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Head Of The Harbor, NY Homes for Sale

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  • /46

    $1,499,000

    • 5 Beds
    • 2.5 Baths
    • 2,753 Sq Ft

    12 Briarwood Ct, Saint James, NY 11780

    Stunning 5BR/3BA Luxury Colonial on 2 Sprawling Acres Welcome to this exceptional home set on two beautifully landscaped acres located at the end of a cul-de-sac in the coveted Head of the Harbor neighborhood. Offering breathtaking views and unmatched privacy, this classic colonial seamlessly blends old-world charm with modern amenities. Inside, you’ll find an updated gourmet kitchen featuring

    Agent Photo

    James Szollosi

    Signature Premier Properties

    (866) 697-5919

    12 Briarwood Ct, Saint James, NY 11780
  • /50

    $1,399,999

    • 5 Beds
    • 5 Baths
    • 5,393 Sq Ft

    23 Bacon Rd, Saint James, NY 11780

    BACK ON MARKET !! - ALL BINDERS ARE OFF, DEAL FELL THROUGH - HOME IS 100% AVAILABLE !Welcome to 23 Bacon Road - The Best Value in the coveted Head of the Harbor ! This Elegant & Expansive Ranch-Style home is nestled on 2.38 beautifully landscaped acres in the heart of Head of the Harbor. Built in 1960 & designed by renowned builder Yablonski - This home offers over 5,300 square feet of

    Agent Photo

    James Szollosi

    Signature Premier Properties

    (844) 552-9045

    23 Bacon Rd, Saint James, NY 11780
  • /23

    $1,599,000

    • 6 Beds
    • 3 Baths
    • 4,403 Sq Ft

    18 Watercrest Ct, Saint James, NY 11780

    Classic charm meets modern living! Set high on a beautiful two-acre property, this timeless cedar Colonial sits proudly on a cul-de-sac in the village of Head of Harbor. The grand two-story foyer leads to spacious living and dining rooms, a chef’s kitchen with Viking gas range and granite countertops, and a cozy family room with fireplace. A sunroom provides year-round views of the sparkling

    Filomena Tortorella Signature Premier Properties

    18 Watercrest Ct, Saint James, NY 11780
  • /10

    $1,599,000

    • 4 Beds
    • 3.5 Baths
    • 3,598 Sq Ft

    30 Cordwood Path, Saint James, NY 11780

    A rare opportunity in Head of the Harbor — over 4 acres of subdivided land offering unmatched potential and panoramic water views. This property includes multiple parcels: the main residence situated on one 2-acre lot, plus two additional parcels (Tax ID: 0801-006-00-01-00-001-002 and 0801-006-00-01-00-001-003), including a 2-acre buildable lot and a 0.3-acre private access road. The existing

    Kyle Roskot The Agency Northshore NY

    30 Cordwood Path, Saint James, NY 11780
  • /33

    $1,099,000

    • 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
  • /24

    $1,099,000

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

    120 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

    120 4th St, Saint James, NY 11780
  • /9

    $958,888

    • 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
  • /42

    $1,295,000 Open House 1/17

    • 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, 11767 and 11755.
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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