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Explore Similar Condos Within 2 Miles of Head of the Harbor, NY

  • /23

    $429,000

    • 1 Bed
    • 1.5 Baths
    • 996 Sq Ft

    501 Drew Dr, Saint James, NY 11780

    This immaculate and spacious end-unit ranch has been thoughtfully updated and meticulously maintained. Featuring Andersen windows and doors with custom blinds, this home is filled with natural light and tasteful finishes throughout. The large open-concept living room and dining area create an inviting space that’s perfect for both everyday living and entertaining. The updated kitchen features

    Donna Memoli Varland Daniel Gale Sothebys Intl Rlty

    501 Drew Dr, Saint James, NY 11780
  • /24

    $499,000

    • 1 Bed
    • 1.5 Baths
    • 929 Sq Ft

    607 Cabot Ct E Unit C607, Saint James, NY 11780

    Welcome to Fairfield at St. James – a Premier 55+ Community!One-bedroom, 1.5 bath condo offering comfort, convenience, and an active lifestyle. Enjoy resort-style living with outstanding amenities including indoor and outdoor pools, pickleball / tennis courts, a clubhouse with gym and billiards, and a peaceful walking trail that winds through beautifully landscaped grounds featuring a

    Kathleen Becker Howard Hanna Coach

    607 Cabot Ct E Unit C607, Saint James, NY 11780
  • /21

    $579,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    155 Knolls Dr Unit 155, Stony Brook, NY 11790

    This beautifully updated 2-bedroom, 2-bath condo is nestled in the charming 55+ community of "The Knolls at Stony Brook." It features a gorgeous custom kitchen with top-of-the-line appliances, modernized bathrooms, luxury vinyl flooring, new windows with custom shades, and a newer HVAC system with upgraded ductwork. Custom built-ins add extra storage, and the condo has been freshly painted,

    Kathy Pagano Daniel Gale Sothebys Intl Rlty

    155 Knolls Dr Unit 155, Stony Brook, NY 11790
  • /35

    $470,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    914 Fenway Rd, Saint James, NY 11780

    Beautiful 2Bedroom 2 Bath Condo (55) with wood floors, attached garage, and balcony views! Formal dining room, EIK, Lots of. closets! Enjoy tennis, Pickleball, Swimming Pool & a friendly clubhouse community. 55 and older community

    Laura Riportella Douglas Elliman Real Estate

    914 Fenway 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.

Home Trends in Head of the Harbor, NY

Housing Trends

Median Sale Price
$1,248,000
Median Single Family Sale Price
$1,375,000
Average Price Per Sq Ft
$436
Number of Homes for Sale
4
Last 12 months Home Sales
13
Months of Supply
3.70
Median List Price
$1,396,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
8%
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