46 properties for sale in Glen Head

Introducing An Unparalleled Masterpiece Of Luxury Living On Estate Suited For A Celebrity. This Prestigious And Exclusive Private Brick Compound Situated On 7 Acres Of Lush, Sprawling Grounds In Upper Brookville Offers A Lifestyle That Seamlessly Combines Timeless Elegance With Modern Luxury. Vaulted Ceilings, Creating A Sense Of Openness. Oversized Windows With An Abundance Of Natural Light & Panoramic Views Of The Property. 6 Oversized Bedrooms W/En-Suite Baths, 7 1/2 baths, Large EIK With Generous Counter Space & Storage. For The Car Lover Enthusiast W/10 Car Garage, Top-Of-The-Line Car Lifts & Car Port. Entertainers Exclusive Front & Backyard. Custom-Designed 22,000 Gallon Koi Pond With Thoughtfully Placed Stone Work, Fountains & Lighting. Newly Resurfaced Har-Tru Tennis Court, Gunite Heated Pool, 8 Person Hot Tub, Pool House W/Kitchenette, Full Bath & Changing Room. Custom Outdoor Kitchen, Premium Speaker System Both Inside & Out. Embrace A Lifestyle In Your Private Sanctuary! Goo

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 Gunite inground gas heated pool. The flat entertaining backyard and brick patio, provides ample space to add tennis, pickleball or sport court. This serene oasis is perfect for relaxation and entertainment. Inside the kitchen features hardwood cabinets, complimented by gleaming hardwood flooring throughout the home. The architectural roof adds to the home's timeless elegance. First floor bedroom with en-suite bath and his and hers walk in closets, laundry, and a versatile bedroom/office with a walkout to the fabulous yard. There is so much more to this exceptional property that must be seen to be fully appreciated. Don't miss this rare opportunity to own a true

Set on 2.61 beautifully landscaped acres in the prestigious enclave of Old Brookville, this stately brick Georgian Colonial offers an exceptional blend of timeless architecture, generous living spaces, privacy, and versatility. A sweeping circular driveway creates a grand arrival, framed by mature plantings and lush grounds that provide a serene and secluded setting. Designed to embrace natural light, the residence features oversized windows throughout all three levels, complemented by natural oak hardwood floors that lend warmth and a refined feel. A two-story entry foyer establishes an elegant first impression, opening to an expansive main level with multiple distinct living spaces, including a formal living room, formal dining room, family room, and a versatile secondary sitting room or private office. The family room features a fireplace, while a thoughtfully designed eat-in kitchen offers a propane gas range, pantry, and sun-filled breakfast area surrounded by walls of windows. Sl

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Dream homes do exist. Perfectly situated on 2+ private, meticulously landscaped acres on a winding country lane, this charming 5-bedroom residence offers an unparalleled lifestyle. Every sun-drenched room provides stunning, expansive views of lush lawns, specimen trees, and vibrant perennial gardens. Exquisite Craftsmanship & Main Level Living. The main level showcases exceptional millwork, fine moldings, and rich hardwood flooring. A vaulted foyer welcomes you, leading to an elegant music room, a spacious living room, and a handsome cherry library with custom built-ins. The gourmet kitchen features premium appliances and custom Wood-Mode cabinetry, overlooking your private backyard oasis. A thoughtfully placed butler’s bar with a Sub-Zero wine cooler connects the kitchen to the formal dining room for seamless entertaining. A first-floor bedroom with a private en-suite bath is ideal for guests or multi-generational living. The second level hosts four additional bedrooms. The serene pri

Set behind private gates in the prestigious Estates at Greenfield, this stately brick Georgian Colonial is perfectly positioned on three + magnificently landscaped acres, offering an exceptional blend of timeless architecture and resort-style living. A gracious approach leads to a generous courtyard, creating a striking first impression and a true sense of arrival. Inside, a dramatic two-story center hall marble foyer showcases a sweeping wrought iron circular staircase and exquisite, detailed millwork that sets the tone for the home’s refined interiors. The formal living room is both elegant and inviting, complete with a custom built-in bar and hardwood floors while the generous dining room is perfectly suited for grand entertaining. A warm and inviting den with a fireplace sits just off the chef’s kitchen and sunlit breakfast nook, creating an ideal flow for everyday living. A richly appointed home office features its own fireplace, custom built-in shelving, and a convenient half bat

Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Ste

Welcome To 18 Quaker Ridge Drive. A Stately Colonial Set On Over Two Private Acres Within The Jericho School District. Along One Of Brookville's Most Picturesque Roads And Nestled In A Cul-De-Sac, This 5 Bedroom, 3.5 Bath Residence Presents The Best Of Both Worlds: Classic Architecture Inside And A Beautiful, Bucolic Setting Outside. Backing A Private Equestrian Property, The Home Offers Solitude And Tranquility With Sweeping Pastoral Views. Flat And Expansively Landscaped, The Grounds Are Designed For Both Relaxation And Entertaining. Featuring A 20'x 40' In-Ground Pool, Cabana, Specimen Plantings And Generous Covered Brick Patio - Creating A True Outdoor Sanctuary. There Is Plenty Of Room To Add Even More Amenities That Suit Your Lifestyle, Such As A Tennis Court Or Even Your Own Horse And Stable. Now Step Inside 18 Quaker Ridge - A Timeless Colonial With Generous Principal Rooms And The Convenience Of A First Floor Bedroom, Full Bathroom And Laundry Room. The Upper Level Boasts A Pr

An extraordinary custom-built estate set within one of Old Brookville’s most prestigious gated communities, this magnificent residence offers an exceptional setting for grand-scale living and refined entertaining. The seven-bedroom, 12-bathroom home is complemented by an impressive eight-car garage and an array of resort-style amenities, including a luxurious pool house, swimming pool, hot tub, and private tennis and multi-sport court. A rare offering that seamlessly combines scale, privacy, and sophistication in one of Long Island’s most coveted enclaves. A grand entrance hall with soaring ceilings introduces the home’s elegant interiors. The main level features a chef’s eat-in kitchen, breakfast room, formal living room, formal dining room, family room, library, and lounge, providing an ideal balance of formal and informal living spaces. The second floor is anchored by a commanding primary suite with expansive his-and-her walk-in closets and separate his-and-her bathrooms. The remain

Opportunity knocks! This charming three-bedroom, one-and-a-half-bath ranch is in desirable Glen Head with North Shore Schools. Convenient to the train, highways, and shops. A blank canvas ready to make your own, with endless possibilities and easy expansion potential!

Discover the pinnacle of everyday living where sophistication meets serenity in Old Brookville. Nestled away on its own private and unique compound, this expansive and meticulous ranch boasts 4 bedrooms, 5.5 baths, finished walkout basement. Spacious living areas perfect for entertaining, custom eat-in chef's kitchen boasting top-of-the-line appliances with two islands, granite counter tops, custom cabinetry & storage. Gunite heated pool with new patio and tennis court set amidst 2.4 acres. The 2 story pool house retreat with full kitchen, 2.5 baths & loft. Charming private guest cottage with 2 beds, 1 bath and kitchen, provides an additional space perfect for visitors or extended family. Award-winning North Shore schools, conveniently located to shopping, fine dining, country clubs and prestigious golf courses. This 1-of-a-kind residence offers a lifestyle of unparalleled opportunity, convenience & sophistication. Must see! Google Maps, Waze

Nestled on 2+ bucolic acres with sweeping golf course views, this stately European-style Manor home offers a rare balance of privacy and refinement. Soaring ceilings and bespoke finishes flow into the formal dining room and a dramatic great room with a floor-to-ceiling fireplace and French doors. The chef's kitchen showcases Calacatta marble, a large island, and premium appliances. The opulent master suite features a fireside sitting room, a boutique-style closet, and a luxurious marble bath with a shower for 2 and a bubble tub. The walk-out lower level is an entertainer’s paradise with 10-foot ceilings, a billiard room, wet bar, wine cellar, and a state-of-the-art movie theater. Outside, a grand loggia with a hearth provides a scenic setting for alfresco dining along the pristine fairways. Balancing grand hosting spaces with a private daily sanctuary, this magnificent Gold Coast retreat is near the shoreline, luxury shopping, and dining, with easy access to Manhattan and The Hamptons

‘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 one-of-a-kind masterpiece sits at the end of a private road on eight pristine acres. Beyond its wrought-iron gates, a long, tree-lined stone driveway leads to the stately residence, where every detail reflects exceptional craftsmanship and sophistication - from antique stone fireplace mantels and hand-painted wallpaper to crystal chandeliers and bespoke finishes throughout. A grand entrance hall with a sweeping marble staircase welcomes you to the main level. The formal living and dining rooms, each adorned with French doors, open seamlessly to the outdoor entertaining terraces and overlook the br

Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a grand living room, banquet-sized dining room, inviting family room, and a serene primary suite with fireplace, sitting area, and generous mirrored closets. A spacious country eat-in kitchen and a lower entertainment level with bar and gym further enhance the home’s appeal. Outdoors, the estate opens to multi-tiered gardens, expansive terraces and patios, an in-ground pool, pool house with full kitchen, 2 full baths and guest quarters, tennis/sport court, golf hole with 3 tee boxes, apple orchard, trellis, and outdoor barbecuing area. A rare offering that captures the privacy, grace, and endurin

Set on 2 private and beautifully landscaped acres at the end of a cul-de-sac in the coveted Broad Hollow development of Brookville, this newly built estate offers over 11,400 square feet of total living space—including a 3,600 SF walk-out lower level and a fully outfitted pool cabana—within the top-rated Jericho School District. Designed with a perfect balance of form and function, this luxurious home features 7 en-suite bedrooms and 10 baths, including a first-floor junior primary suite and a grand second-floor primary retreat with a spa-like bath, steam shower, double vanity and expansive his and her’s closets. Many of the secondary suites also feature access to private balconies with amazing views of the retreat-like landscape. Radiant heat runs throughout, and every detail is elevated with bespoke finishes, custom millwork, and designer craftsmanship. The interiors showcase a custom chef’s kitchen, a marble-wrapped family room feature wall, multiple Davinci fireplaces, and a striki

Welcome to this exceptional 2.29-acre park-like estate, located at the end of a private cul-de-sac in the Jericho School District. This extraordinary contemporary residence offers a unique blend of architectural brilliance and resort-style living, designed for both grand entertaining and comfortable everyday life. As you arrive, a circular driveway paved with cobblestone, flame granite, and Belgium block leads to the impressive granite façade of this sensational home. Expertly crafted with technical precision and architectural artistry, the home features an open, multi-level layout where each room is oriented to maximize views and natural light. The main level is graced by stunning 1860s 2.5-inch marble flooring, offering panoramic perspectives of the home's dramatic design. Walls of glass, bronze entryways, and soaring ceilings create a seamless connection between the indoors and the outdoors. The breathtaking family room serves as the heart of the home, complete with a sensational ma

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

Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors that frame picturesque garden views and flood the interiors with natural light. The gracious living and dining areas are anchored by a striking double-sided stone fireplace, creating architectural interest and a warm, inviting ambiance. A sophisticated bar room with wine refrigeration and custom painted cabinetry enhances the cozy den, offering the perfect setting for entertaining. The expansive kitchen and family room serve as the heart of the home, featuring a dramatic double-height vaulted ceiling with loft above and seamless access to a side terrace ideal for outdoor dining and gatherings. Be

An Exceptional Brookville Estate | Timeless Architecture & Refined Modern Living Privately situated behind electric gates on over 2.53 acres of exquisitely landscaped grounds, this extraordinary custom-built Brookville Colonial presents a sophisticated interpretation of timeless architecture and contemporary luxury. Completed in 2020 and distinguished by its striking slate roof, elegant stonework, and meticulously curated interiors, the residence offers an exceptional combination of architectural grandeur, superior craftsmanship, and resort-inspired living. A sweeping stone driveway introduces the estate, where classic proportions, elegant black-trimmed windows, and beautifully manicured grounds establish an impressive sense of arrival. Inside, soaring ceilings, intricate custom millwork, rich herringbone hardwood floors, oversized windows and interiors designed for both grand-scale entertaining and refined everyday living. A gracious entrance foyer unfolds into a series of beautifully

Set behind the gates of an exclusive community in the Village of Old Brookville, this exceptional modern residence offers more than 7,000 square feet of luxurious living space on over three acres of beautifully manicured, private grounds. Walls of windows fill the home with natural light while showcasing serene views of the surrounding landscape, inground pool and hot tub. A dramatic two-story entry introduces the impressive main level, featuring a soaring two-story great room with a striking stone wet bar, a formal dining room and a private home office. The expansive eat-in kitchen includes a spacious breakfast area and provides an inviting setting for both everyday living and entertaining. A generously sized junior primary suite and an additional bedroom completes the first floor. Upstairs, the expansive primary suite serves as a private retreat with dual walk-in closets, a luxurious primary bathroom and a generous terrace. Three additional bedroom suites each feature their own priva

Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private

Welcome to this commanding five-bedroom contemporary residence, a spectacular home where soaring architecture, abundant natural light, and resort-style amenities combine to create an extraordinary living experience. From the moment you enter the dramatic two-story foyer, you are captivated by three magnificent floor-to-ceiling Palladian windows that frame breathtaking views of the terraced, verdant grounds beyond. The home's impressive two-story ceilings, rich hardwood floors, four fireplaces, and generously proportioned principal rooms create an atmosphere that is both grand and inviting, while seamlessly blending the beauty of the outdoors with every interior space. Designed for both everyday living and elegant entertaining, the home features a stunning culinary kitchen appointed with lacquered cabinetry, dual center islands, and an extraordinary Redwood Triple Glass Conservatory that bathes the space in natural sunlight. After dining in the elegant dinig room enhanced by a fireplace

A long driveway opens to a large courtyard with a classic fountain, revealing a magnificent Château-style Mansion on 2.03 acres of verdant property on a private cul-de-sac. Custom built for grand entertaining and everyday living, this incredible residence masterfully blends old-world European charm with modern luxury. A majestic 2-story entry foyer features a stunning domed-vaulted ceiling with a curved staircase, showcasing antiqued mirrored panels and an ornate wrought iron railing. Through a series of exquisite arches, the foyer leads to an expansive formal living room with a detailed ceiling and wall-to-wall windows as well as a palatial-sized dining room with a butler’s pantry that offers a wet bar and additional storage. The comfortable family room has a unique curved wall and a marble fireplace flanked by marble goddesses. Adjacent is a sitting room with a floor-to-ceiling built-in display wall and a cozy hexagonal built-in bay window seating area. Next door, an elegant study of

Welcome to The Knolls, a beautifully landscaped and meticulously maintained gated condominium community offering effortless, low maintenance living in a prime location. This exceptional 2700 square foot residence features 3 bedrooms and 3 full baths, thoughtfully designed with spacious living areas, abundant natural light, and a highly functional floor plan. The sun-filled gourmet eat-in kitchen offers generous cabinetry, ample workspace, and room for casual dining. The elegant living room is anchored by a wood burning fireplace and open to a private wood deck, creating the perfect setting for indoor-outdoor entertaining and relaxation. The spacious primary suite is a true retreat, featuring deck access, abundant closet space, and the convenience of an upstairs laundry area. A second laundry room on the lower level provides added flexibility and convenience. The expansive lower level offers exceptional additional living space with outside access, making it ideal for a family room, home

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 b

Set within the rarefied landscape of Old Brookville, this striking Mid-Century Modern residence is a study in architectural drama and refined design. Celebrated in Luxe Interiors + Design at the time of its transformation, the home reflects the visionary collaboration between its owners and the acclaimed firm Garcia/Maldonado, Inc. The result is a masterwork where every line, material, and proportion has been considered with uncompromising precision. A rich palette of exotic woods—mahogany, oak, and birch—anchors the interiors with warmth and texture, while the architecture itself unfolds with quiet grandeur. The great room is nothing short of breathtaking: a soaring vaulted ceiling, commanding fireplace, and an expansive wall of glass dissolve the boundary between indoors and out, flooding the space with natural light and framing the surrounding landscape as living art. An elegant dining room overlooks the property and is the perfect venue for entertaining. At the heart of the home, t

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. Inside, the richly paneled foyer and wide pegged oak floors set the stage for exquisite architectural details, including a sweeping staircase and intricate custom millwork. The first floor offers a seamless blend of grandeur and comfort. The magnificent living room and banquet-sized dining room both feature elegant fireplaces, while the gourmet kitchen boasts a spacious center island and a bright breakfast room. A butler’s pantry adds convenience, and the library, adorned with built-in bookcases and a fireplace, offers a cozy retreat. Additional highlights include a sunroom, two en suite guest bedrooms, a first-floor washer/dryer, and a powder ro

Set on over 2.5 exceptionally private and beautifully landscaped acres in the prestigious Village of Brookville, 25 Old Wheatley Road is a distinguished European-inspired estate offering timeless architecture, impressive scale, and an exceptional indoor-outdoor lifestyle. The residence makes an immediate impression with its masonry exterior, slate rooflines, sculptural chimneys, arched windows and openings, wrought-iron balconies, and beautifully articulated architectural detailing. Projecting bays, dormers, and varied roof forms create depth and character, while a sweeping stone-paved motor court provides an elegant approach to the home and its integrated three-car garage. Inside, the residence is defined by grand proportions, refined finishes, and a thoughtful floor plan designed for both formal entertaining and comfortable everyday living. A gracious central entry hall and gallery establish the main axis of the home, connecting an expansive formal living room, private library, forma

Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 15+ 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 just moments from New York City. Originally commissioned in 1924 for noted industrialist and financier Benjamin Brewster Jennings - President and Chairman of Socony-Mobil and a prominent figure in New York's financial and corporate circles - this Georgian Revival brick residence with a cascading slate roof was masterfully designed by renowned architect Walter B. Chambers. The estate's distinguished landscape plan was created by legendary landscape architect Ellen Biddle Shipman, whose formal gardens and thoughtfully designed grounds continue to define the property's enduring beauty. Approached b