$1,200,513Average Value$633Average Price per Sq Ft58Homes For Sale
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
Kristie Paget Werz,
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.
View GreatSchools Rating Methodology
On average, homes in Glen Head, NY sell after 85 days on the market compared to the national average of 56 days. The median sale price for homes in Glen Head, NY over the last 12 months is $1,600,000, down 12% from the median home sale price over the previous 12 months.
Welcome to this beautifully transformed Carriage House, where historic charm meets modern living! This impressive main residence offers a spacious open floorplan, featuring three generous bedrooms and 2.5 bathrooms. The heart of the home is illuminated by a stunning wall of windows, flooding the space with natural light and providing gorgeous views of your serene graveled French garden—perfect
Imagine an exclusive lifestyle redefined within a private HOA gated community, where absolute security meets unparalleled luxury on a flat, beautifully landscaped 2.53-acre parcel. This masterfully constructed 7,000-square-foot estate—boasting an impressive six bedrooms and seven bathrooms, each with their own private balcony—is defined by ultra-high-quality finishes throughout, including radiant
Located in the highly coveted, award-winning North Shore School District.Welcome home to this move-in-ready, newly renovated Colonial perfectly situated at the beginning of a charming, quiet cul-de-sac. This 4-bedroom, 2-full-bath home beautifully balances classic warmth with modern upgrades and an open space concept. The expanded 2,300 sq. ft. layout (1,561 sq. ft. livable) begins on the first
Framed by sweeping pond views and surrounded by over 2 private acres of beautifully landscaped grounds, this beautifully renovated brick estate offers a rare blend of luxury, privacy, and serene waterfront living. Tucked away on a quiet cul-de-sac, the home is perfectly positioned to capture the beauty of the pond from both the interior living spaces and the resort-style outdoor setting.A
Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 33+ acre equestrian estate formally named 'Westward' presents a rare opportunity to acquire a significant piece of North Shore history. Privately nestled amid rolling pastures, mature woodlands, and formal gardens, the estate seamlessly blends timeless architectural elegance with an unparalleled country lifestyle
Welcome to this turn-key Split-level home, featuring beautiful updates and special amenities like CAC,radiant heat, whole-house gas generator and whole-house water filtration system. Located on sought-after Viola Drive, and set on a shy half-acre of professionally landscaped, private property backing to Friend’s Academy with room for a pool, this exceptional residence offers the perfect setting
Experience pristine living in this exquisite diamond Brookville home, offering unsurpassed value in a highly coveted location. The prestigious approach features a long circular driveway, welcoming you to a serene retreat. The exterior boasts mature specimen plantings and estate fencing encircling a country club style yard with a 20x40 Gunite gas heated pool. The flat 2 acres of entertaining
Nestled on two private acres, this stunning 4-bedroom, 3.5-bath ranch combines timeless comfort with resort-style living, featuring over 3,100 square feet, an in-ground pool, and beautifully designed indoor-outdoor spaces, all within the acclaimed North Shore School District.
Set on two meticulously landscaped acres, this exceptional Brookville residence showcases refined design, expansive living spaces, and resort-style outdoor amenities. The grounds feature an inground saltwater pool, elegant stone patio, and outdoor kitchen equipped with a barbecue, refrigerator, and sink. A dramatic entry opens to soaring ceilings and impressive window walls that flood the home
Welcome to an extraordinary estates of timeless elegance located at 27 Victorian Lane, Brookville NY. — a distinguished estate that embodies architectural grace in one of the most prestigious residential setting. Set across approximately 2 acres of professionally landscaped grounds, this exceptional residence spans roughly 7,000 square feet of thoughtfully designed interior space, offering a rare
‘Haut Bois’ is a refined brick-and-stucco French chateau nestled in the heart of Brookville, New York. Inspired by the Louis XIV hunting lodge that later became the Palace of Versailles, this extraordinary 18-room estate is steeped in history, elegance, and timeless beauty. Originally built in 1916 by renowned architect Ogden Codman Jr. and meticulously restored in the late 20th century, this
FULLY AVAILABLE! Southern-facing, spacious, light-filled, and private townhouse featuring sleek black hardwood flooring throughout. The open entry foyer with cathedral ceilings leads to a sunlit living room with sliders to the back deck. Additional highlights include a formal dining room, an eat-in kitchen with quartz countertops and matching backsplash, a kitchen island with extra storage, a
Incredible price reduction! Incredible Value! For the Discerning Client who seeks only the Finest....Welcome to 8 Vista Lane in Brookville--where Timeless Design and Bespoke Materials are blended to create this Sophisticated Modern Luxury. A Grand Courtyard leads to the Entrance of this Spectacular Private Estate. The Tone is set as Guests are greeted in the Breathtaking 30'high Domed Circular
Nestled within the prestigious gated community of The Knolls and adjacent to the renowned Glen Head Country Club, this beautifully appointed residence at 19 The Circle offers a seamless blend of elegance, comfort, and effortless living. Bathed in natural light from an abundance of windows and multiple skylights, the home showcases gleaming hardwood floors, crown and base moldings, recessed
Charming one-level ranch offering easy living and modern updates! This well-maintained home features three spacious bedrooms, a beautifully updated full bath, and a brand-new eat-in kitchen perfect for everyday living and entertaining. The inviting living room includes a door leading directly to the backyard, creating a seamless indoor-outdoor flow. Additional highlights include a versatile bonus
Private Location End Unit, Hard Wood Floors, Granite Counter Tops In Eat In Kitchen, Large Living Room And Dining Room Marble Master Bath, Walk In Closets, Storage Area, 2 Decks Overlooking Beautiful Grounds. Full Finished Basement, 2 Car Garage. No Pets 1 Month Security And $1500 Security To Condo Association. Renters Liability Insurance Policy Required, Credit Check.
The property is in the upscale neighborhood, it is in the most desirable school district on Long Island and, the crime rate is under 0.001%.It is 10-20 minutes away walking distance to Roslyn, Sea Clif, and Glen Head beaches.It is also 10-20 minutes away walking distance to Roslyn Engineer Golf Club, Glen Head Golf Club and, Sea Clif Golf Club.If you love to play tennis, the Sports
$2,800 per month
2 Beds
1 Bath
940 Sq Ft
Light, bright and immaculate recently renovated second floor apt. Stay cool with ductless air conditioners. Attic Storage. Boasts a balcony off the kitchen, and shared use of yard below. Near railroad, universities, shopping and dining.
Renovated Kitchen And Bath, New Flooring And High Hat Lighting. Located On Quiet Cul De Sac. Use Of Yard. Off Street Parking. 1 Month Security Tenant Pays Own Gas And Electric.
Welcome to 13 Sheppard Street in Glen Head. This beautifully maintained young Colonial offers the perfect blend of comfort, space, and functionality. Designed with a seamless flow ideal for entertaining, the home features spacious rooms throughout, including a warm and inviting den with a wood-burning fireplace. The large eat-in kitchen provides ample space for gatherings, while the private
Full house rental in residential Glen Head neighborhood of North Shore Acres. The freshly painted home features 4 bedrooms and 2 updated bathrooms. The first floor includes Living room with fireplace, dining room, kitchen, 2 bedrooms, full bath and a screened in porch off of the kitchen. Second floor features 2 bedrooms and full bath. Plenty of room for storage in basement along with the
Welcome to an Extraordinary Rental opportunity where Privacy, Space, and Luxury converge. Set on approximately 2.5 acres of Lush Manicured Grounds, this stunning 3,000+ sqft Expanded Ranch offers an Unmatched Living Experience within the Prestigious Jericho School District. From the moment you turn down the long, Private Driveway, you know this home is something special. Featuring 6 Spacious
Set on a beautiful flat oversized property this exceptional home offers blend of comfort and space and location. Close to shopping beaches and schools. Great for entertaining, relax poolside with your guests in the backyard oasis. Will consider 3-6 month lease
Nestled on a quiet cul-de-sac in the prestigious village of Old Brookville, this stunning Mediterranean style estate offers the ultimate in luxury rental living. Set on 2 beautifully landscaped acres, this private, resort like retreat combines elegance, space, and exceptional amenities. With over 5,100 square feet of living space, this home features a large foyer that opens into a sophisticated
Renovated and Ready!! Everything is NEW!! Custom Kitchen, Living Room with Hardwood Floors, 4 Bedrooms, Brand New Bathroom, Full Basement, Laundry, Covered Porch, Large Yard, Long Driveway.
Exceptional rental opportunities like this rarely come to market. Welcome to 13 Walnut Street, a beautifully maintained 1893 Colonial Revival offering the perfect blend of historic charm and modern comfort on a private .34-acre property in the heart of Glen Head.Brimming with curb appeal, the home's sunny yellow façade, classic symmetrical architecture, and inviting covered front porch
Sunny Large (1200 sq feet) Three Bedroom Apartment On The Second Floor. Quiet Cul De Sac Location, Shared Backyard. Basement With Separate Entrance With Washer/Dryer and Separate Finished Room. Driveway Parking for 2 Cars and Street Parking. Close to Center of Town, Restaurants, Beaches, and LIRR.
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