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575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2025 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY.LISTING DATA REFRESHED ON MAY 15 2025 AT 3:10 PM.

DOUGLAS ELLIMAN IS A LICENSED REAL ESTATE BROKER IN CALIFORNIA WITH LICENSE # 01947727, COLORADO WITH LICENSE # EC100053892, CONNECTICUT WITH LICENSE # REB.0314827, THE DISTRICT OF COLUMBIA WITH LICENSE # REO40000160, FLORIDA WITH LICENSE # CQ1020232, MARYLAND WITH LICENSE # 645270, MASSACHUSETTS WITH LICENSE # 422764, NEVADA WITH LICENSE # 1454643, NEW JERSEY WITH LICENSE # 0572105, NEW YORK WITH LICENSE # 10991211812, TEXAS WITH LICENSE # 9008706, AND VIRGINIA WITH LICENSE # 0226035659.

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146 Oakside Dr

smithtown, NY 11787

$2,999,000

  • 6 BR
    5 BA, 1 HALF BA
    APPROX. 7,200 SF
  • sold

INTERESTED? LET'S CONNECT

Welcome to "The Oakside", a waterfront estate on the Nissequogue River which offers unobstructed waterviews from every room! This breathtaking "Georgian Colonial" style country manor estate is perfect for those who appreciate a blend of high end custom modern amenities and the understated elegance & feeling of a bygone era. The property includes the spectacular main manor home, a separate 1 bedroom cottage, a detached garage with 3 heated bays, and a heated 20x60' saltwater pool with cabana which all have been meticulously maintained with the utmost attention to detail. This family compound replicates all of one's desires for a peaceful, joyful, and calming feeling of being "away from it all". The current owners have totally renovated this estate to the highest standards of living today, yet still retaining the "wonderful feeling of days gone by" from the Roaring 1920's, where entertainment along the waterfront and many social events were often enjoyed. The magnificent main home consists of three floors of living space which features: 6 Bedrooms, 5.5 Baths, 5 fireplaces, a gorgeous library, wonderful music room, den, banquet size formal dining room, radiant heated floors, all updated windows, custom mill work and fine detailing throughout. The stunning expansive conservatory room with brick fireplace with grill, high ceilings and walls of French doors overlooking the river and lush yard is perfect for hosting large gatherings. There is a professional kitchen with butler's pantry & breakfast room, all with the highest end commercial grade stainless steel appliances and fixtures. The spacious 3 room primary bedroom suite features an updated marble ensuite with fireplace & 2 custom dressing areas. A beautiful "widow's walk" offers spectacular views of the River & lawns. The finished basement features a 2,000 bottle climate-controlled wine cellar, a recreation room, large storage and utility areas. The exterior of all the home has been completely updated with copper roofing, cedar shake siding & a full house generator. An inground heated saltwater pool with full cabana and brick patios makes this the perfect setting to entertain guests or enjoy the quietude. There is a long sweeping driveway to the home with bluestone walkways and special red chip & oil gravel. The grounds are superbly maintained with rolling verdant green lawns to the water, many fine specimen trees and plantings, rose bushes & also includes the largest registered Black Walnut Tree in NYS. There is a new dock and a floating dock, a covered grill house, a school bus stop shed, fresh water springs, a smokehouse and vegetable gardens, as well as inground sprinklers. This is truly a "one a of kind" property for discerning buyers seeking superior quality and tranquility. "The Oakside" is a must-see. Enjoy the feeling of being "away from it all"., Additional information: Appearance:Diamond,Interior Features:Guest Quarters,Marble Bath,Separate Hotwater Heater:Y

Details

7,200 Sq Ft

2.89 Private Acres Exterior Space

Single Family Home

$40,816 Annual Tax

Built in 1927

MLS/Listing ID L3547052

1 Units

Amenities & Features

ADA Inside

ENERGY STAR Qualified Washer

ENERGY STAR Qualified Water Heater

Style - Estate

Association - Roof Deck

Heating - ENERGY STAR Qualified Equipment

Guest Quarters

Marble Bath

Parking - 3 Car Detached

Partial

Heating - Other

Storage

Smart Thermostat

Lot - Near Public Transit

Lot - Level

Parking - Heated Garage

Parking - Detached

Panoramic View

Waterfront

Water Access

River Access

Double Pane Windows

Wine Cooler

Water Purifier Owned

Microwave

Freezer

Community - Park

Construction - Shake Siding

Construction - Cedar

Construction - Brick

Private Entrance

ONEKEY

Source of Data: ONEKEY MLS

Interested in 146 Oakside Dr?