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Upper Brookville, NY Homes

Section Image
  • /47

    $5,698,000

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

    5 Farmwoods Ln, Glen Head, NY 11545

    This gorgeous Brick Colonial, located in Upper Brookville, is a beautiful and elegant estate that sits on 2.53 acres. Built in 2007, this residence offers an impressive 6 bedrooms and 7 bathrooms within its expansive 6,921 square feet of living space. Step inside to find a home designed for both grand entertaining and comfortable living. The first floor features a formal living room, a formal

    Batul Morbi Compass Greater NY LLC

    5 Farmwoods Ln, Glen Head, NY 11545
  • /27

    $20,000 per month

    • 3 Beds
    • 3 Baths
    • House for Rent

    Unlisted Address

    Welcome to Barn Owl, a timeless summer retreat set on beautifully landscaped grounds with peaceful garden views on the North Shore of Long Island. This inviting three-bedroom, three-bath cottage offers a rare blend of tranquility, character, and understated elegance for the summer season. Inside, a dramatic great room with soaring ceilings and exposed rustic beams creates a warm and striking

    Samantha Lordi Compass Greater NY LLC

    Unlisted Address
  • 1263 Pine Valley Rd, Oyster Bay, NY 11771

    $7,950,000 Sold Jul 25, 2025

    1263 Pine Valley Rd, Oyster Bay, NY 11771

    • 7 Beds
    • 7.5 Baths
    • 3,278 Sq Ft
    • Built 2017

    Last Sold Summary

    • $2,425/SF
    • 190 Days On Market

    Current Estimated Value $7,738,085

    Last Listing Agent Lisa Fasano Compass Greater NY LLC

    1263 Pine Valley Rd, Oyster Bay, NY 11771
    • 67 Mill River Rd, Oyster Bay, NY 11771

      Est $3,122,652 Not Listed For Sale

      67 Mill River Rd, Oyster Bay, NY 11771

      • 6 Beds
      • 8 Baths
      • 5,699 Sq Ft
      • Built 2014
      67 Mill River Rd, Oyster Bay, NY 11771

      Last Sold Summary

      • 19% Above List Price
      • $462/SF
      • 255 Days On Market

      Last Sold Price $2,635,000

      Last Listing Agent John Messina Daniel Gale Sotheby's

  • /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
  • /21

    $3,500 per month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    953 Ripley Ln, Oyster Bay, NY 11771

    Charming one-bedroom cottage with an additional room that could easily make a wonderful office space. Set on an estate of 3+ acres, surrounded by beautifully landscaped grounds—very peaceful location.

    Donna Scala LAFFEY REAL ESTATE

    953 Ripley Ln, Oyster Bay, NY 11771
  • 1347 Chicken Valley Rd, Oyster Bay, NY 11771

    $3,000,000 Sold Mar 27, 2026

    1347 Chicken Valley Rd, Oyster Bay, NY 11771

    • 4 Beds
    • 5 Baths
    • 3,683 Sq Ft
    • Built 1928

    Last Sold Summary

    • 8% Below List Price
    • $815/SF
    • 44 Days On Market

    Current Estimated Value $3,156,629

    Last Listing Agent Kimberly Bancroft Daniel Gale Sothebys Intl Rlty

    1347 Chicken Valley Rd, Oyster Bay, NY 11771
    • 999 Wolver Hollow Rd, Oyster Bay, NY 11771

      Est $2,542,068 Not Listed For Sale

      999 Wolver Hollow Rd, Oyster Bay, NY 11771

      • 6 Beds
      • 4.5 Baths
      • 6,595 Sq Ft
      • Built 1958
      999 Wolver Hollow Rd, Oyster Bay, NY 11771

      Last Sold Summary

      • 6% Below List Price
      • $409/SF
      • 15 Days On Market

      Last Sold Price $2,700,000

      Last Listing Agent Lindsey Barnett Compass Greater NY LLC

  • /37

    $7,300,000 Open Sat 2:30PM - 4PM

    • 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
  • /48

    $15,000 per month

    • 6 Beds
    • 5 Baths
    • 3,031 Sq Ft
    • House for Rent

    Unlisted Address

    Experience unparalleled privacy and space in this sprawling 3,000 sq. ft. expanded ranch, nestled on 3 acres of lush, manicured grounds within the prestigious Jericho School District. A long, private driveway leads you to a home designed for both grand entertaining and quiet relaxation.• The Main Level: Features a bright living room with a cozy wood-burning fireplace and an inviting open

    Connie Chan Sung & Associates Real Estate

    Unlisted Address
  • 40 W View Dr, Oyster Bay, NY 11771

    $2,400,000 Sold Feb 10, 2026

    40 W View Dr, Oyster Bay, NY 11771

    • 5 Beds
    • 5.5 Baths
    • 6,219 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Below List Price
    • $386/SF
    • 21 Days On Market

    Current Estimated Value $2,426,794

    Last Listing Agent Barbara Drucker Douglas Elliman Real Estate

    40 W View Dr, Oyster Bay, NY 11771
    • 4 Fairway Ct, Oyster Bay, NY 11771

      Est $4,262,089 Not Listed For Sale

      4 Fairway Ct, Oyster Bay, NY 11771

      • 6 Beds
      • 6.5 Baths
      • 8,390 Sq Ft
      • Built 1998
      4 Fairway Ct, Oyster Bay, NY 11771

      Last Sold Summary

      • 33% Above List Price
      • $381/SF
      • 29 Days On Market

      Last Sold Price $3,200,000

      Last Listing Agent Michael Stanco Compass Greater NY LLC

  • /38

    $6,475,000

    • 6 Beds
    • 6 Baths
    • 8,055 Sq Ft

    10 Colonial Dr, Glen Head, NY 11545

    Set on five flat, impeccably landscaped acres at the end of a quiet cul-de-sac, this stately Georgian brick estate represents one of the most private and desirable settings within Upper Brookville’s prestigious gated Colonial Drive enclave. Positioned on a private road of distinguished luxury estates and further enhanced by its own secondary gated entrance, the property offers a rare double gated

    Nareeta Saini Daniel Gale Sothebys Intl Rlty

    10 Colonial Dr, Glen Head, NY 11545
  • 183 Linden 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
    • 22 W View Dr, Oyster Bay, NY 11771

      Est $2,041,579 Not Listed For Sale

      22 W View Dr, Oyster Bay, NY 11771

      • 5 Beds
      • 4.5 Baths
      • 5,187 Sq Ft
      • Built 1987
      22 W View Dr, Oyster Bay, NY 11771

      Last Sold Summary

      • 13% Above List Price
      • $347/SF
      • 96 Days On Market

      Last Sold Price $1,800,000

      Last Listing Agent Jasleen Sabharwal Douglas Elliman Real Estate

  • /49

    $10,750,000

    • 6 Beds
    • 10 Baths
    • 10,109 Sq Ft

    31 Chestnut Hill Dr, Oyster Bay, NY 11771

    Maison Blanche: An Architectural Icon in Upper BrookvilleExperience the pinnacle of ultra-modern luxury at 31 Chestnut Hill Drive. Set on five flat, private acres at the crest of a premier cul-de-sac, this architectural sanctuary was originally designed by the renowned architect Gary Gallagher and redesigned by award-winning FAIA architect Stuart Narofsky, leading to an extensively renovated

    Ephraim Simon Serhant East End LLC

    31 Chestnut Hill Dr, Oyster Bay, NY 11771
  • 5 Linda Ct, Oyster Bay, NY 11771

    $1,650,000 Sold Dec 22, 2025

    5 Linda Ct, Oyster Bay, NY 11771

    • 5 Beds
    • 3.5 Baths
    • 2,968 Sq Ft
    • Built 1962

    Last Sold Summary

    • 8% Below List Price
    • $556/SF
    • 36 Days On Market

    Current Estimated Value $1,729,085

    Last Listing Agent Dee Dee Brix Compass Greater NY LLC

    5 Linda Ct, Oyster Bay, NY 11771
    • 25 Derby Ct, Oyster Bay, NY 11771

      Est $843,242 Not Listed For Sale

      25 Derby Ct, Oyster Bay, NY 11771

      • 3 Beds
      • 3 Baths
      • 1,917 Sq Ft
      • Built 1982
      25 Derby Ct, Oyster Bay, NY 11771

      Last Sold Summary

      • 16% Above List Price
      • $378/SF
      • 12 Days On Market

      Last Sold Price $725,000

      Last Listing Agent Laura Cochran BERKSHIRE HATHAWAY

  • /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
  • 77 Linden Ln, 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 $3,541,143

    Last Listing Agent Debra Quinn Petkanas Daniel Gale Sothebys Intl Rlty

    77 Linden Ln, Glen Head, NY 11545
    • 3 Donna Dr, Oyster Bay, NY 11771

      Est $5,725,625 Not Listed For Sale

      3 Donna Dr, Oyster Bay, NY 11771

      • 6 Beds
      • 9 Baths
      • 7,000 Sq Ft
      • Built 2024
      3 Donna Dr, Oyster Bay, NY 11771

      Last Sold Summary

      • 1% Above List Price
      • $807/SF
      • 578 Days On Market

      Last Sold Price $5,650,000

      Last Listing Agent Tracey Murray Kupferberg Douglas Elliman Real Estate

  • /50

    $1,995,000

    • 5 Beds
    • 4.5 Baths
    • 3,938 Sq Ft

    195 Cedar Swamp Rd, Glen Head, NY 11545

    A Rare 2-Acre North Shore Estate-Like Setting Offering Privacy, Presence, and Endless Potential Set on approximately 2 acres of private, park-Like grounds, this timeless Colonial with vintage charm presents a truly rare opportunity in the heart of Glen Head. Privately set back and gently elevated from the road along a long, tree-lined approach, the property offers an exceptional sense of space

    Nicole Commisso OverSouth LLC

    195 Cedar Swamp Rd, Glen Head, NY 11545
  • No # Linden Ln, Upper Brookville, NY 11545

    $1,640,000 Sold Jul 24, 2025

    No # Linden Ln, Upper Brookville, NY 11545

    • Land
    • 2.22 Acres
    • $738,739 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 82 Days On Market

    Last Listing Agent Debra Quinn Petkanas Daniel Gale Sothebys Intl Rlty

    No # Linden Ln, Upper Brookville, NY 11545
    • 677 Linda Ct, Oyster Bay, NY 11771

      Est $3,973,819 Not Listed For Sale

      677 Linda Ct, Oyster Bay, NY 11771

      • 6 Beds
      • 6.5 Baths
      • 10,000 Sq Ft
      • Built 2018
      677 Linda Ct, Oyster Bay, NY 11771

      Last Sold Summary

      • 22% Above List Price
      • $325/SF
      • 23 Days On Market

      Last Sold Price $3,250,000

      Last Listing Agent Nicholas Conti Compass Greater NY LLC

  • /31

    $2,895,000

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

    1017 Friendly Rd, Oyster Bay, NY 11771

    UPPER BROOKVILLE. Privately set behind sweeping lawns on over two acres in the Village of Upper Brookville, this elegant North Shore residence offers the privacy, scale, and timeless character synonymous with Gold Coast estate living. The home features 4 bedrooms, with primary suite on the main, and 3 full and 2 half baths, along with sun-filled living spaces, hardwood and tiled (radiant heated)

    Maria Babaev Douglas Elliman Real Estate

    1017 Friendly Rd, Oyster Bay, NY 11771
  • 12 Shelter 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 $2,546,999

    Last Listing Agent Melanie Cogan Compass Greater NY LLC

    12 Shelter Ln, Glen Head, NY 11545
    • 353 Juniper Dr, Oyster Bay, NY 11771

      Est $6,325,788 Not Listed For Sale

      353 Juniper Dr, Oyster Bay, NY 11771

      • 6 Beds
      • 9 Baths
      • 11,200 Sq Ft
      • Built 2013
      353 Juniper Dr, Oyster Bay, NY 11771

      Last Sold Summary

      • 5% Above List Price
      • $536/SF
      • 278 Days On Market

      Last Sold Price $6,000,000

      Last Listing Agent Jason Friedman Daniel Gale Sotheby's

  • /27

    $3,699,000 Pending

    • 5 Beds
    • 4.5 Baths

    5 Peacock Ln, Glen Head, NY 11545

    Rare Opportunity on Private Gated Upper Brookville Lane. Only 11 Homes Built & Seldom Offered For Sale. Pride of Ownership throughout This Turn Key Brick Colonial on Quiet Interior 2A+ Site. Attention to Detail, Functional Floor Plan for Contemporary Living & Entertaining Indoors and Outdoors. Magnificent Landscaped Grounds Complete with Outdoor Kitchen, Oversized Patio, Gunite Pool with

    Peggy Carillo Douglas Elliman Real Estate

    5 Peacock Ln, Glen Head, NY 11545
  • 963 Ripley Ln, Oyster Bay, NY 11771

    $3,000,000 Sold Apr 28, 2025

    963 Ripley Ln, Oyster Bay, NY 11771

    • 7 Beds
    • 8 Baths
    • 7,493 Sq Ft
    • Built 1925

    Last Sold Summary

    • 19% Below List Price
    • $400/SF
    • 240 Days On Market

    Current Estimated Value $3,883,010

    Last Listing Agent Kathryn Zoller Daniel Gale Sothebys Intl Rlty

    963 Ripley Ln, Oyster Bay, NY 11771
    • 43 Chestnut Hill Dr, Oyster Bay, NY 11771

      Est $8,864,515 Not Listed For Sale

      43 Chestnut Hill Dr, Oyster Bay, NY 11771

      • 7 Beds
      • 13 Baths
      • 10,861 Sq Ft
      • Built 1993
      43 Chestnut Hill Dr, Oyster Bay, NY 11771

      Last Sold Summary

      • 10% Below List Price
      • $907/SF
      • 19 Days On Market

      Last Sold Price $9,850,000

      Last Listing Agent Shawn Elliott Nest Seekers LLC

  • /22

    $3,500,000

    • 6 Beds
    • 9 Baths
    • 7,500 Sq Ft

    5 Carol Ln, Glen Head, NY 11545

    Elegance redefined in this stunning gem that blends an eclectic mix of mid-century modern design with a touch of contemporary sophistication, nestled on two lush, gated acres in Upper Brookville. From the moment you enter, the home captivates your imagination with its soaring 30-foot ceilings and dramatic windows and wood architectural elements. Clean lines, warm textures, and artful finishes

    Ken Deutsch Deutsch Realty Inc

    5 Carol Ln, Glen Head, NY 11545
  • 100 Wolver Hollow Rd, 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 $1,724,650

    Last Listing Agent Michael Pesce BERKSHIRE HATHAWAY

    100 Wolver Hollow Rd, Glen Head, NY 11545
    • 35 Chestnut Hill Dr, Oyster Bay, NY 11771

      Est $6,331,058 Not Listed For Sale

      35 Chestnut Hill Dr, Oyster Bay, NY 11771

      • 5 Beds
      • 9 Baths
      • 10,500 Sq Ft
      • Built 1997
      35 Chestnut Hill Dr, Oyster Bay, NY 11771

      Last Sold Summary

      • 12% Above List Price
      • $538/SF
      • 32 Days On Market

      Last Sold Price $5,650,000

      Last Listing Agent Shawn Elliott Nest Seekers LLC

  • /40

    $2,199,000

    • 3 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    89 Mill River Rd, Oyster Bay, NY 11771

    Upper Brookville. Brand New Construction on 5 Serene Acres. Move Right In to this Warm & Comfortable Sun Drenched Home! State of the Art Chef's Kitchen w Top of the Line Wolf & Sub Zero Stainless Steel Appliances Throughout. Oak Wood Floors Throughout Entire 2nd Floor. Primary Suite with Brand New Bathroom w His & Her Sinks, Oversized Shower, Luxurious Free Standing Tub & Private Water Closet. 2

    Michael J. Berman Automatic Real Estate Assoc

    89 Mill River Rd, Oyster Bay, NY 11771
  • 21 Overbrook Ln, Glen Head, NY 11545

    $2,200,000 Sold Mar 19, 2026

    21 Overbrook Ln, Glen Head, NY 11545

    • 6 Beds
    • 4.5 Baths
    • 5,900 Sq Ft
    • Built 1992

    Last Sold Summary

    • 2% Below List Price
    • $373/SF
    • 75 Days On Market

    Current Estimated Value $2,187,520

    Last Listing Agent Dalia Elison Douglas Elliman Real Estate

    21 Overbrook Ln, Glen Head, NY 11545
    • 10 Laurel Woods Dr, Oyster Bay, NY 11771

      Est $3,238,432 Not Listed For Sale

      10 Laurel Woods Dr, Oyster Bay, NY 11771

      • 6 Beds
      • 6.5 Baths
      • 5,017 Sq Ft
      • Built 1978
      10 Laurel Woods Dr, Oyster Bay, NY 11771

      Last Sold Summary

      • 42% Above List Price
      • $455/SF
      • 322 Days On Market

      Last Sold Price $2,284,800

      Last Listing Agent Jared Mandel Automatic Real Estate Assoc

  • /48

    $1,911,111

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

    111 Mill River Rd, Oyster Bay, NY 11771

    Private Hilltop Estate with Mother-Daughter Layout in Upper Brookville Located in the prestigious community of Upper Brookville, this exceptional 4,000 sq. ft. home sits on over 2 private acres at the top of a hill, offering outstanding privacy and beautiful natural surroundings. The property borders the Mill River Club and is surrounded by mature trees, creating a peaceful and secluded setting

    Rosalinda Silver Blackstone Realty

    111 Mill River Rd, Oyster Bay, NY 11771
  • 199 Terrace Ln, Oyster Bay, NY 11771

    $2,300,000 Sold Oct 08, 2025

    199 Terrace Ln, Oyster Bay, NY 11771

    • 5 Beds
    • 5 Baths
    • 6,300 Sq Ft
    • Built 1932

    Last Sold Summary

    • 14% Below List Price
    • $365/SF
    • 91 Days On Market

    Current Estimated Value $2,682,906

    Last Listing Agent Huailing Deng Daniel Gale Sothebys Intl Rlty

    199 Terrace Ln, Oyster Bay, NY 11771
    • 1167 Pine Valley Rd, Oyster Bay, NY 11771

      Est $3,467,441 Not Listed For Sale

      1167 Pine Valley Rd, Oyster Bay, NY 11771

      • 6 Beds
      • 4.5 Baths
      • 5,909 Sq Ft
      • Built 1951
      1167 Pine Valley Rd, Oyster Bay, NY 11771

      Last Sold Summary

      • 22% Above List Price
      • $482/SF
      • 76 Days On Market

      Last Sold Price $2,850,000

      Last Listing Agent Diana Mellone Daniel Gale Sotheby's

  • /23

    $2,750,000

    • 4 Beds
    • 6 Baths
    • 4,453 Sq Ft

    7 Locust Ln, Glen Head, NY 11545

    Beautiful Cape Style Cedar Shake Home, First Floor, Large Entry, Large Living Room W/Fireplace, Formal Dining Room, Large Open Eat In Kitchen With Great Room With Fireplace And Beautiful Wood Beams On Ceiling, Master Bedroom With Her And Him Closet, Primary Bathroom, Office Or Sitting Room Off Primary, Additional Bedroom With Full Bathroom, Landry Room. Second Floor Has Bedroom With Full

    Kim Flanagan Signature Premier Properties

    7 Locust Ln, Glen Head, NY 11545

Showing Results 1 - 40, Page 1 of 18

Home Trends in Upper Brookville, NY

Housing Trends

Median Sale Price
$2,500,000
Number of Homes for Sale
0
Last 12 months Home Sales
1
Months of Supply
0.00
Median List Price
$1,998,000
Median Change From 1st List Price
-25%
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