Head of the Harbor Houses for Sale

/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
/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
/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
/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
/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
/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

New York Saint James 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

Home Trends in Head of the Harbor, NY

On average, homes in Head of the Harbor, Saint James sell after 55 days on the market compared to the national average of 51 days. The median sale price for homes in Head of the Harbor, Saint James over the last 12 months is $1,087,500, down 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,087,500

Median Single Family Sale Price

$1,323,999

Average Price Per Sq Ft

$427

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

6.00

Median List Price

$1,299,999

Median Change From 1st List Price

Median Home Sale Price YoY Change

-6%

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

In Head of the Harbor, there are currently 6 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $1,199,000 to $4,000,000, there's something for every budget. As of July, 2025 the median home price in Head of the Harbor, Saint James is $1,299,999, while the average sale price is $1,314,000, providing insight into local market trends. On average, houses spend 55 days on the market before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options available to suit every lifestyle. Browse properties and houses for sale in Head of the Harbor, Saint James and find the perfect place to call home.

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