5 Bedroom homes for sale & real estate in Glen Head, NY

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Tucked at the end of a quiet cul-de-sac, this timeless contemporary sits on two perfectly level acres offering exceptional privacy and a deep, usable yard. The property features an in-ground heated pool with a waterfall and beautiful outdoor space ideal for gatherings or relaxation. Inside, the home provides plenty of opportunity with its dramatic ceilings and walls of glass that create a bright, open feel throughout. The sunken living room flows into a dining area with a wet bar. The first floor includes a spacious primary suite, a dedicated home office, and both formal and casual living areas—all thoughtfully laid out and generously proportioned. With its solid foundation and impres

$2,799,000

5 beds3.5 baths4,498 sq ft

7 Pin Oak Ct, Glen Head, NY 11545

Wet bar • Waterfall • Primary suite

Listing by Compass Greater NY LLC

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Exquisite 5-bedroom residence on a private cul-de-sac set within the highly-regarded Jericho School District. This home features approximately 3,959 sq ft of living space on a flat, pristine 2-acre parcel. Built in 1952 and lovingly maintained, the property offers timeless appeal with modern comforts — two fireplaces, central air-conditioning, and a fully finished lower level. Outdoors, enjoy a resort-style in-ground gunite pool, adjacent pool-house and bocce court, all tucked away among lush landscaping for ideal entertaining or tranquil everyday living. A rare opportunity to reside in one of the North Shore’s most exclusive enclaves — schedule your private tour today.

$2,480,000

5 beds3.5 baths3,959 sq ft

4 Norgate Rd, Glen Head, NY 11545

Flat 2-acre parcel • Private cul-de-sac • Two fireplaces

Listing by United Real Estate Fortune

NEW CONSTRUCTION

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
High Point Court / Parcel A – Brookville A rare opportunity to create a custom luxury estate in one of the North Shore’s most prestigious settings. Plans designed by Steven E. Homburger AIA with Gallagher Homburger Group , Architects, PLLC. He is known for many Gold Coast Mansions designs. This private cul-de-sac parcel is offered with full architectural estate plans, allowing the buyer to build a residence of exceptional scale and elegance featuring grand entertaining rooms, first-floor guest suite, home office/library, sunroom, four-car garage, and a private primary suite wing with sitting room, terrace, and dual dressing rooms. Buyer has the flexibility to choose finishes, in

$7,900,000

5 beds7.5 baths8,600 sq ft

LOT A High Point Ct, Brookville, NY 11545

4 garage spots • Pool • Built 2025

Listing by Gold Coast Real Estate Group

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Discover this private 2-acre estate nestled in the prestigious Brookville Village, located within the top-rated Jericho School District. Enjoy low property taxes and a peaceful, secluded setting just minutes away from major highways and the train station—perfect for easy commuting and convenient living. This classic-style home features an inground swimming pool, expansive grounds, and endless potential to create your dream residence. Whether you’re looking to renovate, expand, or simply enjoy the timeless charm, this property offers incredible possibilities. Don’t miss this rare opportunity—will not last long! Schedule your private tour today and make it yours!

$1,999,000

5 beds4 baths3,009 sq ft

2177 Cedar Swamp Rd, Glen Head, NY 11545

2 acre lot • 3 garage spots • Pool

Listing by Signature Premier Properties

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
This grand, gated estate blends timeless elegance with modern convenience, showcasing meticulous European craftsmanship throughout. Spanning over 8,000 square feet, this expanded custom ranch features soaring 10–12-foot ceilings and a sun-filled layout that ensures unmatched privacy and presence. A heated, air-conditioned 7-car garage serves as an automotive gallery, while the lower level includes a state-of-the-art gym, spa, wet bar, and ample space for entertainment. Outside, the resort-style 20x50 heated saltwater pool, expansive patio, and designer pool house enhance the lush, manicured grounds. Located in the award-winning Jericho School District, this residence is moments from t

$5,200,000

5 beds6.5 baths5,377 sq ft

167 Brookville Rd, Glen Head, NY 11545

2 acre lot • 7 garage spots • Pool

Listing by Compass Greater NY LLC

Property at 8 High Meadow Ct, Glen Head, NY 11545, 5 beds, 5 baths

$4,295,000

5 beds5 baths6,000 sq ft

8 High Meadow Ct, Glen Head, NY 11545

Listing by Compass Greater NY LLC

Property at 26 Rolling Dr, Glen Head, NY 11545, 5 beds, 3.5 baths

$2,750,000

5 beds3.5 baths3,492 sq ft

26 Rolling Dr, Glen Head, NY 11545

Listing by Compass Greater NY LLC

Property at 8 Vista Ln, Glen Head, NY 11545, 5 beds, 7.5 baths

$5,998,000

5 beds7.5 baths8,800 sq ft

8 Vista Ln, Glen Head, NY 11545

Listing by Compass Greater NY LLC

Property at 25 Longridge Ln, Glen Head, NY 11545, 5 beds, 5.5 baths

$5,900,000

5 beds5.5 baths6,500 sq ft

25 Longridge Ln, Glen Head, NY 11545

Listing by Douglas Elliman Real Estate

Property at 19 Glenwood Rd, Glen Head, NY 11545, 5 beds, 3.5 baths

$2,150,000

5 beds3.5 baths2,577 sq ft

19 Glenwood Rd, Glen Head, NY 11545

Listing by Daniel Gale Sothebys Intl Rlty

Property at 5 Peacock Ln, Glen Head, NY 11545, 5 beds, 4.5 baths

$3,699,000

5 beds4.5 baths— sq ft

5 Peacock Ln, Glen Head, NY 11545

Listing by Douglas Elliman Real Estate

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Welcome to 81 Round Hill Road, a sunny and updated 5-bedroom, 3-bathroom home nestled in the desirable Norgate section of East Hills. This inviting residence boasts beautiful wood floors throughout, enhanced by all-new LED lighting. Recent updates include a newer roof, hot water heater, windows, and a generator, ensuring modern comfort and reliability. The large primary suite is a true retreat, featuring tray ceilings, fabulous closet space, and a luxurious primary bathroom. The all-white kitchen is a chef's delight, equipped with high-end appliances and gas cooking, perfect for culinary enthusiasts. Enjoy the privacy of the flat, fully fenced property, ideal for outdoor gatherings and rela

$2,098,000

5 beds3 baths2,958 sq ft

81 Round Hill Rd, Roslyn Heights, NY 11577

0.28 acre lot • 2 garage spots • Built 1938

Listing by Compass Greater NY LLC

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Anticipate the Extraordinary in Stone Hill. TO BE BuILT! An exquisite new construction transitional home is slated for completion in the highly sought-after, gated community of Stone Hill in Muttontown. This remarkable residence will span approximately 6,000 square feet on an immaculate, perfectly level property, granting access to all exclusive Stone Hill amenities. Step inside the dramatic two-story Entry Foyer and Great Room, where the home's open-concept design seamlessly blends opulence with livability. Crafted by a top local luxury developer, the attention to detail is evident in every curated finish: select White Oak flooring throughout, sophisticated custom wall treatments, designer

$3,995,000

5 beds5.5 baths6,000 sq ft

2 Buckingham Ct, Syosset, NY 11791

Gated community • Open-concept design • New construction

Listing by Compass Greater NY LLC

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Elegant Upper Brookville Colonial on Two Lush Acres Nestled in the heart of Long Island’s famed Gold Coast, this stately brick colonial in the Incorporated Village of Upper Brookville offers a timeless blend of sophistication, privacy, and modern comfort. Situated on two flat, beautifully landscaped acres, the home is approached through impressive electric gates, opening to manicured grounds filled with mature trees and specimen plantings. Step inside the two-story reception hall, where a sweeping staircase, fireplace, and radiantly heated floors create a grand yet inviting first impression. Sunlight floods through oversized windows, illuminating the home’s exquisite architectur

$3,750,000

5 beds4.5 baths7,560 sq ft

12 Donna Dr, Oyster Bay, NY 11771

2 acre lot • 3 garage spots • Pool

Listing by Daniel Gale Sothebys Intl Rlty

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Introducing Luxury & TRANQUILITY at its finest– The Modern Classic Estate, Revitalized in 2024, this 5 bedroom 7.5 bathroom Colonial sits behind a gated entry on 2.06 beautifully landscaped acres in prestigious Old Westbury, with highly desired Jericho School District. A brand-new (2025) cedar shingle roof complements the stone-and-shingle exterior, creating spectacular curb appeal. The grand foyer with 17-ft ceilings leads to sun-filled interiors featuring light oak floors, custom millwork, and soaring vaulted ceilings. The double-height living room with fireplace opens to expansive bluestone terraces. A formal dining room connects to an elegant butler’s pantry with win

$5,795,000

5 beds7.5 baths6,563 sq ft

119 Wheatley Rd, Old Westbury, NY 11568

Light oak floors • Sun filled interiors • Grand foyer

Listing by EXP Realty

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
A truly magnificent and rare find, this renovated two-family residence is ideally situated in the charming Sea Cliff Village. Every detail of the total renovation was carefully considered to allow for a seamless interior access between the two spaces while maintaining the option for complete private separation, making this home perfectly suited for extended family living or as a primary residence with an income-producing unit. Upon entering, you are greeted by a gracious foyer with hardwood floors that flow throughout the main level with 10-foot ceilings. The open design connects a comfortable living room, featuring a classic gas fireplace and views of the water during the winter months, to

$2,299,000

5 beds— baths2,982 sq ft

40 Park Way, Sea Cliff, NY 11579

0.43 acre lot • 6 parking spots • Built 1893

Listing by Daniel Gale Sothebys Intl Rlty

ABOUT THIS HOME
5 Bedroom Homes for Sale in Glen Head, NY
Get ready for this beautiful, traditional dutch colonial. Greenvale, North Shore Schools, Gold Coast location. Rare opportunity! A blank canvas for your new custom home! Private Road

$1,199,000

5 beds3 baths3,264 sq ft

2 Addison Ln, Greenvale, NY 11548

0.26 acre lot • 3 parking spots • Built 1918

Listing by South Shore Marketing

Property at 40 W View Dr, Oyster Bay, NY 11771, 5 beds, 5.5 baths

$2,475,000

5 beds5.5 baths6,219 sq ft

40 W View Dr, Oyster Bay, NY 11771

Listing by Douglas Elliman Real Estate

Property at 65 Mellow Ln, Jericho, NY 11753, 5 beds, 5 baths

$2,280,000

5 beds5 baths3,700 sq ft

65 Mellow Ln, Jericho, NY 11753

Listing by Passerina LLC

Property at 60 Moss Ln, Jericho, NY 11753, 5 beds, 5.5 baths

$2,555,000

5 beds5.5 baths3,196 sq ft

60 Moss Ln, Jericho, NY 11753

Listing by Skylux Realty Inc

Property at 77 Duck Pond Rd, Glen Cove, NY 11542, 5 beds, 3 baths

$1,299,000

5 beds3 baths2,900 sq ft

77 Duck Pond Rd, Glen Cove, NY 11542

Listing by Howard Hanna Coach

Property at 5 Schoolhouse Ct, Oyster Bay, NY 11771, 5 beds, 6 baths

$2,549,000

5 beds6 baths6,816 sq ft

5 Schoolhouse Ct, Oyster Bay, NY 11771

Listing by Douglas Elliman Real Estate

Property at 38 High St, Roslyn Heights, NY 11577, 5 beds, 2 baths

$999,990

5 beds2 baths2,240 sq ft

38 High St, Roslyn Heights, NY 11577

Listing by Signature Premier Properties

Property at 24 Rolling Hill Rd, Old Westbury, NY 11568, 5 beds, 5 baths

$2,899,000

5 beds5 baths4,700 sq ft

24 Rolling Hill Rd, Old Westbury, NY 11568

Listing by BERKSHIRE HATHAWAY

Property at 2 Earle Dr, Syosset, NY 11791, 5 beds, 4.5 baths

$2,998,000

5 beds4.5 baths4,531 sq ft

2 Earle Dr, Syosset, NY 11791

Listing by Compass Greater NY LLC

Property at 300 Ellen Pl, Jericho, NY 11753, 5 beds, 4 baths

$1,599,888

5 beds4 baths3,228 sq ft

300 Ellen Pl, Jericho, NY 11753

Listing by Daniel Gale Sothebys Intl Rlty

Property at 14 Lakeville Dr, Roslyn, NY 11576, 5 beds, 3.5 baths

$2,250,000

5 beds3.5 baths3,638 sq ft

14 Lakeville Dr, Roslyn, NY 11576

Listing by Voro LLC

Property at 99 Warner Ave, Roslyn Heights, NY 11577, 5 beds, 3 baths

$1,768,000

5 beds3 baths3,089 sq ft

99 Warner Ave, Roslyn Heights, NY 11577

Listing by Coldwell Banker American Homes

Property at 5 Morgan Ln, Locust Valley, NY 11560, 5 beds, 4.5 baths

$1,898,000

5 beds4.5 baths3,635 sq ft

5 Morgan Ln, Locust Valley, NY 11560

Listing by NY Space Finders Inc

Property at 32 Valley Rd, Old Westbury, NY 11568, 5 beds, 3.5 baths

$2,246,000

5 beds3.5 baths3,692 sq ft

32 Valley Rd, Old Westbury, NY 11568

Listing by Genstone Properties

Property at 28 Earle Dr, Syosset, NY 11791, 5 beds, 5.5 baths

$5,750,000

5 beds5.5 baths9,000 sq ft

28 Earle Dr, Syosset, NY 11791

Listing by Serhant LLC

Based on information submitted to the MLS GRID as of Mon Dec 01 2025. 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.

5 Bedroom Homes for Sale in Glen Head

There are currently 11 5 bedroom homes in Glen Head. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Glen Head stay on the market for 73 days. Popular neighborhoods include North Hempstead, and Oyster Bay. This map is refreshed with the newest listings in Glen Head every 15 minutes.

In the past month, 4 homes have been sold in Glen Head. In addition to houses in Glen Head, there were also 4 condos, 1 townhouse, and 1 multi-family unit for sale in Glen Head last month. Find your dream home in Glen Head using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Glen Head are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Glen Head. Our Glen Head real estate stats and trends will give you more information about home buying and selling trends in Glen Head. If you're looking to sell your home in the Glen Head area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Glen Head with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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