33

Newest Homes for Sale in Old Brookville, NY

Section Image Section Image
  • /32

    $2,995,000

    • 5 Beds
    • 5.5 Baths
    • 4,892 Sq Ft

    5 Woodfield Ln, Glen Head, NY 11545

    5 Woodfield Lane! Set on beautiful landscaped grounds, this impressive residence offers a wonderful blend of space, comfort, and privacy. Totally renovated in 2019! A gracious entry welcomes you into expansive living areas with soaring ceilings, abundant natural light, Stone and hardwood floors, multiple gathering spaces designed for both everyday living and entertaining. The spacious eat-in

    Irene Racanelli Coldwell Banker American Homes

    5 Woodfield Ln, Glen Head, NY 11545
  • /45

    $5,950,000

    • 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
  • /25

    $3,500,000

    • 3 Beds
    • 3 Baths
    • 2,942 Sq Ft

    1 Stonegate Ln, Glen Head, NY 11545

    Set on two level acres surrounded by mature trees in the sought-after Village of Old Brookville, this distinctive three-bedroom, three-bath residence offers a peaceful setting with expansive lawns and exceptional privacy. A long driveway provides abundant parking in addition to the attached two-car garage. Inside, the main level features a dramatic living room with approximately 16-foot ceilings,

    Agent Photo

    Giulio Ferrante

    Signature Premier Properties

    1 Stonegate Ln, Glen Head, NY 11545
  • /2

    $7,900,000

    • Land
    • 17.18 Acres
    • $459,837 per Acre

    97 B Pound Hollow Rd, Old Brookville, NY 11545

    Set on more than 17 pristine and level acres in the heart of prestigious Old Brookville, this exceptional farm property presents a rare opportunity to own a significant piece of Long Island's North Shore history. Once part of the renowned Westward estate, the grounds were originally assembled in the early 1900s for distinguished industrialist and financier Benjamin Brewster Jennings, President

    Agent Photo

    Linda Faraldo

    Daniel Gale Sothebys Intl Rlty

    97 B Pound Hollow Rd, Old 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
  • /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
  • /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

    Joe Scavo Douglas Elliman Real Estate

    3 Valentine Farm Ct, Glen Head, NY 11545
  • /25

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 4,233 Sq Ft

    738 Motts Cove Rd N, Glen Head, NY 11545

    Just Completed to Perfection. Stunning new construction on a charming tree-lined cul-de-sac shared by only six homes, this exceptional 4-bedroom, 4.5-bath Hamptons-inspired residence offers the perfect blend of luxury, craftsmanship, and location.Filled with natural light, the home features exquisite millwork, designer finishes, and an open floor plan ideal for today's lifestyle. The chef's

    Madeline Moritz Douglas Elliman Real Estate

    738 Motts Cove Rd N, Glen Head, NY 11545
  • /2

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 4,365 Sq Ft

    730 Motts Cove Rd N, Glen Head, NY 11545

    Nearing Completion – See 738 Motts Cove N for Finished Home. Stunning new construction on a charming tree-lined cul-de-sac shared by only six homes, this exceptional 4-bedroom, 4.5-bath Hamptons-inspired residence offers the perfect blend of luxury, craftsmanship, and location. Filled with natural light, the home features exquisite millwork, designer finishes, and an open floor plan ideal for

    Madeline Moritz Douglas Elliman Real Estate

    730 Motts Cove Rd N, Glen Head, NY 11545
  • /2

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 4,365 Sq Ft

    734 Motts Cove Rd N, Glen Head, NY 11545

    Nearing Completion – See 738 Motts Cove N for Finished Home. Stunning new construction on a charming tree-lined cul-de-sac shared by only six homes, this exceptional 4-bedroom, 4.5-bath Hamptons-inspired residence offers the perfect blend of luxury, craftsmanship, and location. Filled with natural light, the home features exquisite millwork, designer finishes, and an open floor plan ideal for

    Madeline Moritz Douglas Elliman Real Estate

    734 Motts Cove Rd N, Glen Head, NY 11545
  • /37

    $2,199,000

    • 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
  • /27

    $1,088,000

    $100K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,561 Sq Ft

    7 Locust St, Glen Head, NY 11545

    Located in the highly coveted, award-winning North Shore School District.Welcome home to this move-in-ready, newly renovated Colonial perfectly situated at the beginning of a charming, quiet cul-de-sac. This 4-bedroom, 2-full-bath home beautifully balances classic warmth with modern upgrades and an open space concept. The expanded 2,300 sq. ft. layout (1,561 sq. ft. livable) begins on the first

    Roger Liu Century Homes Realty Group LLC

    7 Locust St, Glen Head, NY 11545
  • /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
  • /34

    $2,499,999

    • 5 Beds
    • 3.5 Baths
    • 3,594 Sq Ft

    19 Pheasant Hill Ln, Glen Head, NY 11545

    This extraordinary Old Brookville estate at 19 Pheasant Hill Lane, featured in Architectural Digest, is a rare Georgian inspired residence that embodies timeless architecture, exceptional craftsmanship, and refined design. Perfectly positioned on two flat, private acres along one of Old Brookville’s most peaceful and coveted streets, this 5 bedroom, 3.5 bath home offers elevated living within the

    Emil Koniecko Signature Premier Properties

    19 Pheasant Hill Ln, Glen Head, NY 11545
  • /33

    $899,000

    $29K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,944 Sq Ft

    112 The Glen, Glen Head, NY 11545

    Welcome to The Knolls, a beautifully landscaped and meticulously maintained gated condominium community offering effortless, low maintenance living in a prime location. This exceptional 1944 square foot residence features 3 bedrooms and 3 full baths, thoughtfully designed with spacious living areas, abundant natural light, and a highly functional floor plan.The sun-filled gourmet eat-in

    Kimberly Bancroft Daniel Gale Sothebys Intl Rlty

    112 The Glen, 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
  • /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
  • /21

    $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 home

    leonardo tavarez Charles Rutenberg Realty Inc

    12 The Cir Unit 12, Glen Head, NY 11545
  • /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
  • /31

    $765,000

    $35K PRICE DROP
    • 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
  • /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
  • /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
  • /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

    $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
  • /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
  • /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
  • /32

    $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
  • /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
  • /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
  • /19

    $2,799,000

    • 5 Beds
    • 3.5 Baths
    • 4,498 Sq Ft

    7 Pin Oak Ct, Glen Head, NY 11545

    Tucked at the end of a quiet cul-de-sac, this timeless contemporary sits on two perfectly level acres offering exceptional privacy and a deep, usable yard. The property features an in-ground heated pool with a waterfall and beautiful outdoor space ideal for gatherings or relaxation. Inside, the home provides plenty of opportunity with its dramatic ceilings and walls of glass that create a bright,

    Robert Schmertz Compass Greater NY LLC

    7 Pin Oak Ct, 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
  • /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

Frequently Asked Questions

What are the most popular zip codes in Old Brookville, NY?
The most popular zip codes in Old Brookville, NY include 11545, 11560, 11548, 11542 and 11771.
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 Jericho Middle School. Browse all the schools in Old Brookville, NY to learn more.
How to Buy a Home How to Finance a Home How to Sell a Home