Head of the Harbor Houses for Sale

/23
$1,599,000 Open Sat 1PM - 2:30PM
- 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
Explore Head of the Harbor
/48
$2,750,000
- 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
/37
$1,199,000
- 4 Beds
- 3 Baths
- 2,583 Sq Ft
118 Harbor Rd, Saint James, NY 11780

Welcome to 118 Harbor Road in the Beautiful Village of Head of The Harbor, NY. This Lovely Home is Nestled on 2 Acres of Serene and Rustic Property that backs to Multiple Acres of Wooded Land. The Generous-Sized Country Kitchen has a Breakfast Island with a Granite Counter, Built-in Wall Grill, Large Picturesque Window with View of Yard, The Living Room is a Generous Size with a 2-Sided

Christine Stevens Daniel Gale Sothebys Intl Rlty

118 Harbor Rd, Saint James, NY 11780
/27
$1,375,000
- 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

Bonnie Glenn Daniel Gale Sothebys Intl Rlty

91 Harbor Rd, Saint James, NY 11780

New York Suffolk County Head Of The Harbor 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, Head Of The Harbor sell after 72 days on the market compared to the national average of 53 days. The median sale price for homes in Head of the Harbor, Head Of The Harbor over the last 12 months is $1,248,000, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,248,000

Median Single Family Sale Price

$1,375,000

Average Price Per Sq Ft

$436

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.70

Median List Price

$1,396,500

Median Change From 1st List Price

Median Home Sale Price YoY Change

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

In Head of the Harbor, there are currently 4 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $1,199,000 to $2,750,000, there's something for every budget. As of October, 2025 the median home price in Head of the Harbor, Head Of The Harbor is $1,396,500, while the average sale price is $1,593,307, providing insight into local market trends. On average, houses spend 72 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, Head Of The Harbor and find the perfect place to call home.

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