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$1,349,000
5 Beds ⋅ 4 Baths ⋅ 1045111 MLS
Move right into this extended, sprawling 6 BR, 4BA ranch, located in highly desired Mills Pond Estates offering an incredible "in-law" space rarely found in the neighborhood. This open concept home, which boasts hardwood floors throughout the main part of the home, is flooded with natural sunlight and is ideal for entertaining. The principle rooms are spacious, open and airy and overlook the resort-style yard which has an IG heated pool with updated liner, (2026) pump, (2025) and filter (2024), as well as a sports court, outdoor kitchen and built-in firepit. Amazing and rare basement allows for additional living space (with proper permits) or storage. This extended model has a classic brick exterior, designated home office, spacious laundry and functional mudroom spaces you wont find in elsewhere. Natural gas hooked up to the home, just needs to be connected. Current heating system can be converted to gas. Some windows redone 2025 and 2026. Oversized garage. 300 amp service. Solar panels are leased and allow for very low electric bills. Don't miss this truly unique opportunity!

9 Elderwood Drive, Saint James
$899,000
4 Beds ⋅ 3 Baths ⋅ 1048941 MLS
Welcome to 17 White Cliff Lane, a picture-perfect four-bedroom, two-and-a-half-bath splanch offering move-in ready living in desirable Dover Hill Estates. Situated in the Smithtown Central School District, this home boasts tremendous curb appeal with a spacious front yard, mature landscaping, new siding (2024), and updated bedroom windows (2024). Inside, the main living spaces flow together through wide, open doorways. The foyer and formal dining room showcase board-and-batten accent walls, complemented by beautiful wood stair railings. The heart of the home features an inviting eat-in kitchen finished with granite countertops and stainless steel appliances opening to a cozy den with a wood-burning fireplace and views of the backyard garden. Everyday comfort is assured with central air conditioning installed in 2023, along with an updated heating system and oil burner. Practical convenience continues with a partial basement, easy-access attic storage, and a two-car garage. The fully fenced, private quarter-acre backyard is an outdoor sanctuary, complete with an updated irrigation system and an in-ground fiberglass swimming pool featuring a brand-new Loop-Loc cover (2024). With the rear property line bordering a forested recharge basin, the property enjoys added privacy and nature while entertaining or relaxing. Positioned just minutes from the Smith Haven Mall and multiple grocery options, this turnkey home balances peaceful suburban living with everyday convenience.

17 White Cliff Lane, Nesconset
$2,199,000
4 Beds ⋅ 4 Baths ⋅ 1048653 MLS
Beautifully situated directly on Stony Brook Harbor, this exceptional waterfront residence offers captivating water views, remarkable privacy and an extraordinary level of custom craftsmanship. Completed in 2024 with no expense spared, the home is a study in sophisticated design, exceptional materials and meticulous execution. With walls of glass framing the harbor and interiors distinguished by one remarkable detail after another, it has the presence and polish of a home that could have been lifted from the pages of Architectural Digest. Every element feels considered. Soaring ceilings and six-inch-wide white oak flooring establish a sense of warmth and scale, complemented by exceptional millwork, custom solid-wood doors, bespoke cabinetry and authentic 1800s barn beams incorporated as architectural accents. Walls of Andersen casement windows and transoms fill the interiors with natural light, while distinctive ceiling treatments and carefully selected finishes give each room its own character. A sculptural curved staircase creates one of the home’s most memorable architectural moments. Beautifully crafted in solid white oak, its graceful form and open design feel more like a piece of custom architecture than a traditional staircase, bringing another layer of artistry to the interior. The custom chef’s kitchen is a statement in both design and craftsmanship, pairing beautifully crafted white cabinetry and designer hardware with dramatic white marble waterfall countertops, a six-burner Viking range and oven, paneled Sub-Zero refrigeration and top-tier appliances. Authentic antique barn beams introduce warmth and architectural character, while radiant-heated floors, an impressive center island and a window-wrapped dining area with French sliding doors opening to the bluestone patio create an exceptional space for both entertaining and everyday living. The great room takes full advantage of its waterfront setting, with walls of windows framing Stony Brook Harbor, while a gas fireplace, beautifully detailed solid white oak ceilings and custom millwork bring warmth and architectural depth to the space. The entire second floor is devoted to the primary suite, creating an exceptionally private retreat with a custom walk-in closet and spa-like bath beautifully appointed in authentic white marble, featuring a soaking tub, oversized marble shower with built-in bench, radiant-heated floors and a coordinating marble vanity. A separate waterfront sitting room opens through French doors to an expansive Ipe deck overlooking Stony Brook Harbor—a serene place for morning coffee or unwinding as the light changes across the water. A separate private gym completes this remarkable level, creating a retreat devoted entirely to comfort, wellness and privacy. Additional bedrooms and baths continue the home’s bespoke approach, with distinctive materials and custom details giving each space its own character. Even the practical spaces have been thoughtfully considered, including a mudroom and striking custom lower-level entry with wood-paneled walls, integrated lighting and built-in storage. Outside, lush lawns, mature trees, bluestone patios and thoughtfully designed landscaping complement the home and its waterfront surroundings. A full basement, 2.5-car garage, gas heat, whole-house generator, integrated speaker and security systems, and smart-home features complete the residence. Rarely does a home bring together this caliber of craftsmanship, architectural character and waterfront beauty so completely. Created without compromise and entirely one of a kind, this is a residence as extraordinary as its setting—where the beauty of Stony Brook Harbor is ever-present and spectacular sunsets over the water provide an unforgettable backdrop at the end of each day.

31 Thompson Lane, Head Of Harbor
$699,999
3 Beds ⋅ 2 Baths ⋅ 1048457 MLS
Welcome to this beautifully maintained split-ranch home nestled in the highly sought-after East Hills Estates of Smithtown. This 3 bedroom, 2 bath, 1 car garage on 0.3 acres home (currently set up as two bedrooms, can be easily put back to three bedrooms) is filled with natural light and is move-in-ready! This residence offers the perfect blend of comfort, style, and functionality. The inviting main level features a bright and airy living room with soaring cathedral ceilings, a cozy gas fireplace, and an open flow into the eat-in kitchen featuring gas range, refrigerator, microwave, dishwasher (2023) and granite countertops, ideal for both everyday living and entertaining. Upstairs, you'll find a spacious primary bedroom with side-by-side double closets, a generously sized second bedroom, and full hall bath. The lower level offers a sun-filled den with abundant natural light, a full bathroom, laundry room and a convenient outside entrance, providing flexible living space perfect for guests, or a home office. 200-amp electric, Andersen windows, a cesspool with overflow (2021), vinyl fencing, separate hot water heater. and whole-house Generac generator. Situated on a tranquil .34-acre level lot, the private backyard is surrounded by mature specimen trees and lush landscaping and pond. With its mint condition, desirable location, and features, this exceptional home offers everything you are looking for.

1 Rutgers Street, Smithtown
$850,000
4 Beds ⋅ 3 Baths ⋅ 1048431 MLS
Remarkable Custom Built 4 Bedroom, 2.5 Bath Colonial In The Heart Of Saint James. This Classic Residence Has Detailed Architectural Design, Crown Moulding, Mill Work And Elegant Appointments Throughout. Boosting A 2-Story Entry Foyer With Staircase, Formal Dining Room, Formal Living Room with Prominent Gas Fireplace, Family Room With Stone Gas Fireplace, and Siding Glass Doors to Composite Deck. Spacious Eat In Kitchen Complimented With Newer Appliances. Renovated Hall Laundry Area, First Floor Powder Room. Upper Level Includes Primary Bedroom Suite With Vaulted Ceilings, Skylights and His-And-Her Closets, Primary Bath w/ Soaker Tub, Shower and Vanity Counter. All Large Bedrooms with Plush Carpeting and Closet Systems. Upper Level Full Bathroom. All Hardwood Flooring as Seen/Carpet As Seen. Spectacular Fenced Property With Lush Professional Landscape, In-Ground Heated Chlorine Pool. All Composite Decking on Outside Deck, 2 Car Garage and Shed, Valuable Updates Include: 2023 New Roof, Newer Kitchen Appliances, Closets Systems, 2025 Hot Water Heater, Digital Irrigation System, Front Windows Casing Replaced with Azex Trim. Located Close Beaches, Golf Clubs, Renowned Restaurants, Located in the Desirable Smithtown School District.

220 St. James Avenue N, Saint James
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 1047851 MLS
Welcome to 29 Farm Road....nestled in the prestigious Village of Head of the Harbor, where secluded, private & tranquil living awaits! This stunning, beautifully maintained Expanded Ranch features a grand entry foyer, spacious EIK w/ granite countertops, center island, SS appliances, and picturesque views of the surrounding landscape, a warm and inviting Great Room w/ Stone FP and vaulted ceilings w/ 2 skylights and 4 slider doors leading to the wrap around deck, a gorgeous formal dining room, powder room. The 1st floor features 3 spacious bedrooms, including a luxurious Primary Bedroom Ensuite w/ private access to the extensive wrap-around porch, WIC, and primary bath w/ double vanity sink, bathtub, and separate shower. Bedroom 2 features a WIC, chair rail molding, and an ensuite bathroom w/ spa tub. Bedroom 3 offers a private loft space and skylight, and a main floor office space w/ French doors, plus an additional full bath completing the main level. The versatile loft is ideal as a recreation room, home gym, or flex space, with convenient attic access. The lower level offers exceptional flexibility and features a 4th Bedroom (perfect for guests or an in-law suite), a Summer Kitchen w/ quartz countertops, oversized family room, 2 separate gym rooms, full bath, laundry room, ample storage, direct access to the two-car garage, and sliders leading to your own private, resort-like backyard retreat! Additional features include.... CAC (2 zones), Oil Heat (4 zones - burner 2016), 200-amp electric, IGS System (8 zones - redone in 2026), inground saltwater heated pool (Liner - 2025), Whole House Inside & Outside KeyOS wireless app-controlled stereo system, and a portable generator with transfer switch hookup. Surrounded by nature, with an abundance of natural light, oversized windows, and skylights that create a bright, airy, and inviting atmosphere throughout. This exceptional home truly has it all! All this and much more... Set on over 2+ acres of beautiful and secluded property (very private), you do not want to miss this rare opportunity!

29 Farm Road, Head Of Harbor
$2,399,000
6 Beds ⋅ 5 Baths ⋅ 1046808 MLS
Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with expansive living spaces filled with natural light of generous proportion and seamless indoor-outdoor flow creating a tranquil retreat just moments from the harbor, beaches, yacht clubs, vineyards and nature preserves. Set on two private beautifully landscaped level acres of property designed for both everyday enjoyment and sophisticated entertaining. This private estate seamlessly blends timeless elegance, modern luxury, and resort-style living. A grand two-story foyer introduces the home's sophisticated interiors, where soaring cathedral ceilings, gleaming hardwood floors, abundant natural light, and exquisite architectural details create an atmosphere of warmth and refinement. Thoughtfully updated throughout, every space has been designed with both everyday comfort and effortless entertaining in mind. The recently renovated chef's kitchen serves as the heart of the home, featuring a dramatic Crawford ceiling, custom crown and box moldings, quartzite-topped center island, and a suite of premium appliances including a Sub-Zero refrigerator, Bosch range, double ovens, microwave drawer, and dishwasher. The kitchen flows seamlessly into the impressive great room, highlighted by a floor-to-ceiling stone wood-burning fireplace and walls of windows overlooking the picturesque grounds. Elegant entertaining spaces continue with a gracious formal living room accessed through glass pocket doors, and a spacious dining room perfectly suited for hosting intimate gatherings or larger celebrations. The main level offers five generously proportioned bedrooms and three full bathrooms, including two recently renovated baths appointed with refined finishes. Upstairs, an expansive loft with hardwood floors overlooking the great room provides additional living and entertaining space and leads to the luxurious primary suite. This private retreat features hardwood flooring, custom closets, detailed millwork, and a stunning newly renovated spa-inspired bath complete with a soaking tub, oversized glass-enclosed shower, dual vanity, and exquisite Italian tile. The outdoor setting is nothing short of extraordinary. Professionally landscaped grounds surround a tranquil in-ground pool, complemented by multiple paver patios designed for elegant outdoor entertaining and relaxation. A sprawling Trex deck extends nearly the entire length of the home, creating a seamless connection between indoor and outdoor living. Additional highlights include a fully finished lower level with a full bath, offering exceptional flexibility for recreation, fitness, guest accommodations, or extended living space. Car enthusiasts will appreciate the rare offering of four garage spaces, including two attached and two detached garages. Recent improvements include extensive interior and exterior painting, newer windows, newer roof and skylights, custom closet systems, wood flooring throughout most of the house and numerous thoughtful upgrades throughout. A wonderful opportunity awaits for you to own this property and reap the rewards of resort living in the White Spruce Farm Community within the Village of Head of the Harbor. A must see! *Taxes Include Village Taxes of $3,199

15 The Chase, Head Of Harbor
$699,999
2 Beds ⋅ 2 Baths ⋅ 1047297 MLS
Welcome to Country Pointe! This is a private, gated community in Nesconset. The community offers many amenities including a heated salt-water pool, 2 tennis courts, Bocce, a playground and gym. This townhouse is truly beautiful and has a lovely porch. It was completely renovated with a new kitchen put in 2 years ago. It is an elegant and classic design. The open space and natural light in the home is very inviting. The kitchen has nice appliances and offers gas cooking. There is a table with a window for dining. There is also a dining room area for larger parties. This space is open to the living room for easy entertaining. The living room has sliders going out to the fenced deck. It is a very nice location in the community. The primary bedroom features walk-in-closets and an ensuite bathroom that is so pretty. The 2nd bedroom is also very nice and the hallway bathroom is updated. The laundry is in the common hallway. This home features a added bonus with the full finished basement. There is a den area, a recreation area and a spare room. The ulilties are also here in the storage area. CAC 15 years, Stove brand new, Dishwasher 2 years, Bathrooms 5 years, There is a roof assessment that has been fully paid for.

107 Deer Valley Drive, Nesconset
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 1038256 MLS
A Coastal Setting That Makes Every Day Feel Like an Escape. Set on 1.74 beautifully private acres in a private beach community, this distinctive 4-bedroom, 3-bath home captures the relaxed rhythm of coastal living, surrounded by water views and beautiful natural surroundings, with easy access to town beaches and the marina. The property extends to Stony Brook Harbor, creating a peaceful natural backdrop, while mature plantings, gardens and a rare gunite in-ground pool enhance the sense of privacy and connection to the landscape. Inside, a light and bright open floor plan is defined by oversized windows and walls of glass that frame the surrounding beauty and bring nature into nearly every living space. The impressive great room takes full advantage of the setting with a dramatic wall of windows, vaulted ceilings and a stone wood-burning fireplace. Open to the dining room, this inviting space also features sliders to an expansive, updated Trex deck—a wonderful place for outdoor dining, entertaining or simply enjoying the views of Stony Brook Harbor. The spacious eat-in kitchen offers generous counter space, granite countertops, updated stainless steel appliances and a wonderful dinette area overlooking the pool and lush natural property. The primary bedroom suite provides a private retreat with a beautifully appointed ensuite bath featuring tumbled marble, a double vanity with granite counters, Jacuzzi tub and oversized shower with dual shower heads and multiple body sprays. Two additional generously sized bedrooms and a full bath with a custom vanity and granite countertop complete the second floor. Adding exceptional versatility, first-floor guest quarters with a separate private entrance and covered patio features a bedroom, full bathroom and living area, providing a comfortable and private space for guests or additional living space. The finished lower level offers even more room to gather and entertain, with wood floors, a comfortable den, wet bar and separate entry with direct access to the outdoors. Outdoors, the peaceful setting takes center stage. The rare gunite in-ground pool, surrounded by stone patios and complemented by a convenient changing room, creates an inviting place to spend summer days, entertain or simply relax amid the beautiful gardens and natural coastal plantings. Updated vinyl siding, a carport and ample driveway parking add everyday convenience. More than simply a home near the water, this is a property that embraces the character and ease of coastal living. With privacy, harbor views and the natural beauty of its 1.74-acre setting, every season offers another reason to enjoy being here—a coastal retreat that feels wonderfully removed from everyday life.

588 E. Long Beach Road, Nissequogue
$790,000
4 Beds ⋅ 3 Baths ⋅ 1026950 MLS
Contemporary 4-bedroom, 2.5-bath home situated on approximately 0.35 acres in the Smithtown School District. Built in 1967, this spacious residence offers approximately 2,745 square feet of living space, a fireplace, and a partial basement. The generous lot provides ample outdoor space for entertaining, gardening, or recreation. Conveniently located near shopping, restaurants, parks, major roadways, and other everyday amenities. A wonderful opportunity to make this home your own.

12 Kenny Street, Hauppauge
$869,000
4 Beds ⋅ 3 Baths ⋅ 1026666 MLS
Welcome to this exceptional 4-bedroom, 2.5-bath Splanch located in the prestigious East Hill Estates section of Smithtown. Offering approximately 2,380 square feet of beautifully designed living space, this residence seamlessly blends timeless elegance with everyday comfort. A gracious floor plan features sun-filled living areas, a warm and inviting fireplace, spacious formal and casual gathering spaces, and a well-appointed kitchen designed for both entertaining and daily living. The generous primary suite provides a peaceful retreat, while three additional bedrooms offer flexibility for family, guests, or a home office. Enjoy year-round comfort with an updated HVAC system, providing efficient heating and cooling throughout the home. Step outside to your private backyard oasis featuring a heated in-ground salt water swimming pool, expansive patio with gas BBQ connection , and beautifully landscaped grounds—perfect for outdoor entertaining or relaxing all summer long. Additional highlights include an attached two-car garage, a full basement offering abundant storage and future finishing potential, and pride of ownership throughout. Ideally situated in the award-winning Smithtown Central School District, the home is conveniently located near parks, golf courses, shopping, dining, beaches, major parkways, and the Long Island Rail Road. This is a rare opportunity to own a beautifully maintained home in one of Smithtown’s most sought-after neighborhoods, where classic Colonial charm meets modern comfort.

6 Navy Drive, Smithtown
$999,000
4 Beds ⋅ 3 Baths ⋅ 1020597 MLS
When opportunity knocks the door must be opened. Welcome to 57 Brooksite Drive. A stunning single unit home in the heart of Smithtown NY sitting on nearly a half an acre of property. Renovated just over 1 year ago this home is being offered to the market at an amazing opportunity to be purchased as turn key as they come. Enjoy the state of the art renovations throughout the property including a finished basement, a first floor master bedroom, and an open concept dining room & kitchen. Spark up the fire and sit with the entire group as you enjoy the fully functional living room fireplace. Walk out your sliding door and gaze at your massive nearly half acre of land where you can host and entertain your friends. Got a project? Your attached garage gives you plenty of space to park your car and sustain your handyman fix. This property needs absolutely nothing except your willingness to enjoy it's perfection. This is a truly ICONIC home!

57 Brooksite Drive, Smithtown
$2,049,000
4 Beds ⋅ 4 Baths ⋅ 1014240 MLS
Exceptional Custom Estate in the Heart of St. James Proper, Situated on 1 Acre of Meticulously Maintained & Landscaped Property with a Resort Style Bucolic Yard. A Covered Front Porch leads into a Double Height Entry Foyer. Offering Four Bedrooms, Four Full Baths, a Family Room with Wood Burning Fireplace, Hardwood Floors, Built-ins & Custom Millwork Throughout. Private Den, First Floor Full Bath, Primary Ensuite with Two Walkin Closets, Propane Fireplace, Private Balcony & Custom Private Bath with Shower, Whirlpool Tub, Bidet & More. Three Additional Bedrooms on Second Floor & Brand-New Full Bathroom. Finished Basement 9' Ceilings with Custom Millwork, Outside Entrance, Custom Bar, Office, Full Bath, Movie Theatre & Much More. Bucolic Rear Yard Encompasses a Double Height Paver Patio, Outdoor Kitchen, Rear Awning, 35x35' Saltwater Heated Inground Pool with Waterfall, Covered Entertainment Area, Tennis Court with Pickleball & Basketball. Rear Stadium Lighting, Built-in Fireplace, Elevated Gazebo, Two Car Detached Garage & Rear Pool House Area. Four Car Garage Total. 400 Amp Electric. Two Zones CAC, two 275 Gallon Oil Tank in Basement. Central Vacuum, Low Line Septic, Built-in Fishtank. Mature Landscaping, Landscape Lighting, Architectural Roof, Pool Table & Much More. Must See to Appreciate. All information to be verified independently by Buyer/Agent. Inquire About CO's.

67 Sunny Road, Saint James
$1,150,000
5 Beds ⋅ 3 Baths ⋅ 1011636 MLS
Nestled on 2.5 private acres in the picturesque Village of Nissequogue, this beautifully remodeled Colonial offers a rare opportunity to enjoy peaceful country-style living with seasonal water views of the Nissequogue River in one of Long Island’s most sought-after communities. This well-maintained home features numerous updates, including a newer roof, siding, driveway, eat-in kitchen, and hardwood flooring throughout the first floor. The interior was freshly painted in March 2026, creating a bright and welcoming atmosphere. The spacious den is highlighted by a cozy wood-burning fireplace with a stove insert, perfect for relaxing on cooler evenings. Updated bathrooms add modern comfort, while the full basement and attached two-car garage provide ample storage and functionality. Enjoy tranquil outdoor living from the rear patio, where partial river views can be appreciated during the summer months. The backyard is surrounded by mature trees, offering privacy, serenity, and a peaceful natural setting. Ideally located near local beaches, hiking and nature trails, fine dining, shopping, and Stony Brook University and Medical Center. This exceptional property combines scenic beauty, modern updates, and convenient access to area amenities. Smithtown Schools

451 River Road, Nissequogue
$1,890,000
4 Beds ⋅ 3 Baths ⋅ 1008414 MLS
Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a professional contractor as his personal home with attention to detail and premium materials throughout. Situated on a private 1-acre property, this exceptional 4-bedroom, 2 1/2 bath home welcomes you with a striking stone façade and dramatic arched entryway that sets the tone for the extraordinary craftsmanship found throughout. Features include oak hardwood floors, solid hardwood interior doors, custom millwork, marble and tile mosaics, a custom detached 2-car garage with handcrafted garage doors built by the homeowner and features its own electrical panel. The fully finished basement includes an outside entrance, laundry area and epoxy flooring. The large, open kitchen includes custom cabinetry, granite countertops, stainless steel appliances, and custom designed tile work. A breathtaking handcrafted marble fireplace with carved lion statuary serves as the centerpiece of the home and features a heat-circulating system with dedicated venting to the primary suite above. Built with 2x6 construction and blown-in insulation for exceptional energy efficiency, the home was also strategically positioned above grade to promote superior drainage. Smart home features include remote thermostat controls with separate zones in each bedroom and an automatic leak-detection water shutoff system. Extending the living space outdoors, a covered patio overlooks the private grounds and is already pre-wired for cable and has a water line in place, providing a seamless opportunity to create the outdoor kitchen and entertainment area of your dreams. From the handcrafted architectural details to the thoughtful engineering and modern conveniences, no expense was spared in creating this truly exceptional residence. A rare opportunity to own a luxury home unlike anything else on the market.

225 Old Willets Path, Smithtown
$6,400,000
5 Beds ⋅ 10 Baths ⋅ 000034 MLS
Waterfront – Set along 243’ of pristine Long Island Sound frontage, this extraordinary waterfront estate offers a truly rare combination of sweeping unobstructed water views, direct access to a sandy beach, and beautifully manicured level grounds with no high bluff — creating an unparalleled coastal setting rarely found on the North Shore. Privately nestled at the end of a private cul-de-sac on 2 lush acres, this over 7,000 square foot custom residence plus an unbelievable entertainment lower level is surrounded by magnificent specimen plantings, manicured gardens, and expansive Ipe Brazilian walnut decking designed to embrace the breathtaking waterfront backdrop from every angle. Nearly every room captures stunning water views, creating a seamless connection to the shoreline while filling the home with natural light and tranquility. Custom built with uncompromising quality and craftsmanship, the residence showcases high-end custom finishes, exquisite detailed moldings, elegant designer touches, and only the finest materials and systems throughout. Sophisticated yet inviting, the home offers an exceptional blend of refined luxury and relaxed coastal living. Every detail has been thoughtfully curated with no expense spared. Designed for both grand-scale entertaining and intimate everyday living, the property offers exceptional indoor and outdoor gathering spaces where unforgettable memories are waiting to be made. Enjoy breathtaking sunsets over the Long Island Sound with unobstructed views stretching to Connecticut, all from the privacy of your own extraordinary waterfront retreat. Ideally located approximately 60 miles from Manhattan and moments from fine dining, shopping, marinas, Stony Brook University, and Stony Brook University Hospital, the property offers a rare blend of private coastal living and everyday convenience A true private oasis, this remarkable estate offers the feeling of being worlds away while enjoying the beauty, serenity, and prestige of luxury waterfront living at its absolute finest.

6 Pheasant Run, Nissequogue
$10,800,000
5 Beds ⋅ 8 Baths ⋅ 996747 MLS
The great statesman, Daniel Webster, (January 18, 1782-October 24 1852) famously remarked, “Long Island Sound is our American Mediterranean.” Indeed, it is. Summerwind. This waterfront enclave, nestled along a uniquely picturesque stretch of Long Island Sound, boasts epic sunrise and sunset views. With architecture and design by world-renowned CetraRuddy Architects, the carefully curated plan demonstrates timeless elegance and understated luxury. The exterior, clad in white stucco and trimmed in fossilized Atlantic shell stone, is complemented by a striking clay tile roof; a design painstakingly supervised by Ludowici’s renowned Master color specialists. Double 11-foot-tall iron entry doors open into the 50-foot-long entrance hall; its intricately carved, painted wood ceilings, soaring to a height of 24-feet, make an indelible first impression. The antique black and white marble and European smoked oak herringbone floors throughout exude Old World charm, and the hand-forged iron balusters and intricately hand-carved rails of the staircase add a touch of whimsy. Entertaining is a delight in the banquet-sized dining room, where a 17th-century Louis XIII limestone mantel takes center stage, complemented by a wet bar, wine refrigeration, and seating for up to 24 guests. The kitchen is the heart of the home and a chef's dream, featuring a raised fireplace hearth finished with 300-year-old French clay tiles, ideal for wood-fired cooking. The expansive custom cabinetry with brass Waterworks hardware provides abundant storage, with a suite of top-of-the-line Wolf and Sub-Zero appliances. The library boasts a dazzling 1920s Baccarat chandelier and a wood-burning fireplace framed by a meticulously carved stone mantel from Orvieto, Italy, circa 1710. The sunken music room, framed by an entire wall of windows, overlooks Long Island Sound, offering the best interior perch for the most epic golden sunsets. The south-facing Moroccan-themed conservatory is bathed in sunlight from the early morning until mid-afternoon, making for very satisfied plants overwintering in this warm, happy space. By evening, the soft glow of a Murano fixture circa 1940 transforms the room into a moody gathering place. Each of five bedrooms offers en suite baths and outdoor space overlooking the breathtaking Long Island Sound. (Two of the five bedrooms have wood-burning fireplaces). An extraordinarily appointed lounge, inspired by Ralph Lauren’s legendary Polo Bar, defines the lower level of the home. Additional amenities here include a soundproof screening room, full wet bar, a professionally audio-tuned listening lounge for vinyl buffs, fitness room with traditional and infrared sauna, expansive laundry room, 3-car garage, and another en suite bedroom, ensuring every need is met in this exceptional home. The grounds of this very private property include a treillaged rose garden, a stone fire pit, Italian wrought iron day beds, a full outdoor kitchen by Hestan, and a private beach with retractable access stairs. Situated equidistant between Long Beach and Short Beach on Long Island's tony North Shore, any and all aquatic activities are readily available, including nearby docking and mooring rights. Other featured local attractions include the beloved Saint James General Store (a fixture on the National Register of Historic Places), Harmony Vineyards, Avalon Nature Preserve, canoeing and kayaking on the Nissequogue River, equestrian facilities, a private golf club, and boating on Long Island Sound. Broker/Owner.

Nissequogue
$2,599,000
6 Beds ⋅ 8 Baths ⋅ 952372 MLS
Paradise on the Nissequogue River with 65 feet of waterfront, ideal for canoeing, kayaking, and serene relaxation. This impressive 5,500+ sq ft contemporary with traditional accents offers 15 rooms and two fully separate living quarters, each with its own basement—perfect for extended or multi-generational living. Both residences feature updated granite eat-in kitchens with wood cabinetry and stainless-steel appliances, formal dining rooms, living and sitting rooms, and spacious primary suites with baths. Additional living space includes two additional bedrooms and a full bath, plus a lower-level spacious guest suite, entertainment rooms, abundant storage, and outside separate entrance (OSE) with its own designated parking. Set on 1.09 beautifully landscaped acres with specimen trees, brick patios, decks and exterior lighting, a spectacular salt water heated gunite in-ground pool (approx. 43’ x 25’) with waterfall, spa, lighting, and natural rock diving board—perfectly positioned to capture sweeping river views. Enjoy evenings by the wood-burning fire pit, surrounded by nautical wildlife and breathtaking sunsets. Located in the highly sought-after Smithtown community, close to fine dining, boutique shopping, theatre, mall, Caleb Smith Preserve, Sunken Meadow Park, beaches, golf, and Smithtown schools. Smithtown offers a blend of tranquil suburban life, historic charm and easy access to parkways and the LIRR/NYC. Additional Features: 2-car garage, North Wing: electric heat exchanger, CAC, heat/AC, South Wing: 3 mini-splits, 5-ton compressor, oil burner, forced hot air/CAC, 60-panel solar system (shared by both wings), In-ground sprinklers, Central vacuum, Two propane tanks, Two fireplaces (one gas, one wood-burning), Two separate hot water heaters, Additional electric panels, Laundry room with slop sink and storage, Brick patio with built-in BBQ

2 Riverview Terrace, Smithtown

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.