16

Upper Brookville, NY Homes for Sale with Pool

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  • /49

    $8,994,999

    $2M PRICE DROP
    • 6 Beds
    • 10 Baths
    • 10,109 Sq Ft

    31 Chestnut Hill Dr, Oyster Bay, NY 11771

    OFFERS OF $7,000,000 OR GREATER RECEIVED ON OR BEFORE SEPTEMBER 21, 2026 TO BE CONSIDERED. ENTIRE PROPERTY WAS COMPLETELY RENOVATED FROM 2023 T0 2026.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

    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
  • /38

    $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

    $3,500,000

    $300K PRICE DROP
    • 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
  • /37

    $4,998,000

    $290K PRICE DROP
    • 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
  • /38

    $3,999,000

    • 6 Beds
    • 9 Baths
    • 7,402 Sq Ft

    5 Carol Ln, Glen Head, NY 11545

    Elegance redefined. This fully gated extraordinary Upper Brookville estate seamlessly blends mid-century modern design with contemporary sophistication, set on two lush, gated acres. Soaring 30-foot ceilings, dramatic windows, rich wood architectural elements, clean lines, and sculptural details create a striking sense of tranquility. Palatial in scale yet thoughtfully designed for comfortable

    Stuart Caspi Douglas Elliman Real Estate

    5 Carol Ln, Glen Head, NY 11545
  • /30

    $5,250,000

    $245K PRICE DROP
    • 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 residenceoffers grand scale, timeless elegance, luxurious landscaping, and a truelifestyle experience both inside and out. Filled with natural light, the homefeatures vaulted ceilings, oversized windows, sweeping property views,6 spacious

    Julia Krispeal Douglas Elliman Real Estate

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

    $8,995,000

    • 5 Beds
    • 12 Baths
    • 9,500 Sq Ft

    7 Covey Ct, Glen Head, NY 11545

    A long driveway opens to a large courtyard with a classic fountain, revealing a magnificent Château-style Mansion on 2.03 acres of verdant property on a private cul-de-sac. Custom built for grand entertaining and everyday living, this incredible residence masterfully blends old-world European charm with modern luxury. A majestic 2-story entry foyer features a stunning domed-vaulted ceiling with a

    John Messina Daniel Gale Sothebys Intl Rlty

    7 Covey Ct, Glen Head, NY 11545
  • /47

    $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
  • /34

    $4,200,000

    Open Sat 1PM - 3PM
    • 6 Beds
    • 8 Baths
    • 8,286 Sq Ft

    10 Laurel Woods Dr, Oyster Bay, NY 11771

    Welcome to 10 Laurel Woods Drive, an expansive 8,000+ square-foot residence privately situated on 5.45 park-like acres in Upper Brookville. Set behind wrought iron gates at the end of a quiet, tree-lined cul-de-sac, this impressive expanded ranch offers exceptional scale, privacy, and a true estate-like setting.The home features six bedrooms and eight bathrooms, including a spacious

    Ted Kritikos Daniel Gale Sothebys Intl Rlty

    10 Laurel Woods Dr, Oyster Bay, NY 11771
  • /34

    $3,480,000

    Open Sun 2PM - 4:30PM
    • 6 Beds
    • 4.5 Baths
    • 5,156 Sq Ft

    24 Winding Ln, Glen Head, NY 11545

    Step away from the everyday and into this gracious, light-filled ranch, where every room feels like an invitation to relax. Sun-drenched and spacious, the interconnected living areas create an effortless flow — warm, welcoming, and made for both quiet mornings and lively gatherings.Built for entertaining, the home features a gourmet kitchen ready for your next dinner party, a formal

    Lina Wang Compass Greater NY LLC

    24 Winding Ln, Glen Head, NY 11545
  • /45

    $5,950,000

    • 6 Beds
    • 4.5 Baths
    • 6,953 Sq Ft

    898 Chicken Valley Rd, Locust Valley, NY 11560

    Set amid mature, beautifully landscaped grounds in the coveted Village of Matinecock, this distinguished brick North Shore residence, built in 2006, offers an exceptional combination of scale, craftsmanship, privacy, and resort-inspired living. Rich hardwood floors, substantial millwork, designer wallcoverings, and thoughtfully updated interiors create a home that is at once impressive and

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    898 Chicken Valley Rd, Locust Valley, NY 11560
  • /2

    $8,250,000

    • 6 Beds
    • 7.5 Baths
    • 7,036 Sq Ft

    160 Hegemans Ln, Glen Head, NY 11545

    Set behind the gates of an exclusive community in the Village of Old Brookville, this exceptional modern residence offers more than 7,000 square feet of luxurious living space on over three acres of beautifully manicured, private grounds. Walls of windows fill the home with natural light while showcasing serene views of the surrounding landscape, inground pool and hot tub.A dramatic

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    160 Hegemans Ln, Glen Head, NY 11545
  • /36

    $2,995,000

    $355K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,850 Sq Ft

    855 Orchard Ln, Oyster Bay, NY 11771

    - Low Taxes - $36,000- Locust Valley Schools- Village of Muttontown, located on the north side of Northern Boulevard/25A, bordering Upper Brookville-4,850 Sq Ft Colonial- 2 Acres- All Upstairs Bathrooms Fully Renovated with high end finishes- Kitchen features Carrara Marble with new Wolf and Sub-Zero Appliances- Bluestone Patio with fully equipped outdoor kitchen

    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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