20 Rolling Dr Glen Head, NY 11545
Estimated payment $20,467/month
Highlights
- Horses Allowed On Property
- In Ground Pool
- Floor-to-Ceiling Windows
- Jericho Middle School Rated A+
- Eat-In Gourmet Kitchen
- Colonial Architecture
About This Home
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.
Listing Agent
Compass Greater NY LLC Brokerage Phone: 631-387-1772 License #10401290785 Listed on: 09/12/2025
Co-Listing Agent
Compass Greater NY LLC Brokerage Phone: 631-387-1772 License #10301210325
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $50,567
Year Built
- Built in 1969 | Remodeled in 2025
Lot Details
- 2.01 Acre Lot
- Landscaped
- Level Lot
- Front and Back Yard Sprinklers
- Cleared Lot
- Garden
- Back Yard Fenced and Front Yard
Parking
- 3 Car Garage
- Driveway
Home Design
- Colonial Architecture
- Frame Construction
- Cedar
Interior Spaces
- 5,000 Sq Ft Home
- 3-Story Property
- Central Vacuum
- Recessed Lighting
- Wood Burning Fireplace
- New Windows
- Floor-to-Ceiling Windows
- Casement Windows
- ENERGY STAR Qualified Doors
- Entrance Foyer
- Family Room
- Formal Dining Room
- Storage
- Neighborhood Views
Kitchen
- Eat-In Gourmet Kitchen
- Gas Range
- Microwave
- Dishwasher
- Viking Appliances
- Stainless Steel Appliances
- Kitchen Island
Flooring
- Wood
- Tile
Bedrooms and Bathrooms
- 6 Bedrooms
- Main Floor Bedroom
- En-Suite Primary Bedroom
- Walk-In Closet
- Bathroom on Main Level
Laundry
- Laundry Room
- Dryer
- Washer
Finished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Laundry in Basement
Pool
- In Ground Pool
- Outdoor Pool
- Fence Around Pool
- Pool Cover
Outdoor Features
- Patio
- Exterior Lighting
- Rain Gutters
- Private Mailbox
Location
- Property is near schools
- Property is near shops
Schools
- Jeffrey Ratner-Robert Seaman Elementary School
- Jericho Middle School
- Jericho Senior High School
Utilities
- Central Air
- Baseboard Heating
- Heating System Uses Natural Gas
- Underground Utilities
- Natural Gas Connected
- Gas Water Heater
- Cesspool
Additional Features
- Accessible Elevator Installed
- Horses Allowed On Property
Listing and Financial Details
- Legal Lot and Block 2139 / D
- Assessor Parcel Number 2403-18-D-00-2139-0
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $43,216 | $1,949 | $952 | $997 |
| 2024 | $5,253 | $1,949 | $952 | $997 |
| 2023 | $37,491 | $1,949 | $952 | $997 |
| 2022 | $37,491 | $1,949 | $952 | $997 |
| 2021 | $36,519 | $1,922 | $939 | $983 |
| 2020 | $34,750 | $2,437 | $2,140 | $297 |
| 2019 | $31,195 | $2,437 | $2,140 | $297 |
| 2018 | $29,838 | $2,437 | $0 | $0 |
| 2017 | $22,637 | $2,437 | $2,140 | $297 |
| 2016 | $28,872 | $2,437 | $1,823 | $614 |
| 2015 | $3,853 | $2,572 | $1,750 | $822 |
| 2014 | $3,853 | $2,572 | $1,750 | $822 |
| 2013 | $4,079 | $2,860 | $1,946 | $914 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 10/29/2025 10/29/25 | Price Changed | $3,099,000 | -3.1% | $620 / Sq Ft |
| 09/12/2025 09/12/25 | For Sale | $3,199,000 | -- | $640 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Administrators Deed | $1,750,000 | Chicago Title Insurance Co | |
| Administrators Deed | $1,750,000 | Chicago Title Insurance Co | |
| Administrators Deed | $1,750,000 | Chicago Title Insurance Co | |
| Deed | -- | -- | |
| Deed | -- | -- |
Source: OneKey® MLS
MLS Number: 912361
APN: 2403-18-D-00-2139-0
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