789

Old Brookville, NY Homes

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  • 35 Hoaglands Ln, Glen Head, NY 11545
    35 Hoaglands Ln, Glen Head, NY 11545
    35 Hoaglands Ln, Glen Head, NY 11545
    /35

    $3,995,000

    • 6 Beds
    • 6.5 Baths
    • 4,787 Sq Ft

    35 Hoaglands Ln, Glen Head, NY 11545

    At the end of a long private driveway the exceedingly charming Georgian Colonial aptly styled “Twin Pines” awaits. Quiet luxury and classic architecture strikes a harmonious balance with resort-style amenities set amongst 2 lush acres, providing an exceptional lifestyle for the discerning buyer. Step inside the entrance to find a foyer with original palazzo tile and library with a wood-burning

    Jaime Hamm Daniel Gale Sothebys Intl Rlty

    35 Hoaglands Ln, Glen Head, NY 11545
  • 87 Piping Rock Rd, Glen Head, NY 11545
    87 Piping Rock Rd, Glen Head, NY 11545
    87 Piping Rock Rd, Glen Head, NY 11545
    /12

    $4,000 per month

    • 2 Beds
    • 1 Bath
    • 955 Sq Ft
    • House for Rent

    87 Piping Rock Rd, Glen Head, NY 11545

    Welcome to 87 Piping Rock Road, Glen Head — a beautifully appointed 2-bedroom, 1-bath rental tucked within a gated, secluded estate. Surrounded by nature and drenched in natural light, this unique residence offers the privacy and tranquility of estate living with modern comforts. The home features a full chef’s kitchen equipped with a baker’s oven, perfect for culinary enthusiasts, and a formal

    Nicholas Evangelista NY Space Finders Inc

    87 Piping Rock Rd, Glen Head, NY 11545
  • Lot 1189 Hegemans Ln, Old Brookville, NY 11545

    $2,075,000 Sold Apr 09, 2025

    • Land
    • 3.00 Acres
    • $691,667 per Acre
    • 313 Days On Market

    Lot 1189 Hegemans Ln, Old Brookville, NY 11545

    Truly a field of dreams!!! One of the last remaining opportunities to build in this prestigious gated Old Brookville community. Set on over 3 flat acres of property. Vineyards, farm-stands, and beautiful country roads, is what you will find as you approach the neighborhood, yet it is so central and conveniently located. There are currently plans to build a spectacular 8000 + square foot home

    Jacqueline Nathel Daniel Gale Sothebys Intl Rlty

    Lot 1189 Hegemans Ln, Old Brookville, NY 11545
  • 25 Longridge Ln, Glen Head, NY 11545
    25 Longridge Ln, Glen Head, NY 11545
    25 Longridge Ln, Glen Head, NY 11545
    /48

    $6,000,000

    • 4 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    25 Longridge Ln, Glen Head, NY 11545

    Old Brookville | Welcome to 25 Longridge Lane– a custom-built brick center hall colonial nestled on over 2 private acres at the end of a peaceful cul-de-sac. A grand entrance, framed by two stone pillars, leads to a long driveway with ample parking, offering two courtyards, and side access to a spacious 3-car garage. You’re immediately greeted by double iron doors that lead to a two-story foyer

    Joe Scavo Douglas Elliman Real Estate

    25 Longridge Ln, Glen Head, NY 11545
  • 1 Michaels Ln, Glen Head, NY 11545

    $2,000,000 Sold Mar 20, 2025

    • 3,265 Sq Ft
    • $613/SF
    • 13 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1962

    1 Michaels Ln, Glen Head, NY 11545

    Move right in and enjoy North Shore living in an idyllic setting. This classic, renovated 5 bedroom Colonial offers more than 3200 square feet of comfortable living space and a floor plan that makes entertaining, working from home and gathering by the fire, a pleasure. The first floor features a sunny, spacious living room, family room, modern eat-in kitchen and adjoining laundry nook, formal

    Ann Hance Compass Greater NY LLC

    1 Michaels Ln, Glen Head, NY 11545
  • 1132 Cedar Swamp Rd, Glen Head, NY 11545
    1132 Cedar Swamp Rd, Glen Head, NY 11545
    1132 Cedar Swamp Rd, Glen Head, NY 11545
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    $4,299,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 5.5 Baths
    • 5,858 Sq Ft

    1132 Cedar Swamp Rd, Glen Head, NY 11545

    Welcome to 1132 Cedar Swamp Road, a stunning hilltop colonial masterpiece, newly built in 2024, set on over 2.5 acres in the heart of the prestigious Village of Old Brookville, New York. This 5,800+ square foot designer residence seamlessly blends opulence with comfort, offering 6 luxurious bedrooms and 5.5 exquisitely designed bathrooms.Inside, the home is a vision of modern yet warm elegance,

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    1132 Cedar Swamp Rd, Glen Head, NY 11545
  • 1 Hickory Dr, Glen Head, NY 11545

    $3,660,000 Sold Mar 17, 2025

    • 6,156 Sq Ft
    • $595/SF
    • 14 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2000

    1 Hickory Dr, Glen Head, NY 11545

    PERFECT IN EVERY WAY!!! STEP INTO THIS SPACIOUS BRICK COLONIAL AND BE READY FOR ALL OF YOUR NEEDS IN YOUR NEW HOME TO BE MET! IT HAS EVERYTHING...NEW KITCHEN, NEW BATHS, FORMAL LIVING & DINING ROOMS, HOME OFFICE/LIBRARY, HUGE FAMILY ROOM WITH FIREPLACE, GLEAMING WOOD AND PORCELAIN FLOORS! THE 3 FAMILY BEDROOMS ON THE 2ND LEVEL ARE SPACIOUS, ONE IS "JACK & JILL". THE MASTER SUITE IN OVER-SIZED

    Rita Pecora Daniel Gale Sothebys Intl Rlty

    1 Hickory Dr, Glen Head, NY 11545
  • 285 Piping Rock Rd, Locust Valley, NY 11560
    285 Piping Rock Rd, Locust Valley, NY 11560
    285 Piping Rock Rd, Locust Valley, NY 11560
    /32

    $4,195,000

    • 7 Beds
    • 5.5 Baths

    285 Piping Rock Rd, Locust Valley, NY 11560

    Rosegate is a delightful one-of-a-kind residence that appears to have been magically plucked from the English countryside. Originally a Large Cottage on a former Estate, Rosegate has been thoughtfully expanded and updated throughout the years. The brick and clapboard home is now a 7 bedroom Colonial on 2.85 acres . Character and charm encompasses every inch of Rosegate. Hand painted murals cover

    Christina Porter Daniel Gale Sothebys Intl Rlty

    285 Piping Rock Rd, Locust Valley, NY 11560
  • 9 Canterbury Rd, Glen Head, NY 11545

    $2,200,000 Sold Mar 03, 2025

    • 3,850 Sq Ft
    • $571/SF
    • 50 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1956

    9 Canterbury Rd, Glen Head, NY 11545

    This classic center hall Colonial offers a wonderful layout including guest quarters, with 4 bedrooms, 3.5 baths, huge den with vaulted ceiling and wet bar, plus 2-car garage. The spectacular 2-acre property is low-maintenance and features a sparkling 20' x 45' heated, saltwater infinity-edge gunite pool with stunning herringbone brick patio, separate saltwater hot tub and cabana with wet bar,

    Dee Dee Brix Compass Greater NY LLC

    9 Canterbury Rd, Glen Head, NY 11545
  • 19 Ridge Ct, Glen Head, NY 11545
    19 Ridge Ct, Glen Head, NY 11545
    19 Ridge Ct, Glen Head, NY 11545
    /36

    $5,480,000

    • 6 Beds
    • 8.5 Baths
    • 8,416 Sq Ft

    19 Ridge Ct, Glen Head, NY 11545

    Click the link for a full video tour: https://vimeo.com/1025186470 Welcome to 19 Ridge Court, a Gold Coast treasure in Brookville Meadows. Discover the pinnacle of luxury living at this bespoke estate, gracefully nestled on 3 pristine acres in an exclusive cul-de-sac. This 8,400+ sq ft residence combines timeless sophistication with modern amenities, offering the perfect blend of grandeur and

    Ira Gross Daniel Gale Sothebys Intl Rlty

    19 Ridge Ct, Glen Head, NY 11545
  • 1140 Cedar Swamp Rd, Glen Head, NY 11545

    $1,998,000 Sold Jan 31, 2025

    • 2,964 Sq Ft
    • $674/SF
    • 18 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1971

    1140 Cedar Swamp Rd, Glen Head, NY 11545

    FIRST TIME ON MARKET Down a long private drive leads to this timeless Traditional Brick Center Hall Colonial. This Meticulously maintained home is nestled on 2.7 acres of mature plantings and open parklike property. Enjoy the gazebo, fountained pond and tranquil surroundings. Grand 2 story entry welcomes you to the Formal Living room with fireplace, Formal Dining room with french doors which

    Lisa Lauricella Signature Premier Properties

    1140 Cedar Swamp Rd, Glen Head, NY 11545
  • 12 Woodfield Ln, Glen Head, NY 11545
    12 Woodfield Ln, Glen Head, NY 11545
    12 Woodfield Ln, Glen Head, NY 11545
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    $3,988,000 Pending

    • 8 Beds
    • 7.5 Baths

    12 Woodfield Ln, Glen Head, NY 11545

    Priced to Sell! Welcome to your private oasis on two acres of lush greenery! This magnificent colonial residence is a true testament to timeless elegance and luxury. Built in 1989, this home boasts an awe-inspiring two-floor portico that sets the stage for the grandeur within. Upon entering the first-floor grand foyer, prepare to be enchanted by the masterful decorative paintings adorning the

    Connie Pinilla Compass Greater NY LLC

    12 Woodfield Ln, Glen Head, NY 11545
  • Unlisted Address

    $2,875,000 Sold Jan 27, 2025

    • 4,928 Sq Ft
    • $583/SF
    • 44 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2000

    Unlisted Address

    Welcome to this stunning Brick Center Hall Colonial situated on 2+ Acres in the Private Cul de sac of Country View Estates located in the Village of Old Brookville. Within 1-3 miles of Country Clubs, Golf Courses and Shopping as wells as Friends Academy, Portledge, The Green Vale School and North Shore Schools District. Enjoy the privacy afforded by a Natural Mixed Evergreen Perimeter Screening

    Frank Ciotta Luxian International Realty

    Unlisted Address
  • 5 Valentine Farm Ct, Glen Head, NY 11545
    5 Valentine Farm Ct, Glen Head, NY 11545
    5 Valentine Farm Ct, Glen Head, NY 11545
    /5

    $4,499,000 Pending

    • 6 Beds
    • 9 Baths
    • 8,400 Sq Ft

    5 Valentine Farm Ct, Glen Head, NY 11545

    Prime location in the Village of Old Brookville. Custom built at the time with the foresight of having two primary bedroom suites, one on each floor. A private separate wing on the 1st floor is dedicated to an entire suite with music room or den, large bedroom and lux bathroom. The property is situated on 3.19 acres at the end of a cul-de-sac and positioned among some of the most notable

    Michael Stanco Compass Greater NY LLC

    5 Valentine Farm Ct, Glen Head, NY 11545
  • 17 Hickory Dr, Glen Head, NY 11545

    $5,400,000 Sold Jan 17, 2025

    • 14,065 Sq Ft
    • $384/SF
    • 96 Days On Market
    • 6 Beds
    • 7.5 Baths
    • Built 2015

    17 Hickory Dr, Glen Head, NY 11545

    Nestled in the prestigious, gated community of Old Brookville on Long Island, this custom-built colonial masterpiece epitomizes luxury living. Completed in June 2014, this stunning residence spans 14,065 square feet and is set on 3 acres of lushly landscaped grounds, secured by a gated entry and bordered by meticulously maintained fencing. Located within the highly regarded North Shore School

    Ronald Lanzillotta BERKSHIRE HATHAWAY

    17 Hickory Dr, Glen Head, NY 11545
  • 6 Longridge Ln, Glen Head, NY 11545
    6 Longridge Ln, Glen Head, NY 11545
    6 Longridge Ln, Glen Head, NY 11545
    /11

    $3,100,000 Open Sun 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 4,975 Sq Ft

    6 Longridge Ln, Glen Head, NY 11545

    Welcome to this stately columned brick and shingle Colonial, nestled amidst lush landscaping that perfectly complements its timeless architectural elegance within the esteemed Village of Old Brookville. This home offers a harmonious blend of luxurious amenities, gracious living spaces, and thoughtful design elements, making it a true sanctuary for its next homeowner. As you approach the

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    6 Longridge Ln, Glen Head, NY 11545
  • 3 Acorn Ct, Glen Head, NY 11545

    $1,561,113 Sold Jan 13, 2025

    • 2,511 Sq Ft
    • $622/SF
    • 35 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1958

    3 Acorn Ct, Glen Head, NY 11545

    Welcome to this exquisite residence nestled in a serene cul-de-sac in the heart of Old Brookville, perfectly set on one lush acre of landscaped grounds. Privacy holds supreme in this bright spacious home, where oversized picture windows and French doors invite abundant natural light and picturesque outdoor views into nearly every room. The beautiful hardwood flooring throughout the home enhances

    Bart Bleiweiss Integrity Core Realty

    3 Acorn Ct, Glen Head, NY 11545
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /20

    $2,999,999

    • 5 Beds
    • 3.5 Baths
    • 5,840 Sq Ft

    Unlisted Address

    Stunning Old Brookville Estate on 2 Acres with Pool & Outdoor OasisWelcome 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

    Colleen Chase Exit Realty Everyday

    Unlisted Address
  • 20 Carlisle Dr, Glen Head, NY 11545

    $2,100,000 Sold Nov 14, 2024

    • 4,678 Sq Ft
    • $449/SF
    • 18 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1986

    20 Carlisle Dr, Glen Head, NY 11545

    Welcome to 20 Carlisle Drive in Old Brookville, a wonderful North Shore center hall colonial nestled on a serene, tree-lined private cul-de-sac. Offered for the first time since its construction, this residence features 5 bedrooms, 4.5 bathrooms, and is situated on two acres, complete with a gunite pool and tennis court. As you enter the home, you are greeted by a grand two-story foyer.

    Ted Kritikos Compass Greater NY LLC

    20 Carlisle Dr, Glen Head, NY 11545
  • 0 Applewood Estate Unit ONE3578383, Upper Brookville, NY 11545
    0 Applewood Estate Unit ONE3578383, Upper Brookville, NY 11545
    0 Applewood Estate Unit ONE3578383, Upper Brookville, 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
  • 101 McCouns Ln, Glen Head, NY 11545

    $2,900,000 Sold Nov 11, 2024

    • 4,355 Sq Ft
    • $666/SF
    • 22 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2023

    101 McCouns Ln, Glen Head, NY 11545

    Incredible 2023 finished home located in the Village of Old Brookville. Completely rebuilt, with first floor additions as well as an entire second floor addition. Original structure was built in 1930. Beautiful landscaped property with specimen plantings on just under one acre lot. VERY LOW TAXES. The flow of this home is fabulous for entertaining and family living alike. Its open floor plan,

    Alissa Kirk Howard Hanna Rand Realty

    101 McCouns Ln, Glen Head, NY 11545
  • 170 Hegemans Ln, Old Brookville, NY 11545
    170 Hegemans Ln, Old Brookville, NY 11545
    170 Hegemans Ln, Old Brookville, NY 11545
    /16

    $2,400,000

    • Land
    • 3.39 Acres
    • $707,965 per Acre

    170 Hegemans Ln, Old Brookville, NY 11545

    Build your Dream Home in the only gated community within the Village of Old Brookville. Enter this newly developed 23+ acre community through an impressive remote-controlled gate. Proceed on a secluded and lushly landscaped two-lane drive to the quiet sanctuary of a cul-de-sac with six buildable lots ranging from 3 to 4 acres each. Conveniently located only 25 miles from Manhattan and close to

    Neena Chowdhary Daniel Gale Sothebys Intl Rlty

    170 Hegemans Ln, Old Brookville, NY 11545
  • 20 Overbrook Ln, Glen Head, NY 11545

    $1,975,000 Sold Oct 29, 2024

    • 4,849 Sq Ft
    • $407/SF
    • 23 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 1984

    20 Overbrook Ln, Glen Head, NY 11545

    Prime Mid-Block Location, Nestled on 2 Beautiful Level, Rolling Acres. Choice of North Shore Schools and Locust Valley Schools. Large entertaining rooms with high ceilings. Five Fireplaces. Come renovate and customize Kitchen and Bathrooms and make it your own. Embrace the Potential of This Remarkable Property and Let Your Imagination Soar as You Craft the Home of Your Dreams.

    Janet Berookhim LAFFEY REAL ESTATE

    20 Overbrook Ln, Glen Head, NY 11545
  • 143 Piping Rock Rd, Locust Valley, NY 11560
    143 Piping Rock Rd, Locust Valley, NY 11560
    143 Piping Rock Rd, Locust Valley, NY 11560
    /33

    $1,399,000

    • 3 Beds
    • 3 Baths

    143 Piping Rock Rd, Locust Valley, NY 11560

    Into the woods! Not your usual abode--truly amazing property. Privacy & seclusion are a must. Rustic 3 BR, 3 Bath Carriage House has an additional 1/2 acre+, making a total of 1.5 acres surrounded by the 15 Acre Saunders Nature Preserve! Brick and wood floors throughout, tall windows, beamed ceilings, huge fireplace. Seeing is believing. Call for your private showing! Homeowner has the option of

    143 Piping Rock Rd, Locust Valley, NY 11560
  • 16 Overbrook Ln, Glen Head, NY 11545

    $2,950,000 Sold Sep 27, 2024

    • 3,942 Sq Ft
    • $748/SF
    • 42 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1984

    16 Overbrook Ln, Glen Head, NY 11545

    Welcome To 16 Overbrooke Lane - A Hidden Treasure Nestled In The Esteemed Old Brookville Community. Presenting The Sanctuary, A Center Hall Colonial Estate Exuding Sophistication, Comfort, And Natural Allure. Set Amidst Two Sprawling Private Acres, Bordered By A Secluded Horse Farm, This Property Offers An Unmatched Haven Of Serenity And Opulence. Approaching The Sanctuary, One Is Greeted By

    Lisa Fasano Compass Greater NY LLC

    16 Overbrook Ln, Glen Head, NY 11545
  • 172 Hegemans Ln, Old Brookville, NY 11545
    172 Hegemans Ln, Old Brookville, NY 11545
    172 Hegemans Ln, Old Brookville, NY 11545
    /12

    $2,500,000

    • Land
    • 4.09 Acres
    • $611,247 per Acre

    172 Hegemans Ln, Old Brookville, NY 11545

    One of a Kind Offering! Build your Dream Home in the only gated community within the Village of Old Brookville. Enter this newly developed 23+ acre community through an impressive remote-controlled gate. Proceed on a secluded and lushly landscaped two-lane drive to the quiet sanctuary of a cul-de-sac with six buildable lots ranging from 3 to 4 acres each. Conveniently located only 25 miles from

    Neena Chowdhary Daniel Gale Sothebys Intl Rlty

    172 Hegemans Ln, Old Brookville, NY 11545
  • 365 Cedar Swamp Rd, Glen Head, NY 11545

    $1,388,000 Sold Sep 26, 2024

    • 40 Days On Market
    • 4 Beds
    • 6 Baths
    • Built 1700

    365 Cedar Swamp Rd, Glen Head, NY 11545

    This beautiful Colonial is an eclectic merger of the charm of yesterday with the conveniences of today. This restored residence set on 2 flat acres offers 4 lofted detached garages, 5 fireplaces, heated salt water in-ground pool, NEW Central Air Conditioning, boiler, plumbing, cameras, driveway and garage doors. Chef's gourmet Eat-in-Kitchen complete with Butler's Pantry, double oven, pizza oven

    Barbara Sinenberg Daniel Gale Sothebys Intl Rlty

    365 Cedar Swamp Rd, Glen Head, NY 11545

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