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Head Of The Harbor, NY Homes for Sale with Acreage

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  • /23

    $1,699,000

    • 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
  • /37

    $1,199,000

    • 4 Beds
    • 3 Baths
    • 2,583 Sq Ft

    118 Harbor Rd, Saint James, NY 11780

    Welcome to 118 Harbor Road in the Beautiful Village of Head of The Harbor, NY. This Lovely Home is Nestled on 2 Acres of Serene and Rustic Property that backs to Multiple Acres of Wooded Land. The Generous-Sized Country Kitchen has a Breakfast Island with a Granite Counter, Built-in Wall Grill, Large Picturesque Window with View of Yard, The Living Room is a Generous Size with a 2-Sided

    Christine Stevens Daniel Gale Sothebys Intl Rlty

    118 Harbor Rd, Saint James, NY 11780
  • /50

    $1,399,999

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

    23 Bacon Rd, Saint James, NY 11780

    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 exquisite living space, This one-of-a-kind gem features a first floor master bedroom,

    James Szollosi Signature Premier Properties

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

    $1,439,000

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

    91 Harbor Rd, Saint James, NY 11780

    Dropped price!! 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 rare

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    91 Harbor Rd, Saint James, NY 11780
  • /6

    $800,000

    • Land
    • 2.33 Acres
    • $343,348 per Acre

    adj #552 Moriches Rd, Head of the Harbor, NY 11780

    Welcome to one of the most coveted and rare land offerings in the exclusive Village of Head of the Harbor. This extraordinary 2.33 acre lot presents a once-in-a-lifetime opportunity to build your dream estate in one of Long Island’s most desirable and picturesque communities.Situated on a serene and private parcel, this property comes permitted and ready to accommodate a spectacular

    Karyn Flores Compass Greater NY LLC

    adj #552 Moriches Rd, Head of the Harbor, NY 11780
  • /44

    $4,000,000

    • 11 Beds
    • 7 Baths
    • 9,411 Sq Ft

    15 Emmet Dr, Stony Brook, NY 11790

    Step into a world of timeless elegance and unparalleled prestige at The Mallows — the crown jewel of the North Shore and one of the most exclusive waterfront estates in Head of the Harbor Village. Originally commissioned by the illustrious Astor family and masterfully designed by acclaimed architect Charles Platt, this historic masterpiece sprawls across 4+ acres of exquisitely landscaped grounds

    Michael Foley Frontline Realty Group LLC

    15 Emmet Dr, Stony Brook, NY 11790
  • /50

    $9,999,000

    • 14 Beds
    • 14.5 Baths
    • 22,000 Sq Ft

    1 Swan Place, Saint James, NY 11780

    Set on 9 pristine acres with panoramic views of Long Island Sound, this private, gated estate is a masterpiece of history and modern refinement. Once a favored retreat for Hollywood’s golden era icons, including the Barrymores, Buster Keaton, and Myrna Loy, this extraordinary residence sits in the heart of Nissequogue, a town renowned for its charm and exclusivity. Designed by celebrated

    Kyle Roskot The Agency Northshore NY

    1 Swan Place, Saint James, NY 11780
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