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Residential Land with Home for Sale in Glen Head, New York

20 Rolling Dr, Glen Head, NY 11545

$3,099,000
2 acres
Active
$100k drop
Est $19,398/mo

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.

5,000
Sq feet
6
Beds
6
Full baths
1
1/2 bath
1969
Built

Location

Street address
20 Rolling Dr
School district
Jericho
Elevation
207 feet
Coordinates
40.8118, -73.5837

Directions

Cedar Swamp Rd to Wheatley Rd then right onto Rolling Drive.

Property details

Acreage
2.01 acres
MLS #
MLSLI 912361
Posted

Property taxes

2024
$50,567

Parcels

  • 2403-18-D-00-2139-0

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Lot

Features
Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Near School, Near Shops, Sprinklers in Front, Sprinklers in Rear

Exterior

Parking Spaces
10
Parking
Driveway, Garage
Pool
Patio
Structures
Storage
Features
Lighting, Mailbox, Rain Gutters

Structure

Style
Colonial
Stories
3
Water
Public
Sewer
Cesspool
Heating
Baseboard, Natural Gas
Cooling
Central Air
Materials
Cedar, Frame
Windows
Aluminum Frames

Interior

Room Count
13
Rooms
Basement, Bathroom x 7, Bedroom x 6, Dining Room, Family Room
Flooring
Hardwood, Tile
Appliances
Dishwasher, Dryer, Gas Range, Gas Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Accessibility
Accessible Elevator Installed
Features
Central Vacuum, Chefs Kitchen, ENERGY STAR Qualified Door(s), Eat-In Kitchen, Elevator, Entrance Foyer, First Floor Bedroom, First Floor Full Bath, Formal Dining, Kitchen Island, Open Kitchen, Primary Bathroom, Quartz/Quartzite Counters, Recessed Lighting, Walk-In Closet(s)

Property utilities

CategoryTypeStatusDescription
GasNatural GasConnected

Nearby schools

NameLevelDistrictDescription
Jeffrey Ratner-Robert Seaman Elementary SchoolElementaryJericho
Jericho Middle SchoolMiddleJericho
Jericho Senior High SchoolHighJericho

Listing history

DateEventPriceChangeSource
Oct 29, 2025Price drop$3,099,000$100,000 -3.1%MLSLI
Sept 13, 2025New listing$3,199,000MLSLI
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This 2.01-acre property is located at 20 Rolling Dr in Glen Head, NY 11545. The property is available for sale for $3,099,000. It has a 5,000 sq ft 6 bedroom, 6 bath house built in 1969.

Checked 22 mins ago — Updated

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