Smithtown Real Estate

Welcome to Smithtown, a vibrant community nestled in the heart of Suffolk County, New York. Known for its picturesque landscapes and rich history, Smithtown is not just a beautiful place to live; it’s also home to an exceptional school district that prioritizes the education and development of its students.

The Smithtown Central School District is renowned for its commitment to academic excellence, offering a comprehensive curriculum that caters to diverse learning styles. With a strong emphasis on both academics and extracurricular activities, students are encouraged to explore their interests and talents. From advanced placement courses to a wide range of sports and arts programs, Smithtown schools provide a well-rounded educational experience that prepares students for future success.

Parents will appreciate the dedicated staff and innovative teaching methods that foster a nurturing environment. The district boasts a high graduation rate and a strong college readiness program, ensuring that students are not only prepared for high school but also for the challenges of higher education. Community involvement is highly encouraged, with numerous events and programs that connect families and educators, creating a supportive network for students.

The picturesque town of Smithtown itself offers a charming blend of suburban tranquility and easy access to urban amenities. With beautiful parks, shopping, and dining options nearby, families can enjoy all that this welcoming community has to offer. Whether you're looking for a place to raise a family or simply seeking a vibrant community, Smithtown’s exceptional school district is just one of the many reasons to call this area home. Explore the possibilities in Smithtown today!

Newest Listings in Smithtown

$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

$799,990

3 Beds ⋅ 4 Baths ⋅ 1049319 MLS

Experience refined, resort-style living in this magnificent Woodbine 3 bedroom 3.5 bath end unit—the largest model offered in the prestigious Country Pointe–Nesconset community. Ideally positioned in a prime interior location, this exceptional residence offers added privacy, beautiful landscaping, and an impressive combination of space, comfort, and custom upgrades. A dramatic two-story entry with soaring ceilings introduces a bright, open layout featuring gleaming hardwood floors, recessed lighting, a gas fireplace, and central vacuum. The beautifully remodeled chef’s kitchen showcases custom finishes, stainless steel appliances, generous cabinetry, and plenty of space for gathering and entertaining. Conveniently located on the main level, the spacious primary suite features a walk-in closet and a private bathroom with a Jacuzzi soaking tub and separate shower. Upstairs, a large open loft provides flexible living space, along with two additional generously sized bedrooms. The full basement with high ceilings offers abundant storage, as well as a partially finished area ideal for a den, home office, gym, full bath or recreation space. Additional highlights include an attached garage, a heating system that is approximately two years young, and a private rear patio surrounded by professionally landscaped grounds and specimen plantings. Country Pointe residents enjoy 24-hour gated security, a clubhouse, fitness center, heated saltwater pool, tennis, pickleball, basketball and bocce courts, a playground, visitor parking, and meticulously maintained common areas. This non-age-restricted community is conveniently located near Wegmans, Trader Joe’s, Whole Foods, restaurants, parks, beaches, major roadways, and Stony Brook University Hospital. This is a rare opportunity to enjoy luxury, privacy, exceptional amenities, and an unbeatable location.

89 Deer Valley Drive, Nesconset

$649,999

3 Beds ⋅ 3 Baths ⋅ 1041427 MLS

Welcome home to this beautifully maintained 3-bedroom, 3-bath home located in the Smithtown School District, offering a versatile layout, modern updates, and plenty of space inside and out. The updated kitchen features stainless steel appliances, quartz countertops, a tile backsplash, and abundant cabinet and counter space. Just off the kitchen, a screened-in porch provides the perfect spot for relaxing, dining, or entertaining. The main level also features a comfortable den, three spacious bedrooms, and two full bathrooms. Downstairs, the basement features an outside entrance, full bathroom, and generous additional living space, offering endless possibilities. Outside, enjoy a large, flat, fully fenced property along with an oversized detached 2.5-car garage, ideal for vehicles, storage, hobbies, or a workshop. Additional highlights include a brand-new cesspool and 200-amp electric service. With its updated interior, flexible living space, expansive property, and convenient location, this home has so much to offer. Come see all the possibilities and make it your own!

666 Rosevale Avenue, Lake Ronkonkoma

$280,000

1 Beds ⋅ 1 Baths ⋅ 1049471 MLS

Fantastic Opportunity to Own! Why rent when you can buy in Smithtown's Award winning School District. This Updated Corner Unit Has Hard Oak Flooring, Granite Countertops, Stainless Appliances, New Wall AC units, Laundry on site and Large Rooms with Plenty of Closet Space ..

355 Route 111 Unit #30 Route 111 Unit #30, Smithtown

$1,199,000

5 Beds ⋅ 4 Baths ⋅ 1049096 MLS

Welcome to this beautiful & Spacious 5 Bedroom Colonial, ideally situated on a cul de sac & offering 3301Sq Ft of living space ,not including the full basement. From the moment you enter you will appriciate the generous room sizes, beautiful oak floors and the comfortable flow throughout this impressive home. The granite Kitchen is designed for both everyday living and entertaining featuring a center island,ample cabinetry,and a covienient butlers pantry. A warm inviting wood burning fireplace creates a perfect setting for relaxing evenings at home. Step outside and discover your own private backyard oasis. Enjoy the oversized paver patio, perfect for outdoor dining and entertaining overlooking the beautiful heated saltwater inground pool. The basement provides valuble additional space and features an outside entrance offering endless possibilties. With aprroximately 3301 sq ft of living space, a Cul de sac location, this home offers the space,comfort and lifestyle you have been looking for !

5 Keystone Court, Smithtown

$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

$3,575,000

6 Beds ⋅ 7 Baths ⋅ 1048898 MLS

Nestled on two private acres in the Incorporated Village of Nissequogue, this extraordinary estate offers beautifully reimagined living space where luxury, comfort, and timeless design come together. The home underwent a remarkable architectural transformation, completely reimagining the interior and exterior while preserving the character and presence of an established North Shore estate. Every detail was thoughtfully redesigned with an emphasis on exceptional craftsmanship, modern functionality, and elegant living. Rich white oak floors, custom stone surfaces, and exquisite finishes create an atmosphere that is both sophisticated and inviting. Designed for everyday living and exceptional entertaining, the chef’s kitchen features an expansive custom pantry that functions like a second kitchen, built-in wine storage, and a beautifully appointed wet bar. The dramatic great room, highlighted by soaring ceilings and a gas fireplace, serves as the heart of the home, while a separate entertainment room featuring a wood-burning fireplace with easy access to convert to gas provides additional space for gathering and celebrating. Offering six bedrooms and seven baths, including two luxurious suite options with spa-inspired baths, heated floors, generous walk-in closets, and refined finishes, the home provides exceptional flexibility and comfort. A distinctive spiral staircase leads to a charming tower overlooking the estate, creating a truly unique architectural feature. Beautifully integrated infrastructure and modern systems complement the home’s exceptional design, providing the comfort, efficiency, and functionality expected in a residence of this caliber. Outside, a heated saltwater pool with stadium steps and bench seating is surrounded by an expansive paver patio, creating the perfect setting for outdoor entertaining. Mature trees and thoughtfully designed landscaping enhance the privacy and beauty of the level two-acre property. A grandfathered horseshoe driveway with dual Belgian block entrances welcomes you home, a highly sought-after feature in Nissequogue’s renowned horse country. Located less than a mile from two beaches, including one with deeded access, this exceptional property offers a rare opportunity to enjoy luxury North Shore living in one of Long Island’s most renowned communities.

523 Long Beach Road, Nissequogue

$979,000

4 Beds ⋅ 3 Baths ⋅ 1042512 MLS

Welcome to this stunning 4-bedroom, 2.5-bath Colonial, thoughtfully transformed from a Splanch in 2009. Set on a private, meticulously landscaped 1-acre property, this exceptional home offers a perfect blend of classic elegance, modern updates, and resort-style outdoor living. A stone-edged driveway and walkway create a beautiful first impression. Step through the front door into an inviting open foyer, where natural light, rich hardwood floors, and elegant design create an immediate sense of warmth and sophistication. High-hat lighting throughout the home enhances the bright, welcoming atmosphere. The heart of the home is the custom-designed kitchen, featuring quartz countertops and stainless-steel appliances. Conveniently located just off the kitchen are a half bath, laundry area, and an exit leading directly to the spectacular outdoor oasis. The raised formal living room overlooks the den and features a wood-burning fireplace with a removable electric insert, creating a warm and inviting space for relaxing or entertaining. Upstairs, the spacious primary bedroom has been thoughtfully updated and features a luxurious en-suite bathroom, a generous walk-in closet, radiant-heated flooring, and pull-down attic stairs providing convenient storage. The additional three bedrooms offer ample storage, including double closets in each room. Two of the top-floor bedrooms feature beautiful cathedral ceilings. The upstairs hallway includes a walk-in closet and an additional linen closet, providing exceptional storage throughout the home. An updated hall bathroom features quartz countertops, a double vanity, and radiant-heated flooring, combining style and comfort. The fully finished partial basement offers additional living or recreational space, along with enclosed closets for the burner and water tank. During the 2009 renovation, the home was converted to gas-fired hot-water heat. The backyard is truly an entertainer’s and swimmer’s dream, highlighted by a 25-yard official short-course, heated, in-ground saltwater pool, perfect for swimming, relaxing, entertaining, or enjoying your own private resort-like retreat. The beautifully landscaped grounds feature a 13-zone irrigation system and are backed by a private quarter-acre wooded area, creating a peaceful and secluded setting. This exceptional property offers space, style, privacy, abundant storage, and beautifully maintained grounds, along with thoughtful updates throughout. A rare opportunity to enjoy Colonial charm, modern amenities, and an extraordinary outdoor lifestyle all in one.

129 Jefferson Avenue, Saint James

$1,625,000

5 Beds ⋅ 4 Baths ⋅ 1048862 MLS

Welcome to 40 Friendly Rd. A home that redefines style, comfort, and convenience. This turn-key, fully renovated property combined luxury and functionality flawlessly. The exterior showcases a perfect blend of brick, Azek facade and oversized Andersen windows exuding a modern yet timeless appeal. As you step inside, you are greeted by a two-story entry foyer with a grand chandelier and monorail/glass floating staircase. The open floor layouts on both floors provide a seamless flow from room to room, making it perfect for both entertaining and everyday living. The kitchen is a chef's dream, featuring custom 3/4" solid white oak and black glass cabinets, custom quartz hood, Viking appliances with a 6-burner stove, and a double island set up. The hidden walk-in butler's pantry offers plenty of storage and adds a touch of luxury. Kitchen flows into a vaulted ceiling family room with a large concrete fireplace which leads to an oversized Trex deck perfect for outdoor entertaining. The property boasts five bedrooms and three and a half well-appointed bathrooms. Custom millwork throughout with 9" wide plank wood flooring, 6" base moldings and a large wet bar on the first level. The home is equipped with a tankless Navien system and a York HVAC system, ensuring optimal comfort all year round. The meticulously landscaped outdoor area with 9 sprinkler zones and new sod provides a tranquil retreat, perfect for enjoying the outdoors. This home is located close to 347 allowing easy access to all local amenities. Whether you are looking for recreation, shopping centers or dining options, you'll find it all within easy reach.

40 Friendly Road, Smithtown

$855,000

4 Beds ⋅ 3 Baths ⋅ 1047477 MLS

Welcome to this beautifully appointed 4-bedroom, 2.5-bath Colonial, ideally situated in the highly desirable Royal Woods/Hillside neighborhood and within the acclaimed Smithtown School District. Freshly painted throughout, this inviting home offers a bright, move-in-ready feel from the moment you arrive. Sun-filled interiors showcase beautiful hardwood floors, cathedral ceiling, a charming bay window, and skylights that create an airy and welcoming atmosphere throughout the home. The spacious living area is anchored by a stunning floor-to-ceiling, full-wall granite wood-burning fireplace, creating an impressive focal point that brings warmth, character, and timeless elegance to the space. The well-appointed kitchen features stainless steel appliances just three years old, combining modern convenience with functionality. The spacious primary suite offers a private retreat, complete with a walk-in cedar closet and a full bath. Enjoy year-round comfort with a high-efficiency heat pump installed just one year ago, providing reliable heating and cooling. An oil-fired hot water heating system remains available as an additional heating option. Step outside and discover your own backyard sanctuary. The inviting inground pool features a one-year-old liner, steps, and pump, while the expansive stone-paver patio provides the perfect backdrop for outdoor entertainment, summer gatherings, or simply relaxing in your own peaceful outdoor escape. Ideally located near Smithtown beaches and Smithtown Landing Golf & Country Club, this exceptional home offers a wonderful combination of comfort, style, convenience, and lifestyle. With its spacious interiors, beautiful outdoor setting, and prime location, this is an opportunity not to be missed. Come make this special home your own!

22 Sheryl Crescent, Smithtown

$749,990

3 Beds ⋅ 2 Baths ⋅ 1047017 MLS

Welcome to 5 Kenny Street, a charming ranch-style home nestled in the heart of Smithtown. This delightful residence boasts three comfortable bedrooms and two full bathrooms, ensuring ample space for all. Upon arrival, you are greeted by the home's impressive curb appeal, set on a generous .34-acre flat parcel. Inside, discover the hidden treasure of hardwood floors beneath the carpeting, preserved for years and ready to shine. The home is equipped with central air conditioning, an updated heating system, and a modern hot water heater for your comfort. Recessed lighting is throughout the house. The spacious living room invites relaxation, while the separate den, enhanced with a cozy gas fireplace, provides an intimate retreat. The kitchen shines with updated stainless steel appliances, a vaulted ceiling with a skylight, and a convenient formal dining room stands ready for your meals and gatherings. The primary bedroom offers the luxury of an ensuite bathroom. The second full bathroom has a skylit vaulted ceiling. This beautiful home has a two-car garage with electric openers, a partially finished large basement with ample storage, and a laundry area adds to the home's practical appeal. Outside, a low-maintenance Trex deck overlooks the picturesque backyard, an ideal spot for outdoor enjoyment. There is an in ground sprinkler system in the front and back yard. The backyard is very private. This home's location is a gem, with easy access to major highways, public transportation, and shopping venues. Welcome to your future home, where convenience meets charm in Smithtown and within the Smithtown School District.

5 Kenny Street, Smithtown

$2,448,000

7 Beds ⋅ 7 Baths ⋅ 1047513 MLS

AN ADDRESS WORTH SAYING YES TO! There are certain streets that make you slow down before you ever reach the house. Swan Place is one of them. Tucked within the coveted Village of Nissequogue, the approach winds past estate-like homes beneath a canopy of mature trees, quietly setting the tone for what awaits. Set on two naturally beautiful and private acres, this is a home with presence, but also one that feels remarkably warm once inside. The sense of occasion begins the moment you step inside. A dramatic two-story foyer is anchored by a grand curved staircase, its sweeping wood balustrade gracefully arcing above the entry and continuing into an elevated, bridge like balcony overlooking the marble floor below. Beyond, the home opens to a spectacular two to three story Great Room, where soaring ceilings, architectural detail and walls of natural light create a space that feels impressive yet inviting. It is a beautiful first impression, sophisticated in design, and unmistakably special. It is a grand introduction, but one that still feels wonderfully livable, the kind of entrance that reminds you immediately that this is no ordinary home. The kitchen was designed for the way a home like this is meant to be enjoyed, open, welcoming, and always connected to what is happening around it. An impressive, oversized center island anchors the space, surrounded by recently renovated designer cabinetry and premium appliances, with plenty of room for everything from morning coffee to a house full of guests. Completely open to the soaring great room on one side and the spectacular, glass filled sunroom, the kitchen becomes the natural gathering place of the home. Sunlight pours in from every direction, while expansive views of the property create an effortless flow from cooking to conversation to the outdoors beyond. Privately positioned on the first floor, the primary suite feels like a retreat of its own. Generous yet intimate, it features a fireside sitting room, beautifully designed dressing spaces and a spa inspired marble bath. French doors open to a private deck with the hot tub just steps away, a wonderfully peaceful escape any time of the day. Additional rooms on the main level offer wonderful flexibility easily imagined as guest quarters, an au pair suite, private offices, or whatever life happens to require. The upper levels unfold with a wonderful sense of privacy and possibility, offering four beautifully proportioned guest bedrooms along with two additional lounging spaces, perfect for quiet reading, late night conversation, a media retreat or simply giving family and guests a place of their own. But the best surprise is found one level higher on the rooftop deck, where the treetops open to spectacular views toward the harbor and Long Island Sound. It is the kind of unexpected perch made for morning coffee, an evening glass of wine, or simply watching the sky change at the end of the day. Outside is where this property becomes something incredibly special. The grounds feel more like a private retreat than a backyard. A heated Gunite pool, framed in stone and brought to life by three cascading waterfalls, creates a wonderfully serene, spa like setting. Expansive decking, a hot tub, outdoor kitchen and two acres of mature landscape provide plenty of places to entertain, and just as many places to disappear with a book and enjoy the quiet. Then there are the unexpected spaces. A tucked-away bonus room above the three-car garage feels like a hidden discovery within the home, an ideal private lounge, game room, studio, or escape, complete with its own Juliet balcony. Life in Nissequogue has always been about having room to breathe. Beaches, boating, the harbor, parks, and the villages of the North Shore are all part of everyday life here, while New York City and the Hamptons remain within reach. 9 Swan Place is an address worth seeing. WHEN THE HOUSE, THE SETTING & THE VALUE ALL SAY YES

9 Swan Place, Nissequogue

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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.