30

Glen Head, NY Homes for Sale with Pool

Section Image
  • /35

    $5,895,000

    • 6 Beds
    • 7.5 Baths
    • 7,000 Sq Ft

    27 Victorian Ln, Glen Head, NY 11545

    Welcome to an extraordinary estates of timeless elegance located at 27 Victorian Lane, Brookville NY. — a distinguished estate that embodies architectural grace in one of the most prestigious residential setting. Set across approximately 2 acres of professionally landscaped grounds, this exceptional residence spans roughly 7,000 square feet of thoughtfully designed interior space, offering a rare

    Katherine Koniecko Signature Premier Properties

    27 Victorian Ln, Glen Head, NY 11545
  • /50

    $5,300,000

    • 5 Beds
    • 7.5 Baths
    • 7,000 Sq Ft

    8 Vista Ln, Glen Head, NY 11545

    For the Discerning Client who seeks only the Finest....Welcome to 8 Vista Lane in Brookville--where Timeless Design and Bespoke Materials are blended to create this Sophisticated Modern Luxury. A Grand Courtyard leads to the Entrance of this Spectacular Private Estate. The Tone is set as Guests are greeted in the Breathtaking 30'high Domed Circular Reception Gallery adorned with Magnificent

    Ellen Zipes Compass Greater NY LLC

    8 Vista Ln, Glen Head, NY 11545
  • /47

    $5,698,000

    • 6 Beds
    • 9 Baths
    • 6,921 Sq Ft

    5 Farmwoods Ln, Glen Head, NY 11545

    This gorgeous Brick Colonial, located in Upper Brookville, is a beautiful and elegant estate that sits on 2.53 acres. Built in 2007, this residence offers an impressive 6 bedrooms and 7 bathrooms within its expansive 6,921 square feet of living space. Step inside to find a home designed for both grand entertaining and comfortable living. The first floor features a formal living room, a formal

    Batul Morbi Compass Greater NY LLC

    5 Farmwoods Ln, Glen Head, NY 11545
  • /33

    $5,495,000

    • 6 Beds
    • 6.5 Baths
    • 6,885 Sq Ft

    63 Fruitledge Rd, Glen Head, NY 11545

    Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale

    Melanie Cogan Compass Greater NY LLC

    63 Fruitledge Rd, Glen Head, NY 11545
  • /2

    $6,300,000

    • 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
  • /27

    $4,750,000

    • 7 Beds
    • 7.5 Baths
    • 7,605 Sq Ft

    38 Ormond Park Rd, Glen Head, NY 11545

    Set on over 2.8 acres of exquisitely landscaped, park-like grounds with mature specimen plantings, this stately brick center-hall Colonial embodies timeless elegance and superior craftsmanship. Custom built by the renowned Gerald Brothers Construction for its current owner, the home showcases the highest level of finishes, thoughtful design, and enduring quality throughout. A grand two-story

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    38 Ormond Park Rd, Glen Head, NY 11545
  • /30

    $5,495,000

    • 6 Beds
    • 7.5 Baths
    • 8,500 Sq Ft

    45 Wolver Hollow Rd, Glen Head, NY 11545

    Introducing 45 Wolver Hollow Road, an exceptional private brick estate compound set on approximately 7 meticulously manicured acres in Upper Brookville. This impressive residence offers grand scale, timeless elegance, luxurious landscaping, and a true lifestyle experience both inside and out. Filled with natural light, the home features vaulted ceilings, oversized windows, sweeping property

    Julia Krispeal Douglas Elliman Real Estate

    45 Wolver Hollow Rd, Glen Head, NY 11545
  • /20

    $4,700,000

    • 6 Beds
    • 7.5 Baths
    • 5,607 Sq Ft

    17 Quaker Ridge Rd, Glen Head, NY 11545

    A gracious circular driveway welcomes you to this exceptional newly renovated residence, perfectly situated at the end of a coveted cul-de-sac. The home showcases the finest designer finishes throughout, including custom cabinetry, wood flooring, two fireplaces, exotic marble and stone. At the heart of the home is a truly spectacular, top-of-the-line Christopher Peacock kitchen wood cabinetry,

    Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

    17 Quaker Ridge Rd, Glen Head, NY 11545
  • /35

    $9,750,000

    • 7 Beds
    • 14 Baths
    • 11,926 Sq Ft

    4 Red Fox Ln, Glen Head, NY 11545

    Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a

    Pierce Dellafera Daniel Gale Sothebys Intl Rlty

    4 Red Fox Ln, Glen Head, NY 11545
  • /49

    $1,990,000 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,176 Sq Ft

    1678 Cedar Swamp Rd, Glen Head, NY 11545

    Welcome to 1678 Cedar Swamp Road, Brookville! Set on a sprawling 2.01-acre property in Brookville and located within the Jericho School District, this beautifully maintained 4-bedroom, 3.5-bath Colonial offers exceptional space, comfort, and lifestyle amenities. The home features wood floors throughout, new moldings, and a freshly painted interior, creating a bright and inviting atmosphere from

    Hemant Shah LAFFEY REAL ESTATE

    1678 Cedar Swamp Rd, Glen Head, NY 11545
  • /43

    $2,750,000

    • 4 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    26 Dolly Cam Ln, Glen Head, NY 11545

    Extraordinary expanded ranch home at the end of a quiet cul-de-sac on 2.1 private acres in the Village of Old Brookville. Low taxes! Turn-key residence offering a bright, open layout with generously scaled principal rooms that flow with warmth and style upon entering the front door. Designer finishes with all work done in the last few years. Newly run natural gas line, the only house on the block

    Michael Stanco Compass Greater NY LLC

    26 Dolly Cam Ln, Glen Head, NY 11545
  • /48

    $2,499,000

    • 5 Beds
    • 3.5 Baths
    • 3,548 Sq Ft

    18 Quaker Ridge Dr, Glen Head, NY 11545

    Rare Is The Opportunity To Secure Over Two Acres Of Flat, Usuable Land In The Highly Sought-After Jericho School District. Along One Of Brookville's Most Picturesque Roads And Nestled In A Cul-De-Sac, 18 Quaker Ridge Drive Is An Idyllic Retreat Backing Onto A Private Equestrian Property - Providing Unmatched Tranquility And Pastoral Vistas. Currently Featuring A Classic 5 Bedroom Colonial, The

    Joanne Cohen Daniel Gale Sothebys Intl Rlty

    18 Quaker Ridge Dr, 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
  • /41

    $2,790,000 Open Sun 12PM - 2PM

    • 5 Beds
    • 6 Baths
    • 3,048 Sq Ft

    14 Ormond Park Rd, Glen Head, NY 11545

    Welcome to this exceptional home located in Brookville Village, within Jericho School District. Perfectly situated in a peaceful and quiet neighborhood, this property offers both comfort and convenience. Close to schools, making daily routines effortless; Easy access to major highways for a smooth commute; Minutes from shopping, dining, and everyday essentials; New attic insulation for improved

    Lei Liu Signature Premier Properties

    14 Ormond Park Rd, Glen Head, NY 11545
  • /32

    $3,299,888

    • 6 Beds
    • 5.5 Baths
    • 4,400 Sq Ft

    33 High Farms Rd, Glen Head, NY 11545

    Welcome to a rare opportunity to own a fully renovated and extended estate—rebuilt from the studs up and reimagined for modern luxury in the heart of one of Long Island’s most coveted neighborhoods. Set on a beautifully manicured 2 acre lot, this 6-bedroom, 5.5-bathroom smart residence combines sophisticated design, premium finishes, and cutting-edge amenities, offering a seamless blend of

    Katherine Koniecko Signature Premier Properties

    33 High Farms Rd, Glen Head, NY 11545
  • /22

    $3,500,000

    • 6 Beds
    • 9 Baths
    • 7,500 Sq Ft

    5 Carol Ln, Glen Head, NY 11545

    Elegance redefined in this stunning gem that blends an eclectic mix of mid-century modern design with a touch of contemporary sophistication, nestled on two lush, gated acres in Upper Brookville. From the moment you enter, the home captivates your imagination with its soaring 30-foot ceilings and dramatic windows and wood architectural elements. Clean lines, warm textures, and artful finishes

    Ken Deutsch Deutsch Realty Inc

    5 Carol Ln, Glen Head, NY 11545
  • /37

    $8,750,000

    • 6 Beds
    • 9 Baths
    • 8,000 Sq Ft

    30 Wood Acres Rd, Glen Head, NY 11545

    Introducing a newly constructed custom Brookville Colonial crowned with a stunning slate roof, offering an extraordinary blend of classic architecture and elevated designer finishes. Privately set behind an electric gate on over 2.53 fully landscaped acres, this exceptional estate, constructed in 2020, has been thoughtfully designed for both grand-scale entertaining and refined everyday living. A

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    30 Wood Acres Rd, Glen Head, NY 11545
  • /47

    $2,650,000

    • 5 Beds
    • 4.5 Baths
    • 5,644 Sq Ft

    4 Cross Ln, Glen Head, NY 11545

    Tucked away in the sought-after North Shore Acres neighborhood of Glen Head you will find this refined home combining contemporary flair with traditional details set on .53 acre. Reimagined within the last 10 years to include all new wood floors, moldings, stairs, kitchen and baths. This property checks all the boxes, a bespoke wood-mode kitchen w/calcutta marble counters, center island and

    Laura Algios Daniel Gale Sothebys Intl Rlty

    4 Cross Ln, Glen Head, NY 11545
  • /43

    $2,695,000

    • 5 Beds
    • 3.5 Baths
    • 4,100 Sq Ft

    1 Glenby Ln, Glen Head, NY 11545

    Tucked away in the heart of Brookville, this exceptional 2-acre estate at 1 Glenby Lane offers the perfect blend of luxury, privacy, and comfort within the highly regarded Locust Valley Central School District. Surrounded by lush, expansive grounds, the property unfolds into a sprawling, park-like setting complete with a full tennis court and a beautiful in-ground pool creating your own private

    Katherine Koniecko Signature Premier Properties

    1 Glenby Ln, Glen Head, NY 11545
  • /29

    $2,199,999

    • 6 Beds
    • 3.5 Baths
    • 5,103 Sq Ft

    9 Chicken Valley Rd, Glen Head, NY 11545

    Sprawling Brick Expanded Ranch in Prestigious Old Brookville! Welcome to this impressive custom-expanded ranch, rebuilt in 2001 and nestled on 2.2 flat acres in the heart of Old Brookville. Offering over 5,100 sq ft of living space, this 6-bedroom, 3.5-bath home combines generous scale with a versatile open floor plan—perfect for both everyday living and entertaining. Highlights include a large

    Katherine Koniecko Signature Premier Properties

    9 Chicken Valley Rd, Glen Head, NY 11545
  • /6

    $6,500,000

    • 6 Beds
    • 9 Baths
    • 7,500 Sq Ft

    36 Emerson Rd, Glen Head, NY 11545

    36 Emerson Road Introduces A Rare Opportunity To Secure A Custom-Built Estate On Over Two Private Acres Within The Jericho School District. This Masterfully Crafted 7,500+ Square Foot Residence Will Offer Six En-Suite Bedrooms, Three Powder Rooms, With A Seamless Blend Of Scale, Craftsmanship, And Modern Functionality. A Grand Two-Story Entry Sets The Tone, Leading To Expansive Entertaining

    Lisa Fasano Compass Greater NY LLC

    36 Emerson Rd, Glen Head, NY 11545
  • /26

    $5,999,999

    • 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
  • /36

    $7,300,000

    • 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
  • /30

    $8,750,000

    • 7 Beds
    • 10 Baths
    • 11,400 Sq Ft

    30 Evans Dr, Glen Head, NY 11545

    Set on 2 private, beautifully landscaped acres at the end of a cul-de-sac in the coveted Broad Hollow section of Brookville, this brand new construction delivers approximately 11,400 square feet of total living space — including a 3,600 SF walk-out lower level and fully appointed pool cabana. Seven en-suite bedrooms and 10 baths are spread across a floor plan that balances grand scale with

    Zach Elliott Nest Seekers LLC

    30 Evans Dr, Glen Head, NY 11545
  • /44

    $6,475,000

    • 6 Beds
    • 6 Baths
    • 6,474 Sq Ft

    10 Colonial Dr, Glen Head, NY 11545

    Set on 5 flat, impeccably landscaped acres at the end of a quiet cul-de-sac, this stately Georgian brick estate represents one of the most private and desirable settings within Upper Brookville’s prestigious gated Colonial Drive enclave. Positioned on a private road of distinguished luxury estates and further enhanced by its own secondary gated entrance, the property offers a rare double gated

    Nareeta Saini Daniel Gale Sothebys Intl Rlty

    10 Colonial Dr, Glen Head, NY 11545
  • /42

    $6,850,000

    • 7 Beds
    • 11 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
  • /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

    $3,650,000

    • 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
  • /2

    $6,399,999

    • 6 Beds
    • 8 Baths
    • 7,200 Sq Ft

    14 Wenwood Dr, Glen Head, NY 11545

    Brookville | Bring your dream home to life. 14 Wenwood Drive offers an opportunity like no other - a chance to add the final touches to a gorgeous 7,200 sq.ft. new home in the heart of Brookville. Featuring 6 bedrooms, 6 full baths, and one powder, with intricate attention to details throughout. Take advantage of the ability to curate finishes to your own taste. In addition to the open floor plan

    Joe Scavo Douglas Elliman Real Estate

    14 Wenwood Dr, Glen Head, NY 11545

Home Trends in Glen Head, NY

Housing Trends

Median Sale Price
$1,870,000
Median Single Family Sale Price
$2,350,000
Median Townhouse Sale Price
$970,000
Median 2 Bedroom Sale Price
$775,000
Average Price Per Sq Ft
$608
Number of Homes for Sale
42
Last 12 months Home Sales
103
Months of Supply
4.90
Median List Price
$2,350,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
44%
How to Buy a Home How to Finance a Home How to Sell a Home