Glen Head, NY Homes for Sale

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  $5,999,999

  $1M PRICE DROP

  • 6 Beds
  • 5.5 Baths

  89 Pound Hollow Rd, Glen Head, NY 11545

  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

  Karen Sharf Daniel Gale Sothebys Intl Rlty

  89 Pound Hollow Rd, Glen Head, NY 11545
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  /36

  $7,300,000

  $950K 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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  /30

  $8,750,000

  • 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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  /44

  $6,475,000

  • 6 Beds
  • 6 Baths
  • 6,474 Sq Ft

  10 Colonial Dr, Glen Head, NY 11545

  Set on 5 flat, impeccably landscaped acres at the end of a quiet cul-de-sac, this stately Georgian brick estate represents one of the most private and desirable settings within Upper Brookville’s prestigious gated Colonial Drive enclave. Positioned on a private road of distinguished luxury estates and further enhanced by its own secondary gated entrance, the property offers a rare double gated

  Nareeta Saini Daniel Gale Sothebys Intl Rlty

  10 Colonial Dr, Glen Head, NY 11545
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  /23

  $998,000

  • 4 Beds
  • 2 Baths
  • 1,561 Sq Ft

  20 Robert Rd, Glen Cove, NY 11542

  Beautiful Colonial-style home with North shore school and located in a desirable tree-lined community, totally renovated in 2023, modern amenities include curb appeal, when entering you will find a thoughtfully designed layout that maximizes space and lots of natural sunlight, 4 Bedrooms, 2 Full Baths with radiant heated floors, large laundry room with custom cabinetry and window, washer and

  Carolina Boucos Daniel Gale Sothebys Intl Rlty

  20 Robert Rd, Glen Cove, NY 11542
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  /24

  $1,099,999

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  2 Ashley Place, Glen Head, NY 11545

  Welcome to 2 Ashley Place, a charming 3 bedroom, 2 bath home nestled in the heart of Glen Head. Brimming with curb appeal, this inviting residence offers timeless character and warm, inviting living spaces. The first floor has hard wood floors throughout the dining room and living room.The spacious living room has a beautiful beamed ceiling and is centered around a classic wood burning fireplace,

  Regina Ciardullo LAFFEY REAL ESTATE

  2 Ashley Place, Glen Head, NY 11545
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  $6,850,000

  • 7 Beds
  • 11 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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  /43

  $12,800,000

  • 10 Beds
  • 15 Baths
  • 20,000 Sq Ft

  53 Simonson Rd, Glen Head, NY 11545

  Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary. A striking

  Jason Friedman Daniel Gale Sothebys Intl Rlty

  53 Simonson Rd, Glen Head, NY 11545
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  /19

  $710,000

  Open Thu 12PM - 2PM

  • 6 Beds
  • 3 Baths
  • 2,964 Sq Ft

  2 Huron St, Glen Head, NY 11545

  Public online Auction: Bidding opens 5/26/26 @ 1 pm & Ends 5/28/26 1 pm (approx). The price of property exclusively represents the suggested opening bid & not the price of the property. Sold "as-is". Great opportunity for a buyer who does their homework & is looking to purchase a 2 family fixer-upper in Glen Head. Please read all information-your due diligence is necessary. Registration deadline

  Sandi Polinsky David R Maltz And Co Inc

  2 Huron St, Glen Head, NY 11545
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  /37

  $1,688,000

  • 5 Beds
  • 3.5 Baths
  • 2,764 Sq Ft

  1 Kissam Ln, Glen Head, NY 11545

  This Glen Head center hall colonial has been updated and expanded 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. A spacious living room with fireplace opens to the gracious formal dining room with double doors leading to the private rear patio complete with outdoor kitchen.

  Laura Algios Daniel Gale Sothebys Intl Rlty

  1 Kissam Ln, Glen Head, NY 11545
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  /2

  $6,399,999

  • 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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  $4,700,000

  • 6 Beds
  • 7.5 Baths
  • 5,607 Sq Ft

  17 Quaker Ridge Rd, Glen Head, NY 11545

  A gracious circular driveway welcomes you to this exceptional newly renovated residence, perfectly situated at the end of a coveted cul-de-sac. The home showcases the finest designer finishes throughout, including custom cabinetry, wood flooring, two fireplaces, exotic marble and stone. At the heart of the home is a truly spectacular, top-of-the-line Christopher Peacock kitchen wood cabinetry,

  Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

  17 Quaker Ridge Rd, Glen Head, NY 11545
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  /50

  $5,899,999

  New Construction

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

  20 Knollwood Rd, Glen Head, NY 11545

  EXCEPTIONAL NEW CONSTRUCTION! 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 millwork and custom paneling

  Janet Berookhim LAFFEY REAL ESTATE

  20 Knollwood Rd, Glen Head, NY 11545
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  /30

  $788,000

  • 3 Beds
  • 1 Bath
  • 1,412 Sq Ft

  2 Nancy Ct, Glen Cove, NY 11542

  Roxbury Ranch offers Living Room with wood burning Fireplace, dining room, Eat in Kitchen, Den with Vaulted Ceilings, 3 Bedrooms, Hall full bath with double vanities, full basement, part finished with heat, office, laundry, work out area, gym, storage room and utilities, outside front covered porch and deck in rear with lush and beautiful yard. Brand New Roof and CAC.

  Mishelle Berger Calo Compass Greater NY LLC

  2 Nancy Ct, Glen Cove, NY 11542
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  /35

  $738,000

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft

  6 Littleworth Ln, Sea Cliff, NY 11579

  Welcome to this warm and recently updated home in the heart of Sea Cliff, offering the perfect blend of charm, comfort, and convenience. Featuring 3 well-proportioned bedrooms and 1.5 bathrooms, this inviting residence is highlighted by a classic front porch—an ideal space to unwind and enjoy the peaceful surroundings.This home seamlessly integrates modern updates with a cozy, welcoming

  lily zhang ZI Realty LLC

  6 Littleworth Ln, Sea Cliff, NY 11579
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  /4

  $2,750,000

  New Construction Coming Soon

  • 5 Beds
  • 5.5 Baths
  • 4,900 Sq Ft

  8 Club Rd, Sea Cliff, NY 11579

  Poised on nearly half an acre of manicured grounds in one of the North Shore's most storied waterfront villages, this newly constructed residence offers an exceptional standard of living where coastal serenity meets refined modern design. Spanning approximately 4,900 square feet across three thoughtfully finished levels, the home presents five bedrooms, four full and one half bathrooms, and an

  Damian Ross Daniel Gale Sothebys Intl Rlty

  8 Club Rd, Sea Cliff, NY 11579

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