The Main House, The Beach House, The Guest House, and The Gate House. All multi-million dollar residences on their own. In addition, there are 3 separate buildable 4 acre waterfront lots. At the heart of the estate lies a 20, 000 square-foot red-brick mansion. The main house features, 30 ft ceiling entry foyer with a timeless black and white marble floor and wrought iron white marble wrap around staircase, five ensuite bedrooms, including a lavish primary suite with dual luxury baths and a private balcony that overlooks breathtaking water views. The elegant formal living room, complete with a fireplace and French doors, opens to a stunning waterfall view. Additional refined spaces include a formal dining room with a striking white marble fireplace, a mahogany library with a wood and stone fireplace, and a office/bay view parlor, each adding to the home’s grandeur. The state-of-the-art gourmet kitchen features two Calacatta Caldia Marble Center Islands, complimented by Waterstone faucets, bronze and gold farm sink, Officine Gullo Firenze Oven, dual Thermador Dishwashers side by side Sub-Zero refrigerator, paired with a separate professional stainless steel Chef’s Kitchen and a 20-foot ceiling breakfast room. Equipped with an elevator and radiant heat throughout, the estate’s exclusive amenities include a private bowling alley, a wine cellar, a spa, and an impressive ballroom. Outdoors, the estate features a breathtaking waterfall, two swimming pools-one near the main house and another by the Gatehouse-a floating dock, and a boat ramp. Beautifully landscaped grounds offer panoramic waterfront views, cementing this estate’s status as an unparalleled retreat, a mere stone’s throw from New York City. The Bedrooms and Bathrooms listed above reflect the 4 separate houses on the property.
Oyster Bay NY, 11771
ML# :3579080 Beaucort is a consummate 5.17-acre Gold Coast estate. Impressive tall wrought iron gates open to a welcoming forecourt framed by manicured plantings. The seven-bedroom residence is an inspired interpretation of a French manor home. Crowned with a steep slate mansard roof, understated details play across the residence’s stucco facade. Beautifully proportioned principal rooms, rich in architectural details, flow easily from one to the next. The luxurious and spacious primary suite has a fireplace, Juliette balcony and two en suite baths. Idyllic flowering gardens surround the refreshing heated swimming pool. With room for relaxing and outdoor entertaining, a bluestone and red brick terrace spans the back of the home. The tennis court has a hard surface, and two levels of attached garages can accommodate six vehicles. An elevator travels from the first to the second level, and a backup generator services the whole house. Landscape lighting softly illuminates the gardens at night. Beaucort reflects a timeless elegance where classic architecture and artistry meet today’s cultivated aesthetic for luxury. A Masterpiece Collection Listing.
232 Cleft Rd, Oyster Bay, NY, 11765
ML# :3578383 Behold Applewood Estate, an expansive 35+ acre serene property nestled within the prestigious Village of Upper Brookville. This unmatched North Shore architectural masterpiece with 6+ dwellings, offers both grandeur and elegance. The unrivaled property was meticulously designed with professional landscaping, decorated with mature privacy hedges, formal gardens with water features and rolling green lawn space. Rooted in history, this magnificent estate was once an Apple Orchard Farm back in the early 1900’s and was also formerly owned by the celebrated 19th-century American Artist Montague Flagg. The bespoke Main Residence encompasses an impressive 13, 000 Sq.Ft. of living space, was custom built with Slate, Brick and Stone in 2005 and is a testament to high-end design and luxury living. Designer details include Onyx Marble installations, spacious primary rooms, oversized parquet wood floors, handmade iron fireplaces, thick-cut millwork and more. A grand Foyer with a winding staircase, a Great Room with intricate coffered 23 foot ceilings and a magnificent Library loft and a handcrafted Meditation Room, a Billiards/Game room with a Wet-Bar and a Eat-In-Kitchen with a Breakfast Room overlooking the peaceful backyard are just a few of the interior highlights that make this home truly special. Additionally, this unrivaled estate features several detached houses including a 2 Bedroom Colonial Residence and a meticulously reconstructed circa 1914 Stone Barn, now serving as a guest retreat. This distinguished horse-property includes a newly resurfaced tennis court, a separate sports court, a 6-door detached garage, a commercial-grade 150kW generator, a long tree-lined driveway and a secure gated entrance, ensuring peace, beauty and privacy. Equestrian enthusiasts will appreciate the formal horse stables complete with a training ring. The property further boasts a heated in-ground pool pavilion with a jetted jacuzzi spa and a built-in outdoor kitchen, as well as a 1 bedroom Pool House and numerous other refined amenities, making it a Gold Coast sanctuary of relaxation and sophistication.
Applewood Estate, Oyster Bay, NY, 11545
ML# :3578068 Welcome to 896 Hilltop Road, Mill Neck, NY - Built in 2015 an exquisite residence that epitomizes elegance and sophistication. This stunning home boasts 3, 798 square feet of meticulously designed living space, set on a sprawling 14, 932-square-foot lot, offering a harmonious blend of luxury and comfort. Upon entering, you are greeted by a grand foyer that sets the tone for the rest of the home. The main level features an inviting formal dining room, perfect for hosting intimate gatherings. The eat-in kitchen is a chef’s dream, adorned with granite and marble countertops, high-end stainless steel appliances including a stove, refrigerator, microwave, dishwasher, and a wine cooler. A spacious pantry provides ample storage. The living area is anchored by a cozy fireplace, ideal for relaxing evenings. Hardwood floors flow seamlessly throughout the home, enhancing its timeless appeal. The primary suite is a sanctuary, offering a huge closet/dressing room and a luxurious bathroom. Three additional generously sized bedrooms and 2.5 additional bathrooms ensure ample space for all. The home office provides a quiet space for productivity, while the gym caters to your wellness needs. The full basement offers additional living space for home entertainment including kitchen, gym, recreational areas and storage. Step outside to the expansive deck, which offers winter water views, creating a serene backdrop for outdoor entertaining. This smart home is equipped with Savant controls for lights, sprinklers, security, TV, and sound systems, providing seamless integration and ease of use. Experience unparalleled luxury in this distinguished residence. Schedule your private viewing today and step into a world of refined living.
896 Hilltop Rd, Oyster Bay, NY, 11771
ML# :3569827 A private gated driveway winds its way to a beautifully restored manor home, perfectly situated on over 8 lush acres. Originally constructed in 1916 this home has been meticulously renovated, seamlessly blending historic charm with modern day elegance. The grand living and dining rooms showcase exquisite moldings, the gourmet kitchen is an epicurean’s dream perfect for creating wonderful meals, the paneled library is the ideal place to curl up with a book in front of the woodburning fireplace. The custom 23’ X 44’ great room created by Smiros & Smiros showcases 16ft ceilings, & an oversized dramatic stone fireplace, truly amazing for entertaining. A luxurious primary bedroom is comprised of a separate sitting room with half bath & coffee bar, spa like full bath with radiant heated floors & two dressing rooms. Five additional ensuite bedrooms including a fully ADA accessible one, & office overlooking the gardens complete the second level. Special features like a paneled elevator, indoor pool, catering kitchen and dog spa fulfills every need. The exterior features a new slate roof, heated five car garage, heated gunite pool, har tru tennis court with lights, putting green, English gardens, playhouse & play area. Quiet Luxury Living At It’s BEST! Home Is Assessed at $9, 326, 000 Taxes Have Been Successfully Grieved Reduction Of Approximately $22, 000 For The 2025/2026 Year!
393 Mill River Rd, Oyster Bay, NY, 11771
ML# :3569453 Welcome to 1620 Old Cedar Swamp Road- A secluded Sprawling Estate that embodies sophistication and timeless elegance. This 7 bedroom 7 bathroom oasis welcomes you from the moment you enter the long driveway up to the residence. Upon entrance into the Grand Foyer that seamlessly flows into the Great Room with Vaulted Ceilings, to the chefs kitchen perfect for culinary enthusiasts and hosting, to the Sun-Filled Solarium and the Grand Living Room perfect for relaxing and entertaining, you are sure to be impressed throughout. Retreat to the primary suite on the first floor, a haven of tranquility with your very own patio overlooking the estate’s manicured grounds. The spa-like en-suite bathroom features a soaking tub, shower, and dual vanities, while the expansive walk-in closet/dressing room offers ample storage, as well as a cozy office conveniently located steps away. The second floor offers 6 additional well-appointed bedrooms and 4 additional bathrooms. The 2 acres of exquisite private property will take your breath away- with an entertainers backyard featuring an inground pool and captivating grounds to soak in all of Natures Beauty as far as the eye can see. This exceptional one-of-a-kind property is a must see- offering unmatched luxury living with endless possibilities located within the highly rated Jericho School District. Don’t forget about the 3 car garage and the large circular driveway to fit all of your most prized possessions, as well as hosting unforgettable gatherings or having peaceful retreats in your very own paradise.
1620 Old Cedar Swamp Rd, Oyster Bay, NY, 11545
ML# :3566322 Welcome to Meadow Farm, a magical compound located on the north shore’s gold coast and only steps away from the Long Island sound. A one of a kind property set on 8 magical acres, offers a unique, serene, and luxurious lifestyle only one hour from Manhattan. At the center of Meadow Farm is a large 6-bedroom home blending the charm of country living with all the modern comforts of today’s lifestyle. The light and bright cottage style home is thoughtfully and elegantly designed, featuring spacious rooms creating an atmosphere that is warm & inviting. The property also boasts a beautiful 5-stall stable complete with a tack room. Additionally, there are two charming caretaker cottages, and a 4 car garage. Another special feature is the large greenhouse, where a variety of plants and flowers can be grown year-round. Rolling meadows, idyllic gardens, captivating pastures, Meadow Farm is a unique compound and a rare find in today’s world.
Meadow Farm @ Lands End, Oyster Bay, NY, 11560