28 Rolling Drive, Glen Head, NY 11545
OFF MARKET

$4,406,500

Trulia Estimate
  • 6 Beds
  • 6.5 Baths
  • 8,500 sqft (on 2 acres)

28 Rolling Drive, Glen Head, NY 11545

Brookville
Est. Refi. Payment $29,443/mo*
Refinance Your Home
Currently Off Market - Sold Jan 17, 2024 for $3,875,000

Home Value

Trulia Estimate
$4.41M
Since last month
Decreased$8K (-0.2%)
Since last year
Increased$178K (+4.2%)
Since last sale
Increased$532K (+13.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +27% in the last 10 years
MonthEstimated value
2026
September 2026$4.41M
August 2026$4.41M
July 2026$4.38M
June 2026$4.42M
May 2026$4.34M
April 2026$4.3M
March 2026$4.28M
February 2026$4.22M
January 2026$4.24M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20 Rolling Drive, Glen Head, NY
0.18
Single-Family Home
$2,700,000
05/15/26
6
6.5
5,972
355 Wheatley Road, Old Westbury, NY
0.22
Single-Family Home
$3,750,000
10/21/25
9
6.5
8,650
109 Wheatley Road, Glen Head, NY
0.53
Single-Family Home
$3,650,000
03/18/26
6
5.5
5,642
47 Valley Road, Old Westbury, NY
0.49
Single-Family Home
$3,488,888
07/28/26
6
5.5
5,353
16 Horse Hill Road, Brookville, NY
0.54
Single-Family Home
$6,050,000
02/04/26
6
6.5
7,200
8 Rolling Drive, Glen Head, NY
0.30
Single-Family Home
$2,350,000
11/24/25
5
3.5
3,530
46 Morgan Drive, Old Westbury, NY
0.77
Single-Family Home
$3,774,000
03/30/26
6
6.5
6,039
24 Rolling Hill Road, Old Westbury, NY
0.49
Single-Family Home
$2,350,000
05/29/26
5
5
4,700
48 Morgan Drive, Old Westbury, NY
0.70
Single-Family Home
$3,053,500
01/28/26
5
4.5
6,000
32 Valley Road, Old Westbury, NY
0.35
Single-Family Home
$1,834,787
10/15/25
5
3.5
3,692

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
20 Rolling Drive, Glen Head, NY 11545
0.18
$2,700,000
6
6.5
5,972
Recently Sold
355 Wheatley Road, Old Westbury, NY 11568
0.22
$3,914,600
9
6.5
8,650
Off Market
8 Rolling Drive, Glen Head, NY 11545
0.30
$2,438,600
5
3.5
3,530
Off Market
152 Wheatley Road, Glen Head, NY 11545
0.27
$1,940,000
2
2
-
Off Market
38 Meadowood Lane, Glen Head, NY 11545
0.35
$2,734,300
6
3.5
-
Off Market
53 Clock Tower Ln, Old Westbury, NY 11568
0.32
$1,855,400
3
2
-
Off Market
136 Wheatley Road, Greenvale, NY 11545
0.34
$2,915,900
4
3.5
6,030
Off Market
53A Clock Tower Ln, Old Westbury, NY 11568
0.35
-
-
-
-
Off Market
32 Valley Road, Old Westbury, NY 11568
0.35
$1,899,900
5
3.5
3,692
Foreclosure
25 Meadowood Lane, Glen Head, NY 11545
0.41
$4,305,700
7
6.5
-
Off Market
29 Horse Hill Road, Brookville, NY 11545
0.43
$2,893,100
6
4.5
-
Off Market

Local Information

  • Map ViewExplore the area around 28 Rolling Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2005
2 acre lot
8,500 sqft
$518/sqft
Garage

About this House

What's unique:High ceilingsMultiple sets of windowsSports courtCenter islandMarble ensuite bathroomFieldstone fireplace
Welcome to this six-bedroom extraordinary designer owned sprawling brick Ranch. Custom built, superior quality and workmanship with no detail overlooked. The generously scaled interior spaces include formal principal rooms with high ceilings and complement an open floor plan for entertaining and living. For the chef, the kitchen is unsurpassed. Highlights include white cabinetry, center island, state of the art appliances and breakfast room. The den is sun filled, spacious and has multiple sets of windows and doors that open to the expansive bluestone patio and verdant property. A fieldstone fireplace and custom wet bar enhance the room. Luxurious primary suite like no other with office, sitting room, dressing room and marble ensuite bathroom. Lower-Level recreation area features gym and 1000+ temperature-controlled wine cellar. Sublime two-acre lush landscape at the end of a quiet cul-de-sac with a sparkling in-ground pool and sports court. Jericho SD., Additional information: Appearance:Diamond ++,Interior Features:Guest Quarters,Marble Bath,Separate Hotwater Heater:Yes
28 Rolling Drive, Glen Head, NY 11545 is a 6 bedroom, 7 bathroom, 8,500 sqft single-family home in Brookville, built in 2005. It last sold for $3,875,000 on Jan 17, 2024 (3% below the $4,000,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,406,500.
Last check for updates: about 8 hours ago
Listed by Lois Kirschenbaum, (516) 526-7425
Daniel Gale Sothebys Intl Rlty, (516) 626-7600
Bought with: Frank Ko, (718) 886-8110, E Realty International Corp, (718) 886-8110
Source: OneKey® MLS as distributed by MLS GRID, MLS#L3500769

Home Details for 28 Rolling Drive

Interior Features

Interior Details
Basement: Walk-Out Access,Crawl Space,Finished,FullNumber of Rooms: 14
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 8500 Square Feet
Appliances & Utilities
Utilities: Trash Collection PrivateAppliances: Cooktop, Dishwasher, Dryer, Microwave, Oven, Refrigerator, Washer, Gas Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a FireplaceNo Spa
Gas & Electric
Electric: Generator
Windows, Doors, Floors & Walls
Window: Blinds, DrapesFlooring: Carpet, Hardwood
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood
View
Has a ViewView: Panoramic
Security
Security: Security System, Video Cameras

Exterior Features

Exterior Home Features
Patio / Porch: PatioFencing: FencedExterior: Basketball Hoop, Gas Grill, SpeakersHas a Private Pool
Parking & Garage
No CarportGarageParking: Attached,Garage Door Opener,Private
Pool
Pool: In GroundPool
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Cesspool
Farm & Range
Allowed to Raise Horses

Property Information

Year Built
Year Built: 2005Year Renovated: 2010
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Ranch
Building
Construction Materials: BrickNot Attached Property
Property Information
Not Included in Sale: Chandelier(s)Parcel Number: 240318D0021560

Price & Status

Price
List Price: $4,000,000
Status Change & Dates
Off Market Date: Wed Sep 27 2023

Active Status

MLS Status: Sold

Location

Direction & Address
City: Brookville
School Information
Elementary School: JEFFREY RATNER-ROBERT SEAMAN ELEMENTARY SCHOOLJr High / Middle School: Jericho Middle SchoolHigh School: Jericho Senior High SchoolHigh School District: Jericho

Building

Building Area
Building Area: 8500 Square Feet
Community rooms
Fitness Center

Community

Community Features: Fitness CenterNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 2 Acres

Offer

Listing Agreement Type: Exclusive Right To Lease

Miscellaneous

BasementMls Number: L3500769Attic: Full

Additional Information

HOA Amenities: Fitness Center

Price and Tax history

DateEventPrice
Jan 17, 2024
Source: OneKey® MLS as distributed by MLS GRID #L3500769
Sold
$3,875,000
Sep 27, 2023
Source: OneKey® MLS as distributed by MLS GRID #3500769
Pending
$4,000,000
Aug 29, 2023
Source: OneKey® MLS as distributed by MLS GRID #3500769
Listed For Sale
$4,000,000
Dec 29, 2003
Source: N/A
Sold
$2,300,000

Market trends in Glen Head

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
49
1MoM

Around this home

Neighborhood Overview

Brookville
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Brookville

At least 13 Trulia users voted on each feature.

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 88 % Say it's dog friendly

  • 83 % Say parking is easy

  • 82 % Say it's quiet

  • 77 % Say they plan to stay for at least 5 years

  • 69 % Say people would walk alone at night

  • 60 % Say there's wildlife

  • 49 % Say neighbors are friendly

  • 39 % Say there's holiday spirit

  • 27 % Say kids play outside

  • 18 % Say streets are well-lit

  • 11 % Say there are community events

  • 10 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Agatha D.
    "This is a high end community it’s hard to walk around because there’s no sidewalks or public transportation but it’s safe and well maintained. "
    14
    Flag

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-09-25 01:03:16 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information

Frequently asked questions about 28 Rolling Drive

  • What is 28 Rolling Drive estimated to be worth?
    Trulia's estimated value for 28 Rolling Drive in Glen Head, NY is $4,406,500.
  • What is the price history for 28 Rolling Drive?
    28 Rolling Drive in Glen Head, NY last sold for $3,875,000 in January 2024.
  • Is Glen Head a buyer's or seller's market?
    Glen Head is currently a balanced market, based on recent for-sale activity.
  • What do residents say about the Brookville neighborhood?
    Residents describe the Brookville neighborhood in Glen Head, NY as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Brookville, Glen Head.
  • Does 28 Rolling Drive have air conditioning?
    Yes, 28 Rolling Drive in Glen Head, NY has air conditioning.
  • Does 28 Rolling Drive have a pool?
    Yes, 28 Rolling Drive in Glen Head, NY has a pool.

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