587

Head Of The Harbor, NY Homes

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  • 30 Cordwood Path, Saint James, NY 11780
    30 Cordwood Path, Saint James, NY 11780
    30 Cordwood Path, Saint James, NY 11780
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    $1,599,000

    • 4 Beds
    • 3.5 Baths
    • 3,598 Sq Ft

    30 Cordwood Path, Saint James, NY 11780

    A rare opportunity in Head of the Harbor — over 4 acres of subdivided land offering unmatched potential and panoramic water views. This property includes multiple parcels: the main residence situated on one 2-acre lot, plus two additional parcels (Tax ID: 0801-006-00-01-00-001-002 and 0801-006-00-01-00-001-003), including a 2-acre buildable lot and a 0.3-acre private access road. The existing

    Kyle Roskot The Agency Northshore NY

    30 Cordwood Path, Saint James, NY 11780
  • 32 Hitherbrook Rd, Saint James, NY 11780
    32 Hitherbrook Rd, Saint James, NY 11780
    32 Hitherbrook Rd, Saint James, NY 11780
    /42

    $6,500 per month

    • 4 Beds
    • 3 Baths
    • 2,795 Sq Ft
    • House for Rent

    32 Hitherbrook Rd, Saint James, NY 11780

    Rare to find home rental in beautiful Head of the Harbor. Spacious 9 room , 4bdrm, 3 full bath 2,795 square foot Farm Ranch home. Wood floors, fireplace, spacious country kitchen with granite and stainless steel appliances, finished walkout basement with gym, jacuzzi tub, palatial primary suite. Hilltop setting on private, wooded 2acre lot with large patio. Available for immediate occupancy.

    John Sanders Shea & Sanders Real Estate Inc

    32 Hitherbrook Rd, Saint James, NY 11780
  • 3 Nadia Ct, Saint James, NY 11780

    $905,000 Sold Oct 10, 2025

    • 2,500 Sq Ft
    • $362/SF
    • 28 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1964

    3 Nadia Ct, Saint James, NY 11780

    Welcome to 3 Nadia Court, a timeless New England-style Cape nestled on nearly 2.5 wooded acres in the exquisite village of Head of the Harbor. Tucked away on a quiet cul-de-sac, this 5-bedroom, 2-bathroom home offers the perfect blend of classic charm and serene privacy.Step through the front door into a large, welcoming foyer with original millwork that sets the tone for this warm and

    Monica Balsan Daniel Gale Sothebys Intl Rlty

    3 Nadia Ct, Saint James, NY 11780
  • 18 Watercrest Ct, Saint James, NY 11780
    18 Watercrest Ct, Saint James, NY 11780
    18 Watercrest Ct, Saint James, NY 11780
    /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
  • 2 Sunset Dr, Saint James, NY 11780
    2 Sunset Dr, Saint James, NY 11780
    2 Sunset Dr, Saint James, NY 11780
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    $20,000 per month

    • 6 Beds
    • 9.5 Baths
    • 6,500 Sq Ft
    • House for Rent

    2 Sunset Dr, Saint James, NY 11780

    Welcome to 2 Sunset Lane – a stunning 6-bedroom, 10-bath estate set on 3.9 beautifully landscaped acres, complete with a private tennis court and herb garden.Main Floor - Step into a grand foyer featuring a sweeping staircase and chandelier. The main level offers a formal dining room, a spacious open kitchen with breakfast nook, large island, and top-of-the-line Wolf range with double

    carol hurnyak Long Island Homes & Horse Prop

    2 Sunset Dr, Saint James, NY 11780
  • 537 Moriches Rd, Saint James, NY 11780

    $1,150,000 Sold Oct 06, 2025

    • 2,541 Sq Ft
    • $453/SF
    • 29 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1927

    537 Moriches Rd, Saint James, NY 11780

    A Rare Country Retreat on 3.5 Level Acres in Head of the HarborWelcome to a truly special property that captures the charm and serenity of a classic country estate—gracious, private, and full of old-world appeal. Set on an incredibly rare and completely level 3.5-acre parcel, this beautiful setting offers a sense of space and tranquility that’s hard to find. Located just minutes from Long

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    537 Moriches Rd, Saint James, NY 11780
  • 33 Bacon Rd, Saint James, NY 11780
    33 Bacon Rd, Saint James, NY 11780
    33 Bacon Rd, 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
  • 174 Mills Pond Rd Unit 2D, Saint James, NY 11780
    174 Mills Pond Rd Unit 2D, Saint James, NY 11780
    174 Mills Pond Rd Unit 2D, Saint James, NY 11780
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    $2,400 per month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Apartment for Rent

    174 Mills Pond Rd Unit 2D, Saint James, NY 11780

    Rare find! Pristine and beautifully maintained second-floor 2-bedroom apartment in a prime location — just minutes from shopping, dining, Stony Brook University, and Stony Brook Hospital. This light-filled apartment offers the perfect combination of comfort and convenience, featuring a spacious living room, updated full bathroom, and a well-equipped kitchen. With its neutral decor, it provides a

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    174 Mills Pond Rd Unit 2D, Saint James, NY 11780
  • 17 Barn Ln, Saint James, NY 11780

    $2,800,000 Sold Sep 26, 2025

    • 5,340 Sq Ft
    • $524/SF
    • 175 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2020

    17 Barn Ln, Saint James, NY 11780

    A Stunning home, nestled on 2 acres, offering incredible attention to detail. The open floor plan offers in excess of 5000 ft. with five bedrooms and 4 1/2 baths. Upon arrival, you are greeted by a gracious two-story entryway leading to a dramatic great room with gas fireplace and double-height coffered ceiling. The formal living room and dining room have 9 foot ceilings and an abundance of

    Deborah Pirro Daniel Gale Sothebys Intl Rlty

    17 Barn Ln, Saint James, NY 11780
  • 91 Harbor Rd, Saint James, NY 11780
    91 Harbor Rd, Saint James, NY 11780
    91 Harbor 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
  • Lot 1 Timothy Ln, Head of the Harbor, NY 11780

    $780,000 Sold Aug 27, 2025

    • Land
    • 2.4 Acres
    • $325,000 per Acre
    • 49 Days On Market

    Lot 1 Timothy Ln, Head of the Harbor, NY 11780

    Rare opportunity for flat parcel of cleared land on a cul-de-sac in the Incorporated village of Head of the Harbor. Surrounded by 4000-6000 sqft homes. This is an ideal location to build your dream home or a spec house. Water, electric at the property. Road paved in front of property. Located within 10 miles of major highways as well as private beaches.

    Alexia Poulos Douglas Elliman Real Estate

    Lot 1 Timothy Ln, Head of the Harbor, NY 11780
  • 15 Emmet Dr, Stony Brook, NY 11790
    15 Emmet Dr, Stony Brook, NY 11790
    15 Emmet Dr, Stony Brook, NY 11790
    /44

    $3,750,000 Pending

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

    15 Emmet Dr, Stony Brook, NY 11790

    Commanding an incomparable position on Stony Brook Harbor, The Mallows stands as one of the most extraordinary and architecturally significant waterfront estates on Long Island’s North Shore. With over 300 feet of private shoreline and unobstructed panoramic west-facing views, this historic masterpiece captures awe-inspiring sunsets that stretch across the Long Island Sound to the Connecticut

    Michael Foley Frontline Realty Group LLC

    15 Emmet Dr, Stony Brook, NY 11790
  • 1 Meadow Gate E, Saint James, NY 11780

    $2,300,000 Sold Aug 07, 2025

    • 5,130 Sq Ft
    • $448/SF
    • 113 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 1987

    1 Meadow Gate E, Saint James, NY 11780

    Welcome to 1 Meadow Gate East....A Stunning Estate with endless possibilities, set on 2 beautiful acres in the desirable Incorporated Village of Head of the Harbor! As you step through the elegant front doors, you’re welcomed by a bright and inviting atmosphere, w/ natural light pouring in and peaceful views of the natatorium w/ Resort style Indoor Premium PebbleTec Pool, offering a perfect mix

    Deborah Lettieri Signature Premier Properties

    1 Meadow Gate E, Saint James, NY 11780
  • Lot 1.6 Brackenwoods Path, Head of the Harbor, NY 11780
    Lot 1.6 Brackenwoods Path, Head of the Harbor, NY 11780
    Lot 1.6 Brackenwoods Path, Head of the Harbor, NY 11780
    /7

    $445,000 Pending

    • Land
    • 2.64 Acres
    • $168,561 per Acre

    Lot 1.6 Brackenwoods Path, Head of the Harbor, NY 11780

    Wooded 2.64 Acre Lot on a Cul De Sac in Prestigious Head Of Harbor-Buy The Land Or Builders Can Be Provided-Stones Throw From The Water, Wineries, Horse Properties Private Location Custom Build Your Dream Home! Surveys Are Available

    Joseph Bartone Coldwell Banker American Homes

    Lot 1.6 Brackenwoods Path, Head of the Harbor, NY 11780
  • 15 Armand Ct, Saint James, NY 11780

    $2,600,000 Sold Aug 06, 2025

    • 8,000 Sq Ft
    • $325/SF
    • 22 Days On Market
    • 5 Beds
    • 8 Baths
    • Built 1985

    15 Armand Ct, Saint James, NY 11780

    A truly one-of-a-kind gated compound set on 2.4 lush meticulously manicured acres. This remarkable estate exudes a sense of serenity combined with a modern, open concept. Designed for those who appreciate high-end custom features and the finest in craftsmanship, this property offers an extraordinary living experience. This entertainer's paradise boasts an open and sophisticated living space

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    15 Armand Ct, Saint James, NY 11780
  • 3 The Hunt, Saint James, NY 11780

    $1,450,000 Sold Jul 30, 2025

    • 3,600 Sq Ft
    • $403/SF
    • 85 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1999

    3 The Hunt, Saint James, NY 11780

    Spectacular and stately contemporary colonial style home boasting 5 bedrooms, 3 full bathrooms, a powder room off the fantastically open eat – in – kitchen with center island, a den with the warmth of a beautiful fireplace, , exceptional layout, full basement with high ceilings, and a parcel to die for. This tucked away ruby offers all the tranquility and serenity of the Head of the Harbor and

    Todd Yovino Island Advantage Realty LLC

    3 The Hunt, Saint James, NY 11780
  • 17 Timothy Ln, Saint James, NY 11780

    $1,248,000 Sold Apr 07, 2025

    • 139 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1923

    17 Timothy Ln, Saint James, NY 11780

    Absolutely STUNNING only begins to describe this 5 bedroom, 3.5 Bath totally renovated colonial in the Village of Head of the Harbor. Gleaming hardwood floors and board and batten accents greet you as you enter into the foyer which then leads to the living room w/ fireplace. The living room has an entrance into the 4 seasons sun room/den as well as the formal dining room/sitting room. This brings

    Zachary Scher Signature Premier Properties

    17 Timothy Ln, Saint James, NY 11780
  • 30 Hitherbrook Rd, Saint James, NY 11780

    $1,200,000 Sold Mar 27, 2025

    • 3,384 Sq Ft
    • $355/SF
    • 74 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1978

    30 Hitherbrook Rd, Saint James, NY 11780

    This home is fully available- deal on the table died- Welcome to 30 Hitherbrook Road in the beautiful Village of Head of the Harbor NY. Impeccably maintained traditional center hall cedar colonial nestled on a beautifully wooded two acre parcel. The home affords a formal living room, formal dining room, an office or sitting room, a spacious eat in kitchen with granite counters, new stainless

    John Sanders Shea & Sanders Real Estate Inc

    30 Hitherbrook Rd, Saint James, NY 11780
  • 1251 N Country Rd, Stony Brook, NY 11790

    $635,000 Sold Mar 13, 2025

    • 99 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1890

    1251 N Country Rd, Stony Brook, NY 11790

    As you come up the private road and into the driveway you will immediately fall in love with this charming home. Upon Entry, you will be invited into the formal living room with a beautiful mantle & fireplace, custom built-in shelving & archways. The formal dining room can become your home office. The Kitchen is open to a dining area and den with vaulted ceilings and French Doors leading to a

    David Guzzetta American Way Real Estate Inc

    1251 N Country Rd, Stony Brook, NY 11790
  • 178 Harbor Rd, Stony Brook, NY 11790

    $870,000 Sold Dec 17, 2024

    • 1,417 Sq Ft
    • $614/SF
    • 14 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1930

    178 Harbor Rd, Stony Brook, NY 11790

    Welcome to this charming 1930s Colonial nestled on a serene 0.5-acre lot, offering both timeless character and modern convenience. This adorable home features 3 bedrooms, 1.5 baths, and has been beautifully updated throughout. The property backs up to Avalon Nature Preserve, providing an abundance of peace and privacy. As you step inside, you'll be greeted by classic Colonial details like

    Michael O Dwyer Daniel Gale Sothebys Intl Rlty

    178 Harbor Rd, Stony Brook, NY 11790
  • 32 Farm Rd, Saint James, NY 11780

    $890,000 Sold Dec 06, 2024

    • 8 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1963

    32 Farm Rd, Saint James, NY 11780

    Discover a hidden gem nestled in the picturesque Incorporated Village of Head of the Harbor. This sprawling ranch-style home, set on a generous wide two-acre lot, offers the perfect blend of country living and convenience. Surrounded by lush greenery, this property provides a serene retreat while remaining just minutes away from town, shopping, Stony Brook University, restaurants, and

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    32 Farm Rd, Saint James, NY 11780
  • 10 Buckingham Ct, Saint James, NY 11780

    $1,725,000 Sold Nov 22, 2024

    • 48 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1997

    10 Buckingham Ct, Saint James, NY 11780

    This stunning all brick expansive colonial is nestled in a sought after location within the private Village of Head of the Harbor. Comprising of 5 Bedrooms and 3 full Bathrooms, this home exudes timeless elegance with its classic brick exterior and stately presence. Set on a lush 2-acre lot, this property is surrounded by other beautiful homes, creating an ambience of sophistication. Upon

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    10 Buckingham Ct, Saint James, NY 11780

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New York Suffolk County Head Of The Harbor

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