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Old Brookville, NY Homes for Sale with Pool

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  • /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
  • /26

    $13,600,000

    • 10 Beds
    • 9.5 Baths
    • 14,761 Sq Ft

    97 Pound Hollow Rd, Glen Head, NY 11545

    Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 15+ acre equestrian estate formally named 'Westward' presents a rare opportunity to acquire a significant piece of North Shore history. Privately nestled amid rolling pastures, mature woodlands, and formal gardens, the estate seamlessly blends timeless architectural elegance with an unparalleled country lifestyle

    Agent Photo

    Linda Faraldo

    Daniel Gale Sothebys Intl Rlty

    97 Pound Hollow Rd, Glen Head, NY 11545
  • /50

    $2,775,000

    • 4 Beds
    • 3.5 Baths
    • 3,112 Sq Ft

    153 Brookville Ln, Glen Head, NY 11545

    Nestled on two private acres, this stunning 4-bedroom, 3.5-bath ranch combines timeless comfort with resort-style living, featuring over 3,100 square feet, an in-ground pool, and beautifully designed indoor-outdoor spaces, all within the acclaimed North Shore School District.

    Salvatore Vacchio Countryside Realty & Mgmt Svcs

    153 Brookville Ln, Glen Head, NY 11545
  • /13

    $4,795,999

    • 11 Beds
    • 14 Baths
    • 11,304 Sq Ft

    1 Penny Pond Ct, Greenvale, NY 11548

    A truly extraordinary opportunity to create one of Brookville's most distinguished private estates. Nestled on an expansive 15-acre parcel in the prestigious Village of Old Brookville, this remarkable property offers an unparalleled setting on one of the area's most coveted and desirable streets. Plans envision a magnificent 22,000-square-foot luxury residence thoughtfully designed to blend

    Robert Barnes BERKSHIRE HATHAWAY

    1 Penny Pond Ct, Greenvale, NY 11548
  • /47

    $5,498,000

    • 7 Beds
    • 8 Baths
    • 5,764 Sq Ft

    952 Cedar Swamp Rd, Glen Head, NY 11545

    Nestled on approximately 5 landscaped acres in Old Brookville, this distinguished estate offers exceptional space, privacy, and classic Gold Coast character. The property includes a stately main residence, a separate 3-bedroom guest cottage, and a pool house, providing flexible living and entertaining opportunities.The main residence offers approximately 5,764 square feet of living space with

    Ying Xu P R O Links Realty Inc

    952 Cedar Swamp Rd, Glen Head, NY 11545
  • /36

    $3,899,000

    • 6 Beds
    • 4.5 Baths
    • 5,254 Sq Ft

    91 Hoaglands Ln, Glen Head, NY 11545

    Nestled in the heart of Old Brookville, this private oasis offers the perfect blend of luxury, tranquility, and modern living. Set on a sprawling, flat 3.2 -acre lot within the prestigious North Shore School District, this property feels like your own year-round retreat.As you approach via the picturesque private driveway, you're greeted by lush, mature landscaping that ensures complete

    Allison Hollander Compass Greater NY LLC

    91 Hoaglands Ln, Glen Head, NY 11545
  • /15

    $2,699,900

    $50K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,938 Sq Ft

    Unlisted Address

    Stunning Old Brookville Estate on 2 Acres with Pool & Outdoor Oasis Welcome to this exquisite 5-bedroom, 4-bathroom home nestled on 2 acres of beautifully landscaped property in the prestigious area of Old Brookville. This elegant residence offers the perfect blend of luxury, comfort, and privacy. Step inside to discover spacious living areas filled with natural light, including a grand living

    Colleen Chase Signature Premier Properties

    Unlisted Address
  • /50

    $5,499,000

    • 9 Beds
    • 7.5 Baths
    • 8,200 Sq Ft

    8 Stonegate Ln, Glen Head, NY 11545

    Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. Inside, the richly paneled foyer and wide pegged oak

    Lisa Ann Heaney Daniel Gale Sothebys Intl Rlty

    8 Stonegate Ln, Glen Head, NY 11545
  • /48

    $6,999,000

    • 7 Beds
    • 8.5 Baths
    • 12,571 Sq Ft

    3 Valentine Farm Ct, Glen Head, NY 11545

    Old Brookville | Welcome to 3 Valentine Farm Court, where timeless architecture, exceptional craftsmanship, and an unmatched collection of luxury amenities define one of the North Shore's most impressive private estates. Positioned behind double iron gates at the end of a secluded cul-de-sac, this stately brick center hall colonial is situated on more than three meticulously landscaped acres,

    Joe Scavo Douglas Elliman Real Estate

    3 Valentine Farm Ct, Glen Head, NY 11545
  • /45

    $4,399,000

    $400K PRICE DROP
    • 5 Beds
    • 8 Baths
    • 6,049 Sq Ft

    93 Hoaglands Ln, Glen Head, NY 11545

    Set within the rarefied landscape of Old Brookville, this striking Mid-Century Modern residence is a study in architectural drama and refined design. Celebrated in Luxe Interiors + Design at the time of its transformation, the home reflects the visionary collaboration between its owners and the acclaimed firm Garcia/Maldonado, Inc.. The result is a masterwork where every line, material, and

    Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

    93 Hoaglands Ln, Glen Head, NY 11545
  • /39

    $4,150,000

    Open Sun 11AM - 1PM
    • 6 Beds
    • 5.5 Baths
    • 6,404 Sq Ft

    17 Hunt Ct, Glen Head, NY 11545

    Old Brookville with choice of North Shore or Locust Valley Schools. 2 Acre Property Welcome to 17 Hunt Court, nestled within the coveted Pheasant Chase section of Old Brookville and tucked behind the area's renowned equestrian center. This exceptional brick colonial blends timeless architecture with beautifully updated interiors, resort-inspired outdoor living, and the peaceful surroundings that

    Joe Scavo Douglas Elliman Real Estate

    17 Hunt Ct, Glen Head, NY 11545
  • /26

    $5,490,000

    $2M PRICE DROP
    • 6 Beds
    • 5.5 Baths

    89 Pound Hollow Rd, Glen Head, NY 11545

    Where Drama Meets DesignWelcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable.From the moment you step inside, you’re swept into a world of high style and high impact. The

    Karen Sharf Daniel Gale Sothebys Intl Rlty

    89 Pound Hollow Rd, Glen Head, NY 11545
  • /42

    $6,450,000

    $400K PRICE DROP
    • 7 Beds
    • 10 Baths
    • 7,485 Sq Ft

    6 Evergreen Way, Glen Head, NY 11545

    Set behind private gates in the prestigious Estates at Greenfield, this stately brick Georgian Colonial is perfectly positioned on three + magnificently landscaped acres, offering an exceptional blend of timeless architecture and resort-style living. A gracious approach leads to a generous courtyard, creating a striking first impression and a true sense of arrival. Inside, a dramatic two-story

    Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

    6 Evergreen Way, Glen Head, NY 11545
  • /37

    $5,250,000

    • 6 Beds
    • 10 Baths
    • 7,532 Sq Ft

    33 Chicken Valley Rd, Glen Head, NY 11545

    Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase

    Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

    33 Chicken Valley Rd, Glen Head, NY 11545
  • /46

    $3,499,000

    $500K PRICE DROP
    • 6 Beds
    • 9 Baths
    • 7,887 Sq Ft

    12 Ridge Ct, Glen Head, NY 11545

    Welcome to 12 Ridge Ct, located in the heart of Old Brookville in the Brookville Meadows. This is your window of opportunity to live in the Gold Coast on 3.4 acres of flat land. From the moment you turn on to the tree-lined street (White Gate Dr.) entering Brookville Meadows, you will feel the caliber of luxury you are about to enter. This home boasts over 7,800 sq feet, the open layout will give

    Richard Brazzano BERKSHIRE HATHAWAY

    12 Ridge Ct, Glen Head, NY 11545
  • /28

    $3,600,000

    $250K PRICE DROP
    • 7 Beds
    • 5.5 Baths
    • 5,073 Sq Ft

    285 Piping Rock Rd, Locust Valley, NY 11560

    Rosegate is an enchanting mini estate that harkens back to golden age of the North Shore of Long Island. This architectural gem has been thoughtfully expanded over the years into a stately 7-bedroom Colonial, set on 2.85 acres of lush, storybook grounds. Every inch of Rosegate exudes character and charm from its Ludowici style roof to its diamond trellis ivy covered walls. Step through the front

    Robert Hulse Compass Greater NY LLC

    285 Piping Rock Rd, Locust Valley, NY 11560
  • /45

    $3,500,000

    Open Sun 11:30AM - 1PM $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
  • /3

    $1,399,000

    $109K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft

    11 Mary Ln, Greenvale, NY 11548

    Roslyn Harbor, North Shore Schools, on cul-de-sac. 0.86 of an acre, opportunity to build your dream home.

    Derek Greene Greene Realty Group

    11 Mary Ln, Greenvale, NY 11548

Home Price Trends

Median Sale Price
$5,020,000
Median Single Family Sale Price
$5,020,000
Average Price Per Sq Ft
$835
Number of Homes for Sale
0
Last 12 months Home Sales
1
Months of Supply
0.00
Median List Price
$5,350,000
Median Change From 1st List Price
6%
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