Head Of The Harbor, NY Homes for Sale

/31
$2,900,000
- 8 Beds
- 8 Baths
- 6,475 Sq Ft
9 Watercrest Ct, Saint James, NY 11780

Set within the prestigious enclave of Head of the Harbor, 9 Watercrest is a stunning showcase of modern luxury, thoughtfully reimagined with impeccable craftsmanship, design, and attention to detail. This turnkey estate blends sophistication, scale, and state-of-the-art comfort. At the heart of the 5,000 sq ft +/- main level is a spectacular, fully renovated chef’s kitchen by renowned HGTV

Kyle Roskot

The Agency Northshore NY

(866) 412-5083

9 Watercrest Ct, Saint James, NY 11780
Explore Head Of The Harbor
/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
/50
$2,300,000
- 5 Beds
- 5 Baths
- 4,788 Sq Ft
2 Deepwells Ln, Saint James, NY 11780

Welcome to this spacious 5-bedroom, 5-bath Colonial set on 1.70 acres in the desirable Head of the Harbor section of Saint James. This 4,788 sq ft home features a functional layout with a first-floor bedroom and full bath, formal dining room, living room, and an open kitchen with granite countertops, center island, and eat-in area leading to a large family room with fireplace. The second level

Paul Musso Realty Connect USA L I Inc

2 Deepwells Ln, Saint James, NY 11780
/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
/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
/2
$1,199,999
- Land
- 2.4 Acres
- $500,000 per Acre
0 Timothy Ln, Saint James, NY 11780

BUILD YOUR DREAM HOME!!!!!! A rare find....flat piece of land in the Incorporated village of Head of The Harbor. This property is surrounded by 4000-7000 sq foot homes. There is electric, water and gas at the property. Ideal location close to Stony Brook Hospital, and major roads.

Janice Fanelli Signature Premier Properties

0 Timothy Ln, Saint James, NY 11780
/6
$1,099,000
- 4 Beds
- 3 Baths
- 2,416 Sq Ft
122 4th St, Saint James, NY 11780

Why settle for someone else’s dream when you can build your own? Welcome to this brand-new TO BE BUILT colonial-style home designed with today’s lifestyle in mind. Set on a deep 15,840 sqft lot, this to-be-built beauty will offer over 2,400 square feet of fresh, functional living space and the kind of craftsmanship and energy efficiency only new construction can deliver. Inside, you’ll find four

James Haydon Realty Connect USA L I Inc

122 4th St, Saint James, NY 11780
/5
$1,099,000
- 4 Beds
- 3 Baths
- 2,416 Sq Ft
120 4th St, Saint James, NY 11780

Why settle for someone else’s dream when you can build your own? Welcome to this brand-new TO BE BUILT colonial-style home designed with today’s lifestyle in mind. Set on a deep 15,840 sqft lot, this to-be-built beauty will offer over 2,400 square feet of fresh, functional living space and the kind of craftsmanship and energy efficiency only new construction can deliver. Inside, you’ll find four

James Haydon Realty Connect USA L I Inc

120 4th St, Saint James, NY 11780
/9
$958,888
- 10 Beds
- 4.5 Baths
474 Route 25A, Saint James, NY 11780

Builder special extended family with plenty of living space, Hord wood floor through out on the first floor. Home features 10 bedrooms, 4.5 Bathrooms, 2 car garages fireplace, Gas heat, CAC-system. This unique house sits 032 acre of the flat lot close downtown of Saint James, train station. Needs 24 Hours Noticed to show, Appointment only!

Jin Tao Realty Connect USA L I Inc

474 Route 25A, Saint James, NY 11780
/42
$1,099,999 Open House 6/06
- 4 Beds
- 3.5 Baths
- 2,600 Sq Ft
36 Vanderbilt Ave, Saint James, NY 11780

Saint James Colonial in Smithtown Schools, built 1998, on a quiet cul-de-sac. A grand two-story foyer leads to formal living and dining rooms, a fireplace family room, and an eat-in kitchen with granite countertops. Off the rear, a glass-wrapped sunroom overlooks the backyard and opens to a large composite deck. Main level highlights include hardwood floors, powder room, and laundry. Two-car

David Friedman Howard Hanna Coach

36 Vanderbilt Ave, Saint James, NY 11780

New York Suffolk County Head Of The Harbor

Why Live in Head Of The Harbor

Head of the Harbor in Saint James is a three-square-mile, entirely residential neighborhood characterized by its rural and pastoral feel. The area is home to approximately 1,500 residents and features winding country roads, mature oak trees, and properties averaging 3,600 square feet on at least two acres. Housing consists solely of single-family homes, predominantly with five-plus bedrooms. The community borders Stony Brook Harbor and includes pockets of agricultural land, such as Harmony Vineyards and Bird’s Foot Farm. Local schools are highly rated, with Mills Pond Elementary School, The Stony Brook School, and Smithtown High School East all receiving high marks for their academic programs and extracurricular activities. Residents enjoy access to Long Beach and Avalon Nature Preserve, which offer natural beauty and recreational opportunities. The Deepwells Farm Historical Society hosts an annual haunted Halloween event, adding to the local charm. Dining options include The Trattoria for Italian cuisine and Del Fuego for Tex-Mex, while grocery shopping requires a short drive to nearby St. James. The neighborhood is safer than the national average, and while commuting to Manhattan is possible via the LIRR, it can take between 1 hour 20 minutes to over three hours depending on traffic.

Learn more about living in Head Of The Harbor

Frequently Asked Questions

What are the most popular zip codes in Head Of The Harbor, NY?

The most popular zip codes in Head Of The Harbor, NY include 11780, 11790, 11787, 11767 and 11755.

How are the schools in Head Of The Harbor, NY?

Head Of The Harbor, NY has highly rated public and private schools. Some of the best schools in Head Of The Harbor based on Niche Grades are Harbor Country Day School, The Knox School and The Stony Brook School. Browse all the schools in Head Of The Harbor, NY to learn more.

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