Browse All Glen Head NY 5 Bedroom Properties for Sale

Welcome to 8 High Meadow Ct, a stunning classic all brick Colonial spanning 6000sqft of luxury set on a magnificent serene Old Brookville cul de-sac. This 5 bedroom Gem is rich with architectural details, exquisite millwork and designer finishes. A Gracious two-story Foyer introduces expansive principle rooms including Living Room/Fireplace, Formal Dining room, Den/Fireplace and Library/Office /Fireplace for effortless grand entertaining or more intimate gatherings Custom Cabinetry surrounds the fabulous Chef's dream Kitchen for endless storage with separate spacious Breakfast room overlooking pool setting. The primary bedroom is a lavish retreat with sun-lit sitting room, fireplace, wardrobe dressing area and luxurious spa bath occupying the prime position of the 2nd floor . Two spacious bedrooms with shared bath and wrap around hallway leading to 4th en-suite bedroom complete the 2nd floor. Lower level is partially finished with playrooms, storage closets, large cedar closet and 1/2 bath. Step outside to brick-walled patio with built-in BBQ and multiple bluestone patios and walkways lined with vibrant gardens leading to the sparkling gunite heated pool with jacuzzi waterfall, Surrounded by lush landscaping, a covered patio with ceiling heaters opens to the very spacious Guest/Pool House with living room, full kitchen , full bath, laundry room and dressing room for a year round retreat. 3 car garage. 2 magnificent private acres, Locust Valley SD. By Appointment

8 High Meadow Court, Glen Head

$1,699,000

5 Beds ⋅ 6 Baths ⋅ 992632 MLS

Set in the heart of Glen Head, this exceptional expanded farm ranch at 30 Todd Drive is full of surprises — a home that truly goes on and on, offering far more space than you would ever imagine from the moment you arrive. Rebuilt and substantially enlarged in 2002, this meticulously maintained residence features 5 bedrooms with potential for a 6th bedroom, 4 full bathrooms, and 2 powder rooms across an expansive and thoughtfully designed layout, including an additional 1,535 square feet of finished lower-level space with egress access to the backyard. A welcoming foyer introduces beautifully scaled interiors highlighted by oversized rooms, rich hardwood flooring, and custom architectural details throughout. The spectacular eat-in kitchen serves as the heart of the home, featuring a large center island with seating, granite countertops, stainless steel appliances, extensive cabinetry, and generous dining space with sliding glass doors opening to the backyard. The formal dining room is perfectly positioned with oversized windows overlooking the private grounds, filling the space with natural light. The impressive family room showcases soaring vaulted ceilings and a dramatic stone wood-burning fireplace, creating a warm and inviting atmosphere with an additional set of sliding doors leading outdoors. The main-level primary suite offers a peaceful retreat complete with a spa-inspired bath and oversized walk-in closet. A second first-floor ensuite bedroom provides ideal accommodations for guests, extended family, or multigenerational living. Upstairs, an additional ensuite bedroom is complemented by two spacious bedrooms, a shared full bath, and a bonus den. The finished lower level provides exceptional additional living space with approximately 1,535 square feet, including laundry, abundant storage, and an expanded area with direct egress access to the rear property. Outside, the secluded backyard is surrounded by mature landscaping and designed for effortless outdoor enjoyment, featuring a patio, gas cooking hookup, basketball area, and exceptional privacy. An oversized two-car garage completes this outstanding offering. A rare North Shore opportunity combining expansive living space, thoughtful design, and timeless appeal, all conveniently located near shopping, dining, public transportation, and within the acclaimed North Shore School District.

30 Todd Drive E, Glen Head

$1,688,000

5 Beds ⋅ 4 Baths ⋅ 989458 MLS

Room for everyone in this expanded and updated Glen Head center hall colonial offering 5 bedrooms and inviting living spaces. The impressive entrance highlights the custom stairs and millwork. An open floor plan is convenient for today's lifestyle. The spacious living room features a fireplace and opens to the gracious formal dining room with double doors leading to the private rear patio complete with outdoor kitchen. An expansive kitchen offers Wolf gas cooking, double ovens and lots of counter space making cooking and entertaining a breeze. The second floor highlights the sun drenched primary bedroom with soaring 11 ft ceilings and french doors to bath featuring radiant heated floors. The additional 4 bedrooms are all spacious with generous storage spaces. Two additional full baths are located on the second floor. A lower level introduces ample recreation areas, laundry room and full bath. This home does not disappoint. Conveniently located within steps to the North Shore Middle/High Schools, close to LIRR, shopping, dining and Tappen Beach.

1 Kissam Lane, Glen Head

$2,650,000

5 Beds ⋅ 5 Baths ⋅ 992824 MLS

Tucked away in the sought-after North Shore Acres neighborhood of Glen Head you will find this refined home combining contemporary flair with traditional details set on .53 acre. Reimagined within the last 10 years to include all new wood floors, moldings, stairs, kitchen and baths. This property checks all the boxes, a bespoke wood-mode kitchen w/calcutta marble counters, center island and premium appliances. A first floor guest suite includes a new full bath. Soaring ceilings with new skylights drenching the living spaces with natural light. The primary suite w/spa-like marble bath, soaking tub, steam shower and double vanities. Additional 3 bedrooms and new full bath all located on second floor. The full walk-out lower level features additional living spaces, additional bedroom and full bath. Sliders provide access to the outdoor oasis where you will find the in-ground saltwater pool with wading area, hot - tub, firepit, new pavers where you can enjoy it all in complete privacy. A CoverSafe Automtic Pool Cover offers peace of mind. You have a found a home that has been loved and renovated with the utmost quality including a new roof, gutters, skylights and exterior painting all done this year. Nothing to do but enjoy living in this beautiful home in an exclusive neighborhood that is also convenient to schools, LIRR, shopping and dining. Taxes have been successfully grieved for upcoming year. North Shore School District.

4 Cross Lane, Glen Head

$2,699,000

5 Beds ⋅ 4 Baths ⋅ 989507 MLS

Welcome to this exceptional home located in Brookville Village, within Jericho School District. Perfectly situated in a peaceful and quiet neighborhood, this property offers both comfort and convenience. Close to schools, making daily routines effortless; Easy access to major highways for a smooth commute; Minutes from shopping, dining, and everyday essentials; New attic insulation for improved energy efficiency; Brand new roof for long-term peace of mind; Newly installed 22 kW whole-house generator; Chimney recently repointed with new lining; Recently redone gunite pool – perfect for relaxation and entertaining; Spacious outdoor area ideal for gatherings and activities; This home combines modern upgrades with a tranquil setting, offering a rare opportunity to own this move-in ready gem!

14 Ormond Park Road, Glen Head

$1,099,999

5 Beds ⋅ 2 Baths ⋅ 988576 MLS

Welcome home to this charming expanded cape nestled on a quiet street in desirable Glenwood Landing. This 5-bedroom, 2-bath residence is just a short distance from local schools and golf course. The main level features an inviting open-concept layout, highlighted by a warm and welcoming living room with a cozy wood-burning fireplace. The dining area is ideal for entertaining, while the kitchen boasts a peninsula with seating—perfect for casual meals or gathering with guests. A versatile bonus room with sliding glass doors opens to the backyard, creating seamless indoor-outdoor living. Two bedrooms and a full bath with double sinks and a walk-in shower complete this level. Upstairs, you’ll find three additional bedrooms and another full bath. One standout bedroom features vaulted ceilings and sliding glass doors leading to a private deck—an ideal spot to unwind and enjoy sunset views. The full basement offers a separate entrance, generous storage space, and a washer and dryer. Step outside to a beautiful backyard featuring both a deck and patio—perfect for entertaining or relaxing—along with a detached two-car garage. Don’t miss this opportunity to own a beautiful home in a highly sought-after location.

11 Edgewood Avenue, Glen Head

$2,699,900

5 Beds ⋅ 4 Baths ⋅ 974758 MLS

Stunning Old Brookville Estate on 2 Acres with Pool & Outdoor Oasis Welcome to this exquisite 5-bedroom, 4-bathroom home nestled on 2 acres of beautifully landscaped property in the prestigious area of Old Brookville. This elegant residence offers the perfect blend of luxury, comfort, and privacy. Step inside to discover spacious living areas filled with natural light, including a grand living room with a cozy fireplace, a formal dining room, and a gourmet kitchen. The primary suite is a private retreat, complete with a spa-like en-suite bathroom. The fully finished basement is an entertainer’s dream, featuring a custom bar and ample space for gatherings. Outdoors, enjoy a serene backyard paradise with an in-ground pool, a charming gazebo, and a spacious patio—perfect for relaxing or entertaining. This exceptional property offers a rare opportunity to own a piece of paradise in one of Long Island’s most desirable locations. Don’t miss out on this remarkable home!

Glen Head

$1,895,000

5 Beds ⋅ 5 Baths ⋅ 975020 MLS

A Rare 2-Acre North Shore Estate-Like Setting Offering Privacy, Presence, and Endless Potential Set on approximately 2 acres of private, park-like grounds, this timeless Colonial with vintage charm presents a truly rare opportunity in the heart of Glen Head. Privately set back and gently elevated from the road along a long, tree-lined approach, the property offers an exceptional sense of space and seclusion—an increasingly rare offering on the North Shore. Overlooking the surrounding area, the home enjoys beautiful natural light and the opportunity to take in stunning sunset views from its elevated setting. Inside, the home features a classic and functional layout with expansive living areas, a formal dining room, and a bright breakfast nook designed for both everyday living and effortless entertaining. A charming original butler’s pantry adds character and functionality, while central air provides year-round comfort. A standout feature is the detached 3-car garage with electric, offering exceptional flexibility for vehicles, storage, or a workshop. The true highlight remains the land—flat, usable, and rich with possibility—offering the perfect canvas to create a custom outdoor retreat, expand, or simply enjoy the tranquility of your own private setting. Recent updates include a roof and gutters less than one year old, a burner approximately 6 years old, and a hot water heater approximately 3 years old, adding additional value and peace of mind. Ideally located just moments from shopping, dining, and transportation, this property delivers the rare balance of privacy, scale, and convenience.

195 Cedar Swamp Road, Glen Head

$2,480,000

5 Beds ⋅ 4 Baths ⋅ 937836 MLS

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.

4 Norgate Road, 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.

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