Head Of Harbor Homes for Sale

Welcome to Head of Harbor, a picturesque village nestled in the heart of Suffolk County, New York. This charming community, located on the North Shore of Long Island, offers a serene escape from the hustle and bustle of city life while still being conveniently close to all the amenities you could desire. With its lush landscapes, waterfront views, and rich history, Head of Harbor is a hidden gem that captures the essence of suburban living.

The village is known for its stunning homes, many of which boast unique architectural styles and expansive properties that provide ample space for outdoor activities and relaxation. Whether you're seeking a cozy cottage, a luxurious estate, or a contemporary family home, Head of Harbor has something to offer for everyone. The real estate market here is thriving, with a variety of homes for sale that cater to diverse tastes and budgets.

Residents enjoy a close-knit community atmosphere, with tree-lined streets, parks, and recreational facilities that promote an active lifestyle. The nearby beaches, hiking trails, and waterfront access make it easy to embrace the natural beauty of Long Island. Families will appreciate the top-rated schools and safe neighborhoods, while those seeking a vibrant social scene will find local shops, dining, and cultural activities just a short drive away.

If you’re considering making Head of Harbor your new home, now is the perfect time to explore the available homes for sale. Discover the charm and tranquility of this idyllic village, where your dream home awaits!

Newest Head Of Harbor Homes for Sale

$1,899,000

4 Beds ⋅ 4 Baths ⋅ 1023400 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

$3,790,000

5 Beds ⋅ 8 Baths ⋅ 1000931 MLS

Have you ever dreamed of building your own CUSTOM HOME in a small village on Long Island? Look No Further! Set within one of Long Island’s most prestigious and private villages, this extraordinary custom-built estate offers over 7,000 square feet of refined living space with an Elevator to service all Floors, First Floor Primary Suite, radiant floors, 2 Saunas, 2 steam showers, full basement with full bathroom and outside entrance, outside back porch with fireplace and full bathroom from outside only. Private setting on a breathtaking 2.35-acre wooded property, complemented by an additional one-acre private driveway. A seamless blend of timeless architecture and modern luxury, this residence has been thoughtfully designed with superior craftsmanship and uncompromising quality throughout. Home is completed to a point where we can schedule tours. A sweeping asphalt and stone driveway with cobblestone edging welcomes you to this impressive two-story traditional home. Inside, an elevator to service all floors of the home, soaring ceilings create an unparalleled sense of space — including a dramatic 20'6" two-story foyer and family room, 10-foot ceilings on the main level, and a full 10-foot walk-out basement offering endless possibilities. Main Level Elegance. The heart of the home is a spectacular chef’s kitchen featuring: * Custom cabinetry * Granite or Quartz countertops * Expansive center island with prep sink * Radiant-heated porcelain flooring Entertain effortlessly in the formal dining room with built-in cabinetry, elegant millwork, and premium stone surfaces. The two-story family room showcases a modern linear gas fireplace beneath a coffered ceiling, creating a striking focal point. An en-suite bedroom provides flexibility for guests or extended family. Additional highlights include a radiant-heated powder room and a covered rear porch with gas fireplace — perfect for year-round outdoor living. Upper-Level Retreat: The second floor features **four en-suite bedrooms**, each with custom closet systems and wide White Oak flooring. The primary suite is a sanctuary, boasting a spa-inspired bath with a large steam shower, radiant heated floors, and deluxe Kohler fixtures. Exceptional Construction & Infrastructure: Built for longevity and performance, this estate includes: * Engineered wood web floor joists *Oversize 3 Car Attached Garage * 400-amp electric service * Natural gas service for heating, hot water, dryer, future generator & pool * Public water via Suffolk County Water Authority * Seven oversized drywells for optimal drainage Throughout the home, meticulous detailing includes wide White Oak hardwood flooring, heavy base moldings, chair rail and crown moldings, and an extra-wide custom staircase with open railings. In-ground Pool is an option and can be customized. 3D Reality Tours are samples of the builders work, not the exact same model we are building. A rare opportunity to own a masterfully constructed estate in one of Long Island’s most exclusive enclaves — where privacy, luxury, and timeless design converge.

550 Moriches Road, Head Of Harbor

$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

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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.