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$3,790,000
5 Beds ⋅ 8 Baths ⋅ 1000931 MLS
Have you ever dreamed of building your own CUSTOM HOME in a small village on Long Island? Look No Further! Set within one of Long Island’s most prestigious and private villages, this extraordinary custom-built estate offers over 7,000 square feet of refined living space with an Elevator to service all Floors, First Floor Primary Suite, radiant floors, 2 Saunas, 2 steam showers, full basement with full bathroom and outside entrance, outside back porch with fireplace and full bathroom from outside only. Private setting on a breathtaking 2.35-acre wooded property, complemented by an additional one-acre private driveway. A seamless blend of timeless architecture and modern luxury, this residence has been thoughtfully designed with superior craftsmanship and uncompromising quality throughout. Home is completed to a point where we can schedule tours. A sweeping asphalt and stone driveway with cobblestone edging welcomes you to this impressive two-story traditional home. Inside, an elevator to service all floors of the home, soaring ceilings create an unparalleled sense of space — including a dramatic 20'6" two-story foyer and family room, 10-foot ceilings on the main level, and a full 10-foot walk-out basement offering endless possibilities. Main Level Elegance. The heart of the home is a spectacular chef’s kitchen featuring: * Custom cabinetry * Granite or Quartz countertops * Expansive center island with prep sink * Radiant-heated porcelain flooring Entertain effortlessly in the formal dining room with built-in cabinetry, elegant millwork, and premium stone surfaces. The two-story family room showcases a modern linear gas fireplace beneath a coffered ceiling, creating a striking focal point. An en-suite bedroom provides flexibility for guests or extended family. Additional highlights include a radiant-heated powder room and a covered rear porch with gas fireplace — perfect for year-round outdoor living. Upper-Level Retreat: The second floor features **four en-suite bedrooms**, each with custom closet systems and wide White Oak flooring. The primary suite is a sanctuary, boasting a spa-inspired bath with a large steam shower, radiant heated floors, and deluxe Kohler fixtures. Exceptional Construction & Infrastructure: Built for longevity and performance, this estate includes: * Engineered wood web floor joists *Oversize 3 Car Attached Garage * 400-amp electric service * Natural gas service for heating, hot water, dryer, future generator & pool * Public water via Suffolk County Water Authority * Seven oversized drywells for optimal drainage Throughout the home, meticulous detailing includes wide White Oak hardwood flooring, heavy base moldings, chair rail and crown moldings, and an extra-wide custom staircase with open railings. In-ground Pool is an option and can be customized. 3D Reality Tours are samples of the builders work, not the exact same model we are building. A rare opportunity to own a masterfully constructed estate in one of Long Island’s most exclusive enclaves — where privacy, luxury, and timeless design converge.

550 Moriches Road, Head Of Harbor
$669,999
4 Beds ⋅ 3 Baths ⋅ 1001234 MLS
Contract Vendee, As-Is, 4 bedroom, 2.5 bath colonial with full bsmt and 2 car garage on 1/2 acre in Smithtown East SD. First floor features, Living Rm, Dining Rm, EIK, 1/2 bath and Family Room. Property requires full renovation.

7 Michael Place, Nesconset
$6,800,000
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
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 996959 MLS
Experience a true vacation-at-home lifestyle in the heart of the Village of Nissequogue, where every day begins with breathtaking southern water views and ends with spectacular western sunsets from a private beach just moments from your doorstep. Nestled within an exclusive beach community with private beach access (dues required), this exceptional coastal retreat seamlessly blends timeless architecture, sophisticated design, and effortless indoor-outdoor living. Beautifully crafted with a classic cedar shingle exterior, this one-of-a-kind residence showcases panoramic water views from multiple balconies and exceptional attention to detail throughout. Sun-drenched living spaces feature soaring vaulted ceilings, white oak flooring, and expansive windows that capture the beauty and serenity of the surrounding landscape. A wood-burning fireplace creates a warm and inviting focal point, while motorized shades in the living room, kitchen, and dinette area provide everyday comfort and convenience. The chef's kitchen is designed for both everyday living and elegant entertaining, featuring custom cabinetry, a Cooper farmhouse sink, induction cooktop, and premium designer finishes that elevate the space. Step outside to your private outdoor oasis, complete with a spacious deck, retractable awning, outdoor shower, beautifully landscaped grounds, and an in-ground sprinkler system. Whether hosting summer gatherings, enjoying sunset cocktails, or returning from a day at the beach, these thoughtfully designed outdoor spaces are ideal for relaxing, entertaining, and unwinding. The third-floor primary suite is a true seaside sanctuary, offering a private balcony with sweeping water views, a luxurious en suite bath, and custom maple-finished closets with built-in maple drawers. Imagine beginning each morning with coffee overlooking the bay and ending every evening with unforgettable sunsets. Exceptional amenities include radiant heated tile flooring throughout the first floor, heat pump systems servicing the main and third floors, smart thermostats, a Ring doorbell system, Kohler generator, recessed hinges, European magnetic door strikes, and sprinkler protection for third-floor exit access. Additional highlights include a two-car garage, U-shaped driveway, and an unbeatable North Shore location. Enjoy close proximity to Long Beach Town Park, just 0.6 miles from Smithtown Bay Yacht Club and approximately 6 miles from the St. James Long Island Rail Road station. This rare offering captures the essence of refined coastal living in one of Long Island's most sought-after waterfront communities. More than a home, this is a year-round retreat where luxury, tranquility, and breathtaking surroundings create an unparalleled lifestyle.

14 Beach Plum Lane, Nissequogue
$1,999,999
5 Beds ⋅ 5 Baths ⋅ 992489 MLS
Welcome to this spacious 5-bedroom, 5-bath Colonial set on 1.70 acres in the desirable Head of the Harbor section of Saint James. This 4,788 sq ft home features a functional layout with a first-floor bedroom and full bath, formal dining room, living room, and an open kitchen with granite countertops, center island, and eat-in area leading to a large family room with fireplace. The second level includes a primary suite with walk-in closets and a private bath, along with additional generously sized bedrooms. Additional highlights include hardwood flooring, crown molding, high ceilings, central air, and natural gas heating. The full finished basement offers additional living space with a lavatory. Exterior features include a 3-car garage, private driveway, and an in-ground pool. Conveniently located near major roadways, shopping, and Smithtown schools.

2 Deepwells Lane, Saint James
$1,250,000
5 Beds ⋅ 4 Baths ⋅ 975603 MLS
Welcome to this stately and impressive Colonial, ideally situated in one of Smithtown's most sought after and picturesque neighborhoods. This exceptional property offers a rare opportunity to create a custom luxury home in a truly premier setting. Boasting generous living space the home features a traditional and functional layout with a spacious Living Room, Dining Room, and inviting Den-perfect for everyday living and entertaining. The Kitchen with its Brazilian granite countertops offers generous space and serves as the perfect canvas to design the heart of your dream home. A beautiful feature of the home is a 280 ft expansive SunRoom extension, complete with hot tub, providing a unique space to unwind and relax all year long while overlooking the yard. Upstairs are 5 well appointed bedrooms including the Primary Bedroom with a huge ensuite full bathroom as well as an additional 1/2 bath. The backyard features a newly renovated 20x40 inground pool with new liner and all new coping (1 year old), and approx 3 year old filter, trex decking for low maintenance outdoor living, a beautiful pavillion to entertain under, and a gazebo. A 2 car garage, a young roof, an above ground 550 gallon oil tank, a 4 zone in-ground sprinklers, a tranquil rock waterfall, lightning rods and an expansive stone wall all around the front of the property. With its grand scale, coveted Smithtown location and proximity to the water, this is a rare find for someone to create a truly exceptional home in a prestigious neighborhood.

2 Three Pond Road, Smithtown
$849,000
4 Beds ⋅ 3 Baths ⋅ 977202 MLS
Lovely Colonial Split, 3/4 Bedroom (4th Bedroom or Office), Spacious Throughout, Updated Eat in Kitchen with Granite/.Stainless Steel Appliances, Attractive Great Room for Gatherings, Updated Baths, Upgraded Recessed Lighting, Updated Windows and Pella Doors, Custom Moldings/Trim, Renovated Entry Level Laundry Room, Central AC- 3 Yrs, 3 Zone Heating System- 3 Yrs, Expanded Primary BR Suite with Full Bath and Walk-In Closet, Country Club Yard, Prof. Landscaped, 20x40 In Ground Pool (5 Yr Liner, Loop-Loc Cover and New Filter), Widened Drive, Partial Garage Space for Storage, Property Tax with Basic Star $14,619.47. NOTE: Natural Gas Line in Street.

43 Hallock Avenue, Smithtown
$1,169,000
4 Beds ⋅ 3 Baths ⋅ 966893 MLS
Set on 1.25 beautifully maintained, level acres within the highly desirable community of St. James, this exceptional property offers the perfect balance of space, privacy, and versatility — with a rare equestrian component that elevates it beyond the ordinary! The impeccably maintained Center Hall Colonial features 4 bedrooms and 2.5 baths with a gracious, flowing floor plan designed for both comfortable everyday living and effortless entertaining. Rich wood floors run throughout the home, complemented by tasteful neutral décor and abundant natural light. The custom updated eat-in kitchen is thoughtfully appointed with stainless steel appliances, granite countertops, and a charming dinette area overlooking the expansive property — creating a seamless indoor-outdoor connection. Formal living and dining rooms provide an elegant gathering space, while the warm and inviting den has a wood burning fireplace and offers a cozy retreat. The primary bedroom features a private ensuite bath, and three additional generously sized bedrooms complete the second level. Updated windows and bathrooms, central air conditioning, a full finished basement with outside entry, and a two-car garage enhance everyday convenience. Additional improvements include low-maintenance vinyl siding, and a generator transfer switch for added peace of mind. Pride of ownership is evident throughout. For those seeking additional flexibility, the property is thoughtfully equipped for equestrian use. A center aisle working barn includes four 12x10 matted breeding stalls, 50-amp electric service, water, heat and ventilation fans, loft exhaust system, and phone lines. Outdoor amenities feature a riding ring with lighting, sprinkler system for dust control, paddock and grazing areas, wash rack, and full secondary fencing. The grounds provide a private and versatile environment suitable for training, conditioning, or leisure riding — all within the comfort of your own property. Located within the Smithtown School District, this unique property is just minutes from shopping, restaurants, parks, transportation, Stony Brook University, Stony Brook Hospital, and the beaches of the Long Island Sound. Offering a rare combination of space, flexibility, and convenience, this exceptional St. James property presents an outstanding opportunity to create something truly special. Whether enjoyed as-is or tailored to suit your vision, this remarkable offering is ready for its next chapter.

14 Hillside Avenue, Saint James
$1,599,000
6 Beds ⋅ 4 Baths ⋅ 948811 MLS
21 Astor Ave Is Located In The Heart Of Saint James Within The Desirable Smithtown School District. This Custom Built And Architecturally Appealing 6 Bedroom, 3.5 Bath Colonial Is Only 25 Years Young & Sits On 3/4 Of An Acre. A Charming Open Front Porch Greets You Before You Enter The Large 2 Story Foyer With Grand Staircase & A Motorized Chandelier. A Bright Formal Living Room Awaits Your Guests Before You Sit Down For A Meal In The Formal Dining Room Featuring A Tray Ceiling. Lovely Hardwood Floors Throughout The Home. The Spacious Custom Kitchen With Island Has Plenty Of Room For A Dining Table And Is Open To The Family Room With Wood Burning Fireplace. There Is Also A Large Enclosed Porch For More Entertaining Space That Leads To The Rear Yard. You And Your House Guests Or In-Laws Will Appreciate The Privacy Of The 1st Floor Guest Quarters With Full Bath & Separate Entrance Complete With Mud Room And Drop Off Station Or This Could Easily Double As A Home Office. The 2nd Level Has 5 Bedrooms, A Full Bath, Laundry Room, And A Large Private En-Suite With Gas Fireplace, Walk-In Closet, And Full Bath With Tub And Separate Shower Stall. If The 4,147 Square Feet Of Living Space Wasn't Enough For You, Then Maybe The Full Finished Basement With A Home Pub & Half Bath Will Help! Wait! Theres More!! Attached 2 Car Garage, Inground Pool, & BONUS Fully Equipped Pool House With CAC & Heat! An Incredible Value For This Much House! Gas Line In Street. Projected ARV $2,300,000 Owner Motivated. Let’s Talk!

21 Astor Avenue, Saint James
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 936825 MLS
Why settle for someone else’s dream when you can build your own? Welcome to this brand-new TO BE BUILT colonial-style home designed with today’s lifestyle in mind. Set on a deep 15,840 sqft lot, this to-be-built beauty will offer over 2,400 square feet of fresh, functional living space and the kind of craftsmanship and energy efficiency only new construction can deliver. Inside, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and private bath, plus two additional full bathrooms—plenty of space for guests, or a growing household. The open-concept kitchen will shine with granite countertops, stainless steel appliances, and flows right into the formal dining room for easy entertaining. This home will be built with Energy Star-rated systems, a separate hot-water storage tank, and high-quality materials throughout. You’ll also get a full basement with customization potential and a scenic south-facing backyard that’s perfect for relaxing or creating your own outdoor retreat. Located in the Smithtown School District and close to parks, shopping, and transportation—it checks every box for modern living. Now’s the time to secure your future in a brand-new, energy-efficient home in a prime Long Island location. Ask about our Builder Incentives

122 4th Street, Saint James
$990,888
10 Beds ⋅ 5 Baths ⋅ 933897 MLS
Builder special extended family with plenty of living space, Hord wood floor through out on the first floor. Home features 10 bedrooms, 4.5 Bathrooms, 2 car garages fireplace, Gas heat, CAC-system. This unique house sits 032 acre of the flat lot close downtown of Saint James, train station. Needs 24 Hours Noticed to show, Appointment only!

474 Route 25A, Saint James
$1,699,543
4 Beds ⋅ 3 Baths ⋅ 919240 MLS
Step into a world of elegance and tranquility at this stunning Colonial home, nestled in the picturesque Village of Nissequogue. Offering a perfect blend of classic charm and modern convenience, this property is a sanctuary where memories are made and cherished. The main house boasts three generously-sized bedrooms, providing ample space for relaxation and personal retreat. Two full bathrooms ensure that morning routines are a breeze, making this home a perfect fit for families or guests. The large kitchen is a chef’s dream, equipped with modern appliances and abundant counter space. Whether you're hosting a dinner party or enjoying a quiet breakfast, this kitchen serves as the heart of the home, seamlessly connecting with the formal dining room that invites laughter and shared meals. The formal living room is an inviting space that sets the stage for cozy evenings by the fireplace, while the den, complete with a wet bar, offers a perfect retreat for entertaining friends or enjoying a nightcap after a long day. Sprawling across 2.36 acres, this property is a true outdoor paradise. Dive into luxury with your own inground pool, where summer days can be spent basking in the sun or hosting unforgettable poolside gatherings. The allure doesn’t stop there; the charming pool house enhances outdoor living with its own living room, kitchenette, and full bath. Perfect for guests or entertaining, the 13' x 21' loft area above provides a unique space for hobbies, a home office, or additional guest accommodation. This home is more than just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss your chance to own this captivating Colonial retreat in Nissequogue—where every corner of the property invites relaxation, celebration, and cherished moments. Schedule your private tour today, and step into your dream home!

704 Short Beach Road, Nissequogue
$2,476,666
7 Beds ⋅ 7 Baths ⋅ 885277 MLS
HUGE PRICE REDUCTION OF $223,000! SELLERS ARE MOTIVATED! Make this home yours today! 9 Swan Place is a renovated estate offering over 8,300 square feet of luxurious living space in one of Long Island’s most coveted areas. Nestled in a pristine area, just across from Stony Brook Harbor, this private sanctuary embodies the best of North Shore living. The home is surrounded by the charm of Nissequogue, Smithtown, Head of the Harbor, and Stony Brook. Imagine days spent exploring local beaches, enjoying waterfront activities, or unwinding at nearby fine dining establishments, vineyards and local parks. For boating enthusiasts, this lifestyle is a dream come true. This elegant home features 7 spacious bedrooms and 6.5 baths, including 5 newly updated bathrooms in marble and quartz. The sprawling first-floor primary suite is a true retreat, boasting his-and-hers walk-in closets, a marble fireplace-accented sitting room, and a spa-like marble bathroom with a hot tub just steps away on your private deck. Two additional bedrooms and a full bath on the main floor make this home ideal for multigenerational living. Vaulted ceilings and natural light define the expansive great room, sunroom, and chef’s kitchen, complete with premium stainless steel appliances, a granite-topped island, and updated light wood cabinetry. The sunroom’s new French doors lead to a sprawling 3,000 sq. ft. deck, perfect for entertaining or simply soaking in your serene surroundings. Outside, the 2-acre professionally landscaped property offers resort-style amenities: a heated gunite pool with three waterfalls, a fire pit, volleyball court, stone patio, and an outdoor kitchen. Whether hosting or relaxing, this home has it all. RECENTLY RENOVATED: KITCHEN CABINETS, BATHROOMS, ENTERTAINMENT ROOM, HVAC, HARDWOOD FLOORS, LANDSCAPING, POOL & DECKS. Located in the sought-after Smithtown School District and surrounded by the vibrant lifestyle of the North Shore, this home is the epitome of luxury and comfort. Hidden halfway between NYC and The Hamptons, this glorious home is meticulously renovated while overflowing with natural light. Don’t miss the chance to make it yours.

9 Swan Place, Nissequogue
$1,550,000
4 Beds ⋅ 4 Baths ⋅ LP1439479 MLS
Last Home To Be Built In This Cul-de-sac. Rendering/Photo Shown Conveys Craftsmanship of Homes Previously Built. Taxes Are Not Known At This Time. Features Include Hardwood Floors, Granite Kitchen Countertops, Choice Of Cabinets With Dove-Tail Draws & Soft Touch Close, 2 Zone Central Air Conditioning, Colonial Base Moldings & So Much More. Some Optional Features Include Venting Out For Stove, A Fireplace, Tray Ceiling Primary Suite, Shadow-box Molding-- Builder Will Build To Suit- Close Distance To Long Island Railroad, Highways, Shopping And More. No Models Available To Show~ Purchaser To Pay Customary Builders Fees. Prices Are Subject To Change-, Additional information: Appearance:To BeBuilt

6 Keystone Court, Smithtown
$1,499,000
4 Beds ⋅ 4 Baths ⋅ LP1439480 MLS
Serene Location! To Be Built. Please Note That Rendering/Photo Shown Conveys Craftsmanship of Homes Previously Built. Taxes Are Not Known At This Time. Features Include Hardwood Floors, Granite Kitchen Countertops, Choice Of Cabinets With Dove-Tail Draws & Soft Touch Close, 2 Zone Central Air Conditioning, Colonial Base Moldings & So Much More. Some Optional Features Include Venting Out For Stove, A Fireplace, Tray Ceiling Primary Suite, Shadow-box Molding-- Builder Will Build To Suit- Close Distance To Long Island Railroad, Highways, Shopping And More. No Models Available To View~ Purchaser To Pay Customary Builders Fees. Prices Are Subject To Change-, Additional information: Appearance:Tbb,Separate Hotwater Heater:Y

2 Vistas Circle, 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.