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Upper Brookville, NY Homes for Sale with Pool

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  • /49

    $8,995,000

    $2M PRICE DROP
    • 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

    Agent Photo

    Ephraim Simon

    Serhant East End LLC

    31 Chestnut Hill Dr, Oyster Bay, NY 11771
  • /47

    $25,000,000

    • 13 Beds
    • 17 Baths
    • 22,429 Sq Ft

    1 Applewood Estate, Upper Brookville, NY 11545

    Experience Applewood Estate — a generational North Shore compound where timeless architecture, historic provenance, and resort-caliber living unfold across more than 35 secluded acres in the esteemed Village of Upper Brookville. Once an operating apple orchard in the early 1900s and later owned by renowned American artist Montague Flagg, this extraordinary estate carries a legacy as rich as the

    Agent Photo

    Ephraim Simon

    Serhant East End LLC

    1 Applewood Estate, Upper Brookville, NY 11545
  • /43

    $1,980,000

    • 4 Beds
    • 3 Baths
    • 2,917 Sq Ft

    279 Hillcrest Ln, Oyster Bay, NY 11771

    Welcome to 279 Hillcrest Lane — A Rare Gold Coast Retreat on Over 2 Private AcresNestled in the prestigious Village of Upper Brookville on New York's storied North Shore, 279 Hillcrest Lane is a beautifully updated modified ranch offering the perfect blend of timeless elegance, thoughtful modern upgrades, and exceptional outdoor living. Set on over 2 park-like acres (87,133 sq ft) of lush,

    Huailing Deng Daniel Gale Sothebys Intl Rlty

    279 Hillcrest Ln, Oyster Bay, NY 11771
  • /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
  • /45

    $3,800,000

    • 5 Beds
    • 4.5 Baths
    • 4,528 Sq Ft

    61 Linden Ln, Glen Head, NY 11545

    Dream homes do exist. Perfectly situated on 2+ private, meticulously landscaped acres on a winding country lane, this charming 5-bedroom residence offers an unparalleled lifestyle. Every sun-drenched room provides stunning, expansive views of lush lawns, specimen trees, and vibrant perennial gardens. Exquisite Craftsmanship & Main Level Living. The main level showcases exceptional millwork, fine

    Kathryn Maxwell Pournaras Daniel Gale Sothebys Intl Rlty

    61 Linden Ln, Glen Head, NY 11545
  • /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
  • /36

    $5,288,000

    • 6 Beds
    • 6.5 Baths
    • 7,111 Sq Ft

    7 Fairway Ct, Oyster Bay, NY 11771

    A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a

    Michelle Cohen Compass Greater NY LLC

    7 Fairway Ct, Oyster Bay, NY 11771
  • /2

    $6,300,000

    New Construction
    • 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
  • /30

    $5,495,000

    • 6 Beds
    • 7.5 Baths
    • 8,500 Sq Ft

    45 Wolver Hollow Rd, Glen Head, NY 11545

    An exceptional private brick estate compound set on approximately7 meticulously manicured acres in Upper Brookville. This impressive residence offers grand scale, timeless elegance, luxurious landscaping, and a true lifestyle experience both inside and out. Filled with natural light, the home features vaulted ceilings, oversized windows, sweeping property views,6 spacious bedrooms with

    Julia Krispeal Douglas Elliman Real Estate

    45 Wolver Hollow Rd, Glen Head, NY 11545
  • /50

    $3,499,999

    • 6 Beds
    • 5.5 Baths
    • 8,263 Sq Ft

    1095 Pine Valley Rd, Oyster Bay, NY 11771

    Welcome to this exceptional estate tucked away at the end of a long, winding driveway on just over two pristine acres in Upper Brookville. This stunning property offers the perfect blend of luxury, comfort, and versatility.The main residence features 5 bedrooms and 4.5 fully updated bathrooms across two thoughtfully designed levels. The expansive first floor hosts 4 bedrooms and 3.5

    Nicholas Conti Compass Greater NY LLC

    1095 Pine Valley Rd, Oyster Bay, NY 11771
  • /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
  • /48

    $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
  • /40

    $2,995,000

    $355K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,848 Sq Ft

    855 Orchard Ln, Oyster Bay, NY 11771

    Welcome to this renovated 5 Bedroom, 4.5 Bath Colonial set on 2 beautifully landscaped acres, a truly move-in ready home. Located on the North Side of Northern Blvd/25A. The chef’s kitchen is appointed with Carrara Marble countertops, premium Wolf and Sub-Zero appliances, and high-end finishes. The elegant living room offers custom built-ins accented by Imperial Danby marble, beautifully

    Tracey Murray Kupferberg Douglas Elliman Real Estate

    855 Orchard Ln, Oyster Bay, NY 11771

Home Price Trends

Median Sale Price
$2,500,000
Median Single Family Sale Price
$25,000,000
Average Price Per Sq Ft
$1,115
Number of Homes for Sale
1
Last 12 months Home Sales
1
Months of Supply
12.00
Median List Price
$13,499,000
Median Change From 1st List Price
-25%
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