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Head Of The Harbor, NY Homes for Sale

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  • /31

    $2,900,000

    • 8 Beds
    • 8 Baths
    • 6,475 Sq Ft

    9 Watercrest Ct, Saint James, NY 11780

    Set within the prestigious enclave of Head of the Harbor, 9 Watercrest is a stunning showcase of modern luxury, thoughtfully reimagined with impeccable craftsmanship, design, and attention to detail. This turnkey estate blends sophistication, scale, and state-of-the-art comfort. At the heart of the 5,000 sq ft +/- main level is a spectacular, fully renovated chef’s kitchen by renowned HGTV

    Agent Photo

    Kyle Roskot

    The Agency Northshore NY

    (866) 412-5083

    9 Watercrest Ct, Saint James, NY 11780
  • /14

    $3,790,000

    New Construction
    • 5 Beds
    • 7.5 Baths
    • 7,000 Sq Ft

    550 Moriches Rd, Saint James, NY 11780

    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 set on a breathtaking 2.35-acre wooded property, complemented by an additional one-acre

    Karyn Flores Compass Greater NY LLC

    550 Moriches Rd, Saint James, NY 11780
  • /2

    $2,300,000

    • 5 Beds
    • 5 Baths
    • 4,788 Sq Ft

    2 Deepwells Ln, Saint James, NY 11780

    Welcome to this spacious 5-bedroom, 5-bath Colonial set on 1.70 acres in the desirable Head of the Harbor section of Saint James. This 4,788 sq ft home features a functional layout with a first-floor bedroom and full bath, formal dining room, living room, and an open kitchen with granite countertops, center island, and eat-in area leading to a large family room with fireplace. The second level

    Paul Musso Realty Connect USA L I Inc

    2 Deepwells Ln, Saint James, NY 11780
  • /35

    $1,899,990

    • 4 Beds
    • 4 Baths
    • 4,711 Sq Ft

    9 Fox Meadow Ln, Saint James, NY 11780

    Welcome to this beautiful Custom built home located on a cul de sac in the desirable village of Head of the Harbor. Enter into a two story foyer with a magnificent stair case. Spacious rooms with high ceilings, hardwood floors and custom moldings through out. The incredible family room has two story ceilings, wall to wall french doors and a firplace The designer eat in kitchen is open and bright

    Rowena Nedvin Signature Premier Properties

    9 Fox Meadow Ln, Saint James, NY 11780
  • /18

    $899,000

    • 4 Beds
    • 3 Baths
    • 2,583 Sq Ft

    118 Harbor Rd, Saint James, NY 11780

    Incredible opportunity to be in Head of the Harbor in a sprawling farm ranch! Large principle rooms flow seamlessly in this sun-filled, private home. Picturesque, serene views can be seen out every window. The kitchen shares a double-sided fireplace with the living room, and the sunken den has its own additional fireplace. Two master en-suites, one on the main and on the second floor, give

    Robin Rosenberg Signature Premier Properties

    118 Harbor Rd, Saint James, NY 11780
  • /2

    $1,199,999

    • Land
    • 2.4 Acres
    • $500,000 per Acre

    0 Timothy Ln, Saint James, NY 11780

    BUILD YOUR DREAM HOME!!!!!! A rare find....flat piece of land in the Incorporated village of Head of The Harbor. This property is surrounded by 4000-7000 sq foot homes. There is electric, water and gas at the property. Ideal location close to Stony Brook Hospital, and major roads.

    Janice Fanelli Signature Premier Properties

    0 Timothy Ln, Saint James, NY 11780
  • /7

    $699,990

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,690 Sq Ft

    43 Vanderbilt Ave, Saint James, NY 11780

    This Colonial home features three bedrooms, 2 1/2 baths, eat in kitchen, formal dining room, large living room, family room with fireplace, basement, two car garage, large fenced yard - on a Dead End Street!

    Joanne DeMaio Real Broker NY LLC

    43 Vanderbilt Ave, Saint James, NY 11780
  • /6

    $1,099,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,416 Sq Ft

    122 4th St, Saint James, NY 11780

    Why settle for someone else’s dream when you can build your own? Welcome to this brand-new TO BE BUILT colonial-style home designed with today’s lifestyle in mind. Set on a deep 15,840 sqft lot, this to-be-built beauty will offer over 2,400 square feet of fresh, functional living space and the kind of craftsmanship and energy efficiency only new construction can deliver. Inside, you’ll find four

    James Haydon Realty Connect USA L I Inc

    122 4th St, Saint James, NY 11780
  • /50

    $1,100,000

    • 5 Beds
    • 1.5 Baths
    • 2,037 Sq Ft

    522 Moriches Rd, Saint James, NY 11780

    Welcome to this spectacular 5-bedroom, 1.5-bath Colonial nestled on an incredible 1.5-acre property in one of the area's most exclusive locations—north of North Country Road (25A), just steps from the General Store and the charm of Head of the Harbor, and only minutes to Long Beach and Short Beach. This exceptional home combines timeless appeal with extensive modern updates, offering the perfect

    Dari Rudge Gateway to The Hamptons R E

    522 Moriches Rd, Saint James, NY 11780
  • /9

    $958,888

    $22K PRICE DROP
    • 10 Beds
    • 4.5 Baths

    474 Route 25A, Saint James, NY 11780

    Builder special extended family with plenty of living space, Hord wood floor through out on the first floor. Home features 10 bedrooms, 4.5 Bathrooms, 2 car garages fireplace, Gas heat, CAC-system. This unique house sits 032 acre of the flat lot close downtown of Saint James, train station. Needs 24 Hours Noticed to show, Appointment only!

    Jin Tao Realty Connect USA L I Inc

    474 Route 25A, Saint James, NY 11780
  • /34

    $899,000

    Open Sat 11:30AM - 1PM Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    3 Thompson Hill Rd, Saint James, NY 11780

    Located on a pristine, tree-lined street in highly desired St. James, this spacious 4 BR, 3.5BA colonial boasts hardwood floors throughout, 2 fireplaces, 2 car garage, gas heat, full finished basement w OSE, separate home office on first floor and 2 car garage. Andersen windows, flat usable private yard, updated central air, 200 amp service, Cesspool is approx 10 years old. Roof approx 10 years

    Robin Rosenberg Signature Premier Properties

    3 Thompson Hill Rd, Saint James, NY 11780
  • /42

    $1,099,999

    Open Sat 12PM - 1PM $195K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,600 Sq Ft

    36 Vanderbilt Ave, Saint James, NY 11780

    Saint James Colonial in Smithtown Schools, built 1998, on a quiet cul-de-sac. A grand two-story foyer leads to formal living and dining rooms, a fireplace family room, and an eat-in kitchen with granite countertops. Off the rear, a glass-wrapped sunroom overlooks the backyard and opens to a large composite deck. Main level highlights include hardwood floors, powder room, and laundry. Two-car

    David Friedman Howard Hanna Coach

    36 Vanderbilt Ave, Saint James, NY 11780

Why Live in Head Of The Harbor

Head of the Harbor in Saint James is a three-square-mile, entirely residential neighborhood characterized by its rural and pastoral feel. The area is home to approximately 1,500 residents and features winding country roads, mature oak trees, and properties averaging 3,600 square feet on at least two acres. Housing consists solely of single-family homes, predominantly with five-plus bedrooms. The community borders Stony Brook Harbor and includes pockets of agricultural land, such as Harmony Vineyards and Bird’s Foot Farm. Local schools are highly rated, with Mills Pond Elementary School, The Stony Brook School, and Smithtown High School East all receiving high marks for their academic programs and extracurricular activities. Residents enjoy access to Long Beach and Avalon Nature Preserve, which offer natural beauty and recreational opportunities. The Deepwells Farm Historical Society hosts an annual haunted Halloween event, adding to the local charm. Dining options include The Trattoria for Italian cuisine and Del Fuego for Tex-Mex, while grocery shopping requires a short drive to nearby St. James. The neighborhood is safer than the national average, and while commuting to Manhattan is possible via the LIRR, it can take between 1 hour 20 minutes to over three hours depending on traffic.

Frequently Asked Questions

What are the most popular zip codes in Head Of The Harbor, NY?
The most popular zip codes in Head Of The Harbor, NY include 11780, 11790, 11787, 11755 and 11767.
How are the schools in Head Of The Harbor, NY?
Head Of The Harbor, NY has highly rated public and private schools. Some of the best schools in Head Of The Harbor based on Niche Grades are Harbor Country Day School, The Knox School and The Stony Brook School. Browse all the schools in Head Of The Harbor, NY to learn more.
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