Head Of Harbor Real Estate

Welcome to Head of Harbor, a picturesque village nestled in the heart of Suffolk County, New York. Known for its stunning natural beauty and tranquil atmosphere, this charming community offers an idyllic escape from the hustle and bustle of city life while still providing convenient access to all the amenities you could desire.

Head of Harbor is renowned for its lush landscapes, featuring rolling hills, serene waterfronts, and abundant green spaces. The village is situated along the scenic shores of Long Island, providing residents with breathtaking views and opportunities for outdoor recreation. Enjoy leisurely walks along the coastline, or take advantage of the nearby parks and nature preserves, perfect for hiking, birdwatching, or simply soaking in the beauty of the surroundings.

The community is characterized by its friendly atmosphere and strong sense of belonging. With a rich history that dates back to the 17th century, Head of Harbor boasts a blend of historic charm and modern conveniences. The village is home to a variety of local shops, cozy cafes, and fine dining establishments, ensuring that residents can enjoy a vibrant lifestyle without venturing far from home.

Education is a top priority here, with access to highly regarded schools that foster academic excellence and personal growth. Families will appreciate the safe and nurturing environment that Head of Harbor provides, making it an ideal place to raise children.

Whether you’re looking for a serene retreat or a vibrant community to call home, Head of Harbor offers the perfect balance of tranquility and convenience. Discover the charm of this hidden gem and experience the unparalleled lifestyle that awaits you in this delightful village.

Newest Listings in Head Of Harbor

$979,000

4 Beds ⋅ 3 Baths ⋅ 1057272 MLS

Classic Center Hall Colonial in Head of the Harbor, Welcome to this charming 4-bedroom, 2.5-bath Center Hall Colonial, ideally situated on 2.19 acres in the Head of the Harbor area of St. James, NY. Built in 1963, this well-maintained home offers timeless character, spacious living, and an exceptional location. Step inside to discover beautiful wood floors and classic wood doors, adding warmth and character throughout the home. Marvin windows provide quality, natural light, and lasting appeal. The property features a cedar deck, perfect for relaxing outdoors or entertaining while enjoying the privacy and expansive grounds. A detached shed provides additional storage, while the two-car garage offers convenient parking and workspace. The full unfinished basement provides abundant storage and flexible space for future use—whether you envision a recreation area, workshop, home gym, or additional living space. The home's location is a true highlight, with convenient access to the LIRR, St. James town, local shopping and dining, and the beautiful North Shore beaches. The property offers a rare combination of space, privacy, character, and convenience. Roof is 12years old, Oil Burner 5 years old, Cedar Deck 5 years old . A rare opportunity to own a spacious Colonial on over two acres in one of St. James' most private locations. Bring your vision and make this special property your own.

3 Gate Road, Head Of Harbor

$1,999,000

5 Beds ⋅ 4 Baths ⋅ 1054624 MLS

A Rare Waterfront Sanctuary in the Village of Head of the Harbor. For the first time since it was built more than half a century ago, this remarkable waterfront property is being offered for sale. Privately set on 2.75 acres overlooking Stony Brook Harbor, 89 Harbor Road has remained under its original ownership since its creation and is defined by privacy, natural beauty and an extraordinary connection to the surrounding landscape. With 200 feet of waterfront, sweeping views extend across the pristine harbor toward Nissequogue, and Long Island Sound beyond, while private steps lead directly to the beach and water below, where a substantial stone riprap revetment protects the shoreline. A long and winding drive passes through a wooded landscape, leading to a broad opening with a light-filled residence framed by majestic oaks and a backdrop of water and sky. Upon arrival, there is an immediate sense of having left the hustle and bustle of the outside world behind—a peaceful sanctuary where the landscape, changing tides and natural beauty of the harbor become part of everyday life. Designed by architect Geysa Sarkany, the approximately 4,600-square-foot residence was conceived around its remarkable setting. The home was designed to look outward, with walls of glass creating a seamless connection between the interiors and the water and landscape beyond. Beneath this openness is a home of substantial construction, engineered and built with solidity and permanence. From the principal living spaces, kitchen and covered deck, the architecture continually draws the eye outward, framing individual views of the sky, shoreline and ever-changing harbor. Thoughtfully placed windows and glass, cypress siding and natural materials further connect the architecture to its surroundings, while 5 bedrooms and 3.5 baths across three levels provide substantial living space. Here, no two days on the harbor are quite the same. The tides rise and recede, revealing winding channels and broad tidal flats. Herons wander the shoreline while ospreys and eagles soar overhead, and sailboats, kayaks and paddleboarders quietly pass below. Summer brings long evenings on the covered deck and breathtaking sunsets over the water, as the sky and harbor take on an ever-changing palette of color and texture. In autumn, the marsh grasses turn from green to gold, while the shifting light and changing winds transform the landscape. The connection to the waterfront extends beyond the views, with direct beach and harbor access for kayaking, paddleboarding and sailing—making the water an integral part of life here. Lovingly maintained and thoughtfully updated over the years, great care has been taken to retain the home’s architectural character and its remarkable connection to the surrounding landscape. It presents a rare opportunity for its next owner to continue its story—whether embracing the home as it is or thoughtfully making it their own. While the setting feels a world away from everyday life, it is within the Smithtown School District and only minutes from Stony Brook Village, Stony Brook University and Stony Brook University Hospital, along with local restaurants, shopping, Avalon Nature Preserve and Harmony Vineyards—offering an exceptional balance of privacy, natural beauty and convenience. The combination of acreage, privacy, substantial waterfront, elevation, direct beach access and expansive views across a pristine harbor presents a remarkable setting—an opportunity to live surrounded by natural beauty, within an ecosystem and landscape that change with every tide and season. A property offering this combination of features rarely becomes available.

89 Harbor Road, Head Of Harbor

$3,699,000

5 Beds ⋅ 8 Baths ⋅ 1037676 MLS

A Rare Opportunity to Create Your Custom Estate on Long Island Opportunities like this are exceptionally rare on Long Island. Set within one of the area’s most prestigious and private villages, this extraordinary new-construction estate offers the space, privacy and ability to customize that are increasingly difficult to find. Privately positioned on a breathtaking 2.35-acre wooded property with an additional one-acre private driveway, this impressive 7,000+ square-foot residence has been thoughtfully designed to combine timeless architecture with today’s most sought-after luxury amenities. Construction has progressed to the point where private tours can now be scheduled, while still offering the opportunity to personalize select finishes and make this remarkable home your own. A sweeping asphalt and stone driveway with cobblestone edging leads to the grand two-story traditional residence and oversized three-car garage. Inside, dramatic proportions immediately set the home apart, with a 20'6" two-story foyer and family room, 10-foot ceilings on the main level, a full 10-foot walk-out basement, and an elevator servicing all floors. The main level is designed for both everyday luxury and effortless entertaining. A spectacular chef’s kitchen features high-end Subzero separate refrigerator and freezer and Wolf appliances; subzero wine cabinetry and wet bar sub-zero, custom cabinetry with wood buildins, granite or quartz countertops, an expansive center island with prep sink, and radiant-heated porcelain floors. The soaring two-story family room is centered around a modern linear gas fireplace and coffered ceiling, while the formal dining room features custom built-ins and elegant millwork. A highly desirable **first-floor en suite** provides exceptional flexibility and convenience. The home also features a primary en suite wing along with 3 additional en-suite bedrooms, wide White Oak flooring, custom closet systems, radiant-heated floors, **two saunas and two steam showers**. Spa-inspired baths with premium Kohler fixtures complete the experience. Outdoor living is equally impressive. A covered rear porch with its own gas fireplace creates a beautiful setting for year-round entertaining, while a dedicated exterior-access full bathroom is ideal for a future pool. An in-ground pool is optional and may be customized to the buyer’s vision. The full 10-foot walk-out basement, complete with a full bathroom and outside entrance, offers tremendous possibilities for additional recreation, fitness, entertainment or guest space. Behind the beauty is equally impressive construction and infrastructure, including engineered wood-web floor joists, 400-amp electric service, natural gas, public water and seven oversized drywells. The home is also designed to accommodate a future generator and pool. Throughout the residence, wide White Oak hardwood floors, substantial moldings, custom millwork and an extra-wide staircase with open railings reflect the level of craftsmanship invested in every detail. More than a new home, this is an opportunity rarely available on Long Island: a newly built 7,000+ square-foot custom estate on exceptional acreage within an exclusive village — offering privacy, scale, luxury and the chance to make the finishing touches uniquely your own. *3D Reality Tours shown are examples of the builder’s previous work and are intended to demonstrate quality and craftsmanship; they do not depict this exact home.

550 Moriches Road, Head Of Harbor

$1,500,000

3 Beds ⋅ 3 Baths ⋅ 1040036 MLS

Elegant and Unique Colonial set on 2 Beautifully Landscaped Acres in the highly Sought After Village of Head of the Harbor. This Spacious Home Offers 3/4 Bedrooms. 3 Traditional Bedrooms Plus a Versatile Bonus Room That Can Easily Function as a 4th Bedroom. Generous-Size Principal Rooms Create an Inviting Layout for Everyday Living and Entertaining. The Home Features a Warm and Welcoming Living Room, a Formal Dining Room, and a Charming Den Highlighted by a Stunning Stone Fireplace. A Separate Study/Home Office Further Enhances This Home’s Valuable Versatility. The Updated Eat in Kitchen Provides Excellent Workspace and Views of the Serene Property. Additional Features Include: 2.5 Baths, Central Air Conditioning, a Full Finished Basement, 2 Car Garage, an Unfinished Walk-Up Attic with Vaulted Ceilings (see floorplan for dimensions), Spacious Deck Overlooking the Picturesque Grounds, Separate Hot Water Heater, Crown Molding, Numerous Updates, and a Comfortable, Functional Floor Plan Enhancing this Home’s Appeal. Set in a Premier North Shore Village Known for Privacy, Natural Beauty, and Convenience, this Property offers an Exceptional Lifestyle Opportunity.

1 Valleywood Court W, Head Of Harbor

$2,275,000

5 Beds ⋅ 4 Baths ⋅ 1027926 MLS

Tucked away on two acres at the end of a quiet cul-de-sac, in the prestigious enclave of Head of the Harbor, this magnificent five-bedroom, four-bath estate offers an unparalleled blend of modern luxury and serene privacy. The entire residence has undergone a comprehensive transformation over the past six years, resulting in a home that feels brand new while retaining its sophisticated, timeless character. The heart of the home is the stunning new kitchen, designed with a modern aesthetic that features sleek finishes, built-in Sub-zero refrigerator, Wolf oven, Jenn Air cooktop- with an intuitive layout perfect for both daily living and large-scale hosting. The large center island with seating, waterfall-edge quartz countertop and second sink invites entertaining on a grand scale, or just a perfect intimate gathering. The new picture window provides a panoramic view of the pristine outdoor, resort-like grounds. Off the kitchen, enjoy casual meals in the glass-enclosed dining area. The main floor also features a formal dining room, a bedroom and full bathroom, in addition to the entertaining spaces, which include an expansive family room with fireplace and access to the patio, an adjacent living room, and a bright, open sitting room off the kitchen with floor-to-ceiling windows looking out to the parklike property. Each of the four full bathrooms has been exquisitely renovated with designer fixtures, heater floor in the primary suite, and contemporary tiling, providing a spa-like experience in every corner of the house. The home's electric service has been upgraded to 450 amp in 2022, and also has a whole house natural gas generator, providing comfort along with style across the entire living space! Beyond the interior, the property serves as a private sanctuary. A brand-new patio leads to a sparkling pool with all new equipment installed in 2022, creating an outdoor oasis framed by mature trees and fenced-in expansive greenery across the 2 acre property. You will also find a dining pavilion offering shade and comfort, a bar, and a cabana with a changing area, bath and outdoor shower for added convenience. The commitment to quality is evident in the structural upgrades as well, including a new balcony off of the primary suite, new roof and the addition of owned solar panels for exceptional energy efficiency. The lower level reveals a fully finished basement, offering versatile space including a summer kitchen, new full bathroom, home gym, media room and recreation area. With every detail meticulously addressed—from the expansive living spaces to the secluded acreage—this estate represents a rare opportunity to enjoy a turnkey lifestyle in one of the most sought-after locations on the North Shore. This Head of the Harbor home is surrounded by the charm of Nissequogue, Smithtown, Saint James 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. Note: please see the attached document for a full list of upgrades to this home!

5 Meadow Gate W, Head Of Harbor

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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.