53 Simonson Road, Glen Head, NY 11545
Property image
Property image
PENDING
6.28 ACRES

$12,800,000

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

53 Simonson Road, Glen Head, NY 11545

Old Brookville
Est. Mortgage $81,147/mo*
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Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Pool
Price/Sqft
$640
Listed
180+ days ago
Climate Control
Radiant, Natural Gas & Central Air

Local Information

  • Map ViewExplore the area around 53 Simonson Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: 41 minutes 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: 271Days 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
Status Change & Dates
Off Market Date: Mon Jul 13 2026

Active Status

MLS Status: Pending

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

Around this home

Neighborhood Overview

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

What Locals Say about Old Brookville

At least 17 Trulia users voted on each feature.

  • 90 % Say yards are well-kept

  • 81 % Say car is needed

  • 77 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 69 % Say it's dog friendly

  • 68 % Say parking is easy

  • 59 % Say there's holiday spirit

  • 57 % Say there's wildlife

  • 52 % Say people would walk alone at night

  • 47 % Say neighbors are friendly

  • 38 % Say it's walkable to restaurants

  • 33 % Say it's walkable to grocery stores

  • 27 % 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

Market trends in Glen Head

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50
4MoM

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
80 Valentines Lane, Glen Head, NY
0.28
Single-Family Home
$2,500,000
02/26/26
7
8.5
8,162
4 Valentines Farm Court, Old Brookville, NY
0.30
Single-Family Home
$7,500,000
07/16/26
7
8.5
10,000
11 Dupont Court, Greenvale, NY
0.73
Single-Family Home
$8,800,000
08/19/26
7
10
14,000
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
35 Hoaglands Lane, Old Brookville, NY
0.80
Single-Family Home
$2,750,000
04/28/26
6
6.5
4,787
10 Eastview Lane, Glen Head, NY
0.35
Single-Family Home
$1,900,000
01/15/26
4
4
3,628
8 Norgate Road, Glen Head, NY
0.91
Single-Family Home
$3,200,000
02/25/26
6
5.5
6,018

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
12 Woodfield Lane, Glen Head, NY 11545
0.16
$3,874,800
8
7.5
-
Off Market
1 Woodhollow Lane, Glen Head, NY 11545
0.12
$2,319,800
5
3.5
5,000
Off Market
3 Woodhollow Lane, Glen Head, NY 11545
0.18
$6,751,500
7
8
10,100
Off Market
86 Valentines Lane, Glen Head, NY 11545
0.26
$3,693,000
7
6.5
-
Off Market
80 Valentines Lane, Glen Head, NY 11545
0.28
$2,500,000
7
8.5
8,162
Recently Sold
11 Woodfield Lane, Old Brookville, NY 11545
0.34
$3,153,500
6
4.5
5,116
Off Market
4 Valentines Farm Court, Old Brookville, NY 11545
0.30
$7,500,000
7
8.5
10,000
Recently Sold
9 Mary Lane, Roslyn Harbor, NY 11576
0.36
$1,665,100
4
3
-
Off Market
1 Michaels Lane, Glen Head, NY 11545
0.31
$2,190,900
5
3
3,265
Off Market
16 Mary Lane, Greenvale, NY 11548
0.37
$1,360,000
3
2
2,060
Recently Sold
12 Eastview Lane, Glen Head, NY 11545
0.32
$5,311,400
7
8.5
6,009
Off Market
10 Eastview Lane, Glen Head, NY 11545
0.35
$1,900,000
4
4
3,628
Recently Sold

Price and Tax history

DateEventPrice
Jul 13, 2026
Source: OneKey® MLS as distributed by MLS GRID #922932
Pending
$12,800,000
Oct 15, 2025
Source: OneKey® MLS as distributed by MLS GRID #922932
Listed For Sale
$12,800,000
Jan 11, 2016
Source: OneKey® MLS as distributed by MLS GRID #L2791571
Sold
$3,100,000
Nov 3, 2015
Source: Agent Provided
Pending
$3,395,000
Aug 26, 2015
Source: Agent Provided
Listed For Sale
$3,395,000

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 2026-08-31 14:18:24 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

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Frequently asked questions about 53 Simonson Road

  • What is the estimated monthly payment for 53 Simonson Road?
    Based on a $12,800,000 list price with 20% down at today's rates, the estimated monthly payment for 53 Simonson Road in Glen Head, NY is approximately $82,453 (about $66,165 principal & interest, $16,213 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about the Old Brookville neighborhood?
    Residents describe the Old Brookville neighborhood in Glen Head, NY as well-kept, quiet, and established. Most residents say you need a car. See homes for sale in Old Brookville, Glen Head.
  • What are the closest schools to 53 Simonson Road?
    The closest schools to 53 Simonson Road in Glen Head, NY are Glen Head Elementary School (Pre-K, rated 9/10), North Shore Middle School (rated 7/10), North Shore Senior High School (rated 10/10).
  • Does 53 Simonson Road have air conditioning?
    Yes, 53 Simonson Road in Glen Head, NY has air conditioning.
  • Does 53 Simonson Road have a pool?
    Yes, 53 Simonson Road in Glen Head, NY has a pool.
  • Does 53 Simonson Road have laundry facilities?
    Yes, 53 Simonson Road in Glen Head, NY has in-unit laundry.
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.