A country club and quiet downtown near the North Shore
Although Glen Head is landlocked, its local businesses and highly rated public schools bear the names and selling points that define hamlets throughout the Town of Oyster Bay; this section of Long Island is rich with the amenities of the Gold Coast and North Shore. “You’re tucked away up on the North Shore. There’s no hustle and bustle. I raised my four kids here, and all four of them are back now raising my grandkids,” says John Langone, an associate broker with Daniel Gale Sotheby’s International Realty who has lived in Glen Head for nearly 40 years. “People used to call it Dead Head because it’s so quiet. We’ve got a small downtown area, and to the west is Hempstead Harbor. We’re still seeing bidding wars for houses. People want to be here.” North of state Route 25A, Long Island life moves a little slower. In Glen Head, spending an afternoon at the country club, shuttling kids to baseball games and day tripping at North Shore beaches doesn’t require fighting parkway traffic.
Glen Head residents are a short drive from Tappen Beach in Sea Cliff.
Drive the fairway at Glen Head Country Club.
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Single-family homes from across the 20th century in Glen Head
Architectural styles range from stately early 20th-century Federal designs to midcentury suburban staples like Cape Cods and ranch-style homes to modern New Traditionals blend on Glen Head’s residential streets, surrounded by the equally diverse landscaping breaking up tidy front lawns. Smaller homes, typically with three or fewer bedrooms, sell for $550,000 to $1 million. Larger homes with upward of four bedrooms sell for $800,000 to $1.8 million, with especially large estates on small acreages going for $2 million up to $4 million. While spacious lots are sought after, quarter-acre lots on suburban blocks or gently winding roads are much more common. Sidewalks are available on some gridded streets, but are lacking in the winding subdivisions.
Glen Head has a variety of house style for home buyers to choose from.
Multi-family homes are also available in Glen Head.
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Extracurriculars at highly rated North Shore schools
North Shore School District receives high ratings for its entire kindergarten through 12th-grade pipeline, with Glen Head Elementary School, North Shore Middle and North Shore High School all earning an A or higher from Niche. Small class sizes are one key to the district’s success; North Shore High School boasts a student-teacher ratio of 8-to-1, significantly better than the national average of 17-to-1. Extracurriculars help round out the high school’s International Baccalaureate World School education, allowing students to participate in a regional award-winning robotics team or contribute to the school’s newspaper, the Viking View.
The student teacher ratio at Glen Head Elementary School in Glen Head, NY is 11 to 1.
At Friends Academy, we achieve educational excellence.
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Golf, tennis and swimming at Glen Head Country Club
Members at the Glen Head Country Club tee off on an 18-hole golf course, spend time on the tennis courts and swim laps in the outdoor pool. Those wanting to explore membership at a different country club can find other clubhouses and golf courses in almost any direction, sprawling within a few miles of home in neighboring hamlets like Matinecock and Glenwood Landing. The Glen Head Racquet Club is a hub for indoor tennis and has become increasingly popular with pickleball players in the Gold Coast Pickleball Club in recent years. Behind the Glen Head Community Center and American Legion Post 336, Francis M. Gaynor Park provides a hidden-away playground and plenty of fields and parking spaces for Glenwood-Glen Head Junior Baseball games and practices. The waters of Hempstead Harbor are within 3 miles of boaters and beachgoers, meeting at Tappen Beach which welcomes Town of Oyster Bay residents to enjoy the sandy beach, playground and pool or apply to store kayaks on racks and larger boats at the marina.
Shopping and dining off Glen Head Road
A small-town shopping district branches from Glen Head Road, clumped together in old-fashioned strip malls and connected by wide sidewalks to standalone storefronts. Specialty businesses with names like Glen Head Hardware, Glen Head Spa and Glen Head Flower Shop stand down the street from restaurants serving global cuisines. Heirloom Tavern serves American dishes in a dimly lit dining room and shaded outdoor patio, while Kiraku Japanese Restaurant offers sushi and cocktails to diners in booths or at the sushi bar. Groceries and essentials are available at Gemelli's Gourmet Market North, Holiday Farms Supermarket and CVS. St. Hyacinth Catholic Church is the only house of worship within the hamlet, holding most masses in English and one Sunday morning mass in Polish.
Health-focused nutritious items are a focus of Gemelli Gourmet Market in Glen Head.
Honey's in Glen Head is fast-casual bistro serving a variety of soups, salads, and sandwiches.
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Glen Head LIRR Station and driving on the Long Island Expressway
As out of the way as Glen Head is, getting around the North Shore on Route 25A or coastal side roads isn’t a problem. “If the high school and middle school are letting out, I go down past the Harbor which puts me a mile out of the way. Other than that, there’s no traffic,” Langone says. Commuters are more likely to hit congestion on the Long Island Expressway on the roughly 30-mile drive to Manhattan. The Glen Head Long Island Rail Road Station starts riders on the roughly hourlong trip to Penn Station. Northwell Health’s Glen Cove Hospital is a few miles north, and LaGuardia Airport is about 20 miles west.
From GALS to classes at Gold Coast Public Library
While Glen Head doesn’t host many large events or festivals, classes ranging from chair yoga and painting to autumnal spooky story times are regularly held at the Gold Coast Public Library. The small community library was imagined by a Girl Scout and her classmates who formed a youth Get a Library Soon (GALS) committee, kickstarting adult and local government involvement and, eventually, the opening of the current library in 2005. A larger library has been under construction since 2023 and is expected to welcome the public to browse more shelves of books and attend community classes in 2025. Parents and players kick off the Glenwood-Glen Head Junior Baseball season with a parade ending in Glen Head each spring, followed by opening day ceremonies and a barbecue at Francis M. Gaynor Park.
Approximately 140 students attend Tiegerman Elementary in Glen Cove, NY.
Your source for resources and study space is the Gold Coast Public Library in Glen Head.
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Written By
Hannah Rainey
Photography Contributed By
J. Michael DeMeo
Video By
Jake Bell
Interested in learning more about homes in this area?
Reach out to
Alexandra Gregorek,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Glen Head, NY sell after 78 days on the market compared to the national average of 52 days. The median sale price for homes in Glen Head, NY over the last 12 months is $1,650,000, up 11% from the median home sale price over the previous 12 months.
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