Glen Head Real Estate

Welcome to Glen Head, a charming hamlet nestled in the heart of Nassau County, New York. This picturesque community is part of the North Shore of Long Island, offering a delightful blend of suburban tranquility and vibrant local culture. With its tree-lined streets, historic architecture, and welcoming atmosphere, Glen Head is a hidden gem that attracts families, professionals, and retirees alike.

Glen Head boasts a rich history, characterized by its quaint neighborhoods and a strong sense of community. Residents enjoy access to top-rated schools, making it an ideal location for families seeking quality education for their children. The local parks, including the popular Glen Head Park, provide ample opportunities for outdoor recreation, from leisurely strolls to active sports.

One of the standout features of Glen Head is its convenient location. Situated just a short drive from the bustling city of New York, residents can easily enjoy the cultural, culinary, and entertainment offerings of the metropolis while returning home to the serene charm of their hamlet. The Long Island Rail Road offers a quick commute to Manhattan, making Glen Head a desirable choice for city professionals.

Additionally, Glen Head is home to a variety of local shops, cafes, and restaurants, fostering a vibrant community spirit. Whether you’re looking to explore unique boutiques or savor a delicious meal at a local eatery, you’ll find plenty of options right at your doorstep.

In Glen Head, you’ll discover a perfect blend of suburban comfort and urban convenience, making it a wonderful place to call home. Come experience the warmth and charm that this lovely hamlet has to offer!

Newest Listings in Glen Head

$1,118,000

3 Beds ⋅ 3 Baths ⋅ 1058934 MLS

A perfect Colonial, thoughtfully updated for today’s lifestyle, this exceptional Glen Head home seamlessly blends timeless character with modern luxury. At the heart of the home is the chef’s kitchen, featuring a Wolf range, Sub-Zero refrigerator, and oversized center island that opens effortlessly to the living room—creating an ideal space for everyday living and entertaining with sound system inside and out. The formal dining room offers an elegant setting for special occasions, while multiple entrances provide easy access to the expansive outdoor deck, perfect for seasonal dining and gatherings. The meticulously maintained grounds offer a true outdoor retreat, complete with a covered patio that conveniently leads to the heated garage and a lush, level yard with irrigation in the front and back for gardening. Inside, 9-foot ceilings on the main level enhance the sense of space and light, while the vaulted primary suite upstairs provides a private sanctuary, complete with a spa-like bath. Located within the highly regarded North Shore School District, consistently recognized as one of New York State’s top school districts, this home is ideally situated in the charming community of Glen Head. Tree-lined streets, suburban charm, and proximity to Hempstead Harbor and Tappan Beach offer an exceptional lifestyle with plenty of opportunities to enjoy the outdoors. For commuters, the Glen Head train station is just 0.3 miles away, while easy access to the Long Island Expressway makes travel throughout the region convenient. Come see for yourself what makes 11 Cherry Street such a wonderful place to call home—offering the space, amenities, location, and flexibility to accommodate a wide range of lifestyles.

11 Cherry Street, Glen Head

$1,125,000

5 Beds ⋅ 3 Baths ⋅ 1062070 MLS

Wonderful opportunity to own this beautiful 4- to 5-bedroom Colonial with garage, perfectly situated on a lovely block within the North Shore School District! Offering a wonderful flow throughout, featuring a spacious living room with a wood-burning fireplace, dining room, kitchen, FIRST FlOOR bedroom and full bath, plus a den that can easily serve as an additional bedroom or home office. The choice is yours! Upstairs, you'll find three additional bedrooms and two full baths, including a lovely primary suite with its own private bath and steam shower. Step outside to a beautiful, flat backyard with plenty of room for a pool, entertaining, or simply enjoying the outdoors. Full finished basement and shed add to the many conveniences of this home. Conveniently located close to schools, shopping, restaurants, parks, and all that the North Shore has to offer. Pictures coming soon!

11 University Place, Glen Head

$710,000

4 Beds ⋅ 2 Baths ⋅ 1062160 MLS

A rare opportunity in the desirable, quiet neighborhood of The Glen Knolls, near North Shore High School. This 1940s home offers endless potential for buyers looking to restore its original character or take on a renovation project, with the option to rebuild in a sought-after location. The home features 4 bedrooms and 2 full baths, including two bedroom options on the first floor. Wall of storage space available on second floor. Outside, enjoy your backyard shaded by a beautiful elm tree. Bring your vision and make it your own! Please note, this home is sold AS IS.

19 Plymouth Drive S, Glen Head

$959,000

4 Beds ⋅ 3 Baths ⋅ 1057431 MLS

Welcome to 14 Waverly Street, a solid, well-built single-family home perfectly situated in the highly sought-after community of Glen Head. Boasting four spacious bedrooms and three full bathrooms, this residence offers over 1,900 sq ft of versatile living space. The bright, welcoming layout centers on a cozy living area with a fireplace. Set on a generous 0.27-acre lot, the property truly shines in the backyard, your own private oasis complete with a beautifully maintained in-ground pool, perfectly primed for entertaining or relaxing outdoors. An attached garage adds everyday convenience and additional storage. Located within the prestigious North Shore School District, this is a rare opportunity to invest in a great neighborhood.

14 Waverly Street, Glen Head

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 1057516 MLS

'RARE AND REMARKABLE' RANCH . . . . with Understated, Unassuming Elegance. At first glance one may not view this ranch-styled home as anything particularly extraordinary in terms of its size or its form but it has a certain allure that is rather irresistible. You will undoubtedly find time spent within it to be completely restorative. Nature surrounds you here- it envelopes you and it provides a peaceful, serene environment that calms the mind and body. You can consider this property your very own oasis, your home of refuge- private and secluded- a wonderful place to raise your family. Older relatives or guests will be able to comfortably navigate this home since all of its rooms are on one level - just one step up from the street grade. There are a few apple trees to enjoy in the backyard, a small greenhouse, and plenty of room for a vegetable garden and even domesticated livestock! - live off of your own land! When and if you outgrow its ample space, you can add onto it- no need to move! All of these items are what typically render a house that may be initially viewed as ordinary into a home that captivates you - heart and soul- and becomes quite extraordinary. Over time, you will fill it with fond memories of many special family gatherings and occasions- exactly like its original (for 5 years) and current owners (for 42 years) have. . . its unavoidable. The use and thorough enjoyment of this home and property render its value ABSOLUTELY PRICELESS! PERFECTLY POSITIONED in the south-west corner of the Village of Old Brookville, it is not far from the surviving mansions of the bye-gone era responsible for the reference to Nassau County’s northern shore as its ‘gold coast’. The town planners were apparently intent on preserving the nature of the area when they required each residential lot to consist of a minimum of 2 acres. They encouraged owners to continue agriculture, dairying, the keeping of poultry, livestock & horses (with limits), dogs, game and birds for personal use. Owners are also encouraged to pursue their own horticulture interests utilizing the existing greenhouse. Home occupation for various professional uses (there is a separate side entrance) is also possible albeit with some restrictions, or pursue your artistic interests (the tool shed or the attached double garage would make an excellent art or music studio). Ideally located within close proximity to the Greenvale Station on the Oyster Bay line of the LIRR, the North Shore Central School District (K-12), and the LIU-CW Post and NY Institute of Technology campuses. Shopping abounds at the Wheatly Shopping Plaza, which now includes Uncle Giuseppi’s, the Miracle mile, the Roosevelt Mall and all the various shopping centers along Old Country Road in Westbury. Whole Foods and Trader Joes are also nearby. There is a vast number of country clubs and golf courses to choose from surrounding this property in addition to several tennis clubs and the Red Barn and Brookville Farms Equestrian centers. Notable Places of Interest nearby: Theordore Roosevelt Memorial Park; Young's Farm; The Planting Fields Aboretum; Old Westbury Gardens; Nassau County Museum of Art; Sands Point Preserve; Bayville Adventure Park; Rottkamp Brothers Farm; Muttontown Preserve; Christopher Morley Park; Holocaust Center; Sagamore Hill National Historic Site; Raynham Hall Museum; Oyster Bay Waterfront Center; Jericho Cider Mill; Garvies Pt Museum and Preserve

23 Hill House Lane, Glen Head

$3,390,000

6 Beds ⋅ 6 Baths ⋅ 1056792 MLS

Luxurious estate in a private gated neighborhood in the Village of Upper Brookville! This exceptional estate offers a rare combination of expansive acreage, generous living space, and resort-style amenities. Set on more than two acres, the 5,063-square-foot residence features six bedrooms, five full and one-half baths, and an inviting layout designed for both refined everyday living and effortless entertaining. Soaring ceilings, expansive windows, and an open-concept design create a light-filled sense of volume throughout the home. The majority of the living spaces are thoughtfully arranged on the main level, while generously proportioned rooms provide flexibility for both intimate gatherings and larger-scale entertaining. Walls of windows frame serene views of the beautifully landscaped grounds and bring the surrounding setting into the home. Beyond the interiors, the property unfolds as a private outdoor retreat. A sparkling in-ground pool and full tennis court provide an exceptional setting for recreation, relaxation, and summer entertaining, while the expansive grounds offer both privacy and room to enjoy the estate to its fullest. A three-car garage and distinguished circular drive enhance the property's impressive arrival and everyday convenience. A distinctive opportunity to enjoy privacy, scale, and an exceptional collection of amenities in one of Long Island's most sought-after North Shore settings

6 Quail Path, Glen Head

$1,390,000

4 Beds ⋅ 3 Baths ⋅ 1049860 MLS

Welcome to 9 The Promenade! Quiet interior location on oversized lot-4 Bed / 3 Bath - Primary En-Suite + 3 additional bedrooms.-Hi-Ranch-2318sq ft. -2023 updates inside & out-Open floor plan-White Chef’s Kitchen w/ Center Island-Huge Dining Room w/ sliders to fenced yard & patio-Laundry off kitchen-Ground-level guest bedroom room/mother-daughter w/proper permits required-Garage + oversized driveway for parking-

9 The Promenade, Glen Head

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1051579 MLS

This well-maintained Colonial offers four bedrooms and three full baths in a prime Glen Head location within the North Shore School District. A charming white picket-fenced backyard and welcoming fireplace add to its inviting appeal. The oversized kitchen opens to the dining room and backyard, creating an ideal setting for everyday living and entertaining. A spacious living room, convenient mudroom, and first-floor bedroom with full bath provide comfort and flexibility. Upstairs, the primary suite features an en suite bath and large walk-in closet, while two additional sun-filled bedrooms and a full hall bath complete the second level. Recent updates include a two-year-old roof and new washer, dryer, and refrigerator, each with an extended warranty. Numerous improvements reflect the home’s careful maintenance and pride of ownership. Conveniently located near the LIRR, shopping, dining, parks, beaches, Glenwood Landing Elementary School, and all that Glen Head has to offer.

30 Waverly Street, Glen Head

$949,000

2 Beds ⋅ 4 Baths ⋅ 1048063 MLS

Welcome to this sun-drenched and stylish Glen Head fully-updated townhouse in the Fairway View development, perfectly positioned with ideal southern exposure that bathes the home in natural light all day long. Step into a dramatic entry foyer with soaring cathedral ceilings that flow seamlessly into an open-concept living area. Sleek black hardwood floors anchor the residence, creating a sophisticated backdrop for both daily living and effortless entertaining. The gourmet eat-in kitchen features timeless quartz countertops, a matching backsplash, an expansive island with abundant storage, and a dedicated laundry area with pantry space. Step through sliders from the main living space onto your private back deck—an idyllic setting for outdoor dining or peaceful morning coffee. Upstairs, the primary suite serves as a true sanctuary, complete with a generous closet system and a tranquil, Zen-inspired en-suite bathroom. A spacious second bedroom, an additional full bath, and a versatile den/office space with its own private upper-deck access offer endless flexibility for work or guests. The fully finished basement adds exceptional living space, featuring an open layout, a third full bathroom, and an egress window. Situated in the prestigious, award-winning North Shore School District, this home offers the ultimate blend of privacy and convenience—just minutes from top-rated schools, local dining, community amenities, Tappen Beach, and the Glen Head LIRR for a effortless commute.

40 Cedar Lane N Unit #40, Glen Head

$4,190,000

7 Beds ⋅ 7 Baths ⋅ 1043149 MLS

Welcome to 22 Evans Drive, an exceptional residence set on over two acres in the prestigious Village of Brookville. Offering approximately 6,750 square feet of living space, this impressive home combines grand proportions, timeless elegance, and exceptional privacy. Designed for both sophisticated entertaining and comfortable everyday living, the home features expansive living areas, abundant natural light, generously sized bedrooms, and a seamless flow throughout. The beautifully landscaped property provides a peaceful, private setting with plenty of space for outdoor entertaining and relaxation. Located within the highly regarded Jericho School District and surrounded by some of Long Island’s most distinguished estates, this remarkable Brookville property offers a rare combination of space, privacy, and convenience—just minutes from shopping, dining, major roadways, and the LIRR. A truly special opportunity to own an impressive estate in one of Long Island’s most desirable communities.

22 Evans Drive, Glen Head

$699,999

5 Beds ⋅ 2 Baths ⋅ 1040374 MLS

This double dormered Cape Cod features a living room, formal dining room, a kitchen, a den, two bedrooms and a full bath on the main floor and three bedrooms including the primary bedroom ( full with primary bedroom is huge and could easily be divided into two separate bedrooms ) and a bath on the second floor. There is a full basement, a one car garage that is not in good shape, an in-ground pool that needs to be repaired or replaced, hardwood floors, tile floors, a newer main roof, all gas cooking and Heating and a very quiet location that is walk to most things. This house needs a lot of work but is a diamond in the rough.

1 Glen Cove Drive, Glen Head

$4,500,000

1037268 MLS

Two distinctive residential building lots offered individually or together. Lot A consists of approximately 2.26 acres and Lot B approximately 2.12 acres, each with rights and ownership interest in the dedicated private road serving the two properties. The private road area is separate from and additional to the stated building-lot acreage, providing a private and distinctive approach to both homesites. Purchase one lot ($2,250,000/each) or acquire both for a combined private estate opportunity. See subdivision plan and title documents for boundaries and ownership details.

6 Hidden Pond, Glen Head

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.