5 Rolling Dr, Glen Head, NY 11545
OFF MARKET

$2,750,400

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 4,673 sqft (on 2.07 acres)

5 Rolling Dr, Glen Head, NY 11545

Brookville
Est. Refi. Payment $18,109/mo*
Refinance Your Home
Currently Off Market - Sold Mar 30, 1998 for $500,000

Home Value

Trulia Estimate
$2.75M
Since last month
Increased$22K (+0.8%)
Since last year
Increased$218K (+8.5%)
Since last sale
Increased$2M (+456.3%)
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 +37% in the last 10 years
MonthEstimated value
2026
September 2026$2.78M
August 2026$2.76M
July 2026$2.76M
June 2026$2.76M
May 2026$2.69M
April 2026$2.69M
March 2026$2.67M
February 2026$2.63M
January 2026$2.64M
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
8 Rolling Drive, Glen Head, NY
0.16
Single-Family Home
$2,350,000
11/24/25
5
3.5
3,530
20 Rolling Drive, Glen Head, NY
0.18
Single-Family Home
$2,700,000
05/15/26
6
6.5
5,972
109 Wheatley Road, Glen Head, NY
0.39
Single-Family Home
$3,650,000
03/18/26
6
5.5
5,642
32 Valley Road, Old Westbury, NY
0.45
Single-Family Home
$1,834,787
10/15/25
5
3.5
3,692
24 Rolling Hill Road, Old Westbury, NY
0.63
Single-Family Home
$2,350,000
05/29/26
5
5
4,700
14 Farmstead Lane, Glen Head, NY
0.49
Single-Family Home
$2,680,000
02/03/26
5
4
4,000
47 Valley Road, Old Westbury, NY
0.60
Single-Family Home
$3,488,888
07/28/26
6
5.5
5,353
42 Clocktower Lane, Old Westbury, NY
0.62
Single-Family Home
$2,050,000
09/18/26
5
4.5
5,001
16 Horse Hill Road, Brookville, NY
0.43
Single-Family Home
$6,050,000
02/04/26
6
6.5
7,200
20 Rolling Hill Road, Old Westbury, NY
0.62
Single-Family Home
$2,000,000
09/03/26
5
3
4,482

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
8 Rolling Drive, Glen Head, NY 11545
0.16
$2,438,600
5
3.5
3,530
Off Market
28 Rolling Drive, Glen Head, NY 11545
0.14
$4,356,000
6
6.5
8,500
Off Market
20 Rolling Drive, Glen Head, NY 11545
0.18
$2,700,000
6
6.5
5,972
Recently Sold
136 Wheatley Road, Greenvale, NY 11545
0.22
$2,874,300
4
3.5
6,030
Off Market
38 Meadowood Lane, Glen Head, NY 11545
0.23
$2,701,600
6
3.5
-
Off Market
25 Meadowood Lane, Glen Head, NY 11545
0.26
$4,250,100
7
6.5
-
Off Market
152 Wheatley Road, Glen Head, NY 11545
0.23
$1,947,100
2
2
-
Off Market
33 Farmstead Lane, Brookville, NY 11545
0.30
$4,205,200
7
6.5
-
Off Market
134 Wheatley Rd, Glen Head, NY 11545
0.32
$3,890,200
5
3.5
3,827
Off Market
20 Meadowood Lane, Glen Head, NY 11545
0.33
-
-
-
-
Off Market
29 Horse Hill Road, Brookville, NY 11545
0.33
$2,838,000
6
4.5
-
Off Market
36 Farmstead Lane, Glen Head, NY 11545
0.33
$2,294,400
7
4.5
4,495
Off Market

Local Information

  • Map ViewExplore the area around 5 Rolling Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1968
2.07 acre lot
4,673 sqft
$589/sqft
Garage

About this House

Hampton Style Living On 2+ Acres With Pond View From The House. Large Spacious Rooms Through Out. 6 Bedrooms, 4.5 Baths, Wood Burning Fireplace. Finished Basement With Home Theater, Office And Recreation Room. Close To Highways, Easy Commute To Manhattan.
5 Rolling Dr, Glen Head, NY 11545 is a 6 bedroom, 5 bathroom, 4,673 sqft single-family home in Brookville, built in 1968. It last sold for $500,000 on Mar 30, 1998. More recently, it was listed as a rental in December 2012 with an asking price of $12,000 per month. That rental listing was removed on May 14, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,750,400, with a rent estimate of $9,379/month.

Home Details for 5 Rolling Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 9Types of Rooms: Recreation Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 2.07 acres

Price and Tax history

DateEventPrice
May 14, 2013
Source: Agent Provided
ListingRemoved
$9,500
Feb 6, 2013
Source: Agent Provided
PriceChange
$9,500
Price decreased by 21%
Dec 14, 2012
Source: Agent Provided
Listed For Rent
$12,000
Mar 30, 1998
Source: N/A
Sold
$500,000

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

Frequently asked questions about 5 Rolling Dr

  • What is 5 Rolling Dr estimated to be worth?
    Trulia's estimated value for 5 Rolling Dr in Glen Head, NY is $2,750,400.
  • What is the price history for 5 Rolling Dr?
    5 Rolling Dr in Glen Head, NY last sold for $500,000 in March 1998.
  • 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 5 Rolling Dr have air conditioning?
    Yes, 5 Rolling Dr in Glen Head, NY has air conditioning.
  • Does 5 Rolling Dr have laundry facilities?
    Yes, 5 Rolling Dr in Glen Head, NY has in-unit laundry.

Explore by feature - Garage

Explore by feature - Air Conditioning

7 rentals with air conditioning in Glen Head, NY

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Glen Head, NY

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