146 Oakside DriveSmithtown, NY 11787Sale Price: $2,800,000

  • Sale Price: $2,800,000
  • 658 Days Since Sale
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Federal 30-year interest rate: 6.37% last updated on May 7, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $2,800,000Sale Price
  • 6Bedrooms
  • 6Bathrooms
  • 7,200Square Feet

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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

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Listed by Bonnie Glenn of Daniel Gale Sothebys Intl Rlty (631-584-6600)

Listing Sold by Daniel Gale Sothebys Intl Rlty

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of May 15, 2026 11:23 AM EDT. 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. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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