20 Rolling Drive Glen Head, NY $ 3,099,000
20 Rolling Drive
$ 3,099,000
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20 Rolling Drive

Glen Head, NY, 11545
$ 3,099,000
Bedrooms6 Baths6.1 Sq 5,000

Monthly Estimate*

$ 19,334

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Single Family Home for sale in Glen Head, NY

for $3,099,000 with 6 bedrooms and 6 full baths, 1 half bath. This 5,000 square foot home was built in 1969 on a lot size of 2.01.

Welcome to 20 Rolling Drive, Glen Head, NY - Set on a pristine 2 acres of rolling lawn. 6 Bedrooms | 6.5 Bathrooms | 4,868 Sq Ft | Colonial Discover the perfect balance of space, style, and modern updates in this fully renovated 5000 sq ft Colonial, with a basement and garage included it is approximately a 7000 sq ft total structured home, ideally located in prestigious Brookville. With 6 bedrooms, 6.5 bathrooms, and expansive grounds, this home is designed for both elegant entertaining and everyday living. Inside, a sun-filled open floor plan highlights wide-plank hardwood floors, oversized windows, and seamless flow between living spaces. The chef’s kitchen features Viking appliances, quartz countertops, custom cabinetry, dual sinks, an oversized island, a wine fridge, and sliders opening directly to the backyard. A spacious family room with a stone, wood-burning fireplace and multiple dining and living areas creates versatile spaces for gatherings. There is even an elevator that takes you from the garage to the first floor and then to the primary bedroom. Upstairs, the luxurious primary suite includes a spa-inspired bath, while five additional bedrooms and updated bathrooms with LED mirrors and sleek finishes offer comfort and flexibility. The finished full basement adds even more living space, complete with a full bathroom, laundry room, and endless potential for a gym, media room, or guest suite. Outdoors, the property is a true retreat, featuring a sparkling in-ground pool, two large patios, and a sprawling grassy yard ideal for entertaining or recreation. A circle driveway and 3-car garage provide convenience and curb appeal. Peace of mind comes with major updates, 3 brand new CAC systems, Boiler 2017, and a new roof. Situated close to top-rated schools, golf, shopping, dining, and major highways, 20 Rolling Drive offers estate-style living with every modern convenience. Move-in ready, spacious, and built for today’s lifestyle, this Brookville gem has it all. 2 Acres, 3 Car Garage, Boiler 2017 - 5 zones, Natural Gas, Radiant floors in primary bathroom, Elevator, 400 AMP, New Roof, soffits and leaf guards, 25 X 50 gunite pool newly diamond dusted, 12 Zone Sprinkler System in the front and back, CAC.

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Single Family Active

Price

$ 3,099,000

Bedrooms

6

Full Bath

6

Half Bath

1

Property Type

Single Family

Taxes

$ 50,566

Style

Colonial

Lot Size

2.01

Year Built

1969

Town/City

Glen Head

County/Region

Nassau

MLS | Web ID

912361

Features
Interior
Interior Amenities First Floor Bedroom First Floor Full Bath Central Vacuum Chefs Kitchen Eat-in Kitchen Elevator ENERGY STAR Qualified Door(s) Entrance Foyer Formal Dining Kitchen Island Open Kitchen Primary Bathroom
Basement Finished Full Walk-Out Access
Flooring Hardwood Tile
Total Fireplaces 1
Fireplace Features Family Room Wood Burning
Basement Features Finished Full Walk-Out Access
Basement (Y/N) Y
Window Features Aluminum Frames Casement Floor to Ceiling Windows New Windows
Fireplace Y/N Y
Half Baths 1
Total Bedrooms 6
Total Baths 7
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General
Sewer Cesspool
Heating Baseboard Natural Gas
Cooling Central Air
Utilities Electricity Connected Natural Gas Connected Trash Collection Public Underground Utilities Water Connected
Appliances Dishwasher Dryer Gas Range Microwave Refrigerator Stainless Steel Appliance(s) Washer Gas Water Heater
Garage Spaces 3
Patio/Porch Features Patio
Architectural Style Colonial
Pool Features Fenced In Ground Outdoor Pool Pool Cover
Construction Materials Cedar Frame
Year Built 1969
View Neighborhood
Property Subtype Single Family Residence
Tax Year 2024
Parcel Number 2403-18-D-00-2139-0
Accessibility Accessible Elevator Installed
County Nassau County
Property Type Residential
HOA N
Garage Y/N Y
Total Rooms 13
Full Baths 6
Directions Cedar Swamp Rd to Wheatley Rd then right onto Rolling Drive.
High School Jericho Senior High School
City Oyster Bay
Disclosures Seller Property Disclosure
Senior Community Y/N N
High School District Jericho
Carport Y/N N
Elementary School JEFFREY RATNER-ROBERT SEAMAN ELEMENTARY SCHOOL
Property Attached Y/N N
Tax Annual Amount 50566.78
Showing Instructions Listing Agent
Middle/Junior High School Jericho Middle School
Property Condition Updated/Remodeled
Additional Parcels Y/N N
Virtual Tour https://jumpvisualtours.com/u/486574 https://jumpvisualtours.com/486574
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Jericho
Elementary School District Jericho
Tax Lot 2139
Year Built Effective 2025
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Exterior
Exterior Amenities Garden Lighting Mailbox Rain Gutters
Fencing Back Yard
Parking Features Driveway Garage Driveway Garage
Water Source Public
Total Parking 10
Parking Spaces 10
Foundation Details Concrete Perimeter
Spa N
Building Area Total 6000
Waterfront Y/N N
Road Frontage Type Municipal
Road Responsibility Public Maintained Road
Horse Y/N Y
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Internal Only
Street Number 1 20
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* Excluded Features
List By
Christopher Galluzzo

Listing Agent

Compass Greater Ny Llc

Broker

631-387-1772

Contact

Affordability Calculator

$23,548
Per Month
82%
18%
0%
Monthly Principal & Interest
$19,334
Monthly Property Taxes
$4,214
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
5163286 Elementary School
4101292 Middle School
Jericho Senior High School High School
Pricing History
DatePricePrice ChangeDescription
10/29/2025$3,099,000 -3.13% Price Down
9/13/2025$3,199,000 Listed Price

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20 Rolling Drive, Glen Head, NY, 11545 is a Single Family Home for sale at $3,099,000 with 5,000 sqft and a lot size of 2.01. 20 Rolling Drive has 6 bedrooms, 6.1 baths, and was built in 1969. The property's zip code is 11545 which is in Glen Head, NY