Head Of The Harbor

Situated in just three-square miles, Head of the Harbor is 100% residential sprinkled with pockets of agricultural land. Country roads are barely wide enough for two cars wind through thickly wooded forest areas. Homes are shrouded in swathes of mature oak trees. Driveways are outfitted with white picket fence entry gates and flagged mailboxes. Pockets of cropland and farmland include Harmony Vineyards, BB & GG Farms & Nursery and Bird’s Foot Farm. Home to a year-round community of about 1,500 people and approximately 500 homes, this rural community borders Stony Brook Harbor, a pristine harbor along Long Island’s North Shore. “Head of the Harbor is suburban in that people commute to the city to work,” says Marianne Koke, Associate Real Estate Broker at Daniel Gale Sotheby’s International Realty with 40 years of experience selling homes on the North Shore of Long Island. “It has a rural, pastoral feel.” Homes are significantly larger than the national average in Head of the Harbor, averaging 3,600 square feet. “Most properties are on at least two acres. People buying here are looking for a larger property, " says Koke. There is one typology of housing here: single-family homes. While there are a handful of 3-bedroom properties, most houses have five-plus bedrooms. On the lower end, a three-bedroom Colonial-style home with a 2-car garage and stone paved driveway could list for between $600,000 and $750,000. A midrange home with 5-plus bedrooms and amenities like an in-law suite, wet bar and outdoor pool could fetch between $1.3 million and $1.5 million. Extravagant outliers exist, like a 14-bedroom manor with a tennis court, indoor pool house, 4-car garage and home gym with a sauna for start at $8 million plus. Inventory is low, but like many parts of Long Island, views of the bay or harbor will come with a steeper price tag. For elementary school, Head of the Harbor kids can start their education at Mills Pond Elementary School. The pre-K through grade 5 institution has an A rating on Niche for its above-average academics and beloved after school activities, including the fieldtrip to the Mill Pond Art Show and the annual East egg hunt. For middle school, A-rated The Stony Brook School offers a fantastic music program alongside a rigorous academic program. For high school, Smithtown High School East received an A for its diverse range of electives that help students prepare for what they might want to major in college. One of the main reasons someone might move to Head of the Harbor is to enjoy its breezy, calm beaches. Residents frequent Long Beach year-round, a large swath of greenspace – surrounded by Porpoise Channel on one side and the Atlantic Ocean on the other – with bathing beaches and a marina. Locals also have access to Avalon Nature Preserve, a former residential estate made into a 7-acre memorial dedicated to the son of local residents. The preserve was designed for visitors to explore a series of natural gardens interspersed with picturesque paths, overlooks and bridges. Once a year during the month of October, Deepwells Farm Historical Society turns its 19th-century Greek Revival mansion and estate into a haunted Halloween excursion. Residents of Head of the Harbor and surrounding locales come to explore the haunted halls leading to 16 rooms of “unrelenting terror.” The journey continues outside in the “haunted forest” Twisted Fairytale Trail. Along the way out, visitors can visit the spirits of the departed at the Family Graveyard. All proceeds from the fundraiser go to reparations of other Suffolk County landmarks listed on the National Register of Historic Places, most recently including Saint James General Store. Restaurants and shopping can be found along the outskirts of town. Local favorite, The Trattoria, serves rustic Italian dishes, including their famed beef braised in Barolo wine. At Tex-Mex eatery Del Fuego, locals rave about the brisket tacos and say the margaritas are “fire.” Kids get their ice cream fix at Mickey’s Ice Cream Kitchen, where they are known for hosting birthday parties with custom-colored decorations. Meanwhile, there are a handful of fast food and franchise spots, including a Shake Shack in Lake Grove, a Cheesecake Factory at the Smith Haven Mall and a Red Lobster next to Lowes. Delighting visitors with outdoor seating, live music and valet parking, Harmony Vineyards serves a light nosh with its famous wine-tasting prix fixe. For groceries, residents have to drive five to 15 minutes to supermarkets in St James, which include Whole Foods, Trader Joe’s and ALDI. Shopping is limited and mainly made up of big box names, including Ulta Beauty, Old Navy, Warby Parker and Macy’s. Everyone in Head of the Harbor has a car or two parked in their attached garage. Driving winding country roads, residents easily pass through the residential and agricultural sections of the three-square-mile neighborhood. Getting to Manhattan is doable, but it’s not a cake wake. It’s 60 miles from Midtown Manhattan, which could take anywhere from 1 hour 20 minutes to 3 hours 10 minutes, depending on the time of day. Residents can go to the city via LIRR at Stony Brook Station or St. James Station, which takes just under two hours to get to Penn Station.