Residential > House
Active
09/12/2025
List Price
$3,099,000$620/ft²
20 Rolling Dr
Glen Head, NY 11545
- 6Beds
- 7Baths
- 5,000ft²Living Area
- 2acLot Size
- 1Pool
- 10Car
- 1969Year Built
- 91DOM
- -Permit
20 Rolling Dr, Glen Head, NY 11545 is a 6 bed, 7 bath, 5,000 ft² house built in 1969 on a 2.010 acre lot.
Property Valuations
Latest estimates for 20 Rolling Dr based on TopHap automated valuation model (AVM).
TopHap Estimate
$1,908,550
$453/ft²
-$1M below List Price
Updated 2 months ago
20 Rolling Dr is valued at $1,908,550 by TopHap AVM 2 months ago.
MLS Description
The listing agent's description. Original Listing
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 Agents
The listing agent for 20 Rolling Dr is Christopher Galluzzo.
CG
Christopher Galluzzo
Compass Greater NY LLC
Phone: (212) 913-9058
Current Ownership
Information about the current owner(s).
Taxes Billed
Taxes billed in 2025$43,216.03From latest Total Assessed Value2,217.34%Total Assessed Value$1,949=Land+
Assessed Value$952Additions
Assessed Value$997
In 2025, taxes billed for 20 Rolling Dr were $43,216.03, which is 2217.34% from latest Total Assessed Value of $1,949.
Property History
20 Rolling Dr has undefined property events records (listings, deeds, permits, tax, foreclosure, loan).
Property Events
Environment
Environmental factors around 20 Rolling Dr
Hazard Risks
Wind236Hurricane129Lead124Air Pollution115Ozone114Carb Mono105Weather101Nat'l Avg100Earthquake97Particulates93Hail66Tornado36
12 hazards (Carbon Monoxide, Earthquake Risk, Hail Index, Tornado Index, Hurricane Index, Air Pollution Index, Ozone Index, Wind Index, Weather Risk, Lead Index, Particulate Matter, National Average) are above the national average around 20 Rolling Dr.
Walkability Index
0 /20
Most Walkable
20-18
Very Walkable
17-15
Somewhat Walkable
14-10
Car Dependent
9-0
20 Rolling Dr has a walkability score of 0 out of 20, which means that it is in a car dependent area.
Temperature
Seasonal temperature sampled over multiple years
Winter
Average
Low
26°F
High
40°F
Summer
Average
Low
63°F
High
81°F
In the winter at 20 Rolling Dr, temperatures range from 25.73°F to 39.72°F with an average of 32.73°F. In the summer, the temperature ranges from 63°F to 80.94°F with and average of 71.97°F.
School Information
Public Schools
* The school rating is based entirely on the test score performance of each school. It is based on a scale of A-F, A being best.
Nearby public schools serving 20 Rolling Dr have no ratings.
Nearby Properties on Rolling Dr
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- 10 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,434 square foot, 4.25 bathroom, 2.37 acre property. It was built in 1968 and has an estimate of $2,280,559 with a price per ft² of $664.
- 19 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,095 square foot, 5.25 bathroom, 2.22 acre property. It was built in 1969 and has an estimate of $1,779,352 with a price per ft² of $575.
- 9 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,432 square foot, 4.25 bathroom, 2.03 acre property. It was built in 1969 and has an estimate of $2,166,287 with a price per ft² of $631.
- 14 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 4,591 square foot, 5.25 bathroom, 2.04 acre property. It was built in 1967 and has an estimate of $2,615,654 with a price per ft² of $570.
- 8 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,530 square foot, 3.25 bathroom, 2 acre property. It was built in 1968 and has an estimate of $1,902,974 with a price per ft² of $539.
- 12 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 4,164 square foot, 5.25 bathroom, 2.02 acre property. It was built in 1968 and has an estimate of $2,866,180 with a price per ft² of $688.
- 16 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 5,825 square foot, 5.25 bathroom, 2 acre property. It was built in 1998 and has an estimate of $2,388,324 with a price per ft² of $410.
- 18 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,452 square foot, 4.25 bathroom, 2.25 acre property. It was built in 1969 and has an estimate of $2,170,257 with a price per ft² of $629.
- 20 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 4,213 square foot, 4.25 bathroom, 2.01 acre property. It was built in 1969 and has an estimate of $2,484,972 with a price per ft² of $590.
- 22 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 5,086 square foot, 4.25 bathroom, 2 acre property. It was built in 1969 and has an estimate of $4,103,093 with a price per ft² of $807.
- 24 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,597 square foot, 3.25 bathroom, 2 acre property. It was built in 1968 and has an estimate of $2,160,581 with a price per ft² of $601.
- 26 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,492 square foot, 4.25 bathroom, 2.01 acre property. It was built in 1969 and has an estimate of $1,999,286 with a price per ft² of $573.
- 17 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,733 square foot, 5 bedroom, 4.25 bathroom, 2.11 acre property. It was built in 1967 and has an estimate of $2,499,000 with a price per ft² of $669.
- 15 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 5,214 square foot, 5.25 bathroom, 2.03 acre property.
- 5 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 4,673 square foot, 5.25 bathroom, 2.07 acre property. It was built in 1968 and has an estimate of $2,470,853 with a price per ft² of $529.
- 3 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 4,492 square foot, 4.25 bathroom, 2.03 acre property. It was built in 1969 and has an estimate of $2,160,231 with a price per ft² of $481.
- 30 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 6,241 square foot, 5 bedroom, 5 bathroom, 2.25 acre property. It was built in 1969 and has an estimate of $2,272,500 with a price per ft² of $364.
- 28 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 6,301 square foot, 10.25 bathroom, 2 acre property. It was built in 2005 and has an estimate of $3,926,759 with a price per ft² of $623.
- 25 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,989 square foot, 4.25 bathroom, 2.04 acre property. It was built in 1969 and has an estimate of $2,436,241 with a price per ft² of $611.
- 2 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,440 square foot, 4.25 bathroom, 2.02 acre property. It was built in 1967 and has an estimate of $1,860,354 with a price per ft² of $541.
- 4 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,698 square foot, 4.25 bathroom, 2 acre property. It was built in 1971 and has an estimate of $2,176,384 with a price per ft² of $589.
- 6 Rolling Dr, Glen Head, NY 11545 (Brookville) is a 3,705 square foot, 4.25 bathroom, 2.05 acre property. It was built in 1968 and has an estimate of $2,375,413 with a price per ft² of $641.