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$4,999,990
14 Beds ⋅ 15 Baths ⋅ 833470 MLS
Set on 9 pristine acres with panoramic views of Long Island Sound, this private, gated estate is a masterpiece of history and modern refinement. Once a favored retreat for Hollywood’s golden era icons, including the Barrymores, Buster Keaton, and Myrna Loy, this extraordinary residence sits in the heart of Nissequogue, a town renowned for its charm and exclusivity. Designed by celebrated architect Stanford White, known for the Washington Square Arch, the estate reflects timeless grandeur while seamlessly incorporating state-of-the-art amenities. Steeped in rich history and surrounded by breathtaking landscapes, this extraordinary estate has been meticulously restored, blending old-world elegance with modern luxury to create an unrivaled living experience. Spanning more than 20,000 square feet across three distinct residences, the estate offers 14 lavish bedrooms and 14.5 opulent bathrooms. Every space has been crafted with precision, from the slate roofing to the exquisite stonework, ensuring a setting of ultimate luxury and comfort. The estate is a haven of resort-style living, featuring an awe-inspiring two-story great house and an expansive indoor pool pavilion with a Gunite pool, hot tub, fitness center, and sauna. A fully finished lower level offers a wine cellar and tasting room, perfect for intimate gatherings. The property also includes a three-bedroom guest house and dedicated staff quarters, ensuring privacy and convenience. Outside, the grounds are impeccably designed with lush landscaping, a professional-grade tennis court, a cascading waterfall, and custom Italian porcelain walkways. A four-car garage and a high-powered Generac generator provide security and reliability. Located just minutes from beaches, yacht clubs, fine dining, and boutique shopping, this estate offers a rare blend of seclusion and accessibility. Perfectly positioned between New York City and The Hamptons, it is a true sanctuary of elegance and prestige, making it one of the most desirable properties on the North Shore.

1 Swan Place, Nissequogue
$4,900,000
4 Beds ⋅ 5 Baths ⋅ 839882 MLS
Nestled Within The Prestigious Village Of Nissequogue, 4 Pheasant Run Is A Masterpiece Of Waterfront Elegance, Where Timeless Sophistication Meets The Natural Beauty Of The Long Island Sound. Set On An Expansive, Meticulously Landscaped Property, This Exquisite Residence Offers A Private Sanctuary With Unparalleled Water Views, Lush Greenery, And Direct Access To The Shore. A Grand Circular Driveway Leads To The Beautiful Residence, Where Classic Architecture Design Is Complemented By Modern Luxury. Upon Entry, Soaring Ceilings And Walls Of Glass Frame Breathtaking Panoramas Of The Sound, Filling The Home With Natural Light And An Ever-Changing Seascape. The Open, Flowing Layout Seamlessly Connects Formal And Informal Living Spaces, Each Adorned With Custom Millwork, Rich Hardwood Floors, And Refined Finishes That Exude Warmth And Sophistication. The Gourmet Chef's Kitchen, Outfitted With Top Of The Line Appliances, Blends Seamlessly With The Breakfast Nook And Den, Offering A Perfect Space For Both Grand Entertaining And Intimate Gatherings. French Doors Open To An Expansive Deck, Where Gentle Sea Breezes And The Sound Of Lapping Waves Create A Serene Retreat. The Primary Suite, Located On The Main Level, Is A Private Oasis Boasting A Spa Like Bath, Walk In Closets, And A Private Loft Overlooking The Water - An Idyllic Setting To Watch The Sunset Over The Horizon. There Are 3 Additional Bedrooms, Two Of Them En-Suites With Full Bathrooms. Outdoors, Manicured Gardens Lead To A Large, In-Ground Pool With Patio, As Well As A Private Staircase And Sandy Shoreline Where Sun-Soaked Days Can Be Spent Embracing The Tranquility Of Waterfront Living. Additional Amenities Include New Siding, New Trex Deck, New Retaining Walls, Estate Fencing, IG Sprinklers, Central Air, Central Vac, 400 Amp Electricity, New Roof, New Leaf Gutters, New Driveway, Updated Cesspool, Wolf Range Appliances, Security System, 2 Above-Ground Oil Tanks, Owned Solar Panels, A Full-House Generac Generator, And 162 ' Of White Sandy Beach. Whether Hosting Lavish Gatherings Or Enjoying Quiet Moments Of Reflections, 4 Pheasant Run Is More Than A Home - It Is A Legacy Estate Offering A Rare Opportunity To Experience The Beauty, Elegance, And Exclusivity Of Life On The Nissequogue Waterfront.

4 Pheasant Run, Nissequogue
$2,799,000
4 Beds ⋅ 5 Baths ⋅ 878416 MLS
Welcome to "The Hill Valley House," where timeless design and modern luxury come together in perfect harmony. Completed in 2023 with no expense spared, this one-of-a-kind custom estate sits on 2.66 acres of lush, private grounds and offers an extraordinary blend of timeless design and cutting-edge innovation. Step inside to experience an ambiance of sophistication and comfort, with soaring 10' ceilings throughout, high-end custom treatments, and impeccable finishes. The grand great room is anchored by a stunning dual-sided gas stone fireplace and flows seamlessly into the heart of the home—a spectacular, state-of-the-art gourmet kitchen. Designed for both beauty and function, this culinary showpiece features rich custom wood cabinetry, sleek quartzite countertops with a dramatic waterfall edge, and a large center island with ample seating—perfect for casual dining or elegant entertaining. The kitchen is fully outfitted with top-tier stainless steel appliances, including a professional-grade six-burner gas stove, wine fridge, and an inviting dinette area that overlooks the tranquil backyard. The first-floor primary suite is a true sanctuary, boasting walls of glass that invite nature in and a spa-inspired ensuite with exquisite tilework, a soaking tub, walk-in shower, custom wood double vanity, and a spacious walk-in closet. A private first-floor office adds convenience and flexibility. Upstairs, three additional bedrooms each feature their own ensuite baths, including one with a private rooftop deck. A second-floor entertainment area with built in speakers and walk-in storage room or office complete the upper level. One of the crown jewels of "The Hill Valley House" is the screened-in porch—a luxurious outdoor haven designed for year-round enjoyment. Featuring double French doors, a dramatic dual stone gas fireplace, built-in infrared heaters, and a refined dining area, this exceptional space merges indoor elegance with outdoor serenity. The finished basement includes a dedicated home gym and a vast unfinished area with endless potential—ideal for a media room, wine cellar, or additional living space tailored to your lifestyle. Adding to the home’s long list of luxuries are a state-of-the-art solar panel system, whole-house water purification, advanced backup power system, smart home technologies, as well as an oversized three-car garage. Outside, your personal resort awaits—with a heated 19'x36' saltwater in-ground pool, cozy fire pit, and expansive patios—perfect for entertaining or peaceful relaxation. The Hill Valley House offers a lifestyle that feels like a permanent vacation—set on lush, resort-like grounds, yet just minutes from Long Island Sound beaches, local marinas, restaurants, charming town shops, and Stony Brook University. Truly, no detail was overlooked in the creation of this exceptional home. From its superior construction to its thoughtfully curated finishes, this is more than a home—it’s a lifestyle. Make this dream property yours today.

317 Old Mill Road, Nissequogue
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 1018259 MLS
A stunning, fully reimagined luxury home where timeless design meets modern living. Completely renovated from top to bottom in June 2026. This exceptional 4-bedroom, 3.5-bath residence showcases magazine-worthy interiors, wide-plank 9.5-inch white oak flooring, custom millwork, designer lighting, and a dramatic double-sided European concrete fireplace that serves as the architectural centerpiece of the home. The chef's kitchen was designed for both everyday living and entertaining, featuring custom two-tone cabinetry, a handcrafted hood, farmhouse sink, oversized gathering island, walk-in pantry, and a suite of premium Miele appliances. The luxurious primary suite and four designer bathrooms offer spa-inspired finishes, custom tilework, bespoke vanities, luxury fixtures, and illuminated backlit mirrors. Outside, professionally landscaped grounds, lush sod, Cambridge walkways, expansive patios, and a custom fire pit create a private setting ideal for entertaining and relaxation. Additional features include a finished basement, main-level laundry room, three-car garage, Andersen 400 Series windows and doors, new roof, new plumbing, new electrical, new irrigation system, and two new Daikin HVAC systems. Every surface, finish, and detail has been thoughtfully curated to create a truly turnkey home that feels custom built. Rarely does a property of this caliber come to market. Set on a beautiful cul-de-sac in the heart of Nissequogue, and minutes from the beach, this move-in ready residence perfectly blends timeless style, comfort, and sophistication. An exceptional opportunity to enjoy one of the North Shore's most sought-after communities!

4 Short Path, Nissequogue
$1,600,000
4 Beds ⋅ 6 Baths ⋅ 961073 MLS
Set gracefully on 2 private, level acres in the prestigious Village of Nissequogue, this architecturally distinctive 4-bedroom, 4 full bath, 2 half bath residence is a remarkable expression of refined luxury and timeless sophistication. Designed for the buyer with truly discerning taste, the home showcases bespoke details, dramatic architectural elements, and exquisite custom updates throughout—seamlessly blending elegance with elevated comfort. A striking entry introduces the home’s signature curved archways, rich hardwood flooring, and an airy, light-filled floor plan ideal for both grand entertaining and intimate everyday living. At the heart of the residence is a breathtaking great room featuring soaring vaulted wood ceilings, a magnificent floor-to-ceiling stone fireplace, and a beautiful custom wood spiral staircase leading to an enchanting loft library—an extraordinary architectural centerpiece that exudes artistry and refinement. Updated windows throughout the home invite natural light while framing picturesque views of the surrounding grounds. The chef’s kitchen is thoughtfully appointed with high-end stainless steel appliances, double ovens, custom cabinetry, and a dramatic wall of picture windows overlooking the lush property. Flowing seamlessly from the kitchen, an elegant den with a gas fireplace and wet bar provides a refined and inviting space for sophisticated gatherings and relaxed entertaining. A truly exceptional highlight of the home is the spectacular solarium—an extraordinary space designed for year-round entertaining. Enclosed in walls of glass and bathed in natural light, this stunning retreat features a spa pool and radiant heated floors, creating a private resort-like atmosphere in every season. Whether hosting intimate evenings or lively gatherings, this space offers an unparalleled indoor-outdoor living experience. The primary bedroom suite provides a serene and luxurious retreat with generous proportions and a beautifully appointed bath. Three additional bedrooms are equally well-designed, complemented by four full baths and two powder rooms featuring elevated finishes. A full finished basement with outside entry and guest quarters offers exceptional flexibility for extended guests, recreation, or private workspace. Outdoors, the estate-like setting offers total privacy, paver patios, mature landscaping, and a stunning in-ground pool for resort-style living. Additional premium amenities include gas heat, a full-house Generac generator, whole-house water filtration system, updated windows, and a two-car garage—plus much more. An extraordinary offering defined by architectural distinction, luxurious detail, and uncompromising quality, this exceptional residence has been thoughtfully curated to provide a lifestyle of elevated comfort, timeless sophistication, and refined luxury at every turn.

37 Bridle Path, Nissequogue
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 956696 MLS
Beautifully maintained and thoughtfully updated, this classic country colonial is set on a peaceful 2-acre property in the private Village of Nissequogue. Tucked away on a serene cul-de-sac, the home offers a rare sense of tranquility while remaining just minutes from Long Island Sound beaches, local marinas, Stony Brook University Hospital—and approximately 60 miles from New York City, providing the perfect balance of retreat and accessibility. A charming covered front porch invites you to slow down and enjoy the peaceful sounds of nature that surround the property. Inside, the home has been wonderfully updated and features a light-filled, open, and flowing floor plan ideal for both everyday living and entertaining. Gleaming hardwood floors, custom moldings, updated windows, and hi-hat lighting enhance the gracious formal spaces throughout. The elegant formal living room features a wood-burning fireplace, while the formal dining room opens seamlessly to the kitchen, creating a warm and welcoming atmosphere for gatherings. The chef’s kitchen is a true standout, offering granite countertops, generous prep space, a wet bar with wine refrigerator, and updated stainless-steel appliances including a 6-burner Thermador gas range (2022) and a Sub-Zero refrigerator. An expansive dinette area with its own wood-burning fireplace and double French doors leads directly to the patio, perfectly blending indoor and outdoor living. The expansive great room is designed for comfortable living, featuring vaulted ceilings, a wall of windows with views of the yard, rich wood floors, and a stone accent wall—perfect for gatherings or quiet nights at home. A convenient first-floor bedroom suite with a private full bath provides flexible living options. Upstairs, you’ll find three additional bedrooms, including two generously sized secondary bedrooms and a beautiful primary suite with vaulted ceilings, picturesque windows, a walk-in closet, a dressing area with custom cabinetry, and a spa-like bath with Jacuzzi tub and separate shower. A fully updated main bathroom with custom vanity and shower is complemented by a conveniently located second-floor laundry room, making everyday living effortless. A full unfinished basement offers endless potential for additional finished living space. Additional highlights include a two-car attached garage, along with numerous recent improvements such as vinyl perfection shake siding (2019), roof (2019), fencing (2019), cesspool (2018), hot water heater (2019), appliances (2022), burner (2019), updated AC compressors, and more. Outdoors, the level and private backyard feels like a secluded retreat, complete with a paver patio and heated in-ground pool—perfect for summer entertaining, quiet evenings, and enjoying the beauty of the surrounding landscape year-round. Thoughtfully updated and impeccably cared for, this home delivers a rare combination of privacy, comfort, and timeless appeal. Set in a peaceful setting with spaces designed for both everyday living and special moments, it’s an opportunity not to be missed.

1 Tracklot Road, Nissequogue
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 899595 MLS
Elegant classic colonial nestled on a serene cul-de-sac, showcasing gracious, light-filled, and generously sized rooms. The inviting living room features a striking stone fireplace, while the beautifully remodeled gourmet kitchen boasts custom cherry cabinetry, gleaming granite countertops, and top-of-the-line Miele appliances. The warm and welcoming den offers a dramatic full-wall brick fireplace, perfect for cozy gatherings. Throughout the home, rich wood floors and solid wood doors exude quality and character. The oversized primary suite is a true retreat, featuring two generous walk-in closets, and a luxurious ensuite bath complete with a relaxing spa bathtub, a sleek glass enclosed shower and and an elegant double-sink vanity. An additional three bedrooms , one with ensuite bath provide versatility for family and guests. Recent updates include a roof, cement shingle siding, an efficient heating system, energy-saving windows, and well appointed kitchen and bathroom renovations. Additional highlights include a walk up attic, two-car garage and a partial basement which provide for ample storage. Relax and unwind on the charming covered rear porch or the stately front veranda, both overlooking expansive, lush, and manicured lawns. Located in the tranquil Village of Nissequogue and close to area beaches, fine restaurants, local shopping and Stony Brook University and Medical Center. Smithtown Schools

9 Holly Lane, Nissequogue
$1,350,000
4 Beds ⋅ 5 Baths ⋅ 916981 MLS
Welcome to this contemporary farm ranch, gracefully set on 2.16 acres in the scenic Village of Nissequogue. Surrounded by pristine natural beauty and offering seasonal views of the Nissequogue River, this residence provides a rare blend of quiet retreat, modern comfort, and timeless design. Guests will be welcomed in to an open and light filled home with living room and dining room overlooking a mahogany deck that spans the length of that floor. The home features four bedrooms and four-and-a-half baths, including two separate primary suites that offer versatility. Both suites are well appointed, have luxurious baths and provide for private retreats. A recently renovated and well designed kitchen will please any chef. It has top of the line stainless steel appliances, granite countertops, functional island and breakfast bar. The second level loft area is light and airy and has many possible uses. Every detail has been thoughtfully considered, including a fully renovated lower level with a walkout entrance, ideal for additional living space, or for multigenerational living. Geothermal heating and cooling ensure year-round efficiency and comfort. Recent updates include updated kitchen, baths, new skylights, some new windows. and new generator. Outside, the property is a haven for relaxation and entertaining. Beautifully landscaped and hardscaped grounds feature fieldstone edging, a bluestone patio, multilevel decks, and a new hot tub. There is ample space to add a pool, making this the perfect setting for both intimate gatherings and grand celebrations. A newly paved driveway leads to a three-car attached garage, complemented by a detached one-car garage, providing a total of four bays. Nearby is the hamlets of Saint James and Smithtown, hiking trails, Long Island Sound Beaches, fine dining, and Stony Brook University and Medical Center. Smithtown Schools. From its thoughtfully designed interiors to its stunning outdoor spaces, this property embodies the best of Nissequogue living—where natural beauty and refined comfort come together in perfect harmony.

1 Summit Trail, Nissequogue
$1,350,000
4 Beds ⋅ 2 Baths ⋅ 875436 MLS
Nestled in the charming historic village of Nissequogue, this meticulously maintained and freshly painted 4-bedroom, 2-bathroom home is a true gem that blends modern comforts with timeless appeal. As you approach the property, a paved and cobblestone lighted driveway that leads you to the front door, setting the tone for the elegance and quality that awaits inside. Step into the open-concept living space, where maple-stained hardwood floors run throughout the main level, creating a seamless flow. The chef’s kitchen is an entertainer’s dream, featuring high-end stainless KitchenAid appliances, a walk-in pantry, a vented hood, a double sink, and luxurious quartz countertops. The oversized garnet island serves as a central hub for gatherings and culinary creations. French doors open to an oversized mahogany deck, which overlooks the beautifully landscaped grounds, complete with a natural stone patio—ideal for outdoor dining or simply relaxing in the serene surroundings. Inside, the vaulted living room with a wood-burning stove adds warmth and character, creating a cozy atmosphere perfect for every season. The primary bedroom is a peaceful retreat with walk-in closets and ample space, while three additional well-sized bedrooms share a full bathroom. The oversized finished basement is a highlight of the home, offering a laundry area, fitness room, and workshop—ideal for those who love to stay active or need extra storage and space. Outside, the fully fenced property is beautifully landscaped with mature evergreens, maple trees, and colorful flowering perennials. Bluestone and fieldstone patios and walkways invite you to explore every corner of the lush grounds. Enjoy community access to Short Beach, Long Beach, the Nissequogue River, and nearby hiking trails. Plus, benefit from local police and fire services for added peace of mind. The home is also equipped with a generator and a robust 400-amp service, ensuring reliability and peace of mind. This exceptional property in Nissequogue offers the perfect balance of luxury, functionality, and natural beauty—an ideal place to call home.

659 Horse Race Lane, Nissequogue
$1,165,000
4 Beds ⋅ 3 Baths ⋅ 995969 MLS
Panoramic water views from this beautifully updated home located in a lovely beach community . This gorgeous totally updated home is a designer showplace with huge windows looking out to the smithtown bay. There are hardwood floors and custom moldings throughout. The kitchen is spacious with large center island and quartz counters. The family has a fireplace and large sliding patio doors leading a large deck perfect for entertaining or just to relax and take in the views. The primary bedroom is large with ensuite bathroom and walkin closet. There is another set of patio doors leading to a second story deck a perfect place to watch the boats go by. There updated heating system, 2 zone central air, roof windows and siding. This home is steps to private beach access and mooring rights. Feel like you are on vacation the whole year round

17 Beach Plum Lane, Nissequogue
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 930989 MLS
Tucked away within the exclusive Village of Nissequogue, this elegant single-level estate offers an extraordinary sense of peace and privacy. Set on two serene acres at the end of a quiet cul-de-sac, the residence is surrounded by lush landscape and mature trees, creating a natural retreat that feels worlds away from the everyday. Inside, refined architectural details and gracious open spaces define the home’s inviting character. Large windows bathe each room in light and frame views of the tranquil grounds, while thoughtful design seamlessly blends sophistication with warmth. Just minutes from the Long Island Sound and the local marina, this property offers effortless access to sandy beaches, coastal walks, and sailing adventures — all while maintaining the quiet charm of an exclusive residential enclave. This is more than a home; it is a lifestyle — where nature, comfort, and understated luxury come together in perfect harmony.

7 Short Path, Nissequogue
$920,000
5 Beds ⋅ 3 Baths ⋅ 967720 MLS
Welcome to 1 Spring Hollow Road, tucked at the end of a cul de sac in the Village of Nissequogue. Set on approximately 2.5 acres of natural, scenic surroundings, this classic Colonial offers the space, privacy, and timeless North Shore setting that make this community so exceptional. With 5 plus bedrooms and 3 full baths, the home features hardwood floors, generously proportioned rooms, three fireplaces, and a wood burning stove that add warmth and character throughout the year. A true highlight is the sun drenched Oak Room, showcasing soaring ceilings, a custom oak mantle, loft space, and walls of Andersen windows that bring the outdoors in. This versatile space is ideal for a home office, creative studio, guest retreat, or additional living area. Endless possibilities. Offering timeless structure and strong bones, this is a home ready for its next chapter. Enjoy all that Nissequogue is known for, including winding roads, estate like surroundings, access to nature trails, the Nissequogue River, and the Long Island Sound, close to St. James, Stony Brook Village, and Long Island Rail Road access to New York City.

1 Spring Hollow Road, Nissequogue
$850,000
917229 MLS
Incredible improved 1.93 acre property in Nissequogue welcomes custom new construction to take advantage of the existing foundation of the formerly 3500 sq ft home. Extensive landscaping in place with specimen plantings, lighting, irrigation, lawn and garden. Hardscape includes upscale outdoor Kitchen, Fire Pit, impressive stone patio and pool surround for in ground Gunite Pool. All pool equipment and systems recently updated. In ground 1000 gallon Propane tank, newly paved drive with drainage and Belgian block edging. A very rare opportunity. Call for private showing. Do not enter property without confirmed appointment. Security in place.

7 Smith Lane, Nissequogue

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.