166 Oakside Dr, Smithtown, NY 11787
Property image
Property image
OFF MARKET

$1,269,700

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 3,500 sqft (on 2 acres)

166 Oakside Dr, Smithtown, NY 11787

Est. Refi. Payment $8,386/mo*
Refinance Your Home
Currently Off Market - Sold Apr 11, 2018 for $650,000

Home Value

Trulia Estimate
$1.27M
Since last month
Decreased$8K (-0.6%)
Since last year
Increased$59K (+4.9%)
Since last sale
Increased$620K (+95.3%)
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 +65% in the last 10 years
MonthEstimated value
2026
August 2026$1.27M
July 2026$1.28M
June 2026$1.28M
May 2026$1.28M
April 2026$1.25M
March 2026$1.26M
February 2026$1.23M
January 2026$1.21M
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
158 Landing Meadow Road, Smithtown, NY
0.39
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
144 Landing Meadow Road, Smithtown, NY
0.54
Single-Family Home
$1,225,000
08/11/26
5
4.5
3,937
1 Valley Avenue, Smithtown, NY
0.52
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600
56 Rose Street, Smithtown, NY
0.49
Single-Family Home
$680,000
01/22/26
4
2
2,300
17 Thide Court, Smithtown, NY
0.66
Single-Family Home
$1,175,000
04/09/26
5
2.5
3,495
1 Summit Trail, Nissequogue, NY
0.79
Single-Family Home
$1,350,000
04/08/26
4
4.5
3,900
109 Oakside Drive, Smithtown, NY
0.22
Single-Family Home
$1,300,000
03/31/26
4
3.5
2,400
142 Landing Meadow Road, Smithtown, NY
0.58
Single-Family Home
$1,750,000
04/23/26
6
5
4,479
60 Oak Street, Smithtown, NY
0.59
Single-Family Home
$869,000
01/22/26
4
2.5
2,660
4 Nadia Court, Smithtown, NY
0.66
Single-Family Home
$1,900,000
03/04/26
5
4.5
4,677

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
173 Oakside Drive, Smithtown, NY 11787
0.19
$1,022,900
3
2
-
Off Market
109 Oakside Drive, Smithtown, NY 11787
0.22
$1,300,000
4
3.5
2,400
Recently Sold
467 Landing Avenue, Smithtown, NY 11787
0.32
$847,100
4
2.5
-
Off Market
17 Wandering Way, Smithtown, NY 11787
0.31
$1,598,300
4
2.5
-
Off Market
11 Wandering Way, Smithtown, NY 11787
0.36
$1,582,600
5
5
3,667
Off Market
456 Landing Avenue, Smithtown, NY 11787
0.38
$1,033,400
4
3.5
2,200
Off Market
148 Oakside Drive, Smithtown, NY 11787
0.36
$1,634,700
4
4
-
Off Market
445 Landing Avenue, Smithtown, NY 11787
0.39
$854,400
3
1.5
2,500
Off Market
Address Not Disclosed, Smithtown, NY 11787
0.37
$1,499,000
4
3.5
3,000
For Sale
158 Landing Meadow Road, Smithtown, NY 11787
0.39
$1,495,000
4
3.5
3,634
Recently Sold
152 Landing Meadow Road, Smithtown, NY 11787
0.38
$1,940,000
5
4
-
Off Market
156 Landing Meadow Road, Smithtown, NY 11787
0.39
$1,061,600
4
3
-
Off Market

Local Information

  • Map ViewExplore the area around 166 Oakside Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1967
Lot Size
2 acres
Living Area
3,500 sqft
Price/Sqft
$363
Parking
Garage

About this House

This single-family home is located at 166 Oakside Dr, Smithtown, NY. 166 Oakside Dr is in Smithtown, NY and in ZIP code 11787. This property has 5 bedrooms, 4 bathrooms and approximately 3,500 sqft of floor space. This property has a lot size of 2.00 acres and was built in 1967.
166 Oakside Dr, Smithtown, NY 11787 is a 5 bedroom, 4 bathroom, 3,500 sqft single-family home built in 1967. It last sold for $650,000 on Apr 11, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,269,700, with a rent estimate of $5,470/month.

Home Details for 166 Oakside Dr

Interior Features

Interior Details
BasementTypes of Rooms: Dining Room, Family Room, Laundry Room, Master Bath, Recreation RoomCeiling Fan
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: VinylLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1967Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Apr 11, 2018
Source: OneKey® MLS as distributed by MLS GRID #L2959069
Sold
$650,000
Dec 8, 2017
Source: Agent Provided
PriceChange
$689,500
Price decreased by 1%
Nov 24, 2017
Source: Agent Provided
PriceChange
$694,500
Price decreased by 1%
Oct 25, 2017
Source: Agent Provided
PriceChange
$699,000
Price decreased by 4%
Oct 13, 2017
Source: Agent Provided
PriceChange
$729,000
Price decreased by 3%

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 166 Oakside Dr

  • What is 166 Oakside Dr estimated to be worth?
    Trulia's estimated value for 166 Oakside Dr in Smithtown, NY is $1,269,700.
  • What is the price history for 166 Oakside Dr?
    166 Oakside Dr in Smithtown, NY last sold for $650,000 in April 2018.
  • 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 166 Oakside Dr have air conditioning?
    Yes, 166 Oakside Dr in Smithtown, NY has air conditioning.
  • Does 166 Oakside Dr have laundry facilities?
    Yes, 166 Oakside Dr in Smithtown, NY has laundry facilities.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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12 rentals with a washer/dryer in Smithtown, NY

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Off Market Homes Near 166 Oakside Dr

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