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$1,489,999
4 Beds ⋅ 4 Baths ⋅ 1027742 MLS
Welcome to 21 Wilderness Road, an exceptional Colonial set on two private acres in the Village of Nissequogue, where timeless design and thoughtful updates come together in a private, serene setting. Offering 4 bedrooms and 4 bathrooms, this residence delivers generous living spaces, refined finishes, and effortless everyday comfort. Hardwood floors, detailed crown molding, and an inviting floor plan create a warm yet elegant atmosphere throughout. The updated kitchen is appointed with granite countertops, abundant cabinetry, and flows seamlessly into the main living areas, making it ideal for both entertaining and everyday living. A fireside sitting area offers the perfect place to gather, while a dedicated home office provides the flexibility to function as a fifth bedroom, guest suite, or private study. One of the home’s most desirable features is its private deeded access to the pristine Long Island Sound, where scenic water views and shoreline access offer an exceptional coastal lifestyle. Additional highlights include an oversized two-car garage with attic storage, a newer Peerless boiler with a Riello burner, and an indirect hot water system for added efficiency. Surrounded by mature trees and lush landscaping, yet just minutes from the Nissequogue Golf Club, scenic nature preserves, and the charming village of St. James, this exceptional property offers a rare opportunity to enjoy privacy, recreation, and coastal living in one of Long Island’s most distinguished waterfront communities.

21 Wilderness Road, Nissequogue
$1,599,999
6 Beds ⋅ 5 Baths ⋅ 1021330 MLS
Nestled on over 2 private, level acres in the prestigious Village of Nissequogue, this beautifully maintained center hall Colonial offers 6 bedrooms, 4.5 baths, and an exceptional layout designed for comfortable living and entertaining. A grand entry foyer welcomes you into a home featuring soaring cathedral ceilings, spacious living areas, and a spectacular 20.6' x 30' kitchen with abundant cabinetry and workspace that serves as the heart of the home. The oversized formal dining room is ideal for hosting gatherings, while the versatile floor plan includes two primary suites on the main level and a third primary ensuite upstairs, along with three additional generously sized bedrooms and another full bath. Step outside to your private backyard retreat featuring a heated in-ground pool surrounded by mature landscaping. Additional highlights include a two-car garage, beach access, mooring rights, and an exceptional North Shore location offering privacy, tranquility, and estate-style living.

15 Stillwater Road, Saint James
$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
$1,195,000
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
$1,699,543
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

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.