Suffolk, NY Homes

/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
/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
$1,450,000 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

Est $764,826 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

/45
$1,999,999
- 3 Beds
- 3 Baths
- 3,600 Sq Ft
595 Moriches Rd, Saint James, NY 11780

When you enter the driveway on Cordwood Path, you will know you have found your home. Tucked away among mature trees, this stately yet welcoming home offers an exceptional blend of elegance, comfort, and privacy. From the moment you arrive via the interlocking brick walkway, you’re greeted by low-maintenance, manicured landscaping that reflects true pride of ownership—and a home that’s been both

Danielle Lenard Signature Premier Properties

595 Moriches Rd, Saint James, NY 11780
/12
$2,400 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.

Steven Stassi Eric G Ramsay Jr Assoc LLC

174 Mills Pond Rd Unit B, 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 $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

/50
$2,500,000 Pending
- 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
$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 $1,175,855 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

/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
$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

Est $1,217,661 Not Listed For Sale
- 5 Beds
- 4.5 Baths
6 Buckingham Ct, Saint James, NY 11780

6 Buckingham Ct, Saint James, NY 11780

/37
$899,000
- 5 Beds
- 2 Baths
- 2,500 Sq Ft
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
$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 $1,563,119 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

/41
$1,199,000
- 4 Beds
- 3 Baths
- 2,583 Sq Ft
118 Harbor Rd, Saint James, NY 11780

Welcome to 118 Harbor Road, Head of The Harbor, NY – A Charming Retreat in the Heart of Nature Nestled on 2 acres of serene, rustic property that backs onto acres of pristine wooded land, This lovely home offers the perfect blend of privacy, tranquility, and charm. Country Kitchen: The generous-sized kitchen features a breakfast island with a granite countertop, a built-in wall grill, and a

Christine Stevens Howard Hanna Coach

118 Harbor Rd, 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 $1,596,747 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

/50
$1,399,999
- 5 Beds
- 5 Baths
- 5,393 Sq Ft
23 Bacon Rd, Saint James, NY 11780

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 exquisite living space, This one-of-a-kind gem features a first floor master bedroom,

James Szollosi Signature Premier Properties

23 Bacon 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 $1,968,695 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

/27
$1,499,000
- 3 Beds
- 3.5 Baths
- 3,210 Sq Ft
91 Harbor Rd, Saint James, NY 11780

Tucked away in a charming and highly desirable country setting, this sprawling ranch-style residence offers a rare opportunity to enjoy refined living on 2.6 quiet, park-like acres—just moments from the charm and convenience of Stony Brook Village. Perfectly positioned near the tranquil waters of Stony Brook Harbor, Avalon Nature Preserve, local vineyards, and only a short drive to Stony Brook

Bonnie Glenn Daniel Gale Sothebys Intl Rlty

91 Harbor Rd, 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

Est $1,279,145 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

/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 permitted and ready to accommodate a spectacular

Karyn Flores Compass Greater NY LLC

adj #252 Moriches Rd, Head of the Harbor, 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 $1,377,859 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

/44
$4,000,000
- 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
$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 $1,024,527 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

/33
$1,249,000 Pending
- 5 Beds
- 2.5 Baths
- 2,541 Sq Ft
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
$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 $1,267,365 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

/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
$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 $1,172,617 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

/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
$2,600,000 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

Showing Results 1 - 40, Page 1 of 15

New York Suffolk County Head Of The Harbor

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage