Water Views - Eco Friendly
146 Oakside Drive, Smithtown, NY
$ 2,999,000
Property Attributes
  • MLS#3509871
  • TypeSingle Family
  • CountySUFFOLK
  • CitySmithtown
  • NeighborhoodOakside Estate 1927
  • Zip11787
  • StyleColonial
  • Year Built1927
  • Taxes$ 40816
  • Price$ 2,999,000
  • Bedrooms6
  • Full Bathrooms5
  • Half Bathrooms1
  • Sqr Footage125888
  • Lot Size2.89 Acres
Data Source:
OneKey® MLS
Property Description

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".

Elementary School Middle School High School
Accompsett Elementary School Accompsett Middle School Smithtown High School-West
Price History
10/11/2023 Listed $2,999,000

General Features

Architectural Style Colonial
High School Smithtown High School-West
High School District Smithtown
Elementary School Accompsett Elementary School
Middle/Junior High School Accompsett Middle School
Middle/Junior School District Smithtown
Elementary School District Smithtown

Interior Features

Basement Bilco Door(s),Finished,Full,Walk-Out Access


  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Property vs Single Family Average in 11787

AVG $970K
AVG $15,868
AVG 259
Data Provided by Inside Real Estate®
Year Built
AVG 1969
AVG 29
Data Provided by Walkscore® not using MLS data

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