Head of the Harbor Homes

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  /19

  $2,900,000

  • 5 Beds
  • 4.5 Baths
  • 5,340 Sq Ft

  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

  (855) 512-5119

  17 Barn Ln, Saint James, NY 11780
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• 

  

  

  /15

  $4,500 per month

  • 4 Beds
  • 2 Baths
  • 2,500 Sq Ft
  • House for Rent

  445 N Country Rd, Saint James, NY 11780

  Mint colonial,. 4 bedrooms, 2 full bathrooms, large kitchen with French doors that open to family room, formal dining room,, sunroom & front porch. Off street parking, Smithtown schools, Additional information: Appearance:Mint

  Michelle Bender Douglas Elliman Real Estate

  445 N Country Rd, 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
• 

  Est $738,421 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  40 Hitherbrook Rd, Saint James, NY 11780

  40 Hitherbrook Rd, Saint James, NY 11780
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  /6

  $800,000

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

  adj #252 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 fully permitted and ready to accommodate a spectacular 6,000+

  Karyn Flores Compass Greater NY LLC

  adj #252 Moriches Rd, Head of the Harbor, NY 11780
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  /12

  $2,500 per month

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

  174 Mills Pond Rd Unit B, Saint James, NY 11780

  Two bedroom apartment available for immediate occupancy available in Saint James. Landlord to pay all utilities besides electricity.

  Eric Ramsay IV Eric G Ramsay Jr Assoc LLC

  174 Mills Pond Rd Unit B, 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
• 

  Est $1,271,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,254 Sq Ft

  36 Harbor Rd, Saint James, NY 11780

  36 Harbor Rd, Saint James, NY 11780
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  /44

  $4,999,999

  • 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
• 

  $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
• 

  Est $912,640 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,689 Sq Ft

  1 Friends Way, Saint James, NY 11780

  1 Friends Way, Saint James, NY 11780
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  /50

  $2,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,130 Sq Ft

  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
• 

  $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
• 

  Est $1,085,721 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths

  6 Buckingham Ct, Saint James, NY 11780

  6 Buckingham Ct, Saint James, NY 11780
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  /33

  $1,349,000

  • 5 Beds
  • 2.5 Baths
  • 2,541 Sq Ft

  537 Moriches Rd, Saint James, NY 11780

  Incredible Level 3.5 Pastoral Acres..with Detached Cottage with so many possibilities & 2 Stall Horse Bldg./Welcome to this updated classic country colonial where modern amenities blend seamlessly with timeless charm. This thoughtfully renovated home features gas heat, central air, updated Andersen windows, updated baths, gleaming wood floors, and custom millwork. The kitchen shines with

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  537 Moriches 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
• 

  Est $1,613,414 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 5,253 Sq Ft

  21 Buckingham Ct, Saint James, NY 11780

  21 Buckingham Ct, Saint James, NY 11780
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  /45

  $2,699,000 Pending

  • 5 Beds
  • 8 Baths
  • 8,000 Sq Ft

  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
• 

  $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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  Est $1,690,000 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  19 the Chase, Saint James, NY 11780

  19 the Chase, Saint James, NY 11780
• 

  

  /45

  $2,599,000 Pending

  • 6 Beds
  • 5.5 Baths
  • 4,850 Sq Ft

  33 Bacon Rd, Saint James, NY 11780

  Experience luxury living at its finest in this breathtaking and stately Georgian style 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 a truly one of a kind home.Nestled on 3.50 lush, level, professionally manicured acres in the

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  33 Bacon 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
• 

  Est $1,739,667 Not Listed For Sale

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

  4 The Hunt, Saint James, NY 11780

  4 The Hunt, Saint James, NY 11780
• 

  

  /8

  $750,000 Pending

  • Land
  • 2.40 Acres
  • $312,500 per Acre

  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
• 

  $1,450,000 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
• 

  Est $2,577,000 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,394 Sq Ft

  4 Wicks Ln, Saint James, NY 11780

  4 Wicks Ln, Saint James, 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
• 

  $2,450,000 Sold Sep 18, 2024

  • 41 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2022

  16 Gate Rd, Saint James, NY 11780

  Located In The Highly Regarded Village Of Head of The Harbor, This Captivating, Newly Constructed Board And Batten Modern Farmhouse Is Designed For Today's Open Concept Lifestyle. This Four Bedroom, Four And A Half Bathroom Residence Was Constructed With Attention To Every Detail And Every Amenity. Step Into A Spectacular Great Room With Soaring 20 Foot Ceilings And Fireplace, And An Elegant And

  Maria Orlandi Compass Greater NY LLC

  16 Gate Rd, Saint James, NY 11780
• 

  Est $1,243,000 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 4,355 Sq Ft

  29 Deepwells Ln, Saint James, NY 11780

  29 Deepwells Ln, Saint James, NY 11780
• 

  

  /41

  $1,330,000

  • 5 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  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
• 

  $850,000 Sold Aug 21, 2024

  • 2,485 Sq Ft
  • $342/SF
  • 91 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1847

  29 Three Sisters Rd, Saint James, NY 11780

  Immaculate and Well Appointed 1847 Farmhouse Classic Located In Long Islands Quaint Head Of The Harbor Village. Welcoming Wrap Around Front Porch Welcomes You & Your Guests Into This One Of A Kind Beauty. Original Hard Pine Flooring & Hand Hewn Century Old Wood Beams Make The Dining Room & Sitting Area with Fireplace Extra Special. Custom Window Treatments Throughout. Updated Eat In Kitchen With

  Kristen Moriarty Keller Williams Realty Elite

  29 Three Sisters Rd, Saint James, NY 11780
• 

  Est $613,772 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,004 Sq Ft

  531 Moriches Rd, Saint James, NY 11780

  531 Moriches Rd, Saint James, NY 11780
• 

  $610,000 Sold Jul 29, 2024

  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  406 Route 25A Unit A, Saint James, NY 11780

  Nestled in the heart of St. James this captivating hi-ranch home offers an exquisite blend of versatility, comfort, and sophistication, ideal for a range of living dynamics. This residence presents a unique opportunity to enjoy as a spacious family home, accommodate visitors with ease, the perfect work from home space, and so much more. As you step inside, you're greeted by a layout that

  Adam Weisinger NEXTHOME FINEST FIRST

  406 Route 25A Unit A, Saint James, NY 11780
• 

  Est $2,013,000 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 4,293 Sq Ft

  8 Fells Way, Saint James, NY 11780

  8 Fells Way, Saint James, NY 11780
• 

  $1,225,000 Sold Jul 17, 2024

  • 17 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1965

  8 Woodlot Rd, Saint James, NY 11780

  Nestled on 2 private serene acres within the Private Village of Head of the Harbor, this captivating 4-bedroom 4 full bath sprawling ranch offers a lifestyle of comfort and tranquility. As you step inside, you'll be greeted by large windows that seamlessly blend the outdoors with the indoors. Truly a nature lover's paradise this one-of-a-kind home boasts a spacious light-filled interior

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  8 Woodlot Rd, Saint James, NY 11780
• 

  Est $911,568 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,950 Sq Ft

  46 Harbor Hill Rd, Saint James, NY 11780

  46 Harbor Hill Rd, Saint James, NY 11780
• 

  $1,917,500 Sold Jun 13, 2024

  • 4,600 Sq Ft
  • $417/SF
  • 12 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2018

  31 Branglebrink Rd, Saint James, NY 11780

  Stunning Young 4600 Square Foot Colonial Thoughtfully Designed For Today's Living, Exuding The Highest Of Quality, Craftmanship And Designer Millwork. Step Through The Elegant Double Entry Doors Into The Beautiful Foyer, Living Room, Office With French Doors And Formal Dining Room With Coffered Ceilings. The Spectacular Gourmet Chef's Kitchen Is Designed For Entertaining With A Large Quartz

  Maria Orlandi Compass Greater NY LLC

  31 Branglebrink Rd, Saint James, NY 11780
• 

  Est $1,225,000 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,173 Sq Ft

  6 Farm Rd, Saint James, NY 11780

  6 Farm Rd, Saint James, NY 11780
• 

  Est $1,193,000 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,326 Sq Ft

  14 Bacon Rd, Saint James, NY 11780

  14 Bacon Rd, Saint James, NY 11780
• 

  Est $1,859,333 Not Listed For Sale

  • 10 Beds
  • 7 Baths
  • 6,250 Sq Ft

  10 Muffins Meadows, Saint James, NY 11780

  10 Muffins Meadows, Saint James, NY 11780

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