Glen Head, NY Homes

• 

  Est $964,403

  Not Listed For Sale

  18 Polly Ln, Glen Head, NY 11545

  • 3 Beds
  • 1.5 Baths
  • 1,192 Sq Ft
  • Built 1938

  18 Polly Ln, Glen Head, NY 11545

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Sheila Wenger Douglas Elliman Real Estate
• 

  

  

  /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
• 

  $1,200,000

  Sold Oct 30, 2025

  21 Orchard St, Glen Head, NY 11545

  • 3 Beds
  • 1.5 Baths
  • 2,100 Sq Ft
  • Built 1957

  Last Sold Summary

  • 10% Above List Price
  • $571/SF
  • 25 Days On Market

  Current Estimated Value $1,215,783

  Last Listing Agent Irene Nictas Daniel Gale Sothebys Intl Rlty

  21 Orchard St, Glen Head, NY 11545
• 

  Est $1,283,142

  Not Listed For Sale

  3 Tennis Ct, Glen Head, NY 11545

  • 4 Beds
  • 2.5 Baths
  • 2,626 Sq Ft
  • Built 2002

  3 Tennis Ct, Glen Head, NY 11545

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Dee Dee Brix Compass Greater NY LLC
• 

  

  

  /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
• 

  $740,000

  Sold Mar 12, 2026

  20 Collins Rd, Glen Cove, NY 11542

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 1951

  Last Sold Summary

  • 10% Above List Price
  • $607/SF
  • 21 Days On Market

  Current Estimated Value $719,838

  Last Listing Agent Stephanie Valerio Vintage American Realty LLC

  20 Collins Rd, Glen Cove, NY 11542
• 

  Est $987,613

  Not Listed For Sale

  8 Terry Ct, Glen Head, NY 11545

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1965

  8 Terry Ct, Glen Head, NY 11545

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Cheryl Rosenthal Realty Trends Corp
• 

  

  /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
• 

  $875,000

  Sold Jan 28, 2026

  1 William St, Glen Head, NY 11545

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft
  • Built 1928

  Last Sold Summary

  • 5% Above List Price
  • $430/SF
  • 38 Days On Market

  Current Estimated Value $892,924

  Last Listing Agent Kerry Ann Fyne Citizens International Realty

  1 William St, Glen Head, NY 11545
• 

  Est $1,264,189

  Not Listed For Sale

  20 Terry Ct, Glen Head, NY 11545

  • 4 Beds
  • 2.5 Baths
  • 2,289 Sq Ft
  • Built 1966

  20 Terry Ct, Glen Head, NY 11545

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Richard Arnold Branch Real Estate Group
• 

  

  /30

  $3,299,000

  Pending

  • 5 Beds
  • 6 Baths
  • 5,011 Sq Ft

  11 Wenwood Dr, Glen Head, NY 11545

  Welcome to 11 Wenwood Drive, an exceptional residence nestled in the prestigious, highly sought-after Village of Brookville. The home is located within the Jericho Union Free School District and offers convenient access to shopping, dining, parks, major highways and public transportation. From the moment you arrive, you'll be captivated by the home's impressive curb appeal and thoughtfully

  Kate Callan Daniel Gale Sothebys Intl Rlty

  11 Wenwood Dr, Glen Head, NY 11545
• 

  $3,650,000

  Sold Mar 18, 2026

  109 Wheatley Rd, Glen Head, NY 11545

  • 6 Beds
  • 5.5 Baths
  • 5,642 Sq Ft
  • Built 2004

  Last Sold Summary

  • $647/SF
  • 23 Days On Market

  Current Estimated Value $3,617,090

  Last Listing Agent Michael Stanco Compass Greater NY LLC

  109 Wheatley Rd, Glen Head, NY 11545
• 

  Est $2,576,812

  Not Listed For Sale

  10 Central Dr, Glen Head, NY 11545

  • 5 Beds
  • 3 Baths
  • 3,600 Sq Ft
  • Built 1990

  10 Central Dr, Glen Head, NY 11545

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Laura Algios Daniel Gale Sothebys Intl Rlty
• 

  

  /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
• 

  $1,360,000

  Sold Jul 09, 2026

  1 Sandra Ct, Glen Cove, NY 11542

  • 4 Beds
  • 2.5 Baths
  • 2,068 Sq Ft
  • Built 1960

  Last Sold Summary

  • 5% Above List Price
  • $658/SF
  • 15 Days On Market

  Current Estimated Value $1,296,126

  Last Listing Agent Dee Dee Brix Compass Greater NY LLC

  1 Sandra Ct, Glen Cove, NY 11542
• 

  Est $1,121,209

  Not Listed For Sale

  17 Glen Ln, Glen Head, NY 11545

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1943

  17 Glen Ln, Glen Head, NY 11545

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Damian Ross Daniel Gale Sothebys Intl Rlty
• 

  

  /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
• 

  $3,850,000

  Sold Mar 27, 2026

  11 Victorian Ln, Glen Head, NY 11545

  • 6 Beds
  • 6.5 Baths
  • 4,737 Sq Ft
  • Built 2008

  Last Sold Summary

  • 9% Below List Price
  • $813/SF
  • 122 Days On Market

  Current Estimated Value $3,819,913

  Last Listing Agent Zach Elliott Nest Seekers LLC

  11 Victorian Ln, Glen Head, NY 11545
• 

  Est $784,820

  Not Listed For Sale

  1 Maiden Ln, Glen Head, NY 11545

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1956

  1 Maiden Ln, Glen Head, NY 11545

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent John Langone Daniel Gale Sothebys Intl Rlty
• 

  

  /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
• 

  $1,550,000

  Sold May 21, 2026

  270 Frost Pond Rd, Glen Head, NY 11545

  • 6 Beds
  • 4 Baths
  • 3,416 Sq Ft
  • Built 1978

  Last Sold Summary

  • 9% Below List Price
  • $454/SF
  • 37 Days On Market

  Current Estimated Value $1,962,940

  Last Listing Agent Michael Stanco Compass Greater NY LLC

  270 Frost Pond Rd, Glen Head, NY 11545
• 

  Est $915,051

  Not Listed For Sale

  31 Glen Cove Dr, Glen Head, NY 11545

  • 4 Beds
  • 2 Baths
  • 1,330 Sq Ft
  • Built 1954

  31 Glen Cove Dr, Glen Head, NY 11545

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Giuseppe Gregorio NY Space Finders Inc
• 

  

  /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
• 

  $1,833,000

  Sold Nov 18, 2025

  30 Roslyn Dr, Glen Head, NY 11545

  • 5 Beds
  • 3.5 Baths
  • 3,280 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $559/SF
  • 55 Days On Market

  Current Estimated Value $1,930,253

  Last Listing Agent Derek Greene Greene Realty Group

  30 Roslyn Dr, Glen Head, NY 11545
• 

  Est $1,208,448

  Not Listed For Sale

  11 Oak Valley Dr, Glen Head, NY 11545

  • 3 Beds
  • 2 Baths
  • 2,625 Sq Ft
  • Built 1909

  11 Oak Valley Dr, Glen Head, NY 11545

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Laura Algios Daniel Gale Sothebys Intl Rlty
• 

  

  /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
• 

  $1,587,500

  Sold May 11, 2026

  22 Knott Dr, Glen Cove, NY 11542

  • 4 Beds
  • 2.5 Baths
  • 3,051 Sq Ft
  • Built 1996

  Last Sold Summary

  • 6% Above List Price
  • $520/SF
  • 35 Days On Market

  Current Estimated Value $1,520,816

  Last Listing Agent Brian Fagen Compass Greater NY LLC

  22 Knott Dr, Glen Cove, NY 11542
• 

  Est $790,604

  Not Listed For Sale

  45 Glen Cove Dr, Glen Head, NY 11545

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1941

  45 Glen Cove Dr, Glen Head, NY 11545

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Katrina Taylor Clifford Coldwell Banker American Homes
• 

  

  /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
• 

  $2,650,000

  Sold Aug 24, 2026

  4 Cross Ln, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 5,644 Sq Ft
  • Built 1988

  Last Sold Summary

  • $470/SF
  • 36 Days On Market

  Current Estimated Value $2,631,345

  Last Listing Agent Laura Algios Daniel Gale Sothebys Intl Rlty

  4 Cross Ln, Glen Head, NY 11545
• 

  Est $841,019

  Not Listed For Sale

  4 Hillcrest Dr, Glen Head, NY 11545

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft
  • Built 1920

  4 Hillcrest Dr, Glen Head, NY 11545

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Amy Tansill Daniel Gale Sothebys Intl Rlty
• 

  

  /39

  $999,999

  Pending

  • 3 Beds
  • 2 Baths
  • 1,959 Sq Ft

  56 Glen Cove Dr, Glen Head, NY 11545

  Beautifully remodeled home offering a bright, open layout with soaring vaulted ceilings, gleaming hardwood floors, and timeless finishes throughout. The inviting living room is anchored by a stunning fireplace, creating the perfect space to relax or entertain. The updated interior seamlessly blends style and comfort, while large windows fill the home with natural light. Step outside to a private

  Giuseppe Gregorio NY Space Finders Inc

  56 Glen Cove Dr, Glen Head, NY 11545
• 

  $4,520,000

  Sold Jul 01, 2026

  8 Brookville Ln S, Glen Head, NY 11545

  • 6 Beds
  • 11 Baths
  • 6,662 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $678/SF
  • 51 Days On Market

  Current Estimated Value $4,576,007

  Last Listing Agent Karen Sharf Daniel Gale Sothebys Intl Rlty

  8 Brookville Ln S, Glen Head, NY 11545
• 

  Est $1,206,614

  Not Listed For Sale

  2 Cedar Ln, Glen Head, NY 11545

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1931

  2 Cedar Ln, Glen Head, NY 11545

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Andréa Sorrentino Douglas Elliman Real Estate
• 

  

  /37

  $2,675,000

  • 5 Beds
  • 4.5 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
• 

  $950,000

  Sold Jul 23, 2026

  29 Glen Cove Dr, Glen Head, NY 11545

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1954

  Last Sold Summary

  • 105,573% Above List Price
  • $575/SF
  • 59 Days On Market

  Current Estimated Value $896,531

  Last Listing Agent Eduardo Rodriguez Cosmo Group Realty

  29 Glen Cove Dr, Glen Head, NY 11545
• 

  Est $1,637,330

  Not Listed For Sale

  41 William St, Glen Head, NY 11545

  • 4 Beds
  • 3.5 Baths
  • 2,978 Sq Ft
  • Built 1993

  41 William St, Glen Head, NY 11545

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent John Langone Daniel Gale Sothebys Intl Rlty
• 

  

  /3

  $2,499,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,756 Sq Ft

  14 Horse Hill Rd, Glen Head, NY 11545

  Welcome to this exceptional Ranch-style retreat nestled on over 2 private acres in the prestigious Brookville and located within the award-winning Jericho School District. Offering 5 spacious bedrooms and 3 full bathrooms, this move-in ready home perfectly blends warmth, elegance, and serene living. Designed with both comfort and entertaining in mind, the home features an open-concept eat-in

  Geeta Shukla EXP Realty

  14 Horse Hill Rd, Glen Head, NY 11545
• 

  $6,748,000

  Sold Aug 18, 2026

  3 Woodhollow Ln, Glen Head, NY 11545

  • 7 Beds
  • 7.5 Baths
  • 10,000 Sq Ft
  • Built 2025

  Last Sold Summary

  • $675/SF
  • 11 Days On Market

  Current Estimated Value $6,572,840

  Last Listing Agent Traci Clinton Compass Greater NY LLC

  3 Woodhollow Ln, Glen Head, NY 11545
• 

  Est $1,247,154

  Not Listed For Sale

  20 Waverly St, Glen Head, NY 11545

  • 3 Beds
  • 1.5 Baths
  • 2,012 Sq Ft
  • Built 1928

  20 Waverly St, Glen Head, NY 11545

  Last Sold Summary

  • 108 Days On Market

  Last Listing Agent John Langone Daniel Gale Sothebys Intl Rlty

Showing Results 201 - 240, Page 6 of 18