Head Of The Harbor, NY Homes

• 

  

  

  /46

  $1,499,000

  • 5 Beds
  • 2.5 Baths
  • 2,753 Sq Ft

  12 Briarwood Ct, Saint James, NY 11780

  Stunning 5BR/3BA Luxury Colonial on 2 Sprawling Acres Welcome to this exceptional home set on two beautifully landscaped acres located at the end of a cul-de-sac in the coveted Head of the Harbor neighborhood. Offering breathtaking views and unmatched privacy, this classic colonial seamlessly blends old-world charm with modern amenities. Inside, you’ll find an updated gourmet kitchen featuring

  

  James Szollosi

  Signature Premier Properties

  (866) 697-5919

  12 Briarwood Ct, Saint James, NY 11780
• Explore Head Of The Harbor

• 

  

  

  /4

  $1,800 per month

  • 1 Bed
  • 1.5 Baths
  • 400 Sq Ft
  • Apartment for Rent

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

  One Bedroom apartment located in Saint James, NY available for rent immediately. All utilities included besides cable and wifi. Located with close proximity to Stony Brook University and within Smithtown School District.

  Eric Ramsay IV Eric G Ramsay Jr Assoc LLC

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

  $2,600,000 Sold Aug 06, 2025

  15 Armand Ct, Saint James, NY 11780

  • 5 Beds
  • 8 Baths
  • 8,000 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $325/SF
  • 22 Days On Market

  Current Estimated Value $2,631,948

  Last Listing Agent Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  15 Armand Ct, Saint James, NY 11780
• 

  Est $894,186 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,417 Sq Ft

  178 Harbor Rd, Stony Brook, NY 11790

  178 Harbor Rd, Stony Brook, NY 11790
• 

  

  

  /50

  $1,399,999

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

  23 Bacon Rd, Saint James, NY 11780

  BACK ON MARKET !! - ALL BINDERS ARE OFF, DEAL FELL THROUGH - HOME IS 100% AVAILABLE !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

  

  James Szollosi

  Signature Premier Properties

  (844) 552-9045

  23 Bacon Rd, Saint James, NY 11780
• 

  

  /6

  $2,400 per month

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

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

  Updated and spacious two bedroom apartment with occupancy available immediately! Located with close proximity to Stony Brook University with all utilities included besides cable and Wi-Fi.

  Eric Ramsay IV Eric G Ramsay Jr Assoc LLC

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

  $1,200,000 Sold Mar 27, 2025

  30 Hitherbrook Rd, Saint James, NY 11780

  • 4 Beds
  • 2.5 Baths
  • 3,384 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $355/SF
  • 74 Days On Market

  Current Estimated Value $1,228,458

  Last Listing Agent John Sanders Shea & Sanders Real Estate Inc

  30 Hitherbrook Rd, Saint James, NY 11780
• 

  Est $827,362 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
• 

  

  /48

  $2,750,000 Pending

  • 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
• 

  

  /50

  $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
• 

  $2,800,000 Sold Sep 26, 2025

  17 Barn Ln, Saint James, NY 11780

  • 5 Beds
  • 4.5 Baths
  • 5,340 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Below List Price
  • $524/SF
  • 175 Days On Market

  Last Listing Agent Deborah Pirro Daniel Gale Sothebys Intl Rlty

  17 Barn Ln, 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
• 

  

  /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

  $4,200 per month

  • 4 Beds
  • 2 Baths
  • 3,000 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
• 

  $905,000 Sold Oct 10, 2025

  3 Nadia Ct, Saint James, NY 11780

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Above List Price
  • $362/SF
  • 28 Days On Market

  Last Listing Agent Monica Balsan Daniel Gale Sothebys Intl Rlty

  3 Nadia Ct, Saint James, NY 11780
• 

  Est $1,296,333 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
• 

  

  /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
• 

  $1,150,000 Sold Oct 06, 2025

  537 Moriches Rd, Saint James, NY 11780

  • 5 Beds
  • 2.5 Baths
  • 2,541 Sq Ft
  • Built 1927

  Last Sold Summary

  • 8% Below List Price
  • $453/SF
  • 29 Days On Market

  Last Listing Agent Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  537 Moriches Rd, Saint James, NY 11780
• 

  Est $1,197,094 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths

  6 Buckingham Ct, Saint James, NY 11780

  6 Buckingham Ct, Saint James, NY 11780
• 

  

  /10

  $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
• 

  $1,450,000 Sold Jul 30, 2025

  3 The Hunt, Saint James, NY 11780

  • 5 Beds
  • 3.5 Baths
  • 3,600 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Above List Price
  • $403/SF
  • 85 Days On Market

  Current Estimated Value $1,458,494

  Last Listing Agent Todd Yovino Island Advantage Realty LLC

  3 The Hunt, Saint James, NY 11780
• 

  Est $1,705,000 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
• 

  

  /27

  $1,375,000 Pending

  • 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 rare

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  91 Harbor Rd, Saint James, NY 11780
• 

  $2,300,000 Sold Aug 07, 2025

  1 Meadow Gate E, Saint James, NY 11780

  • 5 Beds
  • 5.5 Baths
  • 5,130 Sq Ft
  • Built 1987

  Last Sold Summary

  • 14% Below List Price
  • $448/SF
  • 113 Days On Market

  Current Estimated Value $2,358,493

  Last Listing Agent Deborah Lettieri Signature Premier Properties

  1 Meadow Gate E, Saint James, NY 11780
• 

  Est $1,566,000 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
• 

  $780,000 Sold Aug 27, 2025

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

  • Land
  • 2.4 Acres
  • $325,000 per Acre

  Last Sold Summary

  • 4% Above List Price
  • 49 Days On Market

  Last Listing Agent Alexia Poulos Douglas Elliman Real Estate

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

  Est $1,685,919 Not Listed For Sale

  • 5 Beds
  • 3 Baths

  10 Buckingham Ct, Saint James, NY 11780

  10 Buckingham Ct, Saint James, NY 11780
• 

  $1,248,000 Sold Apr 07, 2025

  17 Timothy Ln, Saint James, NY 11780

  • 5 Beds
  • 3.5 Baths
  • Built 1923

  Last Sold Summary

  • 4% Below List Price
  • 139 Days On Market

  Current Estimated Value $1,272,805

  Last Listing Agent Zachary Scher Signature Premier Properties

  17 Timothy Ln, Saint James, NY 11780
• 

  Est $2,186,667 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
• 

  $3,600,000 Sold Dec 10, 2025

  15 Emmet Dr, Stony Brook, NY 11790

  • 11 Beds
  • 7 Baths
  • 9,411 Sq Ft
  • Built 1906

  Last Sold Summary

  • 28% Below List Price
  • $383/SF
  • 224 Days On Market

  Last Listing Agent Michael Foley Frontline Realty Group LLC

  15 Emmet Dr, Stony Brook, NY 11790
• 

  Est $1,188,360 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,565 Sq Ft

  49 Harbor Hill Rd, Saint James, NY 11780

  49 Harbor Hill Rd, Saint James, NY 11780
• 

  $635,000 Sold Mar 13, 2025

  1251 N Country Rd, Stony Brook, NY 11790

  • 3 Beds
  • 2 Baths
  • Built 1890

  Last Sold Summary

  • 14% Below List Price
  • 99 Days On Market

  Current Estimated Value $1,040,802

  Last Listing Agent David Guzzetta American Way Real Estate Inc

  1251 N Country Rd, Stony Brook, NY 11790
• 

  Est $949,799 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,485 Sq Ft

  29 Three Sisters Rd, Saint James, NY 11780

  29 Three Sisters Rd, Saint James, NY 11780
• 

  Est $1,308,183 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 $2,224,333 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
• 

  Est $1,278,849 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  25 Pinoak Ln, Saint James, NY 11780

  25 Pinoak Ln, Saint James, NY 11780
• 

  Est $945,044 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths

  32 Farm Rd, Saint James, NY 11780

  32 Farm Rd, Saint James, NY 11780
• 

  Est $1,289,333 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths

  120 Harbor Rd, Saint James, NY 11780

  120 Harbor Rd, Saint James, NY 11780
• 

  Est $1,263,333 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,794 Sq Ft

  44 Hitherbrook Rd, Saint James, NY 11780

  44 Hitherbrook Rd, Saint James, NY 11780
• 

  Est $1,412,408 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 2,976 Sq Ft

  72 Harbor Rd, Saint James, NY 11780

  72 Harbor Rd, Saint James, NY 11780

Showing Results 1 - 40, Page 1 of 15