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For sale
  • $12,800,000

    53 Simonson Road, Old Brookville, NY 11545

    10beds
    20,000sqft
    Single Family Residence, Residential
    Built in 2018
    6.28 Acres Lot
    $-- Zestimate®
    $640/sqft
    $-- HOA

    What's special

    Two-story barnFloor-to-ceiling wine display wallPrivate gatesPrivate loungePrivate sitting areaPoolside cabanaSpacious home office
    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.
    168 days
    |
    5,318
    |
    198
    |

    Zillow last checked: 7 hours ago

    Listing updated: October 23, 2025 at 10:09am

    Listing by:

    Daniel Gale Sothebys Intl Rlty 516-466-4036,

    Jason P. Friedman 516-236-6226,

    Sarah R. Friedman 516-466-4036,

    Daniel Gale Sothebys Intl Rlty

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 922932MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 10
      • Bathrooms: 15
      • Full bathrooms: 13
      • 1/2 bathrooms: 2
      Other
      • Description: WALK OUT - Foyer w/ Wine Rack, Office, Bedroom, 2 Full Baths, SittingRm, Golf Sim. Room, Gym and Sauna
      • Level: Basement
      Other
      • Description: Foyer, GreatRm with Wet Bar, Office, 2 PowderRms, Bed with Full Bath, Formal DiningRm, EIK, Butler's Pantry, Den & MudRm
      • Level: First
      Other
      • Description: Primary Bedroom Suite with Attached Bath, 4 Additional Bedrooms with 4 Full Bathrooms, Laundry room
      • Level: Second
      Heating
      • Radiant
      Cooling
      • Central Air
      Appliances
      • Included: Convection Oven, Cooktop, Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Cooktop, Gas Oven, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
      • Laundry: Washer/Dryer Hookup, Multiple Locations
      Features
      • First Floor Bedroom, First Floor Full Bath, Built-in Features, Cathedral Ceiling(s), Central Vacuum, Chefs Kitchen, Crown Molding, Double Vanity, Eat-in Kitchen, Entertainment Cabinets, Entrance Foyer, Formal Dining, 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
      • Flooring: Hardwood, Tile
      • Windows: Floor to Ceiling Windows, Oversized Windows, Wall of Windows
      • Basement: Finished,Full,Walk-Out Access
      • Attic: See Remarks
      • Number of fireplaces: 6
      • Fireplace features: Bedroom, Family Room, Living Room
      Interior area
      • Total structure area: 20,000
      • Total interior livable area: 20,000 sqft

      Property

      Parking
      • Total spaces: 5
      • Parking features: Attached, Heated Garage, Oversized
      • Garage spaces: 4
      • Carport spaces: 1
      Features
      • Levels: Two
      • Patio & porch: Covered, Patio, Porch, Terrace
      • Exterior features: Rain Gutters, Speakers
      • Has private pool: Yes
      • Pool features: In Ground, Outdoor Pool, Pool/Spa Combo
      • Has spa: Yes
      • Fencing: Fenced
      • Has view: Yes
      • View description: Open
      Lot
      • Size: 6.28 Acres
      • Features: Back Yard, Front Yard, Landscaped, Level
      Details
      • Additional structures: Barn(s), Guest House, Pool House
      • Parcel number: 241520J0709480
      • Special conditions: None
      • Other equipment: Generator, Irrigation Equipment, Pool Equip/Cover
      • Horses can be raised: Yes

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Estate
      • Property subtype: Single Family Residence, Residential
      Materials
      • Stone, Stucco
      Condition
      • Actual
      • Year built: 2018

      Utilities & green energy

      • Sewer: Cesspool
      • Water: Public
      • Utilities for property: Electricity Connected, Natural Gas Connected, Trash Collection Public, Water Connected

      Community & HOA

      Community
      • Security: Building Security, Security Gate
      HOA
      • Has HOA: No
      Location
      • Region: Glen Head

      Financial & listing details

      • Price per square foot: $640/sqft
      • Tax assessed value: $6,990,000
      • Annual tax amount: $128,023
      • Date on market: 10/15/2025
      • Cumulative days on market: 168 days
      • Listing agreement: Exclusive Right To Sell
      • Exclusions: Contact Listing Agent(s)
      • Electric utility on property: Yes

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        Price history
        DateEventPrice
        10/15/2025Listed for sale$12,800,000+312.9%$640/sqft
        Source: OneKey® MLS as distributed by MLS GRID #922932 Report a problem
        1/11/2016Sold$3,100,000-8.7%$155/sqft
        Source: OneKey® MLS as distributed by MLS GRID #L2791571 Report a problem
        11/3/2015Pending sale$3,395,000$170/sqft
        Source: Douglas Elliman Report a problem
        8/26/2015Listed for sale$3,395,000-18.2%$170/sqft
        Source: Douglas Elliman Real Estate #2791573 Report a problem
        9/1/2012Listing removed$4,150,000$208/sqft
        Source: Prudential Douglas Elliman Real Estate #2436362 Report a problem
        10/5/2011Listed for sale$4,150,000$208/sqft
        Source: Prudential Douglas Elliman Real Estate #2436362 Report a problem
        8/15/2011Listing removed$4,150,000$208/sqft
        Source: Prudential Douglas Elliman Real Estate #2378629 Report a problem
        3/25/2011Listed for sale$4,150,000-24.5%$208/sqft
        Source: Prudential Douglas Elliman Real Estate #2320040 Report a problem
        5/11/2009Listing removed$5,495,000$275/sqft
        Source: Prudential Real Estate #2129231 Report a problem
        11/1/2008Listed for sale$5,495,000+322.7%$275/sqft
        Source: Prudential Real Estate #2129231 Report a problem
        2/14/2005Sold$1,300,000$65/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2024-- $5,869 -3.5%
        2023-- $6,080 -0.5%
        2022-- $6,111
        2021$36,276 -0.3%--
        2020$36,373 $3,436
        2019-- $3,436 -23.3%
        2018$42,146 +4.6%$4,477
        2017$40,285 +4.3%$4,477 -5.6%
        2016$38,643 +415.4%$4,741 -5.3%
        2015$7,497 -7.8%$5,004 -13.7%
        2013$8,134 -2.9%$5,800 -9%
        2012$8,375 -75.2%$6,376 -3%
        2011$33,826 +3.8%$6,573 -4.7%
        2010$32,594 $6,895 -7.7%
        2009-- $7,471 -1.6%
        2008-- $7,595 -43.8%
        2005-- $13,522 -41%
        2004-- $22,920
        2003-- $22,920 -33.6%
        2002-- $34,510 -5.1%
        2001-- $36,370
        2000-- $36,370

        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: Old Brookville

        Getting around

        16 / 100
        Car-Dependent
        21 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Glen Head Elementary School
        • Middle: North Shore Middle School
        • High: North Shore Senior High School

        Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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