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$2,775,000
4 Beds ⋅ 4 Baths ⋅ 1025463 MLS
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.

153 Brookville Lane, Glen Head
$3,950,000
5 Beds ⋅ 8 Baths ⋅ 1010610 MLS
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
$2,995,000
3 Beds ⋅ 3 Baths ⋅ 1003540 MLS
Built new in 2017 with the highest of standards on an ultra-private 1 acre property in Glen Head. This one level 3 bedroom ranch luxury home offers quality finishes, exceptional craftsmanship and a comfortable floor plan. The main living area is an open concept eat-in-kitchen to a great room with fireplace and formal dining. A separate den with beautiful paneled walls is to the front of the house. Custom millwork, high ceilings and wide plank hardwood floors throughout. Natural gas and full radiant heat. The custom kitchen is equipped with Wolf and Sub-Zero appliances, quality cabinetry, marble countertops, centre island and premium details. Spacious primary bedroom suite with lux primary bathroom. Lots of closets and storage. Full basement with outdoor entrance, complete with gym, office and recreational room, cedar closet and more. Outdoor living is equally impressive with a covered heated lanai, bluestone patio, heated gunite swimming pool, pavilion/pool house, outdoor shower, and lush professional mature landscaping creating a true private retreat. Additional highlights include James Hardie siding, real stone veneer, alarm and camera system, sprinkler system, epoxy-finished 2-car garage, and two hidden storage sheds. A rare North Shore offering combining privacy, luxury and resort-style living. North Shore School District, Glen Head Elementary and quick access to local towns and shops, golf and tennis clubs, beaches and more.

379 Frost Pond Road, 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
$1,375,000
4 Beds ⋅ 2 Baths ⋅ 981017 MLS
As spring arrives, an exceptional opportunity awaits to own this beautifully updated original Stern Family home, thoughtfully reimagined and extensively renovated in 2024, ideally situated in Glen Head’s sought-after Hill Terrace and overlooking the prestigious Engineers Country Club golf course. This high-end center hall Colonial seamlessly blends classic Tudor-inspired design with modern luxury and offers a true turn-key lifestyle where every detail has been thoughtfully addressed. Newly refinished hardwood floors run throughout, complemented by a freshly painted interior, all new Pella windows, updated bathrooms featuring new toilets throughout, and a slate roof that has been professionally cleaned and well maintained. The fully renovated eat-in kitchen is a true showpiece, featuring a quartzite waterfall island, Wolf 6-burner gas range with pasta water spout, Sub-Zero refrigerator, beverage refrigerator, and radiant heated floors. The kitchen flows effortlessly into the dining area with direct access to the backyard. The living room offers a wood-burning fireplace and connects to a heated sunroom with access to the yard, providing additional living space. The second level features a sun-filled primary bedroom along with three additional bedrooms. The fully finished walk-out lower level adds approximately 650 square feet of living space and includes a recreation area and a new, modern laundry room. Step outside to your private outdoor oasis, complete with an in-ground saltwater pool with a new liner, heated spa with waterfall feature, and an outdoor kitchen equipped with a BBQ, sink, and refrigerator. The property is enhanced with mature plantings, in-ground sprinklers, and outdoor lighting. Additional features include a two-car detached garage, oversized driveway, and an electric vehicle charging station conveniently located by the garage. Conveniently located near shopping, dining, transportation, and major roadways, and located within the sought-after North Shore School District. Don’t miss this exceptional opportunity.

60 Roosevelt 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
$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
$2,099,000
4 Beds ⋅ 3 Baths ⋅ 920526 MLS
Exceptional Custom-Built Colonial in the Heart of Glen Head Don’t miss this rare opportunity to own a truly one-of-a-kind custom-built home in the desirable Glen Head community. Thoughtfully designed and built with no expense spared, this residence is a masterpiece of quality craftsmanship, luxury finishes, and modern functionality — far beyond basic or “just to code.” Step into a grand center hall colonial featuring a dramatic entry foyer, stunning custom white oak flooring, and intricate moldings throughout. The expansive open-concept layout flows seamlessly into a gourmet chef’s eat-in kitchen, complete with a massive 2” quartz island, top-of-the-line GE Cafe appliances, LED lighting, and custom cabinetry — ideal for everyday living and entertaining. Unmatched Construction & Features: Radiant heat throughout all levels, including the basement, Superior 2"x6" framing and steel beam construction, 10' ceilings on lower level, 9' on main and 8' upstairs, One-foot-thick foundation for durability and insulation. All principal rooms are generously sized, filled with natural light, and designed for both comfort and elegance. Outside, enjoy your private backyard oasis with a beautiful in-ground pool featuring a smart filtration system and automated retractable cover, plus a sleek outdoor kitchenette area — perfect for relaxing and entertaining year-round. All perfectly situated on over a quarter-acre of manicured property in a prime location. This home is a rare gem offering the perfect blend of timeless design and cutting-edge construction.

9 Hill Drive, Glen Head

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.