15 Emmet Drive, Head Of Harbor (Head Of The Harbor), NY, 11790 | $4,999,999

Step into a world of timeless elegance and unparalleled prestige at The Mallows — the crown jewel of the North Shore and one of the most exclusive waterfront estates in Head of the Harbor Village. Originally commissioned by the illustrious Astor family and masterfully designed by acclaimed architect Charles Platt, this historic masterpiece sprawls across 4+ acres of exquisitely landscaped grounds with over 300 feet of private beachfront on Stony Brook Harbor, offering commanding west-facing sunset views that stretch across the Long Island Sound to Connecticut. This is more than a residence — it’s a statement. A sanctuary where Gilded Age grandeur meets refined modern luxury. From the moment you arrive, you're greeted by an enchanting cobblestone driveway and sweeping limestone patio that set the stage for a resort-style lifestyle. Outdoor amenities rival the finest private clubs—a heated saltwater pool, hot tub, private tennis court, waterfront gazebo, and serene gardens including a vegetable garden and charming chicken coop, all thoughtfully curated for entertaining and tranquility alike. Inside, the estate unfolds with 11 bedrooms, 5. 5 bathrooms, and 14 fireplaces, all artfully restored to preserve the home’s stately character while embracing contemporary sophistication. A 3-bedroom guest cottage offers additional space for hosting in luxury. Every inch of this estate speaks to craftsmanship and distinction: soaring 9. 5-foot ceilings, rich custom millwork, an elegant library, and a breathtaking glass conservatory off the primary suite, framed by hurricane-rated Marvin windows and doors. A four-season glass room seamlessly extends from the family room, offering panoramic harbor views year-round. Entertain in grandeur with a professional-grade chef’s kitchen equipped with Viking appliances, Sub-Zero refrigeration, and a gas range—adjacent to a formal dining room designed for unforgettable gatherings. Additional luxuries include a three-level elevator, a sprawling wine cellar, and every detail one would expect in a world-class estate. Perfectly positioned just moments from Stony Brook Yacht Club, Avalon Nature Preserve, Stony Brook Village, and LIRR access, this remarkable estate also falls within the award-winning Three Village School District. The Mallows is more than a home — it’s a generational legacy, an iconic waterfront retreat, and a once-in-a-lifetime opportunity to own the most coveted estate on the North Shore.

Features

  • Town: Head Of Harbor
  • Rooms: 24
  • Bedrooms: 11
  • Baths: 5 full / 2 half
  • Style: Estate
  • Year Built: 1906
  • Garage: 3-car
  • Heating: Oil, Forced Air
  • Cooling: Central Air
  • Basement: Full, Partially Finished, Walk-Out Access
  • Approx Sq. Feet: 9,411
  • Acreage: 4.1
  • Est. Taxes: $81,693
  • Lot Desc: Level, Historic District, Sprinklers In Front, Sprinklers In Rear
  • View: Water
  • Water Front: Yes
  • Elem. School: Minnesauke Elementary School
  • Middle School: Paul J Gelinas Junior High School
  • High School: Ward Melville Senior High School
  • School District: Three Village
  • Pool: In Ground
  • Appliances: Dishwasher, Dryer, Microwave, Oven, Refrigerator, Washer, Oil Water Heater
  • MLS#: 835698
  • Days on Market: 24 days
  • Website: https://www.raveis.com
    /eprop/835698/15emmetdrive_headofharbor_ny?source=qrflyer
Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to the buying decision should be independently verified.

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Scott PetersenVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 32556

339.224.0866

Scott.Petersen@raveis.com

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15 Emmet Drive, Head Of Harbor (Head Of The Harbor), NY, 11790

$4,999,999

Cheryl Bugley

Sales Associate

William Raveis Real Estate

Phone: 781.749.3007

Cheryl.Bugley@raveis.com

Scott Petersen

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 339.224.0866

Scott.Petersen@raveis.com

NMLS Mortgage Loan Originator ID 32556

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $3,999,999 $3,999,999 $3,999,999
Term 360 months 360 months 180 months
Initial Interest Rate** 5.375% 6.375% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.565% 6.475% 6.183%
Monthly Tax Payment $6,808 $6,808 $6,808
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $22,399 $24,955 $33,754
Total Monthly Payment $29,332 $31,888 $40,687

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.