Head Of The Harbor, NY Homes

• 

  

  

  /46

  $1,499,000 Pending

  • 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

• 

  

  

  /18

  $2,250 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  Unlisted Address

  Quiet and convenience to all in this 2nd story 1 bedroom apartment with 1st floor entry access. Heat, air conditioning, water, trash removal included. driveway parking for 1 car, no laundry on site. NO PETS/SMOKING. Minutes to train/ University SUNY Stony Brook/Hospital, shopping, dining, parks and historic district. driveway parking for 1 car

  Lisa Jaeger Douglas Elliman Real Estate

  Unlisted Address
• 

  $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 $2,753,000

  Last Listing Agent Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  15 Armand Ct, Saint James, NY 11780
• 

  Est $1,254,884 Not Listed For Sale

  30 Hitherbrook Rd, Saint James, NY 11780

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

  30 Hitherbrook Rd, Saint James, NY 11780

  Last Sold Summary

  • 5% Above List Price
  • $355/SF
  • 74 Days On Market

  • Last Sold Price $1,200,000
  • Mar 27, 2025

  Last Listing Agent John Sanders Shea & Sanders Real Estate Inc
• 

  

  

  /46

  $2,900,000

  • 8 Beds
  • 8 Baths
  • 6,475 Sq Ft

  9 Watercrest Ct, Saint James, NY 11780

  Set in the prestigious enclave of Head of the Harbor, 9 Watercrest is an unparalleled masterpiece of modern luxury and masterful design. The heart of the home is a breathtaking, completely reimagined culinary space envisioned by nationally acclaimed HGTV designer Ken Kelly. This expansive main floor, encompassing about 5,000 sqft, features soaring beadboard ceilings with custom engineered beams,

  

  Kyle Roskot

  The Agency Northshore NY

  (866) 412-5083

  9 Watercrest Ct, 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
• 

  $2,700,000 Sold Mar 13, 2026

  33 Bacon Rd, Saint James, NY 11780

  • 6 Beds
  • 5.5 Baths
  • 4,900 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $551/SF
  • 95 Days On Market

  Current Estimated Value $2,667,667

  Last Listing Agent Maria Orlandi Compass Greater NY LLC

  33 Bacon Rd, Saint James, NY 11780
• 

  Est $858,853 Not Listed For Sale

  178 Harbor Rd, Stony Brook, NY 11790

  • 3 Beds
  • 1.5 Baths
  • 1,417 Sq Ft
  • Built 1930

  178 Harbor Rd, Stony Brook, NY 11790

  Last Sold Summary

  • 1% Below List Price
  • $614/SF
  • 14 Days On Market

  • Last Sold Price $870,000
  • Dec 17, 2024

  Last Listing Agent Michael O Dwyer Daniel Gale Sotheby's
• 

  

  /50

  $1,399,999 Pending

  • 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

  (833) 912-5344

  23 Bacon Rd, 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 $835,011 Not Listed For Sale

  40 Hitherbrook Rd, Saint James, NY 11780

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1962

  40 Hitherbrook Rd, Saint James, NY 11780

  Last Sold Summary

  • 34% Above List Price
  • $312/SF
  • 23 Days On Market

  • Last Sold Price $625,000
  • Jan 17, 2024

  Last Listing Agent Danielle Baker Douglas Elliman Real Estate
• 

  

  /17

  $3,790,000

  • 5 Beds
  • 7.5 Baths
  • 7,000 Sq Ft

  550 Moriches Rd, Saint James, NY 11780

  Have you ever dreamed of building your own CUSTOM HOME in a small village on Long Island? Look No Further! Set within one of Long Island’s most prestigious and private villages, this extraordinary custom-built estate offers over 7,000 square feet of refined living space with an Elevator to service all Floors set on a breathtaking 2.35-acre wooded property, complemented by an additional one-acre

  Karyn Flores Compass Greater NY LLC

  550 Moriches 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

  Current Estimated Value $996,984

  Last Listing Agent Monica Balsan Daniel Gale Sothebys Intl Rlty

  3 Nadia Ct, Saint James, NY 11780
• 

  Not Listed For Sale

  1 Friends Way, Saint James, NY 11780

  • 4 Beds
  • 3.5 Baths
  • 2,689 Sq Ft
  • Built 1987

  1 Friends Way, Saint James, NY 11780

  Last Sold Summary

  • $495/SF
  • 33 Days On Market

  • Last Sold Price $1,330,000
  • May 03, 2024

  Last Listing Agent Christina Volz BERKSHIRE HATHAWAY
• 

  

  /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
• 

  $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

  Current Estimated Value $1,189,224

  Last Listing Agent Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  537 Moriches Rd, Saint James, NY 11780
• 

  Est $1,149,490 Not Listed For Sale

  6 Buckingham Ct, Saint James, NY 11780

  • 5 Beds
  • 4.5 Baths
  • Built 1990

  6 Buckingham Ct, Saint James, NY 11780

  Last Sold Summary

  • 24% Above List Price
  • 234 Days On Market

  • Last Sold Price $930,000
  • Jan 09, 2024

  Last Listing Agent Bonnie Glenn Daniel Gale Sotheby's
• 

  

  /35

  $949,000

  • 4 Beds
  • 3 Baths
  • 3,475 Sq Ft

  48 Farm Rd, Saint James, NY 11780

  Nestled in a serene, private setting, this spacious 4 bedroom, 3 full bath bilevel home combines a blend of comfort and nature while providing an opportunity to create your dream space. It offers a comfortable and functional 1st floor primary bedroom featuring an ensuite bath, two closets and sliding glass door that opens to views of the tranquil, wooded backyard. The main living area welcomes

  Gina Amen American Real Estate Assoc Inc

  48 Farm Rd, 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 $1,537,667

  Last Listing Agent Todd Yovino Island Advantage Realty LLC

  3 The Hunt, Saint James, NY 11780
• 

  Est $1,770,862 Not Listed For Sale

  21 Buckingham Ct, Saint James, NY 11780

  • 5 Beds
  • 3.5 Baths
  • 5,253 Sq Ft
  • Built 1986

  21 Buckingham Ct, Saint James, NY 11780

  Last Sold Summary

  • 11% Above List Price
  • $305/SF
  • 280 Days On Market

  • Last Sold Price $1,600,000
  • Apr 26, 2023

  Last Listing Agent Suzanne Scully Charles Rutenberg Realty Inc
• 

  

  /23

  $1,599,000 Pending

  • 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
• 

  $2,300,000 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 $2,369,333

  Last Listing Agent Deborah Lettieri Signature Premier Properties

  1 Meadow Gate E, Saint James, NY 11780
• 

  Est $1,680,667 Not Listed For Sale

  19 the Chase, Saint James, NY 11780

  • 5 Beds
  • 3.5 Baths
  • 4,200 Sq Ft
  • Built 1989

  19 the Chase, Saint James, NY 11780

  Last Sold Summary

  • 15% Above List Price
  • $348/SF
  • 54 Days On Market

  • Last Sold Price $1,460,000
  • Aug 16, 2023

  Last Listing Agent Maria Orlandi Compass Greater NY LLC
• 

  

  /36

  $1,399,999

  • 4 Beds
  • 3 Baths
  • 2,942 Sq Ft

  25 Pinoak Ln, Saint James, NY 11780

  Welcome to this Stunning Renovated 4-Bedroom 3-Bath Expanded Ranch, nestled at the end of a cul-de-sac in the coveted Head of the Harbor Village. Sitting on 2+ Tranquil Acres, this move-in ready home features hardwood floors throughout, 2 spacious living room/great room areas, a wood-burning fireplace, a formal dining room, newly installed 200 AMP electrical panel and a full basement adding

  Anna Star HomeSmart Premier Living Rlty

  25 Pinoak Ln, 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 $1,547,165 Not Listed For Sale

  10 Buckingham Ct, Saint James, NY 11780

  • 5 Beds
  • 3 Baths
  • Built 1997

  10 Buckingham Ct, Saint James, NY 11780

  Last Sold Summary

  • 10% Below List Price
  • 48 Days On Market

  • Last Sold Price $1,725,000
  • Nov 22, 2024

  Last Listing Agent Bonnie Glenn Daniel Gale Sotheby's
• 

  

  /46

  $1,850,000

  • 6 Beds
  • 7.5 Baths
  • 5,800 Sq Ft

  60 Harbor Rd, Saint James, NY 11780

  Perfectly Positioned In The Prestigious Village Of Head Of The Harbor, This Exceptional All-Brick Estate Offers Timeless Sophistication And Refined Luxury On 2 Private Acres Directly Across From The Serene Beauty Of Stony Brook Harbor. Spanning Nearly 5800 SF, This Custom-Designed Residence Showcases Impeccable Craftmanship And Architectural Detail Throughout, Including 10 Ft Ceilings, Rich

  Maria Orlandi Compass Greater NY LLC

  60 Harbor Rd, Saint James, NY 11780
• 

  $1,400,000 Sold Mar 20, 2026

  30 Cordwood Path, Saint James, NY 11780

  • 4 Beds
  • 3.5 Baths
  • 3,598 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Below List Price
  • $389/SF
  • 66 Days On Market

  Current Estimated Value $1,516,120

  Last Listing Agent Kyle Roskot The Agency Northshore NY

  30 Cordwood Path, Saint James, NY 11780
• 

  Est $1,147,662 Not Listed For Sale

  49 Harbor Hill Rd, Saint James, NY 11780

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

  49 Harbor Hill Rd, Saint James, NY 11780

  Last Sold Summary

  • 28% Above List Price
  • $252/SF
  • 89 Days On Market

  • Last Sold Price $900,000
  • Oct 28, 2024

  Last Listing Agent Eduardo Ramirez Fresh Start Properties LLC
• 

  

  /46

  $1,425,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,458 Sq Ft

  76 Harbor Rd, Saint James, NY 11780

  This distinguished custom Neo-Dutch Colonial is a masterclass in timeless architecture, exceptional craftsmanship, and exquisite detailing throughout. Gracefully set on 2.82 acres of exquisitely landscaped grounds in Head of the Harbor, the residence is designed with both elegance and comfort in mind, offering a seamless blend of expansive entertaining spaces and intimate everyday living—creating

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  76 Harbor Rd, Saint James, NY 11780
• 

  $1,300,000 Sold Dec 30, 2025

  91 Harbor Rd, Saint James, NY 11780

  • 3 Beds
  • 3.5 Baths
  • 3,210 Sq Ft
  • Built 1993

  Last Sold Summary

  • 13% Below List Price
  • $405/SF
  • 195 Days On Market

  Current Estimated Value $1,271,458

  Last Listing Agent Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  91 Harbor Rd, Saint James, NY 11780
• 

  Est $913,580 Not Listed For Sale

  29 Three Sisters Rd, Saint James, NY 11780

  • 4 Beds
  • 3 Baths
  • 2,485 Sq Ft
  • Built 1847

  29 Three Sisters Rd, Saint James, NY 11780

  Last Sold Summary

  • 7% Above List Price
  • $342/SF
  • 91 Days On Market

  • Last Sold Price $850,000
  • Aug 21, 2024

  Last Listing Agent Kristen Moriarty Keller Williams Realty Elite
• 

  $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

  Current Estimated Value $3,689,984

  Last Listing Agent Michael Foley Frontline Realty Group LLC

  15 Emmet Dr, Stony Brook, NY 11790
• 

  Not Listed For Sale

  6 Farm Rd, Saint James, NY 11780

  • 6 Beds
  • 3 Baths
  • Built 1964

  6 Farm Rd, Saint James, NY 11780

  Last Sold Summary

  • 41 Days On Market

  • Last Sold Price $1,160,000
  • Dec 18, 2023

  Last Listing Agent Bonnie Glenn Daniel Gale Sotheby's
• 

  Est $1,003,170 Not Listed For Sale

  32 Farm Rd, Saint James, NY 11780

  • 3 Beds
  • 3.5 Baths
  • Built 1963

  32 Farm Rd, Saint James, NY 11780

  Last Sold Summary

  • 13% Above List Price
  • 8 Days On Market

  • Last Sold Price $890,000
  • Dec 06, 2024

  Last Listing Agent Bonnie Glenn Daniel Gale Sotheby's
• 

  Est $1,172,000 Not Listed For Sale

  120 Harbor Rd, Saint James, NY 11780

  • 4 Beds
  • 3.5 Baths
  • Built 1965

  120 Harbor Rd, Saint James, NY 11780

  Last Sold Summary

  • 21% Above List Price
  • 20 Days On Market

  • Last Sold Price $965,000
  • Jun 08, 2023

  Last Listing Agent Marianne Koke Daniel Gale Sotheby's
• 

  Est $1,299,667 Not Listed For Sale

  44 Hitherbrook Rd, Saint James, NY 11780

  • 4 Beds
  • 3 Baths
  • 3,794 Sq Ft
  • Built 1988

  44 Hitherbrook Rd, Saint James, NY 11780

  Last Sold Summary

  • 13% Above List Price
  • $303/SF
  • 44 Days On Market

  • Last Sold Price $1,150,000
  • Apr 30, 2024

  Last Listing Agent Gina Davino Exit Realty Everyday
• 

  Est $1,404,010 Not Listed For Sale

  72 Harbor Rd, Saint James, NY 11780

  • 4 Beds
  • 4.5 Baths
  • Built 1941

  72 Harbor Rd, Saint James, NY 11780

  Last Sold Summary

  • 10% Above List Price
  • 73 Days On Market

  • Last Sold Price $1,275,000
  • May 16, 2024

  Last Listing Agent Robin Ward Howard Hanna Coach
• 

  Est $1,290,751 Not Listed For Sale

  8 Woodlot Rd, Saint James, NY 11780

  • 4 Beds
  • 4 Baths
  • Built 1965

  8 Woodlot Rd, Saint James, NY 11780

  Last Sold Summary

  • 5% Above List Price
  • 17 Days On Market

  • Last Sold Price $1,225,000
  • Jul 17, 2024

  Last Listing Agent Bonnie Glenn Daniel Gale Sotheby's
• 

  Est $1,157,196 Not Listed For Sale

  2 Saddle Rd, Stony Brook, NY 11790

  • 3 Beds
  • 3 Baths
  • Built 1951

  2 Saddle Rd, Stony Brook, NY 11790

  Last Sold Summary

  • 11% Below List Price
  • 71 Days On Market

  • Last Sold Price $1,300,000
  • May 02, 2023

  Last Listing Agent Maria Orlandi Compass Greater NY LLC

Showing Results 1 - 40, Page 1 of 15