Old Brookville, NY Homes

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  $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
• Explore Old Brookville

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  $8,500 per month

  • 5 Beds
  • 3 Baths
  • 2,679 Sq Ft
  • House for Rent

  110 Hegemans Ln, Glen Head, NY 11545

  Amazing views from this 4/5 Bedroom home with 3 Full Baths. Sunny Living Room with fireplace, comfy Family Room plus Kitchen and Dining Room. First floor offers 2 large Bedrooms with updated Bath, as well as, 3rd Office/BR with full Bath. Upstairs offers 2 Bedrooms with Bath. Lower Level Laundry and Rec Room. Fenced In ground pool heated by solar power. Lots of closets and storage. Grounds

  Madeleine Ganis Daniel Gale Sothebys Intl Rlty

  110 Hegemans Ln, Glen Head, NY 11545
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  $4,200,000 Sold Oct 10, 2025

  15 Pound Hollow Rd, Glen Head, NY 11545

  • 5 Beds
  • 8 Baths
  • 7,245 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Below List Price
  • $580/SF
  • 39 Days On Market

  Current Estimated Value $4,350,632

  Last Listing Agent Eileen Krach Daniel Gale Sothebys Intl Rlty

  15 Pound Hollow Rd, Glen Head, NY 11545
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  Est $5,695,712 Not Listed For Sale

  • 6 Beds
  • 7.5 Baths
  • 14,065 Sq Ft

  17 Hickory Dr, Glen Head, NY 11545

  17 Hickory Dr, Glen Head, NY 11545
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  $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
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  $38,000 per month

  • 6 Beds
  • 8 Baths
  • 10,000 Sq Ft
  • House for Rent

  16 Evergreen Way, Glen Head, NY 11545

  Nestled in the prestigious Greenfield Estates of Old Brookville, this 10,000 sq ft brick colonial estate is a masterpiece of luxury and privacy on 6 acres. It boasts both indoor and outdoor swimming pools, an outdoor kitchen perfect for entertaining, and a spacious three-car garage. The entrance welcomes you with a grand double bridal staircase and elegant marble floors, leading to a

  Huailing Deng Daniel Gale Sothebys Intl Rlty

  16 Evergreen Way, Glen Head, NY 11545
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  $3,660,000 Sold Mar 17, 2025

  1 Hickory Dr, Glen Head, NY 11545

  • 5 Beds
  • 5.5 Baths
  • 6,156 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Above List Price
  • $595/SF
  • 14 Days On Market

  Current Estimated Value $3,843,145

  Last Listing Agent Rita Pecora Daniel Gale Sothebys Intl Rlty

  1 Hickory Dr, Glen Head, NY 11545
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  Est $969,435 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,845 Sq Ft

  669 Cedar Swamp Rd, Glen Head, NY 11545

  669 Cedar Swamp Rd, Glen Head, NY 11545
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  $3,995,000

  • 7 Beds
  • 5.5 Baths

  285 Piping Rock Rd, Locust Valley, NY 11560

  Rosegate is a delightful one-of-a-kind residence that appears to have been magically plucked from the English countryside. Originally a Large Cottage on a former Estate, Rosegate has been thoughtfully expanded and updated throughout the years. The brick and clapboard home is now a 7 bedroom Colonial on 2.85 acres . Character and charm encompasses every inch of Rosegate. Hand painted murals cover

  Christina Porter Daniel Gale Sothebys Intl Rlty

  285 Piping Rock Rd, Locust Valley, NY 11560
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  $40,000 per month

  • 9 Beds
  • 7.5 Baths
  • 8,200 Sq Ft
  • House for Rent

  8 Stonegate Ln, Glen Head, NY 11545

  Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes, and sought after by many high profile clients. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. As

  Lisa Ann Heaney Daniel Gale Sothebys Intl Rlty

  8 Stonegate Ln, Glen Head, NY 11545
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  $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 $3,569,805

  Last Listing Agent Michael Stanco Compass Greater NY LLC

  5 Valentine Farm Ct, Glen Head, NY 11545
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  Est $2,699,130 Not Listed For Sale

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

  30 Stirrup Dr, Glen Head, NY 11545

  30 Stirrup Dr, Glen Head, NY 11545
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  $6,499,000

  • 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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  $2,300,000 Sold Mar 28, 2025

  6 Carlisle Dr, Glen Head, NY 11545

  • 3 Beds
  • 4.5 Baths
  • 3,799 Sq Ft
  • Built 1985

  Last Sold Summary

  • 12% Below List Price
  • $605/SF
  • 98 Days On Market

  Current Estimated Value $2,470,193

  Last Listing Agent Joe Scavo Douglas Elliman Real Estate

  6 Carlisle Dr, Glen Head, NY 11545
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  Est $3,142,307 Not Listed For Sale

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

  16 Overbrook Ln, Glen Head, NY 11545

  16 Overbrook Ln, Glen Head, NY 11545
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  $3,788,000

  • 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
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  $3,590,500 Sold May 22, 2025

  12 Woodfield Ln, Glen Head, NY 11545

  • 8 Beds
  • 7.5 Baths
  • 11,046 Sq Ft
  • Built 1989

  Last Sold Summary

  • 27% Below List Price
  • $325/SF
  • 335 Days On Market

  Current Estimated Value $3,942,585

  Last Listing Agent Connie Pinilla Compass Greater NY LLC

  12 Woodfield Ln, Glen Head, NY 11545
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  Est $2,688,888 Not Listed For Sale

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

  20 Overbrook Ln, Glen Head, NY 11545

  20 Overbrook Ln, Glen Head, NY 11545
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  $2,500,000 Pending

  • Land
  • 4.09 Acres
  • $611,247 per Acre

  172 Hegemans Ln, Old Brookville, NY 11545

  One-of-a-Kind Offering! Build your Dream Home in the only gated community within the Village of Old Brookville. Enter this newly developed 23+ acre community through impressive remote-controlled gates. Proceed on a secluded and lushly landscaped two-lane motor court to a quiet sanctuary and cul-de-sac featuring six buildable lots ranging from 3 to 4 acres each. Each lot has already been improved

  Neena Chowdhary Daniel Gale Sothebys Intl Rlty

  172 Hegemans Ln, Old Brookville, NY 11545
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  $2,550,000 Sold Jun 05, 2025

  4 Carlisle Dr, Glen Head, NY 11545

  • 5 Beds
  • 5.5 Baths
  • 3,733 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $683/SF
  • 150 Days On Market

  Current Estimated Value $2,663,164

  Last Listing Agent Batul Morbi Compass Greater NY LLC

  4 Carlisle Dr, Glen Head, NY 11545
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  Est $5,268,378 Not Listed For Sale

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

  289 Piping Rock Rd, Glen Head, NY 11545

  289 Piping Rock Rd, Glen Head, NY 11545
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  $2,799,000

  • 5 Beds
  • 3.5 Baths
  • 4,498 Sq Ft

  7 Pin Oak Ct, Glen Head, NY 11545

  Tucked at the end of a quiet cul-de-sac, this timeless contemporary sits on two perfectly level acres offering exceptional privacy and a deep, usable yard. The property features an in-ground heated pool with a waterfall and beautiful outdoor space ideal for gatherings or relaxation. Inside, the home provides plenty of opportunity with its dramatic ceilings and walls of glass that create a bright,

  Robert Schmertz Compass Greater NY LLC

  7 Pin Oak Ct, Glen Head, NY 11545
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  $2,600,000 Sold Jul 31, 2025

  8 Chicken Valley Rd, Glen Head, NY 11545

  • 5 Beds
  • 9 Baths
  • 7,938 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $328/SF
  • 14 Days On Market

  Last Listing Agent Dana Forbes Compass Greater NY LLC

  8 Chicken Valley Rd, Glen Head, NY 11545
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  Est $3,576,380 Not Listed For Sale

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

  255 Piping Rock Rd, Glen Head, NY 11545

  255 Piping Rock Rd, Glen Head, NY 11545
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  $9,000,000

  • 7 Beds
  • 11 Baths
  • 16,000 Sq Ft

  4 Valentine Farm Ct, Glen Head, NY 11545

  OLD BROOKVILLE Far from ordinary, this extraordinary custom built brick Mansion is designed for luxurious entertaining, Set on a private cul-de-sac, wrought iron gates open to the courtyard of this pristine 3acre estate surrounded by lush landscaping and colorful gardens. You'll greet your guests in the breathtaking Foyer where soaring domed ceiling sits 30' above a double bridal staircase.

  Ellen Zipes Compass Greater NY LLC

  4 Valentine Farm Ct, Glen Head, NY 11545
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  $2,075,000 Sold Apr 09, 2025

  Lot 1189 Hegemans Ln, Old Brookville, NY 11545

  • Land
  • 3 Acres
  • $691,667 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 313 Days On Market

  Last Listing Agent Jacqueline Nathel Daniel Gale Sothebys Intl Rlty

  Lot 1189 Hegemans Ln, Old Brookville, NY 11545
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  Est $2,657,500 Not Listed For Sale

  162 Hegemans Ln, Glen Head, NY 11545

  162 Hegemans Ln, Glen Head, NY 11545
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  $3,288,888

  • 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
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  $2,525,000 Sold Oct 24, 2025

  78 McCouns Ln, Glen Head, NY 11545

  • 7 Beds
  • 6 Baths
  • 5,497 Sq Ft
  • Built 1926

  Last Sold Summary

  • 6% Below List Price
  • $459/SF
  • 21 Days On Market

  Current Estimated Value $3,376,203

  Last Listing Agent Michael Pesce BERKSHIRE HATHAWAY

  78 McCouns Ln, Glen Head, NY 11545
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  Est $3,656,664 Not Listed For Sale

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

  4 Canterbury Rd, Glen Head, NY 11545

  4 Canterbury Rd, Glen Head, NY 11545
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  $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
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  $2,350,000 Sold Sep 02, 2025

  6 Dolly Cam Ln, Glen Head, NY 11545

  • 4 Beds
  • 3.5 Baths
  • 4,284 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $549/SF
  • 29 Days On Market

  Current Estimated Value $2,369,881

  Last Listing Agent Michael Stanco Compass Greater NY LLC

  6 Dolly Cam Ln, Glen Head, NY 11545
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  Est $2,553,179 Not Listed For Sale

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

  22 Pheasant Hill Ln, Glen Head, NY 11545

  22 Pheasant Hill Ln, Glen Head, NY 11545
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  /2

  $2,900,000 Pending

  • 7 Beds
  • 10 Baths
  • 8,162 Sq Ft

  80 Valentines Ln, Glen Head, NY 11545

  Old Brookville Contemporary Home | Stunning and serene property backing lush nature preserve - 80 Valentines Lane offers pure peace and privacy on Long Island's Gold Coast.

  Joe Scavo Douglas Elliman Real Estate

  80 Valentines Ln, Glen Head, NY 11545
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  $2,030,000 Sold Jan 12, 2026

  14 Pheasant Hill Ln, Glen Head, NY 11545

  • 7 Beds
  • 6 Baths
  • 5,494 Sq Ft
  • Built 1964

  Last Sold Summary

  • 14% Below List Price
  • $369/SF
  • 58 Days On Market

  Last Listing Agent Damian Ross Daniel Gale Sothebys Intl Rlty

  14 Pheasant Hill Ln, Glen Head, NY 11545
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  Est $5,612,000 Not Listed For Sale

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

  873 Cedar Swamp Rd, Glen Head, NY 11545

  873 Cedar Swamp Rd, Glen Head, NY 11545
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  $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
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  $1,900,000 Sold Jan 15, 2026

  10 Eastview Ln, Glen Head, NY 11545

  • 4 Beds
  • 5 Baths
  • 3,628 Sq Ft
  • Built 1861

  Last Sold Summary

  • 16% Below List Price
  • $524/SF
  • 69 Days On Market

  Last Listing Agent Catherine Davis Serhant East End LLC

  10 Eastview Ln, Glen Head, NY 11545
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  Est $3,075,452 Not Listed For Sale

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

  18 Pheasant Hill Ln, Glen Head, NY 11545

  18 Pheasant Hill Ln, Glen Head, NY 11545
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  $2,400,000 Pending

  • Land
  • 3.39 Acres
  • $707,965 per Acre

  170 Hegemans Ln, Old Brookville, NY 11545

  One-of-a-Kind Offering! Build your Dream Home in the only gated community within the Village of Old Brookville. Enter this newly developed 23+ acre community through impressive remote-controlled gates. Proceed on a secluded and lushly landscaped two-lane motor court to a quiet sanctuary and cul-de-sac featuring six buildable lots ranging from 3 to 4 acres each. Each lot has already been improved

  Neena Chowdhary Daniel Gale Sothebys Intl Rlty

  170 Hegemans Ln, Old Brookville, NY 11545

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