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Head Of The Harbor, NY Homes for Sale

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  • /31

    $2,699,500

    $201K PRICE DROP
    • 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
  • /50

    $1,050,000

    Open Sat 12:30PM - 1:30PM $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,485 Sq Ft

    29 Three Sisters Rd, Saint James, NY 11780

    Welcome to 29 Three Sisters Road, a unique custom-built residence that effortlessly blends historical charm with modern elegance. Built in 1847 and completely renovated, this 4-bedroom, 3-bathroom home is a testament to timeless design and quality craftsmanship. The heart of the home, a stylish kitchen, offers gas cooking, granite counters, and an inviting dining area. The den area, adorned with

    Nicholas Albanese Douglas Elliman Real Estate

    29 Three Sisters 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
  • /50

    $2,499,999

    • 6 Beds
    • 5 Baths
    • 4,375 Sq Ft

    15 the Chase, Saint James, NY 11780

    Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with

    William Galati Signature Premier Properties

    15 the Chase, Saint James, NY 11780
  • /6

    $1,099,000

    New Construction Open Sat 12PM - 2PM
    • 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

    $999,999

    $100K PRICE DROP
    • 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

    $995,888

    Open Sat 11AM - 1PM $15K PRICE INCREASE
    • 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
  • /30

    $1,295,000

    • 6 Beds
    • 4.5 Baths
    • 3,631 Sq Ft

    1259 N Country Rd, Stony Brook, NY 11790

    House for sale.

    William Feng Winzone Realty Inc

    1259 N Country Rd, Stony Brook, NY 11790
  • /34

    $899,000

    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    3 Thompson Hill Rd, Saint James, NY 11780

    Located on a pristine, tree-lined street north of 25A in highly desired St. James, this spacious 4 BR, 3.5BA colonial boasts hardwood floors throughout, 2 fireplaces, updated natural gas heat, and a full finished basement w OSE offering plenty of room for extended family. First floor offers a separate home office. The spacious 2 car garage has plenty of room for cars and additional storage.

    Robin Rosenberg Signature Premier Properties

    3 Thompson 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 is the average household income in Head Of The Harbor, NY?
The average household income in Head Of The Harbor, NY is $234K.
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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