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Head Of The Harbor, NY Homes for Sale

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  • /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
  • /48

    $2,750,000

    • 6 Beds
    • 5.5 Baths
    • 4,900 Sq Ft

    33 Bacon Rd, Saint James, NY 11780

    Set On 3.5 Private Acres In The Prestigious Village Of Head Of The Harbor, 33 Bacon Road Is A Masterpiece Of Design, Craftmanship And Luxury. Built In 2012, This 4900 Square Foot Georgian Colonial Combines Timeless Architectural Elegance With Modern Conveniences, Offering An Unmatched Lifestyle In One Of Long Island's Most Sought-After Enclaves. The Approach To The Property Is Framed By Lush,

    Maria Orlandi Compass Greater NY LLC

    33 Bacon Rd, Saint James, NY 11780
  • /27

    $1,375,000

    • 3 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    91 Harbor Rd, Saint James, NY 11780

    Must see to appreciate! This Diamond Pristine home is tucked away in a charming and highly desirable country setting. There are many updates throughout this sprawling ranch-style residence - including an abundance of New Hi Hat Lighting in every room, Gleaming hardwood floors, and Fully finished basement level, with a bedroom and customized closets, and a huge storage area. The home offers a

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    91 Harbor Rd, Saint James, NY 11780
  • /42

    $1,295,000 Open House 11/15

    • 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
  • /29

    $750,000

    • 4 Beds
    • 2.5 Baths
    • 1,828 Sq Ft

    14 Hill Rd, Saint James, NY 11780

    Nestled in the Saint James community, this 4-bedroom, 2.5-bath Colonial is full of charm and ready to welcome you home. Step inside to find a cozy living room with a wood-burning fireplace, a formal dining room for hosting, and a bright kitchen with easy access to the one-car garage. Upstairs, the spacious primary bedroom features a recently updated en suite bathroom and a walk-in closet—your own

    Jennifer Hilaire BERKSHIRE HATHAWAY

    14 Hill Rd, 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 Ward Melville Senior High School, Harbor Country Day School and Paul J Gelinas Junior High School. Browse all the schools in Head Of The Harbor, NY to learn more.
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