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$1,649,000

Welcome to 4 Holly Lane in Nissequogue, an impressive estate style residence set behind a sweeping circular driveway and surrounded by beautifully manicured grounds, mature trees, and expansive lawns. Step inside to a dramatic two story foyer that introduces a bright, spacious interior featuring hardwood floors, elegant formal living and dining rooms, and a stunning great room with soaring ceilings and a floor to ceiling stone fireplace. The well appointed kitchen offers abundant cabinetry and counter space, stainless steel appliances, and a sun filled breakfast area overlooking the backyard. A bright sunroom provides seamless access to the home’s exceptional outdoor entertaining spaces. Upstairs, the expansive primary suite features vaulted ceilings, a window lined sitting area, and a generous en-suite bath with dual vanities and soaking tub\. Additional spacious bedrooms and a large bonus room provide tremendous flexibility for today’s lifestyle. Outside is where this property truly shines. An expansive paver patio, fire feature, multiple entertaining areas, sprawling lawn, and mature landscaping create a private setting designed for gatherings and relaxation\. An impressive detached accessory building offers a warm lodge inspired interior complete with lounge space, kitchenette, bath, and additional recreational space. With oversized garage areas, extensive storage, remarkable grounds, and incredible versatility throughout, 4 Holly Lane offers an exceptional combination of space, privacy, character, and indoor outdoor living in Nissequogue.

3 Beds ⋅ 4 Baths ⋅ 1048497 MLS

Welcome to 4 Holly Lane in Nissequogue, an impressive estate style residence set behind a sweeping circular driveway and surrounded by beautifully manicured grounds, mature trees, and expansive lawns. Step inside to a dramatic two story foyer that introduces a bright, spacious interior featuring hardwood floors, elegant formal living and dining rooms, and a stunning great room with soaring ceilings and a floor to ceiling stone fireplace. The well appointed kitchen offers abundant cabinetry and counter space, stainless steel appliances, and a sun filled breakfast area overlooking the backyard. A bright sunroom provides seamless access to the home’s exceptional outdoor entertaining spaces. Upstairs, the expansive primary suite features vaulted ceilings, a window lined sitting area, and a generous en-suite bath with dual vanities and soaking tub\. Additional spacious bedrooms and a large bonus room provide tremendous flexibility for today’s lifestyle. Outside is where this property truly shines. An expansive paver patio, fire feature, multiple entertaining areas, sprawling lawn, and mature landscaping create a private setting designed for gatherings and relaxation\. An impressive detached accessory building offers a warm lodge inspired interior complete with lounge space, kitchenette, bath, and additional recreational space. With oversized garage areas, extensive storage, remarkable grounds, and incredible versatility throughout, 4 Holly Lane offers an exceptional combination of space, privacy, character, and indoor outdoor living in Nissequogue.

4 Holly Lane

$1,489,999

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. Along with Additional highlights include, LOW TAXES, Horse property, 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. This home is surrounded by natural beauty, yet exceptionally connected, this residence is moments from boating, Nissequogue Golf Club, Stony Brook University and charming villages of St. James.

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. Along with Additional highlights include, LOW TAXES, Horse property, 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. This home is surrounded by natural beauty, yet exceptionally connected, this residence is moments from boating, Nissequogue Golf Club, Stony Brook University and charming villages of St. James.

21 Wilderness Road, Nissequogue

$1,150,000

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

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

$6,400,000

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.

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

$1,699,543

Set on 2.36 private acres in the Village of Nissequogue, 704 Short Beach Road offers an exceptional combination of privacy, space and indoor-outdoor living. This distinctive 3,043-square-foot Colonial features an inground pool and separate Pool House, creating a setting equally suited to everyday living and entertaining. Inside, the 20' x 15' kitchen features granite countertops, a center island, Wolf gas burner, two Sub-Zero refrigerators and double ovens. The formal dining room, expansive living room and den provide generous gathering spaces, complemented by fireplaces, built-ins and a wet bar. Multiple rooms open directly to the pool area, creating a natural connection between the home's interior and its private outdoor setting. The second-floor primary suite provides separation from the main-level bedrooms, while the Pool House extends the property's versatility with its own living room, kitchenette, full bath and loft area. Mature surroundings and 2.36 acres provide privacy and room to enjoy the property throughout the seasons. A distinctive Nissequogue property offering substantial grounds, flexible living spaces and an exceptional outdoor setting. Schedule your private showing of 704 Short Beach Road.

4 Beds ⋅ 3 Baths ⋅ 919240 MLS

Set on 2.36 private acres in the Village of Nissequogue, 704 Short Beach Road offers an exceptional combination of privacy, space and indoor-outdoor living. This distinctive 3,043-square-foot Colonial features an inground pool and separate Pool House, creating a setting equally suited to everyday living and entertaining. Inside, the 20' x 15' kitchen features granite countertops, a center island, Wolf gas burner, two Sub-Zero refrigerators and double ovens. The formal dining room, expansive living room and den provide generous gathering spaces, complemented by fireplaces, built-ins and a wet bar. Multiple rooms open directly to the pool area, creating a natural connection between the home's interior and its private outdoor setting. The second-floor primary suite provides separation from the main-level bedrooms, while the Pool House extends the property's versatility with its own living room, kitchenette, full bath and loft area. Mature surroundings and 2.36 acres provide privacy and room to enjoy the property throughout the seasons. A distinctive Nissequogue property offering substantial grounds, flexible living spaces and an exceptional outdoor setting. Schedule your private showing of 704 Short Beach Road.

704 Short Beach Road, Nissequogue