148 Oakside Drive, Smithtown, NY 11787
OFF MARKET

$1,627,900

Trulia Estimate
  • 4 Beds
  • 4 Baths

148 Oakside Drive, Smithtown, NY 11787

Est. Refi. Payment $10,834/mo*
Refinance Your Home
Currently Off Market - Sold Jul 26, 2024 for $1,545,000

Home Value

Trulia Estimate
$1.63M
Since last month
Increased$16K (+1%)
Since last year
Decreased$24K (-1.4%)
Since last sale
Increased$86K (+5.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +133% in the last 10 years
MonthEstimated value
2026
August 2026$1.63M
July 2026$1.62M
June 2026$1.63M
May 2026$1.62M
April 2026$1.59M
March 2026$1.64M
February 2026$1.65M
January 2026$1.68M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1 Summit Trail, Nissequogue, NY
0.49
Single-Family Home
$1,350,000
04/08/26
4
4.5
3,900
37 Bridle Path, Saint James, NY
0.62
Single-Family Home
$1,600,000
06/09/26
4
5
3,856
158 Landing Meadow Road, Smithtown, NY
0.67
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
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
144 Landing Meadow Road, Smithtown, NY
0.72
Single-Family Home
$1,225,000
08/11/26
5
4.5
3,937
109 Oakside Drive, Smithtown, NY
0.49
Single-Family Home
$1,300,000
03/31/26
4
3.5
2,400
9 Holly Lane, Saint James, NY
1.14
Single-Family Home
$1,450,000
11/13/25
4
3.5
2,857
1 Valley Avenue, Smithtown, NY
0.84
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600
142 Landing Meadow Road, Smithtown, NY
0.76
Single-Family Home
$1,750,000
04/23/26
6
5
4,479

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
146 Oakside Drive, Smithtown, NY 11787
0.05
$3,084,300
6
5.5
7,200
Off Market
428 River Road, Saint James, NY 11780
0.20
$1,358,000
4
2.5
3,300
Off Market
Address Not Disclosed, Smithtown, NY 11787
0.24
$1,499,000
4
3.5
3,000
For Sale
432 River Road, Saint James, NY 11780
0.25
$1,246,600
2
3
-
Off Market
100 Riverview Terrace, Smithtown, NY 11787
0.31
$2,358,200
4
4
3,700
Off Market
435 River Road, Saint James, NY 11780
0.32
$1,216,700
5
4
4,824
Off Market
421 River Road, Saint James, NY 11780
0.32
$1,406,600
5
2.5
3,821
Off Market
41 Quail Path, Saint James, NY 11780
0.32
$1,091,800
5
3.5
-
Off Market
2 Riverview Terrace, Smithtown, NY 11787
0.33
$2,599,000
6
6.5
3,946
For Sale
44 Quail Path, Saint James, NY 11780
0.38
$1,400,200
5
4
3,823
Off Market
5 Laurel Hill Path, Saint James, NY 11780
0.39
$1,356,000
5
4
-
Off Market

Local Information

  • Map ViewExplore the area around 148 Oakside Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1966
Lot Size
2 acres
Parking
Open Parking

About this House

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
148 Oakside Drive, Smithtown, NY 11787 is a 4 bedroom, 4 bathroom single-family home built in 1966. It last sold for $1,545,000 on Jul 26, 2024 (12% below the $1,750,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,627,900, with a rent estimate of $5,093/month.
Last check for updates: about 11 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

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

Price and Tax history

DateEventPrice
Jul 26, 2024
Source: OneKey® MLS as distributed by MLS GRID #L3489306
Sold
$1,545,000
Apr 4, 2024
Source: OneKey® MLS as distributed by MLS GRID #3489306
Pending
$1,750,000
Sep 20, 2023
Source: OneKey® MLS as distributed by MLS GRID #3489306
PriceChange
$1,750,000
Price decreased by 12%
Jul 6, 2023
Source: OneKey® MLS as distributed by MLS GRID #3489306
Listed For Sale
$1,999,000
Jun 4, 2014
Source: N/A
Sold
$950,000

Market trends in Smithtown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$808K
$4.33KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
102
20MoM

Around this home

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

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-08-31 03:58:04 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

Frequently asked questions about 148 Oakside Drive

  • What is 148 Oakside Drive estimated to be worth?
    Trulia's estimated value for 148 Oakside Drive in Smithtown, NY is $1,627,900.
  • What is the price history for 148 Oakside Drive?
    148 Oakside Drive in Smithtown, NY last sold for $1,545,000 in July 2024.
  • Is Smithtown a buyer's or seller's market?
    Smithtown is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Smithtown?
    The median sale price in Smithtown is $808K. That is up $4.33K from the prior month.
  • Does 148 Oakside Drive have laundry facilities?
    Yes, 148 Oakside Drive in Smithtown, NY has in-unit laundry.
  • How big is the lot at 148 Oakside Drive?
    The lot at 148 Oakside Drive in Smithtown, NY is about 2 acres.

Explore by feature - Pet Friendly

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Off Market Homes Near 148 Oakside Drive

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