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$990,000
4 Beds ⋅ 3 Baths ⋅ 1029417 MLS
Set on a beautifully landscaped 0.80-acre corner property, this custom Farm Ranch offers space, comfort, and exceptional versatility. A welcoming entry foyer opens to a recently renovated eat-in kitchen featuring a striking double-sided fireplace. The bright and airy den is surrounded by walls of windows, while the formal dining room provides easy access to the deck through sliding glass doors. The main level also includes a spacious living room with a custom window seat and a convenient powder room. The first-floor primary suite is designed as a private retreat, complete with a sitting area or home office, a walk-in closet, and an oversized bath featuring a soaking tub and separate walk-in shower. Three additional bedrooms and a full hall bath provide plenty of room for family or guests. The full, partially finished basement offers an outside entrance, laundry area, utilities, and abundant storage or expansion potential. Additional highlights include radiant heat, hardwood flooring, central air conditioning, in-ground sprinklers, Andersen windows, a 150-amp electrical service, generator hookup, updated paver walkways, a roof replaced in 2021, burner installed in 2020, and a hot water heater replaced in 2021. Ideally located near town beaches, Landing Avenue Golf Course, the LIRR, shopping, and dining. This spacious home offers endless possibilities and is much larger than it appears.

19 Eckernkamp Drive, Smithtown
$899,999
4 Beds ⋅ 2 Baths ⋅ 1028706 MLS
Welcome to 41 Oak Street. This inviting High Ranch offers exceptional curb appeal with stately pillars, shingle style vinyl siding, Fieldstone accents, paver walkways, a charming Arbor enhancing the entrance to the backyard and an oversized Belgian Block lined driveway. The home is surrounded by mature landscaping offering natural privacy and a serene setting. Step inside to discover gleaming hardwood floors, sunlit living spaces enhanced by bay and bow windows, custom hand carved wood detailing and stain glass accents that create a warm inviting ambiance. The beautifully appointed kitchen, expansive den with a large skylight and a tastefully renovated full bathroom further enhance the home’s appeal. The versatile lower level offers excellent potential for extended living with proper permits. The sliding glass doors leads to your own private retreat. Multi-level Trex and wood decking with handcrafted built in benches, tiered wood walkways, a custom awning, tranquil fish pond, and a sparkling 20x40 in ground pool surrounded by stone pavers featuring a new liner complete this thoughtfully designed outdoor space. Additional highlights include a new 275 gallon Roth Oil tank, 200-Amp electrical service, a new first floor central air conditioning system, and a roof and siding that are approximately 10 yrs. old. Conveniently located near Smithtown Beaches, Smithtown Landing Golf and Country Club. All of-this is set on .50 acres in a truly desirable location. Don’t miss this wonderful opportunity to make this home your own and create lasting memories for years to come.

41 Oak Street, Smithtown
$990,000
4 Beds ⋅ 3 Baths ⋅ 1028829 MLS
Welcome home to this Post Modern Colonial, where an impressive two-story entry foyer creates a grand first impression. Beautiful hardwood floors, finished in a modern gray tone, extend throughout the entry foyer, staircase, formal living room, and formal dining room, creating a warm and cohesive flow. Designed for today's lifestyle, the home features a desirable open-concept kitchen and family room with a wood-burning fireplace flanked by custom built-ins, making it the perfect gathering space. The spacious primary suite offers a walk-in closet and a private ensuite bath, while a conveniently located first-floor laundry/mudroom with a new front-load washer and dryer adds everyday functionality. Set on a landscaped .43-acre property in the heart of St. James, the private, fenced backyard is an entertainer's dream, featuring an expansive paver patio with a built-in firepit plus a separately fenced saltwater inground pool with waterfall. Pool updates include new filter, heat pump, and Loop-Loc cover, as well as new pavers surround the pool area, while the gazebo provides the perfect place to relax. Thoughtfully updated for today's modern lifestyle, the home features a Smart Home system allowing you to control lights, doors, and central air from your smartphone, along with a security system with cameras for added peace of mind. Additional improvements include a 2020 roof, a 2024 natural gas heating system, CAC with the second-floor compressor replaced in 2023, a separate gas hot water heater, 200-amp electric service with a dedicated panel for an EV charger, and owned solar panels installed in 2020, providing lower electric costs and valuable property tax exemptions. (Note: Taxes being professionally grieved with an estimated $3,300 reduction; grievance is transferable to the Buyer.) Ideally located on a cul-de-sac and just a short walk to Lake Avenue's shops and restaurants, including the new Galiano Wine Bar. This home also offers beach rights to multiple Town of Smithtown beaches, proximity to parks, hiking trails, and nature preserves, and is situated within the highly regarded Smithtown Central School District.

4 Patricks Way, Saint James
$1,099,999
4 Beds ⋅ 3 Baths ⋅ 1014077 MLS
Welcome to this beautifully updated 4 bedroom, 2.5 bath Colonial, nestled at the end of quiet dead-end street in the desirable Town of Smithtown. From the moment you arrive, the newly paved circular driveway, manicured grounds, and exceptional curb appeal set the stage for what awaits inside. Step through the front door into a stunning open foyer where natural light and elegant design create an immediate sense of warmth and sophistication. Rich hardwood floors flow throughout the home, leading you into a custom designed kitchen featuring quartz countertops, glass tile flooring, abundant cabinetry, and thoughtful finishes that make both everyday living and entertaining a pleasure. A newly renovated powder room off the kitchen has direct access to the yard, perfect for guests enjoying the outdoor amenities. Convenience meets luxury with a spacious mudroom, pantry, and laundry room off the two car garage. A living room, family room with wood burning fireplace and formal dining room complete the layout of the first floor. Upstairs, skylights bathe the landing in natural light, creating a bright and welcoming second floor space. . Four generously sized bedrooms offer comfort and privacy, including a serene primary suite complete with an updated en-suite bath with heated floors, skylight, electric fireplace and two spacious closets. The fully finished basement provides exceptional additional living space and includes a cedar closet for storage and wet bar. Recent updates include a brand new tankless hot water heater, offering efficiency and peace of mind. Outside, prepare to be captivated by an exquisitely landscaped backyard designed for both relaxation and entertaining. Multi level grounds with charming gazebos, a built in heated pool, pool house, two storage sheds and a nine zone sprinkler system combine to create a resort like setting you will never want to leave. Whether hosting summer gatherings or enjoying a quiet evening under the stars, this outdoor oasis is truly unforgettable. A rare opportunity to own a meticulously and thoughtfully updated home in Smithtown.

17 Lower Road, Smithtown
$1,200,000
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
$789,000
4 Beds ⋅ 3 Baths ⋅ 1002364 MLS
Welcome to this beautifully expanded Colonial nestled in the highly sought after College Section of Smithtown. This spacious 4 bedroom, 2.5 bath home offers the perfect blend of classic charm and modern updates. Step inside to discover gleaming hardwood floors, generously sized living spaces, and updated bathrooms designed with todays buyer in mind. The 372 square foot primary suite addition provides a wonderful retreat offering additional space and comfort rarely found in homes of this style. The thoughtfully designed floor plan is ideal for both everyday living and entertaining. A brand new roof (2025) and a young gas burner (2018) are just some of the improvements that provide peace of mind. Situated on .24 acre, enjoy a private backyard setting perfect for relaxing, gardening or hosting outdoor gatherings. A one car-garage, a full unfinished basement and muture landscaping complete the package . Located in one of Smithtowns most desired neighborhoods , this home offers convenient access to parks, shopping, restaurants, transportation all in Smithtown School District. With its spacious layout, desirable updates, and exceptional location, this is an opportunity you won't want to miss.

61 Hofstra Drive, Smithtown
$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
$2,399,999
8 Beds ⋅ 8 Baths ⋅ 976021 MLS
New Price. Fresh Presentation. One Extraordinary Opportunity. *A Private Resort Where Luxury Meets Everyday Living* Motivated seller has thoughtfully repositioned this exceptional estate with a compelling new price, creating a rare opportunity to own one of Head of the Harbor's most distinctive luxury residences. Hidden at the end of a quiet cul de sac in the prestigious Incorporated Village of Head of the Harbor, 9 Watercrest Court is more than a home. It is a private retreat where holidays become traditions, generations gather, and every weekend feels like a vacation. Thoughtfully designed for exceptional entertaining and everyday living, every space encourages connection while offering the privacy and comfort of a true estate. Spanning approximately 10,000 square feet across all levels, the residence seamlessly blends timeless architecture with modern luxury. A dramatic two story foyer leads to expansive living spaces filled with natural light, soaring ceilings, radiant heated floors, custom millwork, and walls of windows. At the center of it all is a spectacular chef's kitchen featuring Wolf, Sub Zero, and Miele appliances, an oversized island, walk in pantry, coffee bar, and effortless flow into the surrounding gathering spaces. The primary suite offers a peaceful retreat with a spa inspired bath and oversized walk in closets, while the private guest residence, complete with its own kitchen, living room, bedroom, full bath, and separate entrance, provides exceptional flexibility for multigenerational living, extended family, long term guests, live in support, or a private executive suite. Designed for entertaining on a level rarely found in residential real estate, the lower level features a professionally designed private bowling alley, fitness area, recreation spaces, and multiple gathering areas that make birthdays, holidays, game nights, and family celebrations unforgettable. Outside, the resort style backyard offers an in ground pool, expansive patios, beautifully landscaped grounds, and multiple outdoor living spaces designed for everything from peaceful mornings with coffee to summer barbecues and evenings with family and friends. Ideally located in one of Long Island's most sought after North Shore communities, Head of the Harbor offers estate living just minutes from Stony Brook University, renowned hospitals, yacht clubs, golf courses, beaches, fine dining, and major transportation. This is more than a luxury home. It is where your family's next chapter begins. Notable Features • Approximately 10,000 square feet across all levels • Private guest residence with separate entrance • Professionally designed private bowling alley • Resort style in ground pool with expansive outdoor entertaining areas • Chef's kitchen with Wolf, Sub Zero, and Miele appliances • Radiant heated floors • Whole house generator • Fitness area and expansive recreation spaces • Located in the prestigious Incorporated Village of Head of the Harbor

9 Watercrest Court, Head Of Harbor
$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
$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
$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

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.