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Glen Head, NY Homes for Sale with Pool

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  • /36

    $6,799,000

    • 6 Beds
    • 8.5 Baths

    12 Quaker Ridge Dr, Glen Head, NY 11545

    Brookville New Construction | Welcome home to 12 Quaker Ridge Drive — a pristine brick, center-hall colonial set on 2 acres at the end of a quiet cul-de-sac. This modern estate features six bedrooms — including a first-floor suite — formal living and dining areas, an open-concept kitchen, 3-car garage, and more.Behind a set of iron doors, you're welcomed by an open foyer and curved oak

    Joe Scavo Douglas Elliman Real Estate

    12 Quaker Ridge Dr, Glen Head, NY 11545
  • /48

    $4,295,000

    • 5 Beds
    • 6 Baths
    • 6,000 Sq Ft

    8 High Meadow Ct, Glen Head, NY 11545

    Welcome to this Magnificent Brick Masterpiece with Guest/Pool House on Two Impeccable Resort Style Acres. This Grand Residence sets High Standards for a lifestyle of luxury offering timeless elegance and luxurious modern amenities. Sophisticated designer finishes are blended with classic appointments throughout it's refined and thoughtfully designed Interior. A stunning marble reception foyer

    Ellen Zipes Compass Greater NY LLC

    8 High Meadow Ct, Glen Head, NY 11545
  • /37

    $7,850,000

    • 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
  • /37

    $6,249,000

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

    63 Fruitledge Rd, Glen Head, NY 11545

    Brookville New Construction | 63 Fruitledge Road offers an unparalleled lifestyle of luxury on Long Island's Gold Coast. This newly completed home features a sleek, modern colonial exterior, with countless, black-encased windows allowing natural light to flood the entire interior. Upon entering, the soaring foyer welcomes you with open space and two convenient coat closets and beautiful powder

    Joe Scavo Douglas Elliman Real Estate

    63 Fruitledge Rd, Glen Head, NY 11545
  • /45

    $5,280,000

    • 8 Beds
    • 8.5 Baths
    • 7,900 Sq Ft

    11 Black Rock Rd, Glen Head, NY 11545

    This custom-built brick estate in the highly sought-after Jericho School District offers over 7,900 square feet of luxurious living space, plus a full walk-out lower level, all set on more than two acres of beautifully landscaped grounds. Behind a dual-gated circular driveway, the home showcases top-quality materials, smart home technology, and radiant heat throughout. Every bedroom is en-suite,

    Yan Chen Charles Rutenberg Realty Inc

    11 Black Rock Rd, Glen Head, NY 11545
  • /50

    $5,850,000

    • 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, and sought after by many high profile clients. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. As

    Lisa Ann Heaney Daniel Gale Sothebys Intl Rlty

    8 Stonegate Ln, Glen Head, NY 11545
  • /32

    $4,250,000

    • 6 Beds
    • 7 Baths
    • 8,098 Sq Ft

    3 Pin Oak Ct, Glen Head, NY 11545

    Magnificent Brick Colonial in Prestigious Old Brookville tucked away on a private cul-de-sac in one of Long Island’s most exclusive enclaves, this stately brick Colonial embodies timeless elegance and refined indoor-outdoor living. Designed with an eye for classic proportions and luxury detail, the 8,500-square-foot residence is crowned with a slate roof and surrounded by manicured, park-like

    Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

    3 Pin Oak Ct, Glen Head, NY 11545
  • /30

    $4,288,000

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

    10 Evans Dr, Glen Head, NY 11545

    Welcome to 10 Evans Drive, an exquisite one of a kind estate nestled on a private street in the prestigious Broadhollow community of the incorporated Village of Brookville. Situated on 2 lush acres, this custom-designed 7-bedroom, 6 full and 2 half-bath residence offers the perfect blend of luxury, privacy, and location.Step inside to impressive soaring ceilings, exquisite custom millwork,

    Patricia Santella Douglas Elliman Real Estate

    10 Evans Dr, Glen Head, NY 11545
  • /46

    $4,600,000

    • 6 Beds
    • 6.5 Baths

    11 Victorian Ln, Glen Head, NY 11545

    *** BY APPT ONLY *** NO WALK IN *** Welcome to 11 Victorian Lane, Brookville! The top JERICHO school district!Nestled in one of Long Island’s most prestigious neighborhoods, this custom-built English-style estate blends timeless elegance with modern luxury. Built in 2008 and set on 2 acres of private land. This GEM offers 6 bedrooms, 6.5 bathrooms, 3-4 car garage, an

    Chuan Wang Chen E Realty International Corp

    11 Victorian Ln, Glen Head, NY 11545
  • /47

    $3,500,000

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

    5 Carol Ln, Glen Head, NY 11545

    Elegance personified in this rare gem that captivates the senses and stirs the soul. Captivating every grandeur where you would never want to leave your home on two lush acres. A show stopper!!. Boasts 30 Ft. high ceilings with classic comtemporary elements brought together with masterful finishes that capture elegance and tranquility. Gated entrance and exit with directory for family

    Ken Deutsch Deutsch Realty Inc

    5 Carol Ln, Glen Head, NY 11545
  • /48

    $8,499,000

    • 6 Beds
    • 8 Baths
    • 8,600 Sq Ft

    8 Dogwood Hill, Glen Head, NY 11545

    Brookville | An immaculate modern colonial has made its debut in Brookville. Sitting on 2.57 acres and totaling over 8,600 sq.ft. of living space, welcome to 8 Dogwood Hill - a newly completed luxury residence located on a lengthy, picturesque street just off of Cedar Swamp Road. Beyond the stone pillar entrance at the end of the driveway are two courtyards with belgium block accents that lead to

    Joe Scavo Douglas Elliman Real Estate

    8 Dogwood Hill, Glen Head, NY 11545
  • /50

    $2,275,000

    • 4 Beds
    • 5 Baths
    • 3,628 Sq Ft

    10 Eastview Ln, Glen Head, NY 11545

    Heritage lives beautifully in this one-of-a-kind residence where timeless architecture and refined design bring both grace and nostalgia. Set on a private, tree-lined lot, the home offers four bedrooms, three full bathrooms, and two half-baths, along with a sun-filled kitchen featuring a wood-burning fireplace, a formal library, music room, office, and a fully finished basement.The

    Catherine Davis Serhant LLC

    10 Eastview Ln, Glen Head, NY 11545
  • /20

    $2,595,000

    • 6 Beds
    • 8 Baths
    • 6,952 Sq Ft

    9 Cherry Ln, Glen Head, NY 11545

    Elegant and spacious, this 4-bedroom traditional Colonial is set on 3.9 beautifully landscaped acres, featuring a pool, a charming two-bedroom guest cottage with central AC, and a detached garage with stables—ideal for additional storage.The main residence showcases timeless architectural details, including oak flooring and a richly paneled library with fireplace and wet bar. A generous

    Alexis Mcandrew Daniel Gale Sothebys Intl Rlty

    9 Cherry Ln, Glen Head, NY 11545
  • /35

    $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
  • /32

    $1,099,999

    • 5 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    15 Shepherd St, Rockville Centre, NY 11570

    Totally renovated, using the finest materials, bright and sunny Colonial in Rockville Centre! This large home boasts new siding, new roof, HVAC (heat and hot water), pavered driveway, two car garage, inground pool plus 5 good sized bedrooms, an eat in kitchen, formal dining room, office/den, 2 and 1/2 baths, a full finished basement, and so much more! The Master bedroom has an ensuite and large

    Donovan Neita LAFFEY REAL ESTATE

    15 Shepherd St, Rockville Centre, NY 11570
  • /31

    $2,750,000

    • 5 Beds
    • 3.5 Baths
    • 3,492 Sq Ft

    26 Rolling Dr, Glen Head, NY 11545

    The Red Door Colonial in Brookville. Prime location by the end of a cul-de-sac within close proximity to major roads tucked away privately and serenely set. Expansive 2 acre property with sweeping lawns and terrific curb appeal, the perfect place to unwind and enjoy nature's beauty. Featuring rare 5 car garage, including a separate structure full 3 car garage plus attached 2 car garage to house.

    Michael Stanco Compass Greater NY LLC

    26 Rolling Dr, Glen Head, NY 11545
  • /50

    $3,699,000

    • 6 Beds
    • 5 Baths
    • 5,500 Sq Ft

    13 Locust Ln, Glen Head, NY 11545

    La Isabella A Gracious 2 Acre Estate In Prestigious Upper Brookville Offering Timeless Colonial Architecture With Modern Luxury. Set Behind A Sweeping Drive And Surrounded By Mature Magnolia, Dogwood, And Maple Trees, This Home Is Crafted For Multigenerational Living With Privacy And Sophistication. Inside, A Dramatic Double-Height Foyer And Sweeping Staircase Welcome You To Spacious Sunlit Rooms

    Lisa Fasano Compass Greater NY LLC

    13 Locust Ln, Glen Head, NY 11545
  • /32

    $2,900,000

    • 5 Beds
    • 5.5 Baths
    • 4,164 Sq Ft

    60 Reid Ave, Port Washington, NY 11050

    Stunning circa 1920 Colonial completely redone with an eye for its vintage yet with a distinct emphasis on the comforts of modern living. From the kitchen's Royal Delft tiles, ancient limestone floor (heated), LaClanche range, SubZero, Viking and Miele appliances, to the handsome Waterworks tiled bathrooms and reclaimed river pine flooring and mahogany doors and window casings throughout, this

    Maggie Keats Douglas Elliman Real Estate

    60 Reid Ave, Port Washington, NY 11050
  • /15

    $2,999,999

    • 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
  • /33

    $8,975,000

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

    30 Evans Dr, Glen Head, NY 11545

    Set on 2 private and beautifully landscaped acres at the end of a cul-de-sac in the coveted Broad Hollow development of Brookville, this newly built estate offers over 11,400 square feet of total living space—including a 3,600 SF walk-out lower level and a fully outfitted pool cabana—within the top-rated Jericho School District.Designed with a perfect balance of form and function, this

    Zach Elliott Nest Seekers LLC

    30 Evans Dr, Glen Head, NY 11545
  • /8

    $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
  • /46

    $5,998,000

    • 5 Beds
    • 7.5 Baths
    • 8,800 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
  • /45

    $2,900,000

    • 7 Beds
    • 10 Baths
    • 8,162 Sq Ft

    80 Valentines Ln, Glen Head, NY 11545

    Old Brookville Contemporary Home | Stunning and serene property backing lush nature preserve - 80 Valentines Lane offers pure peace and privacy on Long Island's Gold Coast.A welcoming and bright foyer leads into an open, two-story formal living and dining area, offering high ceilings, one of two fireplaces, and an unobstructed view of the expansive backyard. The primary suite is tucked

    Joe Scavo Douglas Elliman Real Estate

    80 Valentines Ln, Glen Head, NY 11545
  • /31

    $5,890,000

    • 5 Beds
    • 6.5 Baths
    • 5,377 Sq Ft

    167 Brookville Rd, Glen Head, NY 11545

    This grand, gated estate blends timeless elegance with modern convenience, showcasing meticulous European craftsmanship throughout. Spanning over 8,000 square feet, this expanded custom ranch features soaring 10–12-foot ceilings and a sun-filled layout that ensures unmatched privacy and presence. A heated, air-conditioned 7-car garage serves as an automotive gallery, while the lower level

    Aileen Murstein Compass Greater NY LLC

    167 Brookville Rd, Glen Head, NY 11545
  • /16

    $3,700,000

    • 6 Beds
    • 6 Baths
    • 5,100 Sq Ft

    8 Plaka Ct, Glen Head, NY 11545

    Situated on 2 acres, with an amazing layout including a tennis court, swimming pool, spa, and basketball court, this resort-style home has everything you could ever need. Located in the picturesque and highly sought-after town of Old Brookville, this home was built in 1978 and boasts a spacious and well-maintained living space of 5,100 square feet. Offering privacy and tranquility, this is the

    Mark Karten Karten Real Estate Svcs LLC

    8 Plaka Ct, Glen Head, NY 11545
  • /35

    $3,850,000

    • 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
  • /41

    $6,299,000

    • 6 Beds
    • 7.5 Baths
    • 7,314 Sq Ft

    20 Knollwood Rd, Glen Head, NY 11545

    Muttontown Brand New Brick Center Hall Colonial | Set on over two private acres on a quiet cul-de-sac, 20 Knollwood Road is an exceptional new construction estate that blends timeless architecture with elevated, modern finishes. With six en-suite bedrooms, soaring 10-foot ceilings on every level, and thoughtfully designed indoor and outdoor spaces, this home is perfectly suited for refined living

    Joe Scavo Douglas Elliman Real Estate

    20 Knollwood Rd, Glen Head, NY 11545
  • /49

    $5,900,000

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

    25 Longridge Ln, Glen Head, NY 11545

    Old Brookville New Construction | 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

    Joe Scavo Douglas Elliman Real Estate

    25 Longridge Ln, Glen Head, NY 11545
  • /37

    $3,690,000

    • 6 Beds
    • 5.5 Baths
    • 6,018 Sq Ft

    8 Norgate Rd, Glen Head, NY 11545

    Welcome to your dream home in the prestigious Brookville area, within the top-rated Jericho School District. Situated on over 2 acres of beautifully landscaped grounds, this custom-built colonial blends luxury, comfort, and timeless elegance. Key Features Include: Grand open layout with custom crown molding throughout; Upscale gourmet kitchen with high-end appliances (Clive Christian) and natural

    Lei Liu Signature Premier Properties

    8 Norgate Rd, Glen Head, NY 11545
  • /20

    $2,300,000

    • 5 Beds
    • 3.5 Baths
    • 5,021 Sq Ft

    2 Summerwind Dr, Glen Head, NY 11545

    1981 development, Town of Oyster Bay, Contemporary 1-Family prodigious home, Expanded in 2 acres lot. High ceiling with skylight, Large living room, Family room, Formal dining Room, Den, and Center kitchen. Total of 11 rooms, 5 Bedrooms, 3.5 Bathrooms, all in mint condition; plus, Full finished basement. Tennis court and In-ground swimming pool. Large patio, BBQ Deck, Porch, and 3 Car garage.

    John Liu Chase Global Realty Corp

    2 Summerwind Dr, Glen Head, NY 11545
  • /28

    $6,995,000

    • 6 Beds
    • 6 Baths
    • 6,711 Sq Ft

    10 Colonial Dr, Glen Head, NY 11545

    10 Colonial Drive is a stunning Georgian estate set on 5 impeccably landscaped acres in the prestigious Colonial Drive Estate of Upper Brookville. This 6,711 sq. ft. residence offers 6 bedrooms, 6 bathrooms, 4 fireplaces, a heated gunite pool, tennis court, and a 3-car garage. A Baccarat chandelier graces the double-height foyer, setting the tone for elegant living. The formal dining room flows

    Benjamin Jordan Douglas Elliman Real Estate

    10 Colonial Dr, Glen Head, NY 11545
  • /27

    $3,699,000

    • 5 Beds
    • 4.5 Baths

    5 Peacock Ln, Glen Head, NY 11545

    Rare Opportunity on Private Gated Upper Brookville Lane. Only 11 Homes Built & Seldom Offered For Sale. Pride of Ownership throughout This Turn Key Brick Colonial on Quiet Interior 2A+ Site. Attention to Detail, Functional Floor Plan for Contemporary Living & Entertaining Indoors and Outdoors. Magnificent Landscaped Grounds Complete with Outdoor Kitchen, Oversized Patio, Gunite Pool with

    Peggy Carillo Douglas Elliman Real Estate

    5 Peacock Ln, Glen Head, NY 11545
  • /34

    $14,900,000

    • 7 Beds
    • 9 Baths

    1985- 4 Cedar Swamp Rd, Glen Head, NY 11545

    'Haut Bois' - is an elegant brick and stucco French Chateau located in the heart of Brookville, NY. Drawing inspiration from the Louis XIV Hunting Lodge, now known as the Palace At Versailles, this stunning 18 room estate is rich in history and beauty. Originally built by Ogden Codman Jr. in 1916 and later restored in the late 1900's and also in 2023, this one-of-a-kind masterpiece stands tall at

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    1985- 4 Cedar Swamp Rd, Glen Head, NY 11545
  • /32

    $3,995,000

    • 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

Home Trends in Glen Head, NY

Housing Trends

Median Sale Price
$1,785,000
Median Single Family Sale Price
$2,299,500
Median 2 Bedroom Sale Price
$775,000
Average Price Per Sq Ft
$594
Number of Homes for Sale
43
Last 12 months Home Sales
103
Months of Supply
5.00
Median List Price
$2,276,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
32%
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