148 Oakside Drive, Smithtown, NY 11787
OFF MARKET

148 Oakside Drive
Smithtown, NY 11787

  • 4 Beds
  • 4 Baths

$1,622,800

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $10,444/mo*
Refinance Your Home

$1,622,800

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $10,444/mo*
Refinance Your Home
4 Beds
4 Baths
(on 2 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Breathtaking waterfront on the Nissequogue River! 2 Lush Private Acres with Beautiful Green Lawns to the Water's Edge. Canoe or Kayak from Your Own Backyard! There is unlimited potential to make this sprawling ranch your dream home! Spacious home features: hardwood floors, 4 bedrooms, 4 full bathroom, wood burning fireplace, possible mother/daughter with proper permits, large full basement with access to the 2 car garage. Back Patio Offers Stunning Waterviews of the wide part of the Nissequogue River & LI Sound in the distance. Make this your forever home!, Additional information: Interior Features:Guest Quarters,Separate Hotwater Heater:N
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from March 12, 2025

Home Highlights

Parking
Open Parking
Outdoor
Porch, Patio
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 148 Oakside Drive

Interior Features

Interior Details
Basement: Finished,FullNumber of Rooms: 9Types of Rooms: Auxiliary Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4
Appliances & Utilities
Utilities: Trash Collection PublicAppliances: Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Floors: Hardwood
View
Has a ViewView: Panoramic

Exterior Features

Exterior Home Features
Patio / Porch: Patio, PorchExterior: MailboxNo Private Pool
Parking & Garage
No CarportHas Open ParkingParking: Attached,Driveway,Private
Frontage
WaterfrontWaterfront: River Front, WaterfrontResponsible for Road Maintenance: Public Maintained RoadOn Waterfront
Water & Sewer
Sewer: Cesspool

Property Information

Year Built
Year Built: 1966
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Ranch
Building
Construction Materials: Cedar, Shake SidingNot Attached Property
Property Information
Parcel Number: 0800035000300022000

Price & Status

Price
List Price: $1,750,000
Status Change & Dates
Off Market Date: Thu Apr 04 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

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 2 Acres

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: L3489306Attic: FullAttribution Contact: 631-584-6600Showing Advance Notice: 24Showing Requirements: Call Listing Office

Additional Information

HOA Amenities: Park
Last check for updates: about 5 hours ago
Listed by Bonnie Glenn, (631) 921-1494
Daniel Gale Sothebys Intl Rlty, (631) 584-6600
Bought with: Deborah Lettieri, (631) 827-3056, Signature Premier Properties, (631) 360-2800
Source: OneKey® MLS as distributed by MLS GRID, MLS#L3489306

Price History for 148 Oakside Drive

DatePriceEventSource
07/26/2024$1,545,000Sold
OneKey® MLS as distributed by MLS GRID #L3489306
04/04/2024$1,750,000PendingOneKey® MLS as distributed by MLS GRID #3489306
09/20/2023$1,750,000PriceChange
OneKey® MLS as distributed by MLS GRID #3489306
07/06/2023$1,999,000Listed For SaleOneKey® MLS as distributed by MLS GRID #3489306
06/04/2014$950,000Sold
N/A
03/23/2014$1,100,000PriceChange
Agent Provided
09/30/2013$1,250,500PriceChange
N/A
05/15/2013$1,250,000PriceChange
Agent Provided
04/16/2013$1,299,999PriceChange
Agent Provided
01/07/2013$1,500,000PriceChange
Agent Provided
12/01/2012$1,900,000PriceChange
Agent Provided
08/28/2012$2,100,000PriceChange
N/A
07/31/2012$2,500,000Listed For SaleN/A
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Property Tax and Assessment

Year2025
Tax
Assessment$958,750
Home facts updated by county records

Comparable Sales for 148 Oakside Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
44 Quail Path, Saint James, NY
0.38
Single-Family Home
$1,325,000
07/25/25
5
4
3,823
435 River Road, Saint James, NY
0.32
Single-Family Home
$1,150,000
07/16/25
5
4
4,824
428 River Road, Saint James, NY
0.20
Single-Family Home
$1,225,000
08/26/25
4
2.5
3,300
1 Summit Trail, Nissequogue, NY
0.49
Single-Family Home
$1,350,000
01/21/26
4
4.5
3,900
158 Landing Meadow Road, Smithtown, NY
0.67
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
11 Wandering Way, Smithtown, NY
0.54
Single-Family Home
$1,500,000
08/07/25
5
5
3,667
317 Old Mill Road, Saint James, NY
0.70
Single-Family Home
$2,799,000
09/24/25
4
4.5
4,250
1 Tracklot Road, Saint James, NY
1.04
Single-Family Home
$1,450,000
04/16/26
4
3.5
2,760
11 Woodcutters Path, Saint James, NY
0.82
Single-Family Home
$915,000
05/30/25
4
2.5
2,500

Nearby homes

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Assigned Schools

These are the assigned schools for 148 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 231 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. "
    1
    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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Homes for sale near 148 Oakside Drive

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Off Market Homes Near 148 Oakside Drive

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Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. 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

Homes for rent near 148 Oakside Drive

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148 Oakside Drive, Smithtown, NY 11787 is a 4 bedroom, 4 bathroom single-family home built in 1966. This property is not currently available for sale. 148 Oakside Drive was last sold on Jul 26, 2024 for $1,545,000 (12% lower than the asking price of $1,750,000). The current Trulia Estimate for 148 Oakside Drive is $1,622,800.