82 Oakside Rd, Smithtown, NY 11787
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Property image
OFF MARKET

82 Oakside Rd
Smithtown, NY 11787

  • 4 Beds
  • 1 Bath

$753,300

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,045/mo*
Refinance Your Home

$753,300

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,045/mo*
Refinance Your Home
4 Beds
1 Bath
(on 0.48 acres)

Home Value

Trulia Estimate
$753K
Since last month
Decreased$9K (-1.2%)
Since last year
Increased$42K (+5.9%)
Since last sale
Increased$370K (+94.8%)
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 +123% in the last 10 years
MonthEstimated value
2026
August 2026$760K
July 2026$769K
June 2026$758K
May 2026$742K
April 2026$734K
March 2026$743K
February 2026$726K
January 2026$715K
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
4 Burham Court, Smithtown, NY
0.15
Single-Family Home
$950,000
12/22/25
3
2
1,918
56 Rose Street, Smithtown, NY
0.49
Single-Family Home
$680,000
01/22/26
4
2
2,300
81 Oakside Road, Smithtown, NY
0.03
Single-Family Home
$450,000
11/06/25
4
2
1,100
17 Thide Court, Smithtown, NY
0.16
Single-Family Home
$1,175,000
04/09/26
5
2.5
3,495
335 Landing Avenue, Smithtown, NY
0.44
Single-Family Home
$850,000
03/24/26
4
2.5
2,500
24 Ursular Court, Smithtown, NY
0.53
Single-Family Home
$772,000
01/29/26
3
1.5
2,167
368 Landing Avenue, Smithtown, NY
0.32
Single-Family Home
$850,000
03/20/26
4
2.5
2,000
1 Valley Avenue, Smithtown, NY
0.03
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600
1 Clark Street, Smithtown, NY
0.33
Single-Family Home
$850,000
02/20/26
3
2
1,958
3 Jillit Drive, Smithtown, NY
0.44
Single-Family Home
$690,000
09/24/25
3
1.5
-

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
1 Valley Avenue, Smithtown, NY 11787
0.03
$1,150,000
3
2.5
2,600
Recently Sold
79 Oakside Road, Smithtown, NY 11787
0.03
$1,199,999
4
3
2,800
For Sale
83 Oakside Road, Smithtown, NY 11787
0.03
$876,000
4
3
2,103
Off Market
410 Landing Avenue, Smithtown, NY 11787
0.09
$819,300
4
2.5
2,433
Off Market
3 Tree Top Terrace, Smithtown, NY 11787
0.12
$1,207,100
4
2.5
3,000
Off Market
389 Landing Avenue, Smithtown, NY 11787
0.13
$981,400
4
2.5
2,982
Off Market
445 Landing Avenue, Smithtown, NY 11787
0.14
$854,400
3
1.5
2,500
Off Market
4 Burham Court, Smithtown, NY 11787
0.15
$950,000
3
2
1,918
Recently Sold
17 Thide Court, Smithtown, NY 11787
0.16
$1,175,000
5
2.5
3,495
Recently Sold
48 Oakside Road, Smithtown, NY 11787
0.16
$1,050,100
4
3
3,500
Off Market
158 Landing Meadow Road, Smithtown, NY 11787
0.19
$1,495,000
4
3.5
3,634
Recently Sold
41 Stony Hill Path, Smithtown, NY 11787
0.20
$1,982,500
4
4
4,884
Off Market

Local Information

  • Map ViewExplore the area around 82 Oakside Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1955
Lot Size
0.48 acres

About this House

Quiet Location/Easily Expandable/Parklike Setting/Gar Stor/Gar Ee/10 Yr Rf/Prop Gas Cook/Term K/Yng Kit/More!
82 Oakside Rd, Smithtown, NY 11787 is a 4 bedroom, 1 bathroom single-family home built in 1955. It last sold for $390,000 on Aug 5, 2008. It is currently off market. The Trulia Estimate is $753,300, with a rent estimate of $3,799/month.

Home Details for 82 Oakside Rd

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.48 acres

Price and Tax history

DateEventPrice
Aug 5, 2008
Source: N/A
Sold
$390,000
Dec 8, 2007
Source: Agent Provided
ListingRemoved
$423,000
Nov 24, 2007
Source: Agent Provided
PriceChange
$423,000
Price decreased by 4%
Nov 16, 2007
Source: Agent Provided
Listed For Sale
$439,000

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
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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

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Apartments for Rent

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Explore by feature - Pet Friendly

6 pet-friendly rentals in Smithtown, NY

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9 rentals with air conditioning in Smithtown, NY

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7 rentals with a washer/dryer in Smithtown, NY

Homes for sale near 82 Oakside Rd

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Off Market Homes Near 82 Oakside Rd

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Frequently asked questions about 82 Oakside Rd

  • What is 82 Oakside Rd estimated to be worth?
    Trulia's estimated value for 82 Oakside Rd in Smithtown, NY is $753,300.
  • What is the price history for 82 Oakside Rd?
    82 Oakside Rd in Smithtown, NY last sold for $390,000 in August 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.
  • How big is the lot at 82 Oakside Rd?
    The lot at 82 Oakside Rd in Smithtown, NY is about 0.48 acres (20,908 sq ft).