12

5-Bedroom Houses for Sale in Upper Brookville, NY

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  • /8

    $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
  • /28

    $6,995,000

    • 6 Beds
    • 6 Baths
    • 6,711 Sq Ft

    10 Colonial Dr, Glen Head, NY 11545

    10 Colonial Drive is a stunning Georgian estate set on 5 impeccably landscaped acres in the prestigious Colonial Drive Estate of Upper Brookville. This 6,711 sq. ft. residence offers 6 bedrooms, 6 bathrooms, 4 fireplaces, a heated gunite pool, tennis court, and a 3-car garage. A Baccarat chandelier graces the double-height foyer, setting the tone for elegant living. The formal dining room flows

    Benjamin Jordan Douglas Elliman Real Estate

    10 Colonial Dr, Glen Head, NY 11545
  • /42

    $3,800,000 Open Sat 12:30PM - 2PM

    • 6 Beds
    • 6.5 Baths
    • 6,355 Sq Ft

    412 Mill River Rd, Oyster Bay, NY 11771

    Experience modern luxury in this brand-new contemporary masterpiece. This stunning home features expansive open-concept living, soaring ceilings, statement chandelier lighting, and floor-to-ceiling windows that flood the space with natural light, Hide-A-Hose Central Vacuum, Generator. 4-zone HVAC system ensures year-round comfort, while a fully finished basement provides additional flexible

    Najla Erfan Property Professionals Realty

    412 Mill River Rd, Oyster Bay, NY 11771
  • /36

    $1,800,000

    • 6 Beds
    • 4.5 Baths
    • 4,000 Sq Ft

    1233 The Knolls, Oyster Bay, NY 11771

    Incredible opportunity to own and live in prestigious Upper Brookville! Make this amazing 6 bedroom colonial your next dream home. Beautiful layout and flow along with 2 bedroom guest quarters above garage with back stairs off kitchen. Amazing picturesque wide open flowing and very private stunning 2 acre property with pool. All perfectly located on private cul de sac. Property has been in same

    Allison O Rourke Douglas Elliman Real Estate

    1233 The Knolls, Oyster Bay, NY 11771
  • /49

    $3,200,000

    • 7 Beds
    • 8 Baths
    • 8,286 Sq Ft

    10 Laurel Woods Dr, Oyster Bay, NY 11771

    Welcome to Lions Gate!A Private North Shore Estate of Distinction nestled in the heart of Long Island’s Gold Coast; Lions Gate is a grand and secluded 5-acre country estate offering an unparalleled lifestyle of elegance and comfort. The home features seven bedrooms in total, including five ensuite bedrooms—one of which is a first-floor primary suite, each with its own full bath—while two

    Regina Rogers Douglas Elliman Real Estate

    10 Laurel Woods Dr, Oyster Bay, NY 11771
  • /37

    $7,850,000

    • 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

    $3,699,000

    • 6 Beds
    • 5 Baths
    • 5,500 Sq Ft

    13 Locust Ln, Glen Head, NY 11545

    La Isabella A Gracious 2 Acre Estate In Prestigious Upper Brookville Offering Timeless Colonial Architecture With Modern Luxury. Set Behind A Sweeping Drive And Surrounded By Mature Magnolia, Dogwood, And Maple Trees, This Home Is Crafted For Multigenerational Living With Privacy And Sophistication. Inside, A Dramatic Double-Height Foyer And Sweeping Staircase Welcome You To Spacious Sunlit Rooms

    Lisa Fasano Compass Greater NY LLC

    13 Locust Ln, Glen Head, NY 11545
  • /38

    $2,340,000

    • 5 Beds
    • 4.5 Baths
    • 5,405 Sq Ft

    1 Pine Valley Rd, Oyster Bay, NY 11771

    Tucked away on a fully fenced, over two-acre, park-like, electronic-gated property, stands a sprawling Farm Rach expanded and remodeled in 2007. This 5,400-square-foot mini estate of your dreams is located in the scenic Upper Brookville village. With rolling wooded open spaces rife with wildlife and dotted with grand and historic estates, you will be close to boating, golf, equestrian facilities,

    Regina Rogers Douglas Elliman Real Estate

    1 Pine Valley Rd, Oyster Bay, NY 11771
  • /39

    $2,450,000 Open Sun 11AM - 1PM

    • 6 Beds
    • 4.5 Baths
    • 5,871 Sq Ft

    21 Overbrook Ln, Glen Head, NY 11545

    21 Overbrooke Ln offers savvy investors the perfect canvas for a high-value renovation project in one of the North Shore’s most desirable communities. This property sits on a generous lot and is primed for transformation into a luxury residence that aligns with the area’s strong demand for updated homes.Why This Property is a Flip Opportunity:Strong ARV (After Repair Value): Upper

    Aleksandr Dzhurayev Skyline Residential & Comm Inc

    21 Overbrook Ln, Glen Head, NY 11545
  • /36

    $27,000,000

    • 13 Beds
    • 17 Baths
    • 12,892 Sq Ft

    0 Applewood Estate Unit ONE3578383, Upper Brookville, NY 11545

    Behold Applewood Estate, an expansive 35+ acre serene property nestled within the prestigious Village of Upper Brookville. This unmatched North Shore architectural masterpiece with 6+ dwellings, offers both grandeur and elegance. The unrivaled property was meticulously designed with professional landscaping, decorated with mature privacy hedges, formal gardens with water features and rolling

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    0 Applewood Estate Unit ONE3578383, Upper Brookville, NY 11545
  • /27

    $3,699,000

    • 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
  • /5

    $3,500,000 Coming Soon

    • 6 Beds
    • 9 Baths
    • 8,000 Sq Ft

    5 Carol Ln, Glen Head, NY 11545

    Elegance personified in this rare gem that captivates the senses and stirs the soul. Captivating every grandeur where you would never want to leave your home on two lush acres. A show stopper!!. Boasts 30 Ft. high ceilings with classic comtemporary elements brought together with masterful finishes that capture elegance and tranquility. Gated entrance and exit with directory for family

    Ken Deutsch Deutsch Realty Inc

    5 Carol Ln, Glen Head, NY 11545
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