146 Oakside Drive, Smithtown, NY 11787
OFF MARKET

146 Oakside Drive
Smithtown, NY 11787

  • 6 Beds
  • 5.5 Baths
  • 7,200 sqft (on 2.89 acres)

$3,059,700

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $20,071/mo*
Refinance Your Home

$3,059,700

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $20,071/mo*
Refinance Your Home
6 Beds
5.5 Baths
7,200 sqft
(on 2.89 acres)

Local Information

  • Map ViewExplore the area around 146 Oakside Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1927
Lot Size
2.89 acres
Living Area
7,200 sqft
Price/Sqft
$425
Parking
Garage

About this House

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
146 Oakside Drive, Smithtown, NY 11787 is a 6 bedroom, 6 bathroom, 7,200 sqft single-family home built in 1927. It last sold for $2,800,000 on Jul 26, 2024 (7% below the $2,999,000 asking price). It is currently off market. The Trulia Estimate is $3,059,700, with a rent estimate of $7,125/month.

Home Details for 146 Oakside Drive

Interior Features

Interior Details
Basement: Walk-Out Access,Bilco Door(s),Finished,FullNumber of Rooms: 13Types of Rooms: Auxiliary Room
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 7200 Square Feet
Appliances & Utilities
Utilities: Cable Available, Trash Collection PublicAppliances: Dishwasher, Dryer, ENERGY STAR Qualified Appliances, Freezer, Microwave, Refrigerator, Washer, Oil Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: ENERGY STAR Qualified Equipment,Oil,OtherHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: ENERGY STAR Qualified Equipment
Fireplace & Spa
Number of Fireplaces: 5Has a FireplaceNo Spa
Gas & Electric
Electric: Generator
Windows, Doors, Floors & Walls
Window: Blinds, Double Pane Windows, DrapesFlooring: Hardwood
Levels, Entrance, & Accessibility
Floors: Hardwood
View
Has a ViewView: Panoramic
Security
Security: Fire Sprinkler System, Security System

Exterior Features

Exterior Home Features
Fencing: FencedExterior: Awning(s), Gas Grill, Mailbox, Private EntranceHas a Private Pool
Parking & Garage
No CarportGarageHas Open ParkingParking: Detached,Driveway,Garage Door Opener,Heated Garage,Private
Pool
Pool: In GroundPool
Frontage
WaterfrontWaterfront: River Front, Waterfront, Water AccessResponsible for Road Maintenance: Public Maintained RoadOn Waterfront
Water & Sewer
Sewer: Cesspool

Property Information

Year Built
Year Built: 1927
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Estate
Building
Construction Materials: Brick, Cedar, Shake SidingNot Attached Property
Property Information
Not Included in Sale: See RemarksParcel Number: 0800035000400047000

Price & Status

Price
List Price: $2,999,000
Status Change & Dates
Off Market Date: Thu Jun 13 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: Smithtown
School Information
Elementary School: Accompsett Elementary SchoolJr High / Middle School: Accompsett Middle SchoolHigh School: Smithtown High School-WestHigh School District: Smithtown

Building

Building Area
Building Area: 7200 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 2.89 Acres

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: L3547052Attic: FullAttribution Contact: 631-584-6600Showing Advance Notice: 24Showing Requirements: Call Listing Office

Additional Information

HOA Amenities: Park
Last check for updates: about 2 hours ago
Listed by Bonnie Glenn, (631) 921-1494
Daniel Gale Sothebys Intl Rlty, (631) 584-6600
Bought with: Bonnie Glenn, (631) 921-1494, Daniel Gale Sothebys Intl Rlty, (631) 584-6600
Source: OneKey® MLS as distributed by MLS GRID, MLS#L3547052

Price History for 146 Oakside Drive

DatePriceEventSource
07/26/2024$2,800,000Sold
OneKey® MLS as distributed by MLS GRID #L3547052
06/13/2024$2,999,000PendingOneKey® MLS as distributed by MLS GRID #3547052
04/25/2024$2,999,000Listed For SaleOneKey® MLS as distributed by MLS GRID #3547052
04/25/2024ListingRemovedOneKey® MLS as distributed by MLS GRID #3509871
09/20/2023$2,999,000PriceChange
OneKey® MLS as distributed by MLS GRID #3468663
06/23/2023$3,499,000PriceChange
OneKey® MLS as distributed by MLS GRID #3468663
04/03/2023$5,500,000Listed For SaleOneKey® MLS as distributed by MLS GRID #3468663
10/27/2000$949,000Sold
N/A
06/14/1996$590,000Sold
N/A

Market trends in Smithtown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
122
29MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$2,017,500
Home facts updated by county records

Comparable Sales for 146 Oakside Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
317 Old Mill Road, Saint James, NY
0.66
Single-Family Home
$2,799,000
09/24/25
4
4.5
4,250
428 River Road, Saint James, NY
0.17
Single-Family Home
$1,225,000
08/26/25
4
2.5
3,300
1 Summit Trail, Nissequogue, NY
0.50
Single-Family Home
$1,350,000
04/08/26
4
4.5
3,900
37 Bridle Path, Saint James, NY
0.60
Single-Family Home
$1,600,000
06/09/26
4
5
3,856
601 Moriches Road, Nissequogue, NY
1.06
Single-Family Home
$3,425,000
08/06/25
6
5
5,000
11 Wandering Way, Smithtown, NY
0.53
Single-Family Home
$1,500,000
08/07/25
5
5
3,667
142 Landing Meadow Road, Smithtown, NY
0.75
Single-Family Home
$1,750,000
02/09/26
6
5
4,479
158 Landing Meadow Road, Smithtown, NY
0.68
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
4 Nadia Court, Smithtown, NY
0.91
Single-Family Home
$1,900,000
03/04/26
5
4.5
4,677

Nearby homes

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Assigned Schools

These are the assigned schools for 146 Oakside Drive.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Smithtown

At least 232 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 89 % Say it's dog friendly

  • 88 % Say parking is easy

  • 88 % Say yards are well-kept

  • 85 % Say there's holiday spirit

  • 76 % Say it's quiet

  • 74 % Say people would walk alone at night

  • 67 % Say there's wildlife

  • 60 % Say they plan to stay for at least 5 years

  • 60 % Say kids play outside

  • 57 % Say neighbors are friendly

  • 55 % Say streets are well-lit

  • 41 % Say there are sidewalks

  • 39 % Say it's walkable to restaurants

  • 39 % Say there are community events

  • 37 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • nancy hark
    "I have to commute very far - it takes 1-1/2 to 2 hours. There is always traffic on the route. Working from home would be better for me."
    1
    Flag
  • Madeline Barbera
    "There’s a nice dog area in blydenburgh park but this is a horse neighborhood there are over 10,000 horses living here "
    0
    Flag
  • Jackedon24s
    "I’ve lived here my whole life, and everybody is for the most part, friendly and watch out for each other"
    0
    Flag
  • Elle Tee
    "There are lots of families in this area. It’s very neighborly. Only issue would be the occasional larceny out of cars left unlocked at night. "
    2
    Flag
  • Cgallaer
    "Short drive to from the Deer Park and Smithtown LIRR stations. Not too far from the Huntington or Babylon stations. "
    1
    Flag
  • Kimani J.
    "Most residents do not use public transportation. You will need your own vehicle in order to get around. "
    0
    Flag
  • Cgallaer
    "Great place to raise a family with lots of parks and other outdoor activities. It’s also close to other towns in Suffolk County, beaches, and has several LIRR train lines nearby. "
    4
    Flag
  • Cgallaer
    "I work in Manhattan so I take the LIRR to work. There are several train stations in the area and most have lots of parking and good service. "
    3
    Flag
  • Ejclassicdesign
    "Very nice area, safe and close to the beach. Nice school district. It is pricey to attain entrance into the housing market but the values tend to increase relatively fast over time. "
    6
    Flag
  • Robert B.
    "Very safe neighborhood, friendly residents, good schools, very good shopping areas. Has good parks and hiking areas. "
    4
    Flag
  • A &. J. G.
    "Love this neighborhood and having everything so close. I wish there was more Hispanic restaurants around since we love that type of food and have to go far to get it."
    5
    Flag
  • A &. J. G.
    "Quite neighborhood to take a stroll either alone, with the kids or family, or simply to walk the dog. The streets are clean and you feel safe."
    1
    Flag
  • rg9623
    "Smithtown is a great place to raise a family. Has great public schools and has great parks and recreation. Beach’s are close and well maintained "
    5
    Flag
  • Adrian M.
    "Nice houses, safe, close to shopping and entertainment, limited public transportation and expensive."
    0
    Flag
  • hanalu
    "I live here for two years for now, it’s a quiet and safe place, nice people around, and great schools. The tax is crazy high, but if you can handle the housing price and the tax, you are all good to go. Many restaurants nearby, although not very diversity, but still satisfy your basic needs. "
    1
    Flag
  • Laura N.
    "Dog loving community. Great family town. Great school district. Enjoyed 23 years here. Highly recommended."
    0
    Flag
  • Adrian M.
    "The commute itime depends on the time of the day. At noon, traffic can be heavy downtown. Smithtown bypass traffic is usually good."
    0
    Flag
  • Alidalang4
    "Great community and accessibility to shopping and stores . The neighborhoods and neighbor are nice and maintained. Quiet clean neighborhood. "
    1
    Flag
  • Danielle M.
    "Amazing place to raise kids. Great school Districts and opportunities for students to do extra curricular activities as well as sports. The neighborhood is really community oriented and children are often seen in the area playing. One of the biggest benefits is there are many great families and places for the kids to play. I think you will be impressed with the schools and the participation of the staff and teachers. "
    0
    Flag
  • Unspecified
    "Neighbors look out for one another. The homes are well kept. Good schools. Town services are good. Great bars and restaurants nearby."
    1
    Flag
  • Mpyles1982
    "Great schools, early morning drop off available for working parents. A lot of activities to keep your children busy. The only downside is the area lacks diversity."
    0
    Flag
  • Heavensentforeva
    "Great family location. There are also tons of dog people where I currently reside. We usually all walk our dogs together. It is a tight knit community. Everyone pretty much knows everyone on our block. "
    0
    Flag
  • Robertaglasser
    "The homes are very unique many different styles of homes from capes to ranches to split levels nice neighborhoods for raising family "
    1
    Flag
  • Mayivalenzuela
    "We have a very safe, clean and peaceful environment. Near public and private beaches and parks. Great School district. "
    1
    Flag
  • Marissa
    "I’ve lived here for 9 years and everything is centrally located. Wonderful for families especially young ones. "
    1
    Flag

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Off Market Homes Near 146 Oakside Drive

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Based on information submitted to the MLS GRID as of 2026-08-03 13:28:18 PDT 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. Some IDX listings have been excluded from this website. Click here for more information