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Head Of The Harbor, NY Homes for Sale

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  • /50

    $1,999,999

    Open Sun 2:30PM - 4:30PM $300K PRICE DROP
    • 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 BH&G R E Realty Connect

    2 Deepwells Ln, Saint James, NY 11780
  • /14

    $3,699,000

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

    550 Moriches Rd, Saint James, NY 11780

    A Rare Opportunity to Create Your Custom Estate on Long IslandOpportunities like this are exceptionally rare on Long Island. Set within one of the area’s most prestigious and private villages, this extraordinary new-construction estate offers the space, privacy and ability to customize that are increasingly difficult to find.Privately positioned on a breathtaking 2.35-acre wooded

    Karyn Flores Compass Greater NY LLC

    550 Moriches Rd, Saint James, NY 11780
  • /50

    $1,899,000

    • 4 Beds
    • 3.5 Baths
    • 4,831 Sq Ft

    29 Farm Rd, Saint James, NY 11780

    Welcome to 29 Farm Road....nestled in the prestigious Village of Head of the Harbor, where secluded, private & tranquil living awaits! This stunning, beautifully maintained Expanded Ranch features a grand entry foyer, spacious EIK w/ granite countertops, center island, SS appliances, and picturesque views of the surrounding landscape, a warm and inviting Great Room w/ Stone FP and vaulted

    Deborah Lettieri Signature Premier Properties

    29 Farm Rd, Saint James, NY 11780
  • /50

    $2,399,000

    • 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
  • /34

    $1,500,000

    • 3 Beds
    • 2.5 Baths
    • 3,140 Sq Ft

    1 Valleywood Ct W, Saint James, NY 11780

    Elegant and Unique Colonial set on 2 Beautifully Landscaped Acres in the highly Sought After Village of Head of the Harbor. This Spacious Home Offers 3/4 Bedrooms. 3 Traditional Bedrooms Plus a Versatile Bonus Room That Can Easily Function as a 4th Bedroom.Generous-Size Principal Rooms Create an Inviting Layout for Everyday Living and Entertaining. The Home Features a Warm and Welcoming

    Christine Stevens Howard Hanna Coach

    1 Valleywood Ct W, Saint James, NY 11780
  • /50

    $2,375,000

    Open Sat 1PM - 3PM
    • 5 Beds
    • 4 Baths
    • 4,578 Sq Ft

    5 Meadow Gate W Unit KEY1027926, Saint James, NY 11780

    Tucked away on two acres at the end of a quiet cul-de-sac, in the prestigious enclave of Head of the Harbor, this magnificent five-bedroom, four-bath estate offers an unparalleled blend of modern luxury and serene privacy. The entire residence has undergone a comprehensive transformation over the past six years, resulting in a home that feels brand new while retaining its sophisticated, timeless

    Lisa Minuto Compass Greater NY LLC

    5 Meadow Gate W Unit KEY1027926, Saint James, NY 11780
  • /10

    $799,988

    Open Sat 11:30AM - 12:30PM $181K 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 BH&G R E Realty Connect

    474 Route 25A, 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 11754.
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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