Glen Head, NY Homes

• 

  $720,000 Sold Aug 19, 2025

  29 The Glen Unit 29, Glen Head, NY 11545

  • 2 Beds
  • 2.5 Baths
  • 1,569 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $459/SF
  • 64 Days On Market

  Last Listing Agent Lori Farber BERKSHIRE HATHAWAY

  29 The Glen Unit 29, Glen Head, NY 11545
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• 

  Est $1,309,212 Not Listed For Sale

  9 Rini Ct, Glen Head, NY 11545

  • 5 Beds
  • 2.5 Baths
  • 2,756 Sq Ft
  • Built 1968

  9 Rini Ct, Glen Head, NY 11545

  Last Sold Summary

  • 10% Above List Price
  • $432/SF
  • 60 Days On Market

  Last Sold Price $1,190,000

  Last Listing Agent Dee Dee Brix Compass Greater NY LLC
• 

  

  

  /48

  $3,750,000

  • 5 Beds
  • 4.5 Baths
  • 4,934 Sq Ft

  51 Linden Ln, Glen Head, NY 11545

  Perfectly set on a winding country lane, this charming colonial combines timeless craftsmanship with modern luxury on over two level, landscaped acres designed by Steven Dubner. The home showcases fine millwork and mouldings with hardwood flooring throughout the first floor. A welcoming entry leads to a gracious living room with a gas fireplace, dentil moulding surround, and built -in bookcases

  Kathryn Maxwell Pournaras Daniel Gale Sothebys Intl Rlty

  51 Linden Ln, Glen Head, NY 11545
• 

  $5,425,000 Sold Aug 28, 2025

  21 Old Wheatley Rd, Glen Head, NY 11545

  • 6 Beds
  • 6.5 Baths
  • 6,484 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $837/SF
  • 55 Days On Market

  Current Estimated Value $5,191,130

  Last Listing Agent Kristin Purcell Compass Greater NY LLC

  21 Old Wheatley Rd, Glen Head, NY 11545
• 

  Est $1,344,567 Not Listed For Sale

  315 Frost Pond Rd, Glen Head, NY 11545

  • 4 Beds
  • 2.5 Baths
  • 2,450 Sq Ft
  • Built 1967

  315 Frost Pond Rd, Glen Head, NY 11545

  Last Sold Summary

  • 8% Above List Price
  • $510/SF
  • 13 Days On Market

  Last Sold Price $1,249,500

  Last Listing Agent Maria Corigliano Douglas Elliman Real Estate
• 

  

  /15

  $2,750,000

  • 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
• 

  $855,000 Sold Oct 31, 2025

  1 Smith St, Glen Head, NY 11545

  • 4 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 1980

  Last Sold Summary

  • 32% Below List Price
  • $561/SF
  • 367 Days On Market

  Current Estimated Value $947,656

  Last Listing Agent Robert Scarito Douglas Elliman Real Estate

  1 Smith St, Glen Head, NY 11545
• 

  Est $1,198,396 Not Listed For Sale

  311 Frost Pond Rd, Glen Head, NY 11545

  • 5 Beds
  • 2.5 Baths
  • 2,753 Sq Ft
  • Built 1968

  311 Frost Pond Rd, Glen Head, NY 11545

  Last Sold Summary

  • 34% Above List Price
  • $325/SF
  • 108 Days On Market

  Last Sold Price $895,000

  Last Listing Agent Myla Borucke Daniel Gale Sotheby's
• 

  

  /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
• 

  $2,350,000 Sold Jun 26, 2025

  30 Glenby Ln, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 4,644 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $506/SF
  • 178 Days On Market

  Current Estimated Value $2,590,117

  Last Listing Agent Shawn Elliott Nest Seekers LLC

  30 Glenby Ln, Glen Head, NY 11545
• 

  Est $1,207,681 Not Listed For Sale

  233 Lawrence Ln, Glen Cove, NY 11542

  • 3 Beds
  • 2.5 Baths
  • 2,564 Sq Ft
  • Built 2006

  233 Lawrence Ln, Glen Cove, NY 11542

  Last Sold Summary

  • 8% Above List Price
  • $437/SF
  • 91 Days On Market

  Last Sold Price $1,120,000

  Last Listing Agent Jesse Geser Daniel Gale Sotheby's
• 

  

  /38

  $3,288,888 Pending

  • 6 Beds
  • 6.5 Baths
  • 4,787 Sq Ft

  35 Hoaglands Ln, Glen Head, NY 11545

  At the end of a long private driveway the exceedingly charming Georgian Colonial aptly styled “Twin Pines” awaits. Quiet luxury and classic architecture strikes a harmonious balance with resort-style amenities set amongst 2 lush acres, providing an exceptional lifestyle for the discerning buyer. Step inside the entrance to find a foyer with original palazzo tile and library with a wood-burning

  Jaime Hamm Daniel Gale Sothebys Intl Rlty

  35 Hoaglands Ln, Glen Head, NY 11545
• 

  $2,700,000 Sold Feb 24, 2026

  183 Linden Ln, Glen Head, NY 11545

  • 3 Beds
  • 4 Baths
  • 3,602 Sq Ft
  • Built 2016

  Last Sold Summary

  • 19% Above List Price
  • $750/SF
  • 9 Days On Market

  Current Estimated Value $2,551,941

  Last Listing Agent Alexis Mcandrew Daniel Gale Sothebys Intl Rlty

  183 Linden Ln, Glen Head, NY 11545
• 

  Est $727,252 Not Listed For Sale

  206 Lawrence Ln, Glen Cove, NY 11542

  • 3 Beds
  • 1 Bath
  • 1,126 Sq Ft
  • Built 1951

  206 Lawrence Ln, Glen Cove, NY 11542

  Last Sold Summary

  • 25% Above List Price
  • $515/SF
  • 29 Days On Market

  Last Sold Price $580,000

  Last Listing Agent Robert Bressingham Realty Connect USA LLC
• 

  

  /50

  $2,499,000

  • 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
• 

  $990,000 Sold Sep 09, 2025

  13 The Promenade, Glen Head, NY 11545

  • 3 Beds
  • 2 Baths
  • 1,769 Sq Ft
  • Built 1958

  Last Sold Summary

  • 14% Above List Price
  • $560/SF
  • 12 Days On Market

  Current Estimated Value $992,626

  Last Listing Agent Linda OConnor Luxian International Realty

  13 The Promenade, Glen Head, NY 11545
• 

  Est $955,652 Not Listed For Sale

  20 Robert Rd, Glen Cove, NY 11542

  • 4 Beds
  • 1 Bath
  • 1,190 Sq Ft
  • Built 1951

  20 Robert Rd, Glen Cove, NY 11542

  Last Sold Summary

  • 72% Above List Price
  • $466/SF
  • 47 Days On Market

  Last Sold Price $555,000

  Last Listing Agent Vivian Parisi Compass Greater NY LLC
• 

  

  /50

  $2,850,000 Pending

  • 6 Beds
  • 6.5 Baths
  • 5,972 Sq Ft

  20 Rolling Dr, Glen Head, NY 11545

  Nicely renovated Traditional Colonial Ready For Your Finishing Touches Perfectly Situated on 2 Acres with Southern Exposure Along A Tree-Lined Cul-de-sac. This Home Boasts 6 Bedrooms, 6.5 Baths in 7000 Square Feet of Living Space (which includes Finished Basement and Garage). The Open Chef’s Kitchen includes Viking Appliances, Quartz Countertops, Custom Cabinetry, Dual Sinks, Oversized Island

  Phyllis DiNardo Century 21 Crown Homes

  20 Rolling Dr, Glen Head, NY 11545
• 

  $2,400,000 Sold Dec 19, 2025

  1 Coolidge Ave, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 4,382 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Above List Price
  • $548/SF
  • 13 Days On Market

  Current Estimated Value $2,450,703

  Last Listing Agent Vivian Parisi Daniel Gale Sothebys Intl Rlty

  1 Coolidge Ave, Glen Head, NY 11545
• 

  Est $892,815 Not Listed For Sale

  14 Robert Rd, Glen Cove, NY 11542

  • 4 Beds
  • 2 Baths
  • 1,746 Sq Ft
  • Built 1951

  14 Robert Rd, Glen Cove, NY 11542

  Last Sold Summary

  • 1% Above List Price
  • $504/SF
  • 17 Days On Market

  Last Sold Price $880,000

  Last Listing Agent Patrick Hall Branch Real Estate Group
• 

  

  /32

  $2,495,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,811 Sq Ft

  11 Quaker Ridge Dr, Glen Head, NY 11545

  Pull into this Brookville gem, nestled on a quiet private cul-de-sac, and enjoy serenity on two flat acres of beautifully landscaped flat property. This renovated and expanded five-bedroom split-level home is ready for immediate occupancy and features a circular driveway with ample courtyard parking and a three-car attached garage. The scenic grounds offer complete privacy with a fabulous

  Michael Stanco Compass Greater NY LLC

  11 Quaker Ridge Dr, Glen Head, NY 11545
• 

  $2,050,000 Sold Sep 30, 2025

  31 Wenwood Dr, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 3,900 Sq Ft
  • Built 1960

  Last Sold Summary

  • 7% Below List Price
  • $526/SF
  • 56 Days On Market

  Current Estimated Value $2,196,333

  Last Listing Agent Maria Babaev Douglas Elliman Real Estate

  31 Wenwood Dr, Glen Head, NY 11545
• 

  Est $721,195 Not Listed For Sale

  1 Keith Place, Glen Cove, NY 11542

  • 4 Beds
  • 1.5 Baths
  • 1,620 Sq Ft
  • Built 1951

  1 Keith Place, Glen Cove, NY 11542

  Last Sold Summary

  • 25% Above List Price
  • $355/SF
  • 87 Days On Market

  Last Sold Price $575,000

  Last Listing Agent Thomas Knoell Douglas Elliman Real Estate
• 

  

  /21

  $2,850,000

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

  10 Dorchester Dr, Glen Head, NY 11545

  Set on a distinguished two-acre property in the heart of Muttontown, New York, and nestled within a beautiful, sprawling neighborhood, this expansive ranch residence exudes privacy, scale, and timeless sophistication. Tucked well back from the road and surrounded by meticulously maintained landscaping, the home welcomes guests through a double-door entrance to an oversized foyer that immediately

  Jason Friedman Daniel Gale Sothebys Intl Rlty

  10 Dorchester Dr, Glen Head, NY 11545
• 

  $999,000 Sold Jun 23, 2025

  65 The Cir Unit 65, Glen Head, NY 11545

  • 3 Beds
  • 3.5 Baths
  • Built 1988

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Sandi Lefkowitz Daniel Gale Sothebys Intl Rlty

  65 The Cir Unit 65, Glen Head, NY 11545
• 

  Est $662,237 Not Listed For Sale

  3 Sands Rd, Glen Cove, NY 11542

  • 3 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 1952

  3 Sands Rd, Glen Cove, NY 11542

  Last Sold Summary

  • 9% Above List Price
  • $645/SF
  • 19 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Myla Borucke Daniel Gale Sotheby's
• 

  

  /35

  $9,750,000

  • 7 Beds
  • 14 Baths
  • 11,926 Sq Ft

  4 Red Fox Ln, Glen Head, NY 11545

  Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a

  Pierce Dellafera Daniel Gale Sothebys Intl Rlty

  4 Red Fox Ln, Glen Head, NY 11545
• 

  $1,825,000 Sold Oct 30, 2025

  18 Roosevelt Ave, Glen Head, NY 11545

  • 5 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 2023

  Last Sold Summary

  • 3% Above List Price
  • $652/SF
  • 38 Days On Market

  Current Estimated Value $1,895,934

  Last Listing Agent Jordan Caruso Compass Greater NY LLC

  18 Roosevelt Ave, Glen Head, NY 11545
• 

  Est $753,186 Not Listed For Sale

  74 East Ave, Glen Cove, NY 11542

  • 3 Beds
  • 1 Bath
  • 986 Sq Ft
  • Built 1951

  74 East Ave, Glen Cove, NY 11542

  Last Sold Summary

  • 1% Above List Price
  • $760/SF
  • 110 Days On Market

  Last Sold Price $749,000

  Last Listing Agent Eileen Heimer Daniel Gale Sotheby's
• 

  

  /50

  $7,999,999

  • 6 Beds
  • 8 Baths
  • 8,600 Sq Ft

  8 Dogwood Hill, Glen Head, NY 11545

  Brookville | An immaculate modern colonial has made its debut in Brookville. Sitting on 2.57 acres and totaling over 8,600 sq.ft. of living space, welcome to 8 Dogwood Hill - a newly completed luxury residence located on a lengthy, picturesque street just off of Cedar Swamp Road. Beyond the stone pillar entrance at the end of the driveway are two courtyards with belgium block accents that lead to

  Joe Scavo Douglas Elliman Real Estate

  8 Dogwood Hill, Glen Head, NY 11545
• 

  $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 $2,641,983

  Last Listing Agent Therese DiRenzo Compass Greater NY LLC

  14 Chelmsford Dr, Glen Head, NY 11545
• 

  Est $2,588,213 Not Listed For Sale

  30 Stirrup Dr, Glen Head, NY 11545

  • 5 Beds
  • 4.5 Baths
  • 5,826 Sq Ft
  • Built 1995

  30 Stirrup Dr, Glen Head, NY 11545

  Last Sold Summary

  • 8% Above List Price
  • $412/SF
  • 38 Days On Market

  Last Sold Price $2,400,000

  Last Listing Agent Michael Stanco Compass Greater NY LLC
• 

  /2

  $725,000

  • 3 Beds
  • 1.5 Baths
  • 1,426 Sq Ft

  24 Smith St, Glen Head, NY 11545

  his classic 1940s colonial in Glen Head presents an opportunity for restoration or full renovation. Select charming details remain, including a slate roof with decorative snow guards, a wood-burning fireplace with wooden mantle, and a built-in corner cabinet in the dining room - features that may inspire preservation. With 3 bedrooms, 1.5 bathrooms, a spacious yard, and garage, the home offers

  Vivian Parisi Daniel Gale Sothebys Intl Rlty

  24 Smith St, 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 $1,023,990

  Last Listing Agent Molly Deegan Branch Real Estate Group

  43 Scudders Ln, Glen Head, NY 11545
• 

  Est $2,836,784 Not Listed For Sale

  16 Overbrook Ln, Glen Head, NY 11545

  • 4 Beds
  • 4.5 Baths
  • 3,942 Sq Ft
  • Built 1984

  16 Overbrook Ln, Glen Head, NY 11545

  Last Sold Summary

  • 4% Below List Price
  • $748/SF
  • 42 Days On Market

  Last Sold Price $2,950,000

  Last Listing Agent Lisa Fasano Compass Greater NY LLC
• 

  

  /50

  $1,950,000

  • 4 Beds
  • 2.5 Baths
  • 2,985 Sq Ft

  2 Knoll Ln, Glen Head, NY 11545

  Welcome to this impeccably maintained and beautifully updated 4-bedroom center hall colonial, where timeless elegance meets modern luxury. A grand two-story foyer creates a stunning first impression, setting the tone for the thoughtfully designed interior. The heart of the home is a state-of-the-art eat-in kitchen, perfectly equipped for both everyday living and entertaining. Featuring quartz

  Margaret Burkett Signature Premier Properties

  2 Knoll 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 $854,180

  Last Listing Agent Amy Tansill Daniel Gale Sothebys Intl Rlty

  4 Hillcrest Dr, Glen Head, NY 11545
• 

  Est $2,748,785 Not Listed For Sale

  20 Overbrook Ln, Glen Head, NY 11545

  • 6 Beds
  • 5.5 Baths
  • 4,849 Sq Ft
  • Built 1984

  20 Overbrook Ln, Glen Head, NY 11545

  Last Sold Summary

  • 39% Above List Price
  • $407/SF
  • 23 Days On Market

  Last Sold Price $1,975,000

  Last Listing Agent Janet Berookhim LAFFEY REAL ESTATE
• 

  

  /29

  $1,475,000

  • 4 Beds
  • 2 Baths
  • 2,401 Sq Ft

  25 Jaegger Dr, Glen Head, NY 11545

  Welcome to this lovely ranch home nestled near the end of a serene private cul-de-sac in the Village of Old Brookville. Set far back from the road, this wonderful residence sits on over one acre of beautifully landscaped grounds, providing exceptional privacy and tranquility. The bright and spacious interior features oversized wall-to-wall picture windows and French sliding doors that fill the

  Bart Bleiweiss Integrity Core Realty

  25 Jaegger Dr, 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

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