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Recently Sold Head Of The Harbor, NY Homes

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  • 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
  • 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
  • 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
  • 30 Cordwood Path, Saint James, NY 11780

    $975,000 Sold Jan 08, 2025

    • 3,598 Sq Ft
    • $271/SF
    • 10 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1969

    30 Cordwood Path, Saint James, NY 11780

    House being Sold As Is. Located in Historic Village of Head of The Harbor this 4 Bedroom 3.5 Bathroom Ranch with Stunning views of Stony Brooke Harbor. Easy to show, Property being sold with an additional 2-acre plot next door.

    Shawn Rogol Compass Greater NY LLC

    30 Cordwood Path, Saint James, NY 11780
  • 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
  • 49 Harbor Hill Rd, Saint James, NY 11780

    $900,000 Sold Oct 28, 2024

    • 3,565 Sq Ft
    • $252/SF
    • 89 Days On Market
    • 5 Beds
    • 3.5 Baths

    49 Harbor Hill Rd, Saint James, NY 11780

    Stunning Colonial Featuring 5 Bedrooms, 3.5 Bathrooms, 2-Car Garage Featuring Spacious Guest Quarters With Full Bathroom. High Ceilings, Crown Molding, And Hardwood Floors Throughout. A Large Gourmet Kitchen And Ample Cabinet Space. The Formal Dining Room Provides An Elegant Setting. Large Living Room W/ Fireplace, Main Floor Office. Upstairs, The Luxurious Master Suite Awaits, Boasting A

    Eduardo Ramirez Fresh Start Properties LLC

    49 Harbor Hill Rd, Saint James, NY 11780
  • 3 Cordwood Path, Saint James, NY 11780

    $1,450,000 Sold Oct 07, 2024

    • 3,086 Sq Ft
    • $470/SF
    • 21 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1979

    3 Cordwood Path, Saint James, NY 11780

    Welcome to 3 Cordwood Path, a rare gem nestled in the prestigious Head of Harbor section of Saint James, NY. Once part of the historic Stanford White estate, this property spans 2.61 acres of serene, partially wooded land, offering unparalleled privacy and a deep connection to nature. At the heart of this home is a stunning atrium adorned with natural plantings, a tranquil koi fish pond, and a

    Ricardo Pena The Agency Northshore NY

    3 Cordwood Path, Saint James, NY 11780
  • 33 Bacon Rd, Saint James, NY 11780

    $2,600,000 Sold Jul 17, 2025

    • 4,850 Sq Ft
    • $536/SF
    • 13 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2012

    33 Bacon Rd, Saint James, NY 11780

    Expansive 6 BR "Better than New"Georgian Colonial . Every Detail and Amenity possible ! Experience luxury living at its finest in this breathtaking and stately and unsurpassed in quality colonial, where timeless elegance and modern sophistication blend seamlessly. With its striking stone front exterior and inviting paver walkways, this extraordinary property is for the discerning buyer seeking

    Bonnie Glenn Daniel Gale Sothebys Intl Rlty

    33 Bacon Rd, Saint James, NY 11780
  • 342 Northern Blvd, Saint James, NY 11780

    $725,000 Sold Sep 10, 2025

    • 1,748 Sq Ft
    • $415/SF
    • 42 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1953

    342 Northern Blvd, Saint James, NY 11780

    This home has a charming cottage style with arched cased opening and hand crafted builtins and custom cabinetry. The living room boasts a wood burning fireplace while the den has a gas insert stove. Hardwood floors and beautiful mouldings in the bedrooms and living areas on the main level increase its loveliness. With a brick patio and remote controlled retractable awning you can enjoy its

    Beth Agliato Daniel Gale Sothebys Intl Rlty

    342 Northern Blvd, Saint James, NY 11780
  • 1 Thompson Hill Rd, Saint James, NY 11780

    $840,000 Sold Sep 05, 2025

    • 2,230 Sq Ft
    • $377/SF
    • 11 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1964

    1 Thompson Hill Rd, Saint James, NY 11780

    Spacious 5-Bedroom High-Ranch on Corner Lot with Pool & UpgradesWelcome to this beautifully maintained 5-bedroom, 3-bath high-ranch home, perfectly situated on a generous 0.6-acre corner property. This spacious home with room for extended family offers versatile living with plenty of room to spread out, including a freshly painted interior that feels bright and inviting throughout.Enjoy

    Jamie DelCore Signature Premier Properties

    1 Thompson Hill Rd, Saint James, NY 11780
  • 55 Tillotson Ave, Saint James, NY 11780

    $925,000 Sold Aug 25, 2025

    • 2,100 Sq Ft
    • $440/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1962

    55 Tillotson Ave, Saint James, NY 11780

    WELCOME to your dream modern farmhouse in the heart of Saint James. This beautifully designed residence combines rustic charm with contemporary elegance, offering the perfect retreat for those seeking comfort and style. Featuring three spacious bedrooms with three and half bathrooms. The warm and inviting interior showcases a large family room enhanced by natural light and stunning architectural

    Angela Alaimo Douglas Elliman Real Estate

    55 Tillotson Ave, Saint James, NY 11780
  • 292 Northern Blvd, Saint James, NY 11780

    $825,000 Sold Jun 20, 2025

    • 2,645 Sq Ft
    • $312/SF
    • 91 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1964

    292 Northern Blvd, Saint James, NY 11780

    Nestled in the idyllic hamlet of Saint James on Long Island's picturesque north shore, this mid-century Farm Ranch effortlessly blends timeless elegance with modern comforts.As you enter, natural sunlight welcomes you into a bright and airy living room, where large windows offer serene views of the private backyard and sparkling in-ground pool. French doors off the entry hallway lead to a cozy

    Richard LeDoux Realty Connect USA L I Inc

    292 Northern Blvd, Saint James, NY 11780
  • 465 Moriches Rd, Saint James, NY 11780

    $500,000 Sold May 01, 2025

    • 1,042 Sq Ft
    • $480/SF
    • 80 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1929

    465 Moriches Rd, Saint James, NY 11780

    This 2 bed/2 bath colonial is located in the beautiful town of St James within the highly sought after Smithtown School District! Full basement with OSE. Detached garage. Walking distance to Lake Ave shopping & dining. Close to Schools, Smithtown Beaches, Stony Brook Harbor and Avalon Park. Low taxes of $8,659! Home needs some TLC. Zoned for residential and/or light commercial use. This is a

    John Depasquale Evolution Realty of L I

    465 Moriches Rd, Saint James, NY 11780
  • 180 Fifty Acre Rd S, Smithtown, NY 11787

    $920,000 Sold Mar 18, 2025

    • 3,150 Sq Ft
    • $292/SF
    • 124 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1968

    180 Fifty Acre Rd S, Smithtown, NY 11787

    Head on over to this stunner of a home and keep your sneakers on because you'll need them with 5 finished levels, 6 bedrooms and 3 1/2 bathrooms! This manicured .28 acre parcel set right beside Smithtown East High School is appointed with sterling flower beds, a lush green lawn with IGS, paver driveway [2011], 1 car garage, outdoor kitchen with natural-gas BBQ and patio with firepit right outside

    Nicholas Colonna Aliano Real Estate

    180 Fifty Acre Rd S, Smithtown, NY 11787
  • 22 Overton Pass, Saint James, NY 11780

    $735,000 Sold Jan 13, 2025

    • 2,038 Sq Ft
    • $361/SF
    • 167 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1897

    22 Overton Pass, Saint James, NY 11780

    Charming Updated Colonial, Rocking Chair Front Porch with Trex, Vinyl Siding, Andersen Thermopane Windows, Updated Eat-in-Kitchen with Stainless Steel Applicances, Gas Cooking, Granite Bar Counter, Hardwood Floors throughout, 200amp Electric, Dual Gas Navien Tankless for Heat and Hot Water, Rear Deck, Pre-cast Cesspools, Belgian Block Lined Blacktop Driveway, Partially Finished Basement, 3 Zone

    Eric Neitzel DeBarbieri Assoc Inc

    22 Overton Pass, Saint James, NY 11780
  • 78 Clinton Ave, Saint James, NY 11780

    $925,000 Sold Dec 20, 2024

    • 2,937 Sq Ft
    • $315/SF
    • 17 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1952

    78 Clinton Ave, Saint James, NY 11780

    Welcome to this exquisite, fully remodeled Post Modern home, ideally located in the heart of Saint James. Step inside to experience a custom-designed interior where no detail has been spared. This stunning 4-Bedroom residence offers nearly 3,000 square feet of beautifully crafted living space in a desirable, open-concept layout. Originally expanded and rebuilt from the studs in 2012, the home was

    Jason Kaiser Fortune Realty of LI Inc

    78 Clinton Ave, Saint James, NY 11780
  • 345 Northern Blvd, Saint James, NY 11780

    $905,000 Sold Dec 04, 2024

    • 2,026 Sq Ft
    • $447/SF
    • 40 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    345 Northern Blvd, Saint James, NY 11780

    Welcome to your own private oasis right here in the heart of Saint James! Take a seat on your front porch and take in the scenary! This stunning, meticuliosly maintained 4 Bedroom, 2.5 bath home boasts gleaming hardwood floors, designer kitchen with high end appliances and a gorgeous slate floor. This kitchen is a chefs dream come true! Ease into the family room and cuddle up by the fire!

    Gail Carillo Coldwell Banker American Homes

    345 Northern Blvd, Saint James, NY 11780
  • 3 Elm Ln, Stony Brook, NY 11790

    $650,000 Sold Nov 25, 2024

    • 2,300 Sq Ft
    • $283/SF
    • 33 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1955

    3 Elm Ln, Stony Brook, NY 11790

    This home is a secluded nature retreat tucked away on a 0.5A wooded lot on a quiet street. This home is deceivingly large, a must see. Featuring a permitted 340sf accessory apartment (TOB -AA15851) - Approx 1000 ft. to Stony Brook University (Tabler Quad) - 5 minute drive to University Hospital. This 2300 sf home boasts a formal living room with fireplace, formal dining room, gigantic family room

    Laura Pellizzi Signature Premier Properties

    3 Elm Ln, Stony Brook, NY 11790
  • 0 N Country Rd, Saint James, NY 11780

    $600,000 Sold Nov 20, 2024

    • Land
    • 5.74 Acres
    • $104,530 per Acre
    • 23 Days On Market

    0 N Country Rd, Saint James, NY 11780

    Zoned already for 2 New Homes by Village of Head of Harbor. New Cul-De-Sac location to be built off village road. One Home will sit on 3.59acres and 2nd home will sit on 2.15acres on cul-de-sac. Homes will be in Head of Harbor and Smithtown Schools. Survey Attached showing how homes will be located on property.

    Michael Scarito RE/MAX Integrity Leaders

    0 N Country Rd, Saint James, NY 11780
  • 3 Red Oak Rd, Saint James, NY 11780

    $900,000 Sold Nov 01, 2024

    • 3,300 Sq Ft
    • $273/SF
    • 63 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1972

    3 Red Oak Rd, Saint James, NY 11780

    Welcome To 3 Red Oak Road! This Picturesque Colonial Boasts A Classic Center Hall Colonial Design And Is Situated In A Highly Desired Tree-Lined Street In The Heart Of Saint James. The Main Floor Has An Easy Flow That Includes An Entry Foyer, Powder Room, Large Eat-In Kitchen, Formal Dining Room, Formal Living Room With Fireplace, A Spacious Den With Fireplace, As Well As A Beautiful Sunroom/All

    Maria Orlandi Compass Greater NY LLC

    3 Red Oak Rd, Saint James, NY 11780
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