53 Simonson Road, Glen Head, NY 11545
FOR SALE
6.28 ACRES

53 Simonson Road
Glen Head, NY 11545

Old Brookville
  • 10 Beds
  • 14 Baths
  • 20,000 sqft (on 6.28 acres)

$12,800,000

Est. Mortgage $78,474/mo*
Get Pre-Qualified

$12,800,000

Est. Mortgage $78,474/mo*
Get Pre-Qualified
10 Beds
14 Baths
20,000 sqft
(on 6.28 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary.

A striking stone and stucco facade with oversized black-trim windows sets a sophisticated tone upon arrival. Inside, a dramatic marble foyer with a sweeping spiral staircase unveils the heart of the home: a voluminous great room featuring soaring ceilings, a sleek gas fireplace, bespoke wet bar, and walls of glass that dissolve the boundary between indoors and out. Every inch of this residence speaks to thoughtful luxury. The chef’s kitchen is clad in two-toned cabinetry, boasts a suite of chef-grade stainless steel appliances and thick-cut stone countertops. The welcoming family room has a warm fireplace with a custom, stone mantel and beautiful natural wood built-ins. Entertain effortlessly in the formal dining room, designed to host 14+ guests, supported by a fully outfitted butler’s pantry.

Designed for both grand entertaining and intimate day-to-day living, the main level also features a spacious home office with a private sitting area, two elegant powder rooms, a guest-ready first-floor bedroom suite, an elevator and a mudroom conveniently located off of the 4-car attached garage.

Upstairs, the primary wing evokes the atmosphere of a five-star hotel, complete with a private lounge, dressing and vanity area, spa-like bath with an oversized rain shower and soaking tub, radiant heated floors, and multiple walk-in closets, with custom wardrobe installations. There are four additional bedrooms, four marble full-bathrooms and an expansive laundry room.

The walk-out lower level is a world unto itself, beginning with a dramatic foyer framed by a floor-to-ceiling wine display wall. Details include a one-bedroom guest suite, media or den space, full bath, a state-of-the-art gym with sound system and sauna, and a full-scale golf simulator for year-round recreation.

Outdoors, the resort-quality amenities continue with a covered patio with a fireplace, a built-in kitchen, and a sparkling in-ground pool and spa. A poolside cabana offers yet another luxe retreat, complete with a kitchenette, lounge, changing rooms, and full bath. Beyond the main residence, a two-story barn with a loft serves as an 8-stall equestrian facility or an extraordinary car collector's gallery, accompanied by a fully-appointed 3/4 bedroom guest house for extended stays or guest quarters.

Nestled in a picturesque and ultra-private setting, this 20,000+ Sq.Ft. Old Brookville masterpiece redefines modern estate living with unmatched elegance, scale, and functionality. Located within the North Shore School District.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$640
Listed
180+ days ago
Last check for updates: about 9 hours ago
Listing by: Daniel Gale Sothebys Intl Rlty, (516) 626-7600
Jason P. Friedman, (516) 236-6226
Daniel Gale Sothebys Intl Rlty, (516) 626-7600
Sarah R. Friedman, (516) 626-7600
Source: OneKey® MLS as distributed by MLS GRID, MLS#922932
Also Listed on OneKey® MLS as distributed by MLS GRID.

Home Details for 53 Simonson Road

Interior Features

Interior Details
Basement: Finished,Full,Walk-Out AccessNumber of Rooms: 25Types of Rooms: Auxiliary RoomWet Bar
Beds & Baths
Number of Bedrooms: 10Number of Bathrooms: 15Number of Bathrooms (full): 13Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 20000 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Natural Gas Connected, Trash Collection Public, Water ConnectedAppliances: Convection Oven, Cooktop, Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Cooktop, Gas Oven, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Wine RefrigeratorDishwasherDryerLaundry: Washer/Dryer Hookup,Multiple LocationsMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Natural Gas,Radiant,Radiant FloorHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa
Number of Fireplaces: 6Fireplace: Bedroom, Family Room, Living RoomHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Floor to Ceiling Windows, Oversized Windows, Wall of WindowsFlooring: Hardwood, Tile
Levels, Entrance, & Accessibility
Levels: TwoElevatorFloors: Hardwood, Tile
View
Has a ViewView: Open
Security
Security: Building Security, Security Gate

Exterior Features

Exterior Home Features
Patio / Porch: Covered, Patio, Porch, TerraceFencing: FencedOther Structures: Barn(s), Guest House, Pool HouseExterior: Balcony, Rain Gutters, SpeakersHas a Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Carport Spaces: 1Number of Covered Spaces: 4Has a CarportHas a GarageParking Spaces: 5Parking: Attached,Heated Garage,Oversized
Pool
Pool: In Ground, Outdoor Pool, Pool/Spa ComboPool
Water & Sewer
Sewer: Cesspool
Farm & Range
Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 181Days on Market: 180+

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Estate
Building
Construction Materials: Stone, StuccoNot Attached Property
Property Information
Condition: ActualNot Included in Sale: Contact Listing Agent(s)Parcel Number: 241520J0709480

Price & Status

Price
List Price: $12,800,000Price Per Sqft: $640

Active Status

MLS Status: Active

Location

Direction & Address
City: Old Brookville
School Information
Elementary School: Glen Head Elementary SchoolJr High / Middle School: North Shore Middle SchoolHigh School: North Shore Senior High SchoolHigh School District: North Shore

Agent Information

Listing Agent
Listing ID: 922932

Building

Building Area
Building Area: 20000 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 6.28 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 922932Attic: See RemarksAttribution Contact: 516-466-4036Showing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent

Price History for 53 Simonson Road

DatePriceEventSource
10/15/2025$12,800,000Listed For SaleOneKey® MLS as distributed by MLS GRID #922932
01/11/2016$3,100,000Sold
OneKey® MLS as distributed by MLS GRID #L2791571
11/03/2015$3,395,000PendingAgent Provided
08/26/2015$3,395,000Listed For SaleAgent Provided
09/01/2012$4,150,000ListingRemovedAgent Provided
10/05/2011$4,150,000Listed For SaleAgent Provided
08/15/2011$4,150,000ListingRemovedAgent Provided
03/25/2011$4,150,000Listed For SaleAgent Provided
05/11/2009$5,495,000ListingRemovedAgent Provided
11/01/2008$5,495,000Listed For SaleAgent Provided
02/14/2005$1,300,000Sold
N/A

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Property Tax and Assessment

Year2024
Tax
Assessment$6,990,000
Home facts updated by county records

Comparable Sales for 53 Simonson Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
80 Valentines Lane, Glen Head, NY
0.28
Single-Family Home
$2,500,000
02/26/26
7
8.5
8,162
3 Woodhollow Lane, Glen Head, NY
0.18
Single-Family Home
$6,201,000
08/04/25
7
8
10,100
12 Eastview Lane, Glen Head, NY
0.32
Single-Family Home
$5,020,000
08/14/25
7
8.5
6,009
78 McCouns Lane, Glen Head, NY
0.58
Single-Family Home
$2,525,000
10/24/25
7
6
5,497
25 Longridge Lane, Glen Head, NY
0.45
Single-Family Home
$5,600,000
03/27/26
5
5.5
6,500
820 Bryant Avenue, Roslyn, NY
0.76
Single-Family Home
$4,500,000
01/23/26
6
5.5
9,800
6 Longridge Lane, Glen Head, NY
0.45
Single-Family Home
$2,500,000
01/06/26
5
3.5
4,975
8 Chicken Valley Road, Glen Head, NY
1.02
Single-Family Home
$2,600,000
07/31/25
5
8
7,938
35 Hoaglands Lane, Old Brookville, NY
0.80
Single-Family Home
$2,750,000
04/28/26
6
6.5
4,787

Nearby homes

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Assigned Schools

These are the assigned schools for 53 Simonson Road.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

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

What Locals Say about Old Brookville

At least 16 Trulia users voted on each feature.

  • 90 % Say yards are well-kept

  • 81 % Say it's quiet

  • 80 % Say car is needed

  • 69 % Say it's dog friendly

  • 68 % Say they plan to stay for at least 5 years

  • 68 % Say parking is easy

  • 63 % Say there's holiday spirit

  • 55 % Say there's wildlife

  • 48 % Say people would walk alone at night

  • 46 % Say neighbors are friendly

  • 40 % Say it's walkable to restaurants

  • 33 % Say it's walkable to grocery stores

  • 28 % Say there are community events

  • 23 % Say kids play outside

  • 21 % Say streets are well-lit

  • 15 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Chris A.
    "Although Old Brookville is close to supermarkets, convenience stores, etc, it maintains a feeling of privacy. Since property zoning here is two acres, houses are spread out and there are plenty of wooded areas. Its a relatively quiet town and a great place to relax outside, go for a walk, or take the family on a bike ride. "
    21
    Flag
  • Demimax57
    "Private, safe, great schools, bucolic, vineyards and horse farms and golf courses - nothing more need be said."
    1
    Flag

LGBTQ Local Legal Protections

Jason P. Friedman, Daniel Gale Sothebys Intl Rlty, (516) 626-7600
Agent Phone: (516) 236-6226
Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. 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
53 Simonson Road, Glen Head, NY 11545 is a 10 bedroom, 15 bathroom, 20,000 sqft single-family home built in 2018. 53 Simonson Road is located in Old Brookville, Glen Head. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Oct 15, 2025. The MLS # for this home is MLS# 922932.