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Upper Brookville, NY Homes for Sale

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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

    $8,994,999

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

    31 Chestnut Hill Dr, Oyster Bay, NY 11771

    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 originally designed by the renowned architect Gary Gallagher and redesigned by award-winning

    Agent Photo

    Ephraim Simon

    Serhant East End LLC

    31 Chestnut Hill Dr, Oyster Bay, NY 11771
  • /4

    $6,000,000

    $2M PRICE DROP
    • Land
    • 12.62 Acres
    • $475,436 per Acre

    5694 Northern Blvd, East Norwich, NY 11732

    12.6 Acres of Prime Land for Sale – Planned for 4 Homes – 3-Acre Zoning – Cul-de-Sac AccessA rare development opportunity awaits with this 12.6-acre parcel of land, ideally situated at the end of a peaceful cul-de-sac. Zoned for 3-acre minimum lots, this property comes with a concept plan for 4 single-family homes, making it perfect for a small subdivision, custom home builder, or a private

    Agent Photo

    Khalidah Arifee

    Property Professionals Realty

    5694 Northern Blvd, East Norwich, NY 11732
  • /38

    $2,749,000

    $146K PRICE DROP
    • 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
  • /45

    $5,599,000

    Open Sun 1PM - 3:30PM
    • 6 Beds
    • 6.5 Baths
    • 7,300 Sq Ft

    730 Remsens Ln, Oyster Bay, NY 11771

    Introducing an Extraordinary new Construction Estate in the prestigious Village of Muttontown, Set on approximately 3 Private acres overlooking a Picturesque Golf Couse. This Exceptional 2026 built residence offers the perfect blend of Modern Luxury , Elegance, and Sophistication.Featuring Six (6) Spacious Bedrooms and 6.5 designer bathrooms, with Radiant Heated Floors. The home showcases

    Maria Priovolos Keller Williams Points North

    730 Remsens Ln, Oyster Bay, NY 11771
  • /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
  • /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
  • /37

    $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
  • /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

    $5,250,000

    $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
  • /49

    $3,700,000

    $300K PRICE DROP
    • 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

    Kathryn Maxwell Pournaras Daniel Gale Sothebys Intl Rlty

    343 Chicken Valley 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
  • /34

    $4,200,000

    • 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

    • 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

    Open Sun 12PM - 2PM
    • 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
  • /37

    $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
  • /37

    $2,895,000

    $455K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,850 Sq Ft

    855 Orchard Ln, Oyster Bay, NY 11771

    - Low Taxes - $36,000 total- Heated Saltwater Gunite Pool- Locust Valley Schools- Village of Muttontown- 4,850 Sq Ft- 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 featuring DCS Gas Grill, Lynx Pizza Oven, Lynx

    Tracey Murray Kupferberg Douglas Elliman Real Estate

    855 Orchard Ln, Oyster Bay, NY 11771
  • /16

    $289,999

    $15K PRICE DROP
    • 1 Bath
    • 650 Sq Ft

    200 Lexington Ave Unit 12E, Oyster Bay, NY 11771

    Beautifully landscaped and well maintained co-op apartment complex with walkways, patios and sitting areas with on-site superintendent.Second floor studio with high ceilings, 1 AC, open layout, and kitchen with stainless steel appliances.Basement common level offers storage and laundry facilities including bicycle storage room.Conveniently located in the heart of Oyster Bay

    Allan Obando Fave Realty Inc

    200 Lexington Ave Unit 12E, Oyster Bay, NY 11771

Why Live in Upper Brookville

Upper Brookville, NY, is characterized by its winding roads lined with large estates, woods, and farms, creating a calming rural atmosphere. Residents enjoy privacy and nature, with homes on parcels of land starting at a minimum of 2 acres. The village is split between the highly rated Oyster Bay-East Norwich Central School District and Locust Valley Central School District, offering excellent public school options such as Theodore Roosevelt School, James H. Vernon School, Oyster Bay High School, Ann MacArthur Primary School, Locust Valley Intermediate School, Locust Valley Middle School, and Locust Valley High School. Outdoor enthusiasts can explore Hope Iselin Preserve and Planting Fields Arboretum, which features 409 acres of gardens, greenhouses, and historic sites like Coe Hall Historic House Museum. The arboretum hosts community events, including twilight tours and 5K runs. The Mill River Club offers amenities like an 18-hole golf course, pool, and tennis courts. North Shore beaches are less than 4 miles away, providing opportunities for swimming and enjoying sunsets. Shopping and dining options are available in nearby Oyster Bay and East Norwich, with easy access to the Northern State Parkway and an 80-minute train ride to New York City from Oyster Bay Station. Upper Brookville’s mix of large homes, rural atmosphere, and proximity to essentials and entertainment features make it a desirable place to live.

Upper Brookville, NY Home Prices

Upper Brookville, NY
Median Home Price
$13,499,000
Median Sale Price
$2,500,000
% YoY
Avg. Price per Square Foot
$1,115
Median Single Family Price
$25,000,000
Total Active Listings
22 listings
Market Conditions
12 Months of Supply
Buyer's Market

Frequently Asked Questions

What is the average home price in Upper Brookville, NY?
Homes for sale in Upper Brookville, NY have an average home price of $13,499,000.
How many homes have sold over the last 12 months in Upper Brookville, NY?
1 home has sold in Upper Brookville, NY over the last 12 months.
What is the average household income in Upper Brookville, NY?
The average household income in Upper Brookville, NY is $202K.
What are the most popular zip codes in Upper Brookville, NY?
The most popular zip codes in Upper Brookville, NY include 11771, 11545, 11560, 11732 and 11765.
How much do you need to make to afford a house in Upper Brookville?
The median home price in Upper Brookville is $13,499,000. If you put a 20% down payment of $2,699,800 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $71,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $3M a year to afford the median home price in Upper Brookville. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Upper Brookville is $202K.
How are the schools in Upper Brookville, NY?
Upper Brookville, NY has highly rated public and private schools. Some of the best schools in Upper Brookville based on Niche Grades are Friends Academy, Green Vale School and Jericho Middle School. Browse all the schools in Upper Brookville, NY to learn more.
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