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Upper Brookville, NY Homes for Sale with Garage

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  • /41

    $3,795,000

    • 6 Beds
    • 5.5 Baths
    • 5,911 Sq Ft

    23 Overbrook Ln, Glen Head, NY 11545

    Framed by sweeping pond views and surrounded by over 2 private acres of beautifully landscaped grounds, this beautifully renovated brick estate offers a rare blend of luxury, privacy, and serene waterfront living. Tucked away on a quiet cul-de-sac, the home is perfectly positioned to capture the beauty of the pond from both the interior living spaces and the resort-style outdoor setting.A

    Agent Photo

    Jagmeet Bedi

    Compass Greater NY LLC

    23 Overbrook Ln, Glen Head, NY 11545
  • /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
  • /49

    $9,850,000

    $900K 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
  • /39

    $2,988,000

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    110 Linden Ln, Glen Head, NY 11545

    Welcome to luxury living in Upper Brookville's most desirable location. This stunning furnished residence features 6 bedrooms, 5 bathrooms, an office, and a luxurious master suite with a steam shower, jacuzzi tub and a huge walk-in closet. Spread across beautifully landscaped grounds, enjoy amenities such as a Har-Tru tennis court, a heated Olympic-size pool with a spa, and a sun filled deck with

    Anastasiya Franke F2 Firm Inc

    110 Linden Ln, Glen Head, 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
  • /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
  • /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
  • /18

    $2,295,000

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

    7 Locust Ln, Glen Head, NY 11545

    Diamond in the Rough. Oversized cedar shake Cape Cod style home, offers 4453SF of living space on 2 flat acres in Upper Brookville. Traditional Colonial layout features a two-story entry foyer flanked by a formal living room with wood burning fireplace and formal dining rooms, both with large picture windows. An open concept kitchen/great room w/ fireplace is the heart of the home, with high

    Kristine Livadas Compass Greater NY LLC

    7 Locust 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
  • /44

    $2,500,000

    • 7 Beds
    • 4.5 Baths
    • 4,075 Sq Ft

    1117 Cedar Ridge Rd, Oyster Bay, NY 11771

    Short Sale - cash offers only- it is only unable to be financed. Offer subject to third-party approvals

    eva boccio Clear Coast Realty LLC

    1117 Cedar Ridge Rd, Oyster Bay, NY 11771
  • /40

    $2,199,000

    New Construction
    • 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
  • /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

    $6,498,000

    $2M 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
  • /49

    $4,000,000

    • 4 Beds
    • 3.5 Baths
    • 6,122 Sq Ft

    343 Chicken Valley Rd, Glen Head, NY 11545

    Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors

    Kathryn Maxwell Pournaras Daniel Gale Sothebys Intl Rlty

    343 Chicken Valley Rd, Glen Head, NY 11545
  • /44

    $3,850,000

    • 6 Beds
    • 4.5 Baths
    • 6,100 Sq Ft

    735 Remsens Ln, Oyster Bay, NY 11771

    Welcome to Orchard Fields set on over 2 acres of beautifully flat and private grounds, this stunning 6-bedroom, 5-bathroom Colonial blends timeless elegance with modern comfort in one of Upper Brookville’s most prestigious enclaves. Completely and tastefully renovated, this home offers an effortless indoor-outdoor lifestyle perfect for both everyday living and entertaining.The thoughtfully

    Nicholas Conti Compass Greater NY LLC

    735 Remsens Ln, Oyster Bay, NY 11771
  • /49

    $1,990,000

    $508K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,176 Sq Ft

    1678 Cedar Swamp Rd, Glen Head, NY 11545

    Welcome to 1678 Cedar Swamp Road, Brookville! Set on a sprawling 2.01-acre property in Brookville and located within the Jericho School District, this beautifully maintained 4-bedroom, 3.5-bath Colonial offers exceptional space, comfort, and lifestyle amenities. The home features wood floors throughout, new moldings, and a freshly painted interior, creating a bright and inviting atmosphere from

    Hemant Shah LAFFEY REAL ESTATE

    1678 Cedar Swamp Rd, Glen Head, NY 11545

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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