Glen Head, NY Homes for Sale

• 

  

  

  /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
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /34

  $2,499,999

  • 5 Beds
  • 3.5 Baths
  • 3,594 Sq Ft

  19 Pheasant Hill Ln, Glen Head, NY 11545

  This extraordinary Old Brookville estate at 19 Pheasant Hill Lane, featured in Architectural Digest, is a rare Georgian inspired residence that embodies timeless architecture, exceptional craftsmanship, and refined design. Perfectly positioned on two flat, private acres along one of Old Brookville’s most peaceful and coveted streets, this 5 bedroom, 3.5 bath home offers elevated living within the

  Emil Koniecko Signature Premier Properties

  19 Pheasant Hill Ln, Glen Head, NY 11545
• 

  

  /50

  $8,995,000

  • 5 Beds
  • 12 Baths
  • 9,500 Sq Ft

  7 Covey Ct, Glen Head, NY 11545

  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

  John Messina Daniel Gale Sothebys Intl Rlty

  7 Covey Ct, Glen Head, NY 11545
• 

  

  /47

  $5,295,000

  • 6 Beds
  • 9 Baths
  • 6,921 Sq Ft

  5 Farmwoods Ln, Glen Head, NY 11545

  Imagine an exclusive lifestyle redefined within a private HOA gated community, where absolute security meets unparalleled luxury on a flat, beautifully landscaped 2.53-acre parcel. This masterfully constructed 7,000-square-foot estate—boasting an impressive six bedrooms and seven bathrooms, each with their own private balcony—is defined by ultra-high-quality finishes throughout, including radiant

  Batul Morbi Compass Greater NY LLC

  5 Farmwoods Ln, Glen Head, NY 11545
• 

  

  /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
• 

  

  /50

  $3,480,000

  • 5 Beds
  • 4.5 Baths
  • 5,446 Sq Ft

  7 Mac Lean Dr, Glen Head, NY 11545

  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,

  Huailing Deng Daniel Gale Sothebys Intl Rlty

  7 Mac Lean Dr, Glen Head, NY 11545
• 

  

  /37

  $2,675,000

  Open Sat 12PM - 1:30PM Coming Soon

  • 5 Beds
  • 3.5 Baths
  • 4,421 Sq Ft

  10 Dorchester Dr, Glen Head, NY 11545

  Located within a picture perfect community of pristine properties, this striking sprawling Ranch Residence is set on 2 acres of rolling green lawns, professional gardens, and mature evergreens. This Gracious Home welcomes Guests through the handsome Double Door Entry to an Expansive Reception Foyer where classic Wrought Iron Railings line a Circular Staircase. Ideal for Grand Entertaining, the

  Ellen Zipes Compass Greater NY LLC

  10 Dorchester Dr, Glen Head, NY 11545
• 

  /2

  $649,000

  $114K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,499 Sq Ft

  31 Glenwood Rd, Glen Head, NY 11545

  AUCTION/OCCUPIED. 3- bedroom, 2 bath 1,499 square feet home sitting on 6,200 square foot lot inGlenwood Landing. Home is a short distance from Glen Head LIRR station, 3 different golf courses and SeaCliff Beach. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interiorphotos, NO lease in place, NO access- The seller does not represent or guarantee

  Neven Spralja REALHome Services & Solutions

  31 Glenwood Rd, Glen Head, NY 11545
• 

  

  /50

  $5,799,999

  New Construction $999K 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
• 

  

  /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
• 

  

  /23

  $888,000

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  38 Hill Dr, Glen Head, NY 11545

  Charming Corner Property "The Promenade" – Glen Head Tucked into one of Glen Head's most walkable and welcoming pockets, this Charming 3-bedroom, 1-bath ranch sits proudly on a coveted corner lot along The Promenade — offering both character and convenience in equal measure. Step inside and be greeted by warm, original wood floors that flow throughout the home, adding timeless charm to every

  Michelle Rich Branch Real Estate Group

  38 Hill Dr, Glen Head, NY 11545
• 

  

  /37

  $5,250,000

  • 6 Beds
  • 10 Baths
  • 7,532 Sq Ft

  33 Chicken Valley Rd, Glen Head, NY 11545

  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

  Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

  33 Chicken Valley Rd, Glen Head, NY 11545
• 

  

  /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
• 

  

  /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
• 

  

  /27

  $1,088,000

  Open Sat 11AM - 12:30PM $100K PRICE DROP

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

  7 Locust St, Glen Head, NY 11545

  Located in the highly coveted, award-winning North Shore School District.Welcome home to this move-in-ready, newly renovated Colonial perfectly situated at the beginning of a charming, quiet cul-de-sac. This 4-bedroom, 2-full-bath home beautifully balances classic warmth with modern upgrades and an open space concept. The expanded 2,300 sq. ft. layout (1,561 sq. ft. livable) begins on the first

  Roger Liu Century Homes Realty Group LLC

  7 Locust St, Glen Head, NY 11545
• 

  

  /34

  $3,480,000

  • 6 Beds
  • 4.5 Baths
  • 5,156 Sq Ft

  24 Winding Ln, Glen Head, NY 11545

  Step away from the everyday and into this gracious, light-filled ranch, where every room feels like an invitation to relax. Sun-drenched and spacious, the interconnected living areas create an effortless flow — warm, welcoming, and made for both quiet mornings and lively gatherings.Built for entertaining, the home features a gourmet kitchen ready for your next dinner party, a formal

  Lina Wang Compass Greater NY LLC

  24 Winding Ln, Glen Head, NY 11545
• 

  

  /35

  $4,295,000

  • 5 Beds
  • 6 Baths
  • 6,652 Sq Ft

  3 Rock Hill, Glen Head, NY 11545

  BROOKVILLE. Perfectly nestled on two private acres at the end of a quiet cul-de-sac in the heart of Brookville, this exceptional residence offers a harmonious blend of timeless architecture, modern sophistication, and resort-inspired living. Offering five bedrooms, with primary suite on the main, four full and two half baths, this remarkable home welcomes you with a striking two-story arched

  Maria Babaev Douglas Elliman Real Estate

  3 Rock Hill, Glen Head, NY 11545
• 

  /2

  $929,000

  • 4 Beds
  • 2 Baths
  • 1,578 Sq Ft

  35 Washington Ave, Glen Head, NY 11545

  A Builder’s Dream in Hill Terrace!Bring your vision and your contractor—this well-located home offers an exciting opportunity for buyers looking to renovate, customize, and create their dream home. Nestled in the desirable Hill Terrace neighborhood of Glen Head, this property is surrounded by beautiful homes and offers incredible potential.Enjoy a top-rated school district and a

  Terry Sciubba Signature Premier Properties

  35 Washington Ave, Glen Head, NY 11545
• 

  /2

  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 4,365 Sq Ft

  734 Motts Cove Rd N, Glen Head, NY 11545

  Nearing Completion – See 738 Motts Cove N for Finished Home. Stunning new construction on a charming tree-lined cul-de-sac shared by only six homes, this exceptional 4-bedroom, 4.5-bath Hamptons-inspired residence offers the perfect blend of luxury, craftsmanship, and location. Filled with natural light, the home features exquisite millwork, designer finishes, and an open floor plan ideal for

  Madeline Moritz Douglas Elliman Real Estate

  734 Motts Cove Rd N, Glen Head, NY 11545
• 

  

  /50

  $5,499,999

  New Construction Open Sun 12PM - 2PM $400K 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
• 

  

  /48

  $4,595,000

  • 6 Beds
  • 7.5 Baths
  • 9,485 Sq Ft

  24 Emerson Rd, Glen Head, NY 11545

  Set on 2.5 private, beautifully landscaped acres in Brookville, this dramatic 9,485-square-foot contemporary offers exceptional scale, architectural interest and resort-style amenities within the Jericho School District. The 18-room residence features 6 bedrooms and 7 full and 1 half baths, including an expansive main-level primary suite with a spa-like bath and multiple walk-in closets. A grand

  Michael Pesce BERKSHIRE HATHAWAY

  24 Emerson Rd, Glen Head, NY 11545
• 

  

  /21

  $1,550,000

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  12 The Cir Unit 12, Glen Head, NY 11545

  Welcome to The Knolls, a Prestigious Gated Community located in the North Shore Coveted Gold Coast. This Sun-Drenched, Spacious Residence Set in a Prime Location, features a Secluded Backyard. A True Sanctuary that Offers a Combination of Tranquility, Privacy, and Beauty. This Elegant Multi-Level Home has a flowing Open Floor Plan, Hardwood Floors, and an abundance of Natural Light. This home

  leonardo tavarez Charles Rutenberg Realty Inc

  12 The Cir Unit 12, Glen Head, NY 11545
• 

  

  /33

  $848,000

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  8 Anthony Marangiello St, Glen Cove, NY 11542

  Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in Glen Cove, offering a wonderful blend of comfort, functionality, and modern updates. Featuring a spacious primary bedroom en suite, this home is designed for both everyday living and entertaining. The newly updated kitchen features stainless Steele appliances. Throughout the home, hardwood floors add warmth and character,

  Anthony Guerriero First Realty Properties Inc

  8 Anthony Marangiello St, Glen Cove, NY 11542
• 

  

  /27

  $780,000

  • 2 Beds
  • 1.5 Baths
  • 1,162 Sq Ft

  71 Valentine Ave, Glen Cove, NY 11542

  Move right into this Expanded Ranch style home, with full basement, 1-car garage, updated designer kitchen w/ quartz counters and stainless-steel appliance, updated bathrooms, updated flooring, new carpeting, fresh paint, new siding, etc. Mid-block location. Close to shopping, transportation, and local amenities. Don’t miss out on this opportunity!

  Todd Yovino Island Advantage Realty LLC

  71 Valentine Ave, Glen Cove, NY 11542
• 

  

  /34

  $1,395,000

  $40K PRICE INCREASE

  • 5 Beds
  • 3 Baths
  • 2,521 Sq Ft

  34 Nassau Ave, Glen Cove, NY 11542

  Built in 2007 and lovingly maintained by its original and only owner, 34 Nassau Ave reflects true pride of ownership throughout. This well-cared-for duplex offers two residential units and a spacious, flexible layout, making it an excellent opportunity for an owner-occupant or investor.The finished basement provides valuable additional space with a separate walk-out entrance, and multiple

  Luz Hurtado LAFFEY REAL ESTATE

  34 Nassau Ave, Glen Cove, NY 11542
• 

  

  /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

Showing Results 41 - 70, Page 2 of 2