Glen Head, NY Homes

• 

  $2,500,000 Sold Nov 21, 2025

  14 Chelmsford Dr, Glen Head, NY 11545

  • 5 Beds
  • 3.5 Baths
  • 5,349 Sq Ft
  • Built 1974

  Last Sold Summary

  • $467/SF
  • 20 Days On Market

  Current Estimated Value $2,478,635

  Last Listing Agent Therese DiRenzo Compass Greater NY LLC

  14 Chelmsford Dr, Glen Head, NY 11545
• 

  Est $911,902 Not Listed For Sale

  289 Piping Rock Rd, Glen Head, NY 11545

  • 8 Beds
  • 12 Baths
  • 11,647 Sq Ft
  • Built 1928

  289 Piping Rock Rd, Glen Head, NY 11545

  Last Sold Summary

  • 90% Below List Price
  • $756/SF
  • 451 Days On Market

  Last Sold Price $8,800,000

  Last Listing Agent Paul Mateyunas Douglas Elliman Real Estate
• 

  

  

  /26

  $849,888 Pending

  • 2 Beds
  • 1 Bath

  8 Dumond Place, Glen Head, NY 11545

  This charming home features two cozy bedrooms and a sunlit sunroom. The foyer is beautiful when the natural light that comes through the front door, The living room has a warm gas fireplace and elegant wood floors throughout. The home includes a newly renovated bathroom with radiant floor heating, ensuring comfort in every season. The eat-in kitchen is a chef’s dream with granite countertops. The

  Mary Stanco BERKSHIRE HATHAWAY

  8 Dumond Place, Glen Head, NY 11545
• 

  $985,000 Sold Aug 22, 2025

  43 Scudders Ln, Glen Head, NY 11545

  • 3 Beds
  • 2 Baths
  • 1,793 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Above List Price
  • $549/SF
  • 14 Days On Market

  Current Estimated Value $962,661

  Last Listing Agent Molly Deegan Branch Real Estate Group

  43 Scudders Ln, Glen Head, NY 11545
• 

  Est $3,718,183 Not Listed For Sale

  255 Piping Rock Rd, Glen Head, NY 11545

  • 5 Beds
  • 6.5 Baths
  • 3,687 Sq Ft
  • Built 2023

  255 Piping Rock Rd, Glen Head, NY 11545

  Last Sold Summary

  • 8% Below List Price
  • $1,098/SF
  • 150 Days On Market

  Last Sold Price $4,050,000

  Last Listing Agent Xuerong Hou LAFFEY REAL ESTATE
• 

  

  /23

  $1,350,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  20 Michaels Ln, Glen Head, NY 11545

  Brookville ranch 4 bedrooms 3 baths on 1 acre. Living room, dining room, den with wood burning fireplace. Primary king bedroom suite with bath and large closet, 2nd king bedroom, 3 full size bedroom and hall bath with double sink. Guest twin bedroom and bath, laundry area. Full unfinished basement with 2022 oil burner and water tank. 200 AMP electric panel. 2 Car garage, in ground sprinklers,

  Charles Maione Douglas Elliman Real Estate

  20 Michaels Ln, Glen Head, NY 11545
• 

  $790,000 Sold Jul 15, 2025

  4 Hillcrest Dr, Glen Head, NY 11545

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

  Last Sold Summary

  • 9% Above List Price
  • $476/SF
  • 29 Days On Market

  Current Estimated Value $823,389

  Last Listing Agent Amy Tansill Daniel Gale Sothebys Intl Rlty

  4 Hillcrest Dr, Glen Head, NY 11545
• 

  Est $2,840,500 Not Listed For Sale

  162 Hegemans Ln, Glen Head, NY 11545

  • Built 1926

  162 Hegemans Ln, Glen Head, NY 11545

  Last Sold Summary

  • 46% Above List Price
  • $574/SF
  • 121 Days On Market

  Last Sold Price $1,950,000

  Last Listing Agent Neena Chowdhary Daniel Gale Sotheby's
• 

  

  /39

  $8,750,000

  • 6 Beds
  • 9 Baths
  • 8,000 Sq Ft

  30 Wood Acres Rd, Glen Head, NY 11545

  Introducing a newly constructed custom Brookville Colonial crowned with a stunning slate roof, offering an extraordinary blend of classic architecture and elevated designer finishes. Privately set behind an electric gate on over 2.53 fully landscaped acres, this exceptional estate, constructed in 2020, has been thoughtfully designed for both grand-scale entertaining and refined everyday living. A

  Jason Friedman Daniel Gale Sothebys Intl Rlty

  30 Wood Acres Rd, Glen Head, NY 11545
• 

  $2,100,000 Sold Jan 20, 2026

  76 Brookville Rd, Glen Head, NY 11545

  • 6 Beds
  • 4.5 Baths
  • Built 1928

  Last Sold Summary

  • 26% Below List Price
  • 205 Days On Market

  Last Listing Agent Diana Hiotis BERKSHIRE HATHAWAY

  76 Brookville Rd, Glen Head, NY 11545
• 

  Est $2,699,753 Not Listed For Sale

  4 Revere Ct, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 3,718 Sq Ft
  • Built 1973

  4 Revere Ct, Glen Head, NY 11545

  Last Sold Summary

  • 40% Above List Price
  • $518/SF
  • 21 Days On Market

  Last Sold Price $1,925,000

  Last Listing Agent Sandi Lefkowitz Daniel Gale Sotheby's
• 

  

  /33

  $5,699,000

  • 6 Beds
  • 6.5 Baths
  • 6,885 Sq Ft

  63 Fruitledge Rd, Glen Head, NY 11545

  Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale

  Melanie Cogan Compass Greater NY LLC

  63 Fruitledge Rd, Glen Head, NY 11545
• 

  $2,801,000 Sold Jul 09, 2025

  4 Paddock Ct, Glen Head, NY 11545

  • 6 Beds
  • 7.5 Baths
  • 5,732 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $489/SF
  • 45 Days On Market

  Current Estimated Value $2,811,451

  Last Listing Agent Michelle Zhao ZI Realty LLC

  4 Paddock Ct, Glen Head, NY 11545
• 

  Est $3,579,809 Not Listed For Sale

  4 Canterbury Rd, Glen Head, NY 11545

  • 5 Beds
  • 6.5 Baths
  • 3,900 Sq Ft
  • Built 1956

  4 Canterbury Rd, Glen Head, NY 11545

  Last Sold Summary

  • 1% Above List Price
  • $910/SF
  • 19 Days On Market

  Last Sold Price $3,548,000

  Last Listing Agent Julia Krispeal Serhant LLC
• 

  /2

  $6,300,000

  • 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
• 

  $820,000 Sold Jan 16, 2026

  16 Wagon Ln, Glen Head, NY 11545

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Built 1973

  Last Sold Summary

  • 6% Below List Price
  • $631/SF
  • 37 Days On Market

  Current Estimated Value $849,211

  Last Listing Agent Lynda Torel Daniel Gale Sothebys Intl Rlty

  16 Wagon Ln, Glen Head, NY 11545
• 

  Est $4,093,448 Not Listed For Sale

  12 Locust Ln, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 7,200 Sq Ft
  • Built 2003

  12 Locust Ln, Glen Head, NY 11545

  Last Sold Summary

  • 13% Above List Price
  • $505/SF
  • 285 Days On Market

  Last Sold Price $3,635,000

  Last Listing Agent Kathleen Dodd Daniel Gale Sotheby's
• 

  

  /42

  $2,099,000

  • 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
• 

  $1,357,000 Sold Oct 03, 2025

  46 Garfield Ave, Glen Head, NY 11545

  • 4 Beds
  • 2 Baths
  • 2,524 Sq Ft
  • Built 1951

  Last Sold Summary

  • 9% Above List Price
  • $538/SF
  • 20 Days On Market

  Current Estimated Value $1,237,442

  Last Listing Agent Myla Borucke Daniel Gale Sothebys Intl Rlty

  46 Garfield Ave, Glen Head, NY 11545
• 

  Est $3,144,632 Not Listed For Sale

  343 Chicken Valley Rd, Glen Head, NY 11545

  • 4 Beds
  • 3 Baths
  • 3,070 Sq Ft
  • Built 1949

  343 Chicken Valley Rd, Glen Head, NY 11545

  Last Sold Summary

  • 8% Above List Price
  • $945/SF
  • 53 Days On Market

  Last Sold Price $2,900,000

  Last Listing Agent Christina Porter Daniel Gale Sotheby's
• 

  

  /33

  $1,325,000 Open Sun 1PM - 2:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  1 Pine Hill Terrace, Glen Head, NY 11545

  Spacious Colonial on 1 Acre in the North Shore School District. Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial, ideally set on one acre of level property tucked away and set back from the road for added privacy, this home offers the perfect blend of space, comfort, and value all with low taxes.A gracious entry hall leads to the sun-filled Living Room and Formal Dining

  Janet Berookhim LAFFEY REAL ESTATE

  1 Pine Hill Terrace, Glen Head, NY 11545
• 

  $3,359,999 Sold Jun 27, 2025

  77 Linden Ln, Glen Head, NY 11545

  • 6 Beds
  • 5.5 Baths
  • Built 1964

  Last Sold Summary

  • 4% Below List Price
  • 45 Days On Market

  Current Estimated Value $3,385,522

  Last Listing Agent Debra Quinn Petkanas Daniel Gale Sothebys Intl Rlty

  77 Linden Ln, Glen Head, NY 11545
• 

  Est $2,739,894 Not Listed For Sale

  22 Pheasant Hill Ln, Glen Head, NY 11545

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft
  • Built 1966

  22 Pheasant Hill Ln, Glen Head, NY 11545

  Last Sold Summary

  • 37% Above List Price
  • $400/SF
  • 201 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Judy Milman Daniel Gale Sotheby's
• 

  /2

  $5,900,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  25 Longridge Ln, Glen Head, NY 11545

  Old Brookville New Construction | Welcome to 25 Longridge Lane– a custom-built brick center hall colonial nestled on over 2 private acres at the end of a peaceful cul-de-sac.

  Joe Scavo Douglas Elliman Real Estate

  25 Longridge Ln, Glen Head, NY 11545
• 

  $2,500,000 Sold Jul 15, 2025

  12 Shelter Ln, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 5,470 Sq Ft
  • Built 1981

  Last Sold Summary

  • $457/SF
  • 11 Days On Market

  Current Estimated Value $2,551,821

  Last Listing Agent Melanie Cogan Compass Greater NY LLC

  12 Shelter Ln, Glen Head, NY 11545
• 

  Not Listed For Sale

  873 Cedar Swamp Rd, Glen Head, NY 11545

  • 6 Beds
  • 8 Baths
  • 1,150 Sq Ft
  • Built 1928

  873 Cedar Swamp Rd, Glen Head, NY 11545

  Last Sold Summary

  • 25% Below List Price
  • $6,529/SF
  • 254 Days On Market

  Last Sold Price $7,508,800

  Last Listing Agent Nancy Cuite BERKSHIRE HATHAWAY
• 

  

  /31

  $1,848,988 Pending

  • 4 Beds
  • 3 Baths
  • 2,584 Sq Ft

  22 Wenwood Dr, Glen Head, NY 11545

  Nestled Mid -Block On Quiet Street In The Heart Of Brookville! This Ranch Style Home Is An Exceptional Opportunity To Create Your Dream Home! Set On Two Flat Useable Acres, This Property Offers Privacy, Mature Landscaping And Endless Potential For Customization. Ideal For Buyers Looking To Make It Their Own. Bring Your Vision And Transform This Special Property Into Something Truly Extraordinary.

  Paris Rosvolos Paris T Rosvolos

  22 Wenwood Dr, Glen Head, NY 11545
• 

  $890,000 Sold Aug 08, 2025

  82 The Glen Unit 82, Glen Head, NY 11545

  • 3 Beds
  • 2.5 Baths
  • 2 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $445,000/SF
  • 172 Days On Market

  Last Listing Agent Sandi Lefkowitz Daniel Gale Sothebys Intl Rlty

  82 The Glen Unit 82, Glen Head, NY 11545
• 

  Est $2,822,084 Not Listed For Sale

  18 Pheasant Hill Ln, Glen Head, NY 11545

  • 4 Beds
  • 6 Baths
  • 3,354 Sq Ft
  • Built 1926

  18 Pheasant Hill Ln, Glen Head, NY 11545

  Last Sold Summary

  • 34% Above List Price
  • $626/SF
  • 15 Days On Market

  Last Sold Price $2,100,000

  Last Listing Agent Michael J. Berman Automatic Real Estate Assoc
• 

  

  /24

  $670,000 Pending

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

  20 Collins Rd, Glen Cove, NY 11542

  Charming ranch within the North Shore School District. This sun-filled 2-bedroom, 2-bath home offers easy one-level living with hardwood floors throughout. The primary suite features a jacuzzi bathtub with walk-in shower. Eat-in kitchen with granite countertops and stainless steel appliances. Additional highlights include a second full bath, washer/dryer, newly installed oil tank, large yard, and

  Stephanie Valerio Vintage American Realty LLC

  20 Collins Rd, Glen Cove, NY 11542
• 

  $3,196,000 Sold Nov 12, 2025

  184 High Farms Rd, Glen Head, NY 11545

  • 5 Beds
  • 5.5 Baths
  • 4,488 Sq Ft
  • Built 1999

  Last Sold Summary

  • $712/SF
  • 15 Days On Market

  Current Estimated Value $3,146,545

  Last Listing Agent Karen Sharf Daniel Gale Sothebys Intl Rlty

  184 High Farms Rd, Glen Head, NY 11545
• 

  Est $3,260,416 Not Listed For Sale

  101 Brookville Ln, Glen Head, NY 11545

  • 4 Beds
  • 4.5 Baths
  • 3,172 Sq Ft
  • Built 1954

  101 Brookville Ln, Glen Head, NY 11545

  Last Sold Summary

  • 72% Above List Price
  • $599/SF
  • 124 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Racanelli Orioli Team Coldwell Banker American Homes
• 

  

  /47

  $5,399,999

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

  35 Chicken Valley Rd, Glen Head, NY 11545

  Welcome to 35 Chicken Valley Road, an extraordinary, gated estate set far off the road and approached by an approximately 825-foot private driveway entrance, culminating in a prestigious circular drive that announces arrival with quiet grandeur. Nestled within the coveted enclave of Old Brookville, this Brick Center Hall Colonial—masterfully built by the renowned Worrell Group—rests on 4.5 acres

  Amar Jeet Chhibbar LAFFEY REAL ESTATE

  35 Chicken Valley Rd, Glen Head, NY 11545
• 

  $930,000 Sold Sep 30, 2025

  44 Glenwood Rd, Glen Head, NY 11545

  • 5 Beds
  • 2.5 Baths
  • 2,453 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $379/SF
  • 51 Days On Market

  Current Estimated Value $974,236

  Last Listing Agent John Langone Daniel Gale Sothebys Intl Rlty

  44 Glenwood Rd, Glen Head, NY 11545
• 

  Est $3,175,881 Not Listed For Sale

  167 High Farms Rd, Glen Head, NY 11545

  • 6 Beds
  • 4.5 Baths
  • 4,892 Sq Ft
  • Built 2005

  167 High Farms Rd, Glen Head, NY 11545

  Last Sold Summary

  • 11% Above List Price
  • $585/SF
  • 31 Days On Market

  Last Sold Price $2,860,000

  Last Listing Agent Debra Quinn Petkanas Daniel Gale Sotheby's
• 

  

  /28

  $4,250,000 Pending

  • 6 Beds
  • 6.5 Baths

  11 Victorian Ln, Glen Head, NY 11545

  Perfectly situated on over two acres in the heart of Brookville, this stately stone residence combines classic European architecture with modern comfort. Built in 2008 with meticulous attention to detail, the home showcases a full stone exterior with limestone accents and refined finishes throughout. Inside, double entry doors open to a grand interior with soaring ceilings—9 feet on the main

  Zach Elliott Nest Seekers LLC

  11 Victorian Ln, Glen Head, NY 11545
• 

  $1,600,000 Sold May 08, 2025

  100 Wolver Hollow Rd, Glen Head, NY 11545

  • 4 Beds
  • 3.5 Baths
  • 2,737 Sq Ft
  • Built 1941

  Last Sold Summary

  • 2% Below List Price
  • $585/SF
  • 35 Days On Market

  Current Estimated Value $1,662,770

  Last Listing Agent Michael Pesce BERKSHIRE HATHAWAY

  100 Wolver Hollow Rd, Glen Head, NY 11545
• 

  Est $2,963,404 Not Listed For Sale

  163 High Farms Rd, Glen Head, NY 11545

  • 7 Beds
  • 4.5 Baths
  • 4,269 Sq Ft
  • Built 1928

  163 High Farms Rd, Glen Head, NY 11545

  Last Sold Summary

  • 14% Above List Price
  • $609/SF
  • 230 Days On Market

  Last Sold Price $2,600,000

  Last Listing Agent Lindsey Barnett Compass Greater NY LLC
• 

  

  /19

  $1,699,000 Pending

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

  270 Frost Pond Rd, Glen Head, NY 11545

  A versatile and desirable property located in the Village of Old Brookville, NY. This colonial style house is positioned on 2.138 level acres, all flat and usable, providing space for recreation, expansion or future customization. A separate structure oversized concrete garage with high ceilings can be accessed by a long driveway in from the road. Bring your vision to renovate this 6 bedroom

  Michael Stanco Compass Greater NY LLC

  270 Frost Pond Rd, Glen Head, NY 11545
• 

  $3,350,000 Sold May 27, 2025

  5 Valentine Farm Ct, Glen Head, NY 11545

  • 6 Beds
  • 9 Baths
  • 8,400 Sq Ft
  • Built 2001

  Last Sold Summary

  • 44% Below List Price
  • $399/SF
  • 394 Days On Market

  Current Estimated Value $3,754,923

  Last Listing Agent Michael Stanco Compass Greater NY LLC

  5 Valentine Farm Ct, Glen Head, NY 11545

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