27

Old 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
  • /50

    $4,199,999

    • 4 Beds
    • 4.5 Baths
    • 4,288 Sq Ft

    22 Eastview Ln, Glen Head, NY 11545

    Why escape to a luxury resort for the weekend when you can come home to one every single day?This extraordinary residence delivers the kind of lifestyle most people only experience on vacation—private, peaceful, and effortlessly elegant. A rare opportunity to own a home that feels like a permanent getaway. Welcome to "Casa De Luce" a French Chateau style palace, a truly exceptional luxury

    Agent Photo

    Giulio Ferrante

    Signature Premier Properties

    22 Eastview Ln, Glen Head, NY 11545
  • /33

    $21,500,000

    • 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 33+ 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

    $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

    $2,750,000

    • 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

    $3,950,000

    • 5 Beds
    • 8 Baths
    • 5,902 Sq Ft

    8 High Meadow Ct, Glen Head, NY 11545

    Welcome to 8 High Meadow Ct, a stunning classic all brick Colonial spanning 6000sqft of luxury set on a magnificent serene Old Brookville cul de-sac. This 5 bedroom Gem is rich with architectural details, exquisite millwork and designer finishes. A Gracious two-story Foyer introduces expansive principle rooms including Living Room/Fireplace, Formal Dining room, Den/Fireplace and Library/Office

    Ellen Zipes Compass Greater NY LLC

    8 High Meadow Ct, Glen Head, NY 11545
  • /2

    $3,800,000

    $300K PRICE DROP
    • Land
    • 7.09 Acres
    • $535,966 per Acre

    559 Cedar Swamp Rd, Glen Head, NY 11545

    Lovely 7.09 Acres of Residential Land a Great Builders Opportunity! This is not all flat land, it has beautiful hills. Located in Village of Old Brookville, The Address can be Brookville or Glen Head according to Village of Old Brookville same postal zip code. There is 2 acres zoning for this property, so 3 Beautiful Homes can be built on this property. All approvals would go to Village of Old

    Donna Greiner- Fisher Signature Premier Properties

    559 Cedar Swamp Rd, 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
  • /26

    $5,999,999

    $1M PRICE DROP
    • 6 Beds
    • 5.5 Baths

    89 Pound Hollow Rd, Glen Head, NY 11545

    Where Drama Meets Design Welcome 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

    $6,850,000

    • 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
  • /13

    $4,795,999

    • Land
    • 15.8 Acres
    • $303,544 per Acre

    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
  • /5

    $1,700,000

    $699K PRICE DROP
    • Land
    • 2.97 Acres
    • $572,391 per Acre

    12 Hickory Dr, Brookville, NY 11545

    Last Remaining Parcel in Old Brookville Gated Community! Almost 3-acres of land located on cul-de-sac, ready for you to bring your dream home to life. Secure and serene location, with easy access to Northern Boulevard and other main roads. Add your mark on the North Shore, surrounded by beautiful brick-center hall colonial residences and well-maintained landscaping. With natural gas already

    Joe Scavo Douglas Elliman Real Estate

    12 Hickory Dr, Brookville, NY 11545
  • /43

    $12,800,000

    • 10 Beds
    • 15 Baths
    • 20,000 Sq Ft

    53 Simonson Rd, Glen Head, NY 11545

    Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary. A striking

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    53 Simonson 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
  • /39

    $3,100,000

    • 5 Beds
    • 7 Baths
    • 5,480 Sq Ft

    10 Overbrook Ln, Glen Head, NY 11545

    Built by the renowned Farrell Building Company in 1996, whose homes are recognized among Long Island’s finest for their exceptional quality and enduring craftsmanship, this exceptional brick Gold Coast estate blends timeless architecture with today’s luxury amenities, offering over 5,480 square feet of elegantly appointed living space on two private acres in the heart of prestigious Old

    Jodi Locke BERKSHIRE HATHAWAY

    10 Overbrook Ln, Glen Head, NY 11545
  • /28

    $3,850,000

    • 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
  • /32

    $800,000

    • 2 Beds
    • 2 Baths
    • 2,169 Sq Ft

    19 The Cir, Glen Head, NY 11545

    Nestled within the prestigious gated community of The Knolls and adjacent to the renowned Glen Head Country Club, this beautifully appointed residence at 19 The Circle offers a seamless blend of elegance, comfort, and effortless living. Bathed in natural light from an abundance of windows and multiple skylights, the home showcases gleaming hardwood floors, crown and base moldings, recessed

    Mustafa Uruk Exit Realty Island Elite

    19 The Cir, Glen Head, NY 11545
  • /41

    $2,399,000

    • 5 Beds
    • 4.5 Baths
    • 4,667 Sq Ft

    23 Wildwood Ln, Greenvale, NY 11548

    Welcome to 23 Wildwood Lane - an expansive modern contemporary located on a Old Brookville Street and set on .60 flat usable acres. This spacious home includes 5 oversized bedrooms and 5 well-appointed baths, including two primary ensuites with one located on the main level. Designed with flexibility in mind, this layout is ideal for multi-generational living. A dramatic entry foyer features

    Kristen Vlahopoulos Compass Greater NY LLC

    23 Wildwood Ln, Greenvale, NY 11548
  • /44

    $3,680,000

    • 5 Beds
    • 4.5 Baths
    • 6,076 Sq Ft

    14 Norgate Rd, Glen Head, NY 11545

    Welcome to 14 Norgate Road, a magnificent estate nestled in the prestigious Brookville, offering timeless elegance, exceptional craftsmanship, and luxurious living throughout. A grand two-story entry foyer welcomes you into this distinguished residence, setting the tone for the exquisite details found in every room.Designed for both sophisticated entertaining and everyday comfort, the home

    Janet Berookhim LAFFEY REAL ESTATE

    14 Norgate Rd, 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
  • /50

    $10,300,000

    $5M PRICE DROP
    • 7 Beds
    • 12 Baths
    • 14,000 Sq Ft

    11 Dupont Ct, Greenvale, NY 11548

    Nestled on a meticulously landscaped 6-acre+ property, 11 Dupont Court epitomizes architectural sophistication and resplendence. This stately Brookville Brick Colonial, constructed in 2007, spans over 15,000 Sq.Ft. and encompasses 7 Bedrooms and 12 Bathrooms. Its graceful design is distinguished by bespoke features such as elaborate woodwork, spiral staircases, marble flooring and soaring

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    11 Dupont Ct, Greenvale, NY 11548
  • /28

    $1,708,000

    $72K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    106 Woods Dr, Roslyn, NY 11576

    Stunning Hi-Ranch in East Hills, Roslyn! Set on .35 acres, this beautifully maintained home offers 5 spacious bedrooms and 4.5 baths. The main level welcomes you with an inviting entry foyer featuring a coat closet and powder room. Just ahead, a sun-filled family room boasts soaring ceilings, a skylight, fireplace, and sliding doors that open directly to the backyard, along with stairs leading to

    Anthoane Peralta A Class Realty

    106 Woods Dr, Roslyn, NY 11576
  • /50

    $2,995,000

    • 3 Beds
    • 2.5 Baths
    • 3,042 Sq Ft

    379 Frost Pond Rd, Glen Head, NY 11545

    Built new in 2017 with the highest of standards on an ultra-private 1 acre property in Glen Head. This one level 3 bedroom ranch luxury home offers quality finishes, exceptional craftsmanship and a comfortable floor plan. The main living area is an open concept eat-in-kitchen to a great room with fireplace and formal dining. A separate den with beautiful paneled walls is to the front of the

    Panagiotis Athanasopoulos Compass Greater NY LLC

    379 Frost Pond Rd, Glen Head, NY 11545
  • /23

    $1,550,000

    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    12 The Cir Unit 12, Glen Head, NY 11545

    Welcome to The Knolls, a Prestigious Gated Community located in the North Shore Coveted Gold Coast. This Sun-Drenched, Spacious Residence Set in a Prime Location, features a Secluded Backyard. A True Sanctuary that Offers a Combination of Tranquility, Privacy, and Beauty. This Elegant Multi-Level Home has a flowing Open Floor Plan, Hardwood Floors, and an abundance of Natural Light. THIS CO-OP IS

    leonardo tavarez Charles Rutenberg Realty Inc

    12 The Cir Unit 12, Glen Head, NY 11545

Why Live in Old Brookville

Old Brookville, NY, is a village that exudes a rural and secluded charm, characterized by its tree-shaded streets, expansive fields, and horse pastures. The area is known for its luxurious homes and gated estates, often set back on large properties with meticulously maintained landscaping. This privacy is a significant draw for residents, offering a peaceful retreat from the hustle and bustle of city life. Despite its seclusion, Old Brookville is conveniently located near Northern Boulevard, providing easy access to nearby areas. Commuters can reach Glen Head Station in under 2 miles, with trains to New York City's Pennsylvania Station taking about an hour. The North Shore Central School District, highly rated and recognized among the top in New York, serves the village, adding to its appeal for families. Local features include horse stables, riding centers, and the Brookville Country Club, which offers an 18-hole golf course and swimming pool. The village's commercial area includes Holiday Farms Supermarket and Brookville Deli & Caterers, while dining options like Heirloom Tavern in nearby Glen Head are just a short drive away. Tappen Beach, located 3 miles from the village, provides a nearby escape for beachgoers. The combination of luxury, privacy, and convenient amenities makes Old Brookville a sought-after location for those seeking a tranquil yet accessible lifestyle.

Frequently Asked Questions

What is the average home price in Old Brookville, NY?
Homes for sale in Old Brookville, NY have an average home price of $5,350,000.
How many homes have sold over the last 12 months in Old Brookville, NY?
1 home has sold in Old Brookville, NY over the last 12 months.
What are the most popular zip codes in Old Brookville, NY?
The most popular zip codes in Old Brookville, NY include 11545, 11771, 11542, 11568 and 11560.
How much do you need to make to afford a house in Old Brookville?
The median home price in Old Brookville is $5,350,000. If you put a 20% down payment of $1,070,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $26,970 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $1M a year to afford the median home price in Old Brookville. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Old Brookville, NY?
Old Brookville, NY has highly rated public and private schools. Some of the best schools in Old Brookville based on Niche Grades are Friends Academy, Green Vale School and Long Island Lutheran Middle & High School. Browse all the schools in Old Brookville, NY to learn more.

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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