Newest Homes for Sale in Glen Head, NY

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  /50

  $5,499,000

  • 9 Beds
  • 7.5 Baths
  • 8,200 Sq Ft

  8 Stonegate Ln, Glen Head, NY 11545

  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

  Lisa Ann Heaney Daniel Gale Sothebys Intl Rlty

  8 Stonegate Ln, Glen Head, NY 11545
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  /35

  $999,000

  $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,885 Sq Ft

  7 Cedar Ln, Glen Head, NY 11545

  Lovingly updated, this warm and inviting home in the Promenade section of prime Glen Head offers a versatile multi-level layout with 3 bedrooms and 2.5 bathrooms, including a spacious primary ensuite. Featuring multiple living and entertaining spaces across different levels, including a lower-level den/playroom and a generous backyard with multi-level decking. This home blends comfort and

  Vivian Parisi Daniel Gale Sothebys Intl Rlty

  7 Cedar Ln, Glen Head, NY 11545
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  /50

  $5,888,000

  New Construction

  • 6 Beds
  • 5.5 Baths
  • 7,855 Sq Ft

  2 Chelmsford Dr, Glen Head, NY 11545

  Discover unparalleled luxury in the heart of Muttontown at 2 Chelmsford Drive, a striking post-modern custom-designed new construction set on a breathtaking 2-acre country club setting. Surrounded by specimen plantings and professionally curated landscaping, this extraordinary estate offers exceptional craftsmanship, sophisticated design, and resort-style amenities throughout. A dramatic custom

  Janet Berookhim LAFFEY REAL ESTATE

  2 Chelmsford Dr, Glen Head, NY 11545
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  /49

  $3,700,000

  $300K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 6,122 Sq Ft

  343 Chicken Valley Rd, Glen Head, NY 11545

  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

  Kathryn Maxwell Pournaras Daniel Gale Sothebys Intl Rlty

  343 Chicken Valley Rd, Glen Head, NY 11545
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  /40

  $14,900,000

  • 7 Beds
  • 9 Baths
  • 15,743 Sq Ft

  1985- 4 Cedar Swamp Rd, Glen Head, NY 11545

  ‘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

  Jason Friedman Daniel Gale Sothebys Intl Rlty

  1985- 4 Cedar Swamp Rd, Glen Head, NY 11545
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  /45

  $2,595,000

  $280K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,240 Sq Ft

  4 Roads End, Glen Head, NY 11545

  An exceptional piece of North Shore history, “Lily Pond Hollow” is nestled in the heart of Brookville. This gentleman’s farmhouse was seamlessly and thoughtfully expanded with a great room, grand primary suite, and 3 car garage to make it comfortable for modern living. Standing as a reminder of Long Island’s rich history, the estate spreads out over two spectacular acres with an arboretum-like

  Paul Mateyunas Douglas Elliman Real Estate

  4 Roads End, Glen Head, NY 11545
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  /28

  $3,600,000

  $250K PRICE DROP

  • 7 Beds
  • 5.5 Baths
  • 5,073 Sq Ft

  285 Piping Rock Rd, Locust Valley, NY 11560

  Rosegate is an enchanting mini estate that harkens back to golden age of the North Shore of Long Island. This architectural gem has been thoughtfully expanded over the years into a stately 7-bedroom Colonial, set on 2.85 acres of lush, storybook grounds. Every inch of Rosegate exudes character and charm from its Ludowici style roof to its diamond trellis ivy covered walls. Step through the front

  Robert Hulse Compass Greater NY LLC

  285 Piping Rock Rd, Locust Valley, NY 11560
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  /50

  $5,688,000

  New Construction $212K PRICE DROP

  • 6 Beds
  • 7.5 Baths
  • 7,000 Sq Ft

  20 Knollwood Rd, Glen Head, NY 11545

  EXCEPTIONAL NEW CONSTRUCTION! Luxury Living at it's finest! Welcome to 20 Knollwood Road, Muttontown in the Jericho School District. Experience the pinnacle of luxury living in this newly built estate, offering approximately 7,000 square feet of refined design and superior craftsmanship by a highly regarded builder. Every inch of this home reflects meticulous attention to detail, from the bespoke

  Janet Berookhim LAFFEY REAL ESTATE

  20 Knollwood Rd, Glen Head, NY 11545
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  /45

  $4,399,000

  $400K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 6,049 Sq Ft

  93 Hoaglands Ln, Glen Head, NY 11545

  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

  Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

  93 Hoaglands Ln, Glen Head, NY 11545
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  /41

  $3,795,000

  • 6 Beds
  • 5.5 Baths
  • 5,911 Sq Ft

  23 Overbrook Ln, Glen Head, NY 11545

  Framed by sweeping pond views and surrounded by over 2 private acres of beautifully landscaped grounds, this beautifully renovated brick estate offers a rare blend of luxury, privacy, and serene waterfront living. Tucked away on a quiet cul-de-sac, the home is perfectly positioned to capture the beauty of the pond from both the interior living spaces and the resort-style outdoor setting.A

  

  Jagmeet Bedi

  Compass Greater NY LLC

  23 Overbrook Ln, Glen Head, NY 11545
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  /42

  $6,450,000

  $400K PRICE DROP

  • 7 Beds
  • 10 Baths
  • 7,485 Sq Ft

  6 Evergreen Way, Glen Head, NY 11545

  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

  Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

  6 Evergreen Way, Glen Head, NY 11545
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  /30

  $5,495,000

  • 6 Beds
  • 7.5 Baths
  • 8,500 Sq Ft

  45 Wolver Hollow Rd, Glen Head, NY 11545

  An exceptional private brick estate compound set on approximately7 meticulously manicured acres in Upper Brookville. This impressive residenceoffers grand scale, timeless elegance, luxurious landscaping, and a truelifestyle experience both inside and out. Filled with natural light, the homefeatures vaulted ceilings, oversized windows, sweeping property views,6 spacious

  Julia Krispeal Douglas Elliman Real Estate

  45 Wolver Hollow Rd, Glen Head, NY 11545
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  /5

  $6,399,999

  New Construction

  • 6 Beds
  • 8 Baths
  • 7,200 Sq Ft

  14 Wenwood Dr, Glen Head, NY 11545

  Brookville | Bring your dream home to life. 14 Wenwood Drive offers an opportunity like no other - a chance to add the final touches to a gorgeous 7,200 sq.ft. new home in the heart of Brookville. Featuring 6 bedrooms, 6 full baths, and one powder, with intricate attention to details throughout. Take advantage of the ability to curate finishes to your own taste. In addition to the open floor plan

  Joe Scavo Douglas Elliman Real Estate

  14 Wenwood Dr, Glen Head, NY 11545
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  /32

  $3,899,000

  • 6 Beds
  • 4.5 Baths
  • 5,254 Sq Ft

  91 Hoaglands Ln, Glen Head, NY 11545

  Nestled in the heart of Old Brookville, this private oasis offers the perfect blend of luxury, tranquility, and modern living. Set on a sprawling, flat 3.2 -acre lot within the prestigious North Shore School District, this property feels like your own year-round retreat.As you approach via the picturesque private driveway, you're greeted by lush, mature landscaping that ensures complete

  Allison Hollander Compass Greater NY LLC

  91 Hoaglands Ln, Glen Head, NY 11545
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  /30

  $8,350,000

  New Construction $400K PRICE DROP

  • 7 Beds
  • 10 Baths
  • 11,400 Sq Ft

  30 Evans Dr, Glen Head, NY 11545

  Set on 2 private, beautifully landscaped acres at the end of a cul-de-sac in the coveted Broad Hollow section of Brookville, this brand new construction delivers approximately 11,400 square feet of total living space — including a 3,600 SF walk-out lower level and fully appointed pool cabana.Seven en-suite bedrooms and 10 baths are spread across a floor plan that balances grand scale with

  Zach Elliott Nest Seekers LLC

  30 Evans Dr, Glen Head, NY 11545
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  /42

  $2,399,000

  $100K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 3,818 Sq Ft

  22 Brookville Rd, Glen Head, NY 11545

  Welcome to this beautifully transformed Carriage House, where historic charm meets modern living! This impressive main residence offers a spacious open floorplan, featuring three generous bedrooms and 2.5 bathrooms. The heart of the home is illuminated by a stunning wall of windows, flooding the space with natural light and providing gorgeous views of your serene graveled French garden—perfect

  Maria Mejia Blackstone Realty

  22 Brookville Rd, Glen Head, NY 11545
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  /35

  $5,488,888

  $406K PRICE DROP

  • 6 Beds
  • 7.5 Baths
  • 7,000 Sq Ft

  27 Victorian Ln, Glen Head, NY 11545

  Welcome to an extraordinary estates of timeless elegance located at 27 Victorian Lane, Brookville NY. — a distinguished estate that embodies architectural grace in one of the most prestigious residential setting. Set across approximately 2 acres of professionally landscaped grounds, this exceptional residence spans roughly 7,000 square feet of thoughtfully designed interior space, offering a rare

  Katherine Koniecko Signature Premier Properties

  27 Victorian Ln, Glen Head, NY 11545
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  /32

  $3,299,888

  • 6 Beds
  • 5.5 Baths
  • 4,400 Sq Ft

  33 High Farms Rd, Glen Head, NY 11545

  Welcome to a rare opportunity to own a fully renovated and extended estate—rebuilt from the studs up and reimagined for modern luxury in the heart of one of Long Island’s most coveted neighborhoods. Set on a beautifully manicured 2 acre lot, this 6-bedroom, 5.5-bathroom smart residence combines sophisticated design, premium finishes, and cutting-edge amenities, offering a seamless blend of

  Katherine Koniecko Signature Premier Properties

  33 High Farms Rd, Glen Head, NY 11545
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  /15

  $2,699,900

  $50K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,938 Sq Ft

  Unlisted Address

  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

  Colleen Chase Signature Premier Properties

  Unlisted Address
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  /2

  $3,800,000

  $300K PRICE DROP

  • Land
  • 7.09 Acres
  • $535,966 per Acre

  559 Cedar Swamp Rd, Glen Head, NY 11545

  Lovely 7.09 Acres of Residential Land a Great Builders Opportunity! This is not all flat land, it has beautiful hills. Located in Village of Old Brookville, The Address can be Brookville or Glen Head according to Village of Old Brookville same postal zip code. There is 2 acres zoning for this property, so 3 Beautiful Homes can be built on this property. All approvals would go to Village of Old

  Donna Greiner- Fisher Signature Premier Properties

  559 Cedar Swamp Rd, Glen Head, NY 11545
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  /42

  $2,099,000

  New Construction $186K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  9 Hill Dr, Glen Head, NY 11545

  Exceptional Custom-Built Colonial in the Heart of Glen HeadDon’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

  Brian Pryke Douglas Elliman Real Estate

  9 Hill Dr, Glen Head, NY 11545
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  /46

  $3,499,000

  $500K PRICE DROP

  • 6 Beds
  • 9 Baths
  • 7,887 Sq Ft

  12 Ridge Ct, Glen Head, NY 11545

  Welcome to 12 Ridge Ct, located in the heart of Old Brookville in the Brookville Meadows. This is your window of opportunity to live in the Gold Coast on 3.4 acres of flat land. From the moment you turn on to the tree-lined street (White Gate Dr.) entering Brookville Meadows, you will feel the caliber of luxury you are about to enter. This home boasts over 7,800 sq feet, the open layout will give

  Richard Brazzano BERKSHIRE HATHAWAY

  12 Ridge Ct, Glen Head, NY 11545
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  /22

  $3,500,000

  • 6 Beds
  • 9 Baths
  • 7,500 Sq Ft

  5 Carol Ln, Glen Head, NY 11545

  Elegance redefined in this stunning gem that blends an eclectic mix of mid-century modern design with a touch of contemporary sophistication, nestled on two lush, gated acres in Upper Brookville. From the moment you enter, the home captivates your imagination with its soaring 30-foot ceilings and dramatic windows and wood architectural elements. Clean lines, warm textures, and artful finishes

  Ken Deutsch Deutsch Realty Inc

  5 Carol Ln, Glen Head, NY 11545
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  /50

  $5,999,000

  New Construction $800K PRICE DROP

  • 6 Beds
  • 8.5 Baths

  12 Quaker Ridge Dr, Glen Head, NY 11545

  Brookville New Construction | Welcome home to 12 Quaker Ridge Drive — a pristine brick, center-hall colonial set on 2 acres at the end of a quiet cul-de-sac. This modern estate features six bedrooms — including a first-floor suite — formal living and dining areas, an open-concept kitchen, 3-car garage, and more.Behind a set of iron doors, you're welcomed by an open foyer and curved oak

  Joe Scavo Douglas Elliman Real Estate

  12 Quaker Ridge Dr, Glen Head, NY 11545
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  /36

  $5,585,000

  $3M PRICE DROP

  • 9 Beds
  • 12 Baths
  • 17,587 Sq Ft

  60 Piping Rock Rd, Glen Head, NY 11545

  Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless

  Aileen Murstein Compass Greater NY LLC

  60 Piping Rock Rd, Glen Head, NY 11545
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  /2

  $6,300,000

  New Construction

  • 7 Beds
  • 7.5 Baths
  • 7,500 Sq Ft

  1629 Cedar Swamp Rd, Glen Head, NY 11545

  Beautiful Flat 2 Acre Home in Jericho SD in Upper Brookville. Cabana with Gunite Pool, Elevator, Top Appliances, High Ceilings, Great Room w/ Linear Fire Place, Chefs Kitchen+Spice Kitchen, Top Appliances. Hide-A-Hose Central Vacuum. 5 Central Air Zones. Huge Backyard, Professionally designed landscaping. 10 ft first Floor, 10 ft basement, 12” 2nd floor in bedrooms. 4 Panel Slider in Basement!!

  Najla Erfan Property Professionals Realty

  1629 Cedar Swamp Rd, Glen Head, NY 11545
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  /50

  $4,500,000

  $2M PRICE DROP

  • 5 Beds
  • 7.5 Baths
  • 7,000 Sq Ft

  8 Vista Ln, Glen Head, NY 11545

  Incredible price reduction! Incredible Value! For the Discerning Client who seeks only the Finest....Welcome to 8 Vista Lane in Brookville--where Timeless Design and Bespoke Materials are blended to create this Sophisticated Modern Luxury. A Grand Courtyard leads to the Entrance of this Spectacular Private Estate. The Tone is set as Guests are greeted in the Breathtaking 30'high Domed Circular

  Ellen Zipes Compass Greater NY LLC

  8 Vista Ln, Glen Head, NY 11545
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  /26

  $5,490,000

  $2M PRICE DROP

  • 6 Beds
  • 5.5 Baths

  89 Pound Hollow Rd, Glen Head, NY 11545

  Where Drama Meets DesignWelcome 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

  Karen Sharf Daniel Gale Sothebys Intl Rlty

  89 Pound Hollow Rd, Glen Head, NY 11545

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