5 Oakside Rd, Smithtown, NY 11787
OFF MARKET

5 Oakside Rd
Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 2,000 sqft (on 0.27 acres)

$745,000

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $4,999/mo*
Refinance Your Home

$745,000

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $4,999/mo*
Refinance Your Home
3 Beds
2 Baths
2,000 sqft
(on 0.27 acres)

Home Value

Trulia Estimate
$745K
Since last month
Increased$800 (+0.1%)
Since last year
Increased$41K (+5.8%)
Since last sale
Increased$348K (+87.4%)
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 +88% in the last 10 years
MonthEstimated value
2026
August 2026$746K
July 2026$745K
June 2026$748K
May 2026$745K
April 2026$729K
March 2026$728K
February 2026$715K
January 2026$717K
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
159 Saint Nicholas Avenue, Smithtown, NY
0.15
Single-Family Home
$720,000
02/04/26
4
2
1,366
37 Ashland Drive, Kings Park, NY
0.58
Single-Family Home
$720,000
05/06/26
3
1.5
1,800
29 Ashland Drive, Kings Park, NY
0.47
Single-Family Home
$780,000
12/22/25
3
2.5
1,700
6 Nowick Lane, Smithtown, NY
0.43
Single-Family Home
$780,000
02/20/26
4
3
2,488
32 Derby Place, Smithtown, NY
0.44
Single-Family Home
$785,000
06/23/26
3
2.5
1,609
16 Maywood Place, Kings Park, NY
0.43
Single-Family Home
$855,000
10/24/25
3
3
3,000
10 Grand Street, Smithtown, NY
0.19
Single-Family Home
$600,000
05/12/26
3
2.5
1,800
16 Dexter Lane, Kings Park, NY
0.69
Single-Family Home
$800,000
03/20/26
3
2
1,717
24 Ursular Court, Smithtown, NY
0.56
Single-Family Home
$772,000
01/29/26
3
1.5
2,167
18 Ursular Court, Smithtown, NY
0.54
Single-Family Home
$909,130
07/23/26
3
2
1,730

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
10 Riviera Drive, Smithtown, NY 11787
0.05
$870,300
4
2
3,000
Off Market
15 Oakside Road, Smithtown, NY 11787
0.05
$723,100
4
2
-
Off Market
6 Oakside Road, Smithtown, NY 11787
0.06
$885,100
4
2.5
-
Off Market
8 Lower Road, Smithtown, NY 11787
0.09
$824,000
3
2
1,700
Off Market
159 Saint Nicholas Avenue, Smithtown, NY 11787
0.15
$720,000
4
2
1,366
Recently Sold
125 Route 25A, Smithtown, NY 11787
0.13
$766,600
3
3
-
Off Market
1 Grand Street, Smithtown, NY 11787
0.15
$683,700
4
2
-
Off Market
2 Iris Lane, Smithtown, NY 11787
0.16
$716,100
3
2
1,370
Off Market
4 Grand Street, Smithtown, NY 11787
0.15
$717,100
3
2
-
Off Market
26 Riviera Drive, Smithtown, NY 11787
0.19
$822,900
3
1.5
-
Off Market
23 Riviera Drive, Smithtown, NY 11787
0.20
$699,999
3
2
1,370
For Sale
10 Grand Street, Smithtown, NY 11787
0.19
$600,000
3
2.5
1,800
Recently Sold

Local Information

  • Map ViewExplore the area around 5 Oakside Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1973
Lot Size
0.27 acres
Living Area
2,000 sqft
Price/Sqft
$373
Parking
Garage

About this House

Stunning Split In Smithtown Schools Everything New. Sidewalk Community. Lovely Grounds
5 Oakside Rd, Smithtown, NY 11787 is a 3 bedroom, 2 bathroom, 2,000 sqft single-family home built in 1973. It last sold for $398,000 on Jul 23, 2008. It is currently off market. The Trulia Estimate is $745,000, with a rent estimate of $3,942/month.

Home Details for 5 Oakside Rd

Interior Features

Interior Details
BasementAtticTypes of Rooms: Breakfast Nook, Dining Room, Family Room, Mud Room, PantryCeiling Fan
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: VinylGardenLawnPatioSprinkler System
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1973Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Split-level

Community

Units in Building: 1

Lot Information

Lot Area: 0.27 acres

Price and Tax history

DateEventPrice
Jul 23, 2008
Source: N/A
Sold
$398,000
May 29, 2008
Source: Agent Provided
PriceChange
$395,000
Price decreased by 5%
May 14, 2008
Source: Agent Provided
PriceChange
$414,000
Price decreased by 0%
Apr 21, 2008
Source: Agent Provided
PriceChange
$415,000
Price decreased by 2%
Apr 1, 2008
Source: Agent Provided
Listed For Sale
$424,500

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

Frequently asked questions about 5 Oakside Rd

  • What is 5 Oakside Rd estimated to be worth?
    Trulia's estimated value for 5 Oakside Rd in Smithtown, NY is $745,000.
  • What is the price history for 5 Oakside Rd?
    5 Oakside Rd in Smithtown, NY last sold for $398,000 in July 2008.
  • 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 5 Oakside Rd have air conditioning?
    Yes, 5 Oakside Rd in Smithtown, NY has air conditioning.
  • Does 5 Oakside Rd have laundry facilities?
    Yes, 5 Oakside Rd in Smithtown, NY has in-unit laundry.

Explore by feature - Pet Friendly

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Apartments for Rent

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Off Market Homes Near 5 Oakside Rd

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Homes for sale near 5 Oakside Rd

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