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.
Single-familyProperty Type
2018Year Built
6.28 acresLot Size
$640Price/Sq.Ft.
4 garage spacesParking
Listing by Jason Friedman• Daniel Gale Sothebys Intl Rlty
Listing by Sarah Friedman• Daniel Gale Sothebys Intl Rlty
Oyster Bay, located between Cold Spring Harbor and Bayville, is a waterfront and historic Glen Cove neighborhood with a working harbor and leafy, estate-era streetscapes. The neighborhood’s character concentrates around Audrey Avenue at Spring Street, where coffee counters, independent boutiques, and old-school storefronts set a walkable, small-town cadence. The Oyster Bay Railroad Museum, the Oyster Bay Historical Society’s Earle-Wightman House, and the Planting Fields Arboretum State Historic Park act as cultural anchors. Shingle-style homes and classic Colonials mix with village-era cottages near the shore. Waterfront paths and marinas frame daily routines with salt-air views. Beaches and preserves shape the landscape from cove to bluff.
Provided by Walk Score and Local Logic
Market insights
53 Simonson Rd · $12,800,000
DAYS ON MARKET
271 days
The average home goes pending in 30 days.
SALE-TO-LIST
101.3%
Most homes are selling 1% above list price.
LIST PRICE
$12,800,000
Median sale price in this area is $858,225. (93% lower than this home)
PRICE DROP
0 price drops
17% of homes in this area have had a price drop in the past month.
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
First-floor bedroom and full bath
Built-in features
Cathedral ceilings
Central vacuum
Chef's kitchen
Crown molding
Double vanities
Eat-in kitchen
Elevator
Entertainment cabinets
Entrance foyer
Formal dining room
High ceilings
His and hers closets
Kitchen island
Marble counters
Natural woodwork
Open floorplan
Open kitchen
Pantry
Primary bathroom
Sauna
Soaking tub
Sound system / speakers
Stone counters
Storage
Walk-in closets
Washer/dryer hookup
Wet bar
Floor-to-ceiling, oversized, and wall-of-windows
Bedrooms
Multiple bedrooms (25 total rooms; includes first-floor bedroom)
Bathrooms
13 full bathrooms
2 half bathrooms
Kitchen
Convection oven
Cooktop (including gas cooktop)
Gas range
Gas oven
Range
Oven
Microwave
Dishwasher
Refrigerator
Freezer
Stainless steel appliances
Wine refrigerator
Laundry & utility
Washer
Dryer
Washer and dryer present (multiple laundry locations)
Washer/dryer hookup
Flooring
Hardwood
Tile
Heating & cooling
Central air conditioning
Natural gas heating
Radiant heating
Exterior features
Balcony
Covered patio, porch, and terrace
Rain gutters
Exterior speakers
Fenced yard
Landscaped front and back yard
Level lot
Barn(s)
Guest house
Pool house
Private in-ground outdoor pool with spa (pool/spa combo)
Home design
Single-family residence
Two levels
Finished full walk-out basement
Actual property condition
Parking
Attached heated oversized garage
4 garage spaces
1-car carport
Security
Building security
Security gate
Construction
Stone and stucco construction
Measured living area
Utilities
Cesspool sewer
Electricity connected
Natural gas connected
Public trash collection
Water connected
Generator
Irrigation equipment
Pool equipment/cover
Electricity and solar
View estimated energy costs and solar savings for this home
Prime 6.28 Acres Includes Main House, Separate 3 Bedroom Guest Cottage, Inground Heated Pool, Har-Tru Tennis Court, 3-Car Garage With Artist's Studio, Paddocks & Mint 8-Stall Barn With Caretaker's Apartment (Can Be Multi-Car Garage Too). Opportunity To Own A French Country Home Only 22 Miles To Nyc. Superb Location Beautifully Landscaped. Possible Subdivision Into 2 Lots., Additional information: Appearance:Mint,ExterioFeatures:Tennis,Separate Hotwater Heater:Yes
OneKey® MLS as Distributed by MLS Grid #L2791573
Jan 11, 2016
Sold
$3,100,000
$155/sq ft
Aug 25, 2015
Listed
$3,395,000
$170/sq ft
Special 6.28 Acres With Possible Subdivision Into Two 3 Acre Parcels. Existing Structures On Site. Or Use As Compound With Main House, Guest Cottage, Pool & Tennis. Ideal Location In The Village Of Old Brookville Just 22 Miles To Nyc. Idyllic Landscaping On Level Property. Also Includes Horse Paddocks & 8-Stall Barn Or Space For Car Collection. Picturesque Private Setting., Additional information: Minimum Plot Size:3 Acres
Year
Property tax
Land + Additions
Assessment*
2025
$104,946 (+0.3%)
$1,374 + $5,616
$6,990
2024
$104,594 (−9.3%)
$1,374 + $5,616
$6,990
2023
$115,375 (−1.3%)
$1,374 + $5,522
$6,896
2022
$116,909 (−16.2%)
$1,374 + $5,522
$6,896
2021
$139,438 (+286.0%)
$1,374 + $5,522
$6,896
2020
$36,128 (−0.7%)
$1,374 + $5,522
$6,896
2019
$36,373 (+4.8%)
$1,536 + $88
$1,624
2018
$34,695 (−17.7%)
$3,435 + $1
$3,436
2017
$42,145 (+4.6%)
$3,435 + $1,042
$4,477
2016
$40,285 (+1.1%)
$3,435 + $1,042
$4,477
2015
$39,832 (−8.8%)
$3,435 + $2,941
$6,376
2014
$43,684 (−3.5%)
$3,435 + $2,941
$6,376
2013
$45,249 (+9.1%)
$3,435 + $2,941
$6,376
2012
$41,491 (+4.0%)
$3,435 + $3,138
$6,573
2011
$39,901 (+6.5%)
$3,435 + $3,138
$6,573
2010
$37,458 (+0.5%)
$3,435 + $3,460
$6,895
2009
$37,285
$3,435 + $4,036
$7,471
Public record
Beds
—
Baths
7
Stories
2
Lot width
—
Lot depth
—
Lot size
6.28 Acres
Year renovated
—
Finished Sq. Ft.
10,546
Unfinished Sq. Ft.
—
Total Sq. Ft.
10,546
Year built
2018
Style
Single Family Residential
County
Nassau County
APN
20 J0709480
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 97° expected this year, 16 days in 30 years
6/10 Wind Factor
59% chance of strong winds in next 30 years
4/10 Air Factor
4 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Old Brookville, NY • 11545
Average low and high temperatures (°F)
35
23
38
24
53
36
62
44
69
53
81
63
85
69
80
63
76
60
66
50
55
40
41
28
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
76/ 100
Good sunlight
Sunscore
This home receives average direct sun exposure in Old Brookville. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.3 hrs
4.9 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 53 Simonson Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $2,099,000 and $7,500,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $2.1M to $7.5M.