Head Of Harbor Real Estate

Head Of Harbor Real Estate

Welcome to Head of the Harbor, a picturesque village nestled in the heart of Suffolk County, New York. This charming community offers a unique blend of tranquility and sophistication, making it an ideal location for those seeking a serene lifestyle while still being close to the vibrant culture of Long Island.

Head of the Harbor is renowned for its stunning waterfront views, lush landscapes, and an abundance of recreational opportunities. With its proximity to the picturesque Stony Brook Harbor, residents can enjoy boating, fishing, and leisurely strolls along the scenic shoreline. The village is also home to a variety of parks and nature reserves, perfect for outdoor enthusiasts and families looking to explore the great outdoors.

This enchanting village boasts a rich history and a strong sense of community. With its quaint streets lined with beautiful homes, Head of the Harbor exudes charm and elegance. The local schools are highly regarded, providing an excellent education for children, while the nearby cultural attractions, including theaters, museums, and art galleries, offer residents a vibrant social scene.

Head of the Harbor is conveniently located near major highways, making it easy to access nearby towns and cities, including the bustling community of Stony Brook. Whether you're looking for a peaceful retreat or a place to raise a family, Head of the Harbor offers a unique lifestyle that combines the best of both worlds.

Discover the allure of Head of the Harbor, where serene living meets the charm of Long Island’s rich history. Your dream home awaits in this idyllic village!

Newest Listings in Head Of Harbor

$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

$1,899,000
4 Beds 4 Baths 1047851 MLS
Welcome to 29 Farm Road....nestled in the prestigious Village of Head of the Harbor, where secluded, private & tranquil living awaits! This stunning, beautifully maintained Expanded Ranch features a grand entry foyer, spacious EIK w/ granite countertops, center island, SS appliances, and picturesque views of the surrounding landscape, a warm and inviting Great Room w/ Stone FP and vaulted ceilings w/ 2 skylights and 4 slider doors leading to the wrap around deck, a gorgeous formal dining room, powder room. The 1st floor features 3 spacious bedrooms, including a luxurious Primary Bedroom Ensuite w/ private access to the extensive wrap-around porch, WIC, and primary bath w/ double vanity sink, bathtub, and separate shower. Bedroom 2 features a WIC, chair rail molding, and an ensuite bathroom w/ spa tub. Bedroom 3 offers a private loft space and skylight, and a main floor office space w/ French doors, plus an additional full bath completing the main level. The versatile loft is ideal as a recreation room, home gym, or flex space, with convenient attic access. The lower level offers exceptional flexibility and features a 4th Bedroom (perfect for guests or an in-law suite), a Summer Kitchen w/ quartz countertops, oversized family room, 2 separate gym rooms, full bath, laundry room, ample storage, direct access to the two-car garage, and sliders leading to your own private, resort-like backyard retreat! Additional features include.... CAC (2 zones), Oil Heat (4 zones - burner 2016), 200-amp electric, IGS System (8 zones - redone in 2026), inground saltwater heated pool (Liner - 2025), Whole House Inside & Outside KeyOS wireless app-controlled stereo system, and a portable generator with transfer switch hookup. Surrounded by nature, with an abundance of natural light, oversized windows, and skylights that create a bright, airy, and inviting atmosphere throughout. This exceptional home truly has it all! All this and much more... Set on over 2+ acres of beautiful and secluded property (very private), you do not want to miss this rare opportunity!

29 Farm Road, Head Of Harbor

$2,399,000
6 Beds 5 Baths 1046808 MLS
Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with expansive living spaces filled with natural light of generous proportion and seamless indoor-outdoor flow creating a tranquil retreat just moments from the harbor, beaches, yacht clubs, vineyards and nature preserves. Set on two private beautifully landscaped level acres of property designed for both everyday enjoyment and sophisticated entertaining. This private estate seamlessly blends timeless elegance, modern luxury, and resort-style living. A grand two-story foyer introduces the home's sophisticated interiors, where soaring cathedral ceilings, gleaming hardwood floors, abundant natural light, and exquisite architectural details create an atmosphere of warmth and refinement. Thoughtfully updated throughout, every space has been designed with both everyday comfort and effortless entertaining in mind. The recently renovated chef's kitchen serves as the heart of the home, featuring a dramatic Crawford ceiling, custom crown and box moldings, quartzite-topped center island, and a suite of premium appliances including a Sub-Zero refrigerator, Bosch range, double ovens, microwave drawer, and dishwasher. The kitchen flows seamlessly into the impressive great room, highlighted by a floor-to-ceiling stone wood-burning fireplace and walls of windows overlooking the picturesque grounds. Elegant entertaining spaces continue with a gracious formal living room accessed through glass pocket doors, and a spacious dining room perfectly suited for hosting intimate gatherings or larger celebrations. The main level offers five generously proportioned bedrooms and three full bathrooms, including two recently renovated baths appointed with refined finishes. Upstairs, an expansive loft with hardwood floors overlooking the great room provides additional living and entertaining space and leads to the luxurious primary suite. This private retreat features hardwood flooring, custom closets, detailed millwork, and a stunning newly renovated spa-inspired bath complete with a soaking tub, oversized glass-enclosed shower, dual vanity, and exquisite Italian tile. The outdoor setting is nothing short of extraordinary. Professionally landscaped grounds surround a tranquil in-ground pool, complemented by multiple paver patios designed for elegant outdoor entertaining and relaxation. A sprawling Trex deck extends nearly the entire length of the home, creating a seamless connection between indoor and outdoor living. Additional highlights include a fully finished lower level with a full bath, offering exceptional flexibility for recreation, fitness, guest accommodations, or extended living space. Car enthusiasts will appreciate the rare offering of four garage spaces, including two attached and two detached garages. Recent improvements include extensive interior and exterior painting, newer windows, newer roof and skylights, custom closet systems, wood flooring throughout most of the house and numerous thoughtful upgrades throughout. A wonderful opportunity awaits for you to own this property and reap the rewards of resort living in the White Spruce Farm Community within the Village of Head of the Harbor. A must see! *Taxes Include Village Taxes of $3,199

15 The Chase, 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

$2,375,000
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.