151 Oakside Dr, Smithtown, NY 11787
OFF MARKET

$1,049,500

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,800 sqft (on 2 acres)

151 Oakside Dr, Smithtown, NY 11787

Est. Refi. Payment $6,983/mo*
Refinance Your Home
Currently Off Market - Sold Jan 4, 2005 for $308,019

Home Value

Trulia Estimate
$1.05M
Since last month
Decreased$6K (-0.6%)
Since last year
Increased$32K (+3.2%)
Since last sale
Increased$741K (+240.7%)
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 +64% in the last 10 years
MonthEstimated value
2026
August 2026$1.05M
July 2026$1.06M
June 2026$1.06M
May 2026$1.06M
April 2026$1.03M
March 2026$1.04M
February 2026$1.02M
January 2026$991K
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
0.46
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
1 Valley Avenue, Smithtown, NY
0.62
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600
56 Rose Street, Smithtown, NY
0.68
Single-Family Home
$680,000
01/22/26
4
2
2,300
1 Summit Trail, Nissequogue, NY
0.70
Single-Family Home
$1,350,000
04/08/26
4
4.5
3,900
144 Landing Meadow Road, Smithtown, NY
0.52
Single-Family Home
$1,225,000
08/11/26
5
4.5
3,937
109 Oakside Drive, Smithtown, NY
0.28
Single-Family Home
$1,300,000
03/31/26
4
3.5
2,400
277 River Road, Saint James, NY
0.83
Single-Family Home
$1,325,000
06/25/26
4
2.5
3,015
341 River Road, Saint James, NY
0.81
Single-Family Home
$954,000
02/13/26
4
2
2,360
60 Oak Street, Smithtown, NY
0.78
Single-Family Home
$869,000
01/22/26
4
2.5
2,660
368 Landing Avenue, Smithtown, NY
0.89
Single-Family Home
$850,000
03/20/26
4
2.5
2,000

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
Address Not Disclosed, Smithtown, NY 11787
0.18
$1,750,000
4
3.5
3,000
For Sale
148 Oakside Drive, Smithtown, NY 11787
0.22
$1,628,700
4
4
-
Off Market
146 Oakside Drive, Smithtown, NY 11787
0.23
$3,080,200
6
5.5
7,200
Off Market
2 Riverview Terrace, Smithtown, NY 11787
0.25
$2,599,000
6
6.5
3,946
For Sale
100 Riverview Terrace, Smithtown, NY 11787
0.26
-
4
4
3,700
Off Market
17 Wandering Way, Smithtown, NY 11787
0.28
$1,598,300
4
2.5
-
Off Market
109 Oakside Drive, Smithtown, NY 11787
0.28
$1,300,000
4
3.5
2,400
Recently Sold
8 Riverview Terrace, Smithtown, NY 11787
0.29
-
5
4
5,600
Off Market
10 Riverview Terrace, Smithtown, NY 11787
0.31
$2,849,300
5
4
6,798
Off Market
11 Wandering Way, Smithtown, NY 11787
0.33
-
5
5
3,667
Off Market
173 Oakside Drive, Smithtown, NY 11787
0.33
$1,026,200
3
2
-
Off Market
421 River Road, Saint James, NY 11780
0.38
$1,410,000
5
2.5
3,821
Off Market

Local Information

  • Map ViewExplore the area around 151 Oakside Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1971
Lot Size
2 acres
Living Area
2,800 sqft
Price/Sqft
$375
Parking
Garage

About this House

LARGE WINDOWS GREAT ROOM
INDOOR OUTDOOR ARE AS ONE . TREETOP VIEWS DECKS VERY NATURAL LIVING WOOD BURNING STOVE VERY SECLUDED
151 Oakside Dr, Smithtown, NY 11787 is a 4 bedroom, 3 bathroom, 2,800 sqft single-family home built in 1971. It last sold for $308,019 on Jan 4, 2005. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,049,500, with a rent estimate of $5,315/month.

Home Details for 151 Oakside Dr

Interior Features

Interior Details
BasementIn-law unitNumber of Rooms: 11Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Wall
Security
Security System

Property Information

Year Built
Year Built: 1971
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

Exterior Home Features
DeckExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Mar 24, 2021
Source: N/A
ListingRemoved
Jan 4, 2008
Source: N/A
ListingRemoved
$975,500
Mar 5, 2007
Source: N/A
Listed For Sale
$975,500
Jan 4, 2005
Source: N/A
Sold
$308,019
Feb 10, 1999
Source: N/A
Sold
$201,500

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 151 Oakside Dr

  • What is 151 Oakside Dr estimated to be worth?
    Trulia's estimated value for 151 Oakside Dr in Smithtown, NY is $1,049,500.
  • What is the price history for 151 Oakside Dr?
    151 Oakside Dr in Smithtown, NY last sold for $308,019 in January 2005.
  • 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 151 Oakside Dr have air conditioning?
    Yes, 151 Oakside Dr in Smithtown, NY has air conditioning.
  • Does 151 Oakside Dr have laundry facilities?
    Yes, 151 Oakside Dr 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 151 Oakside Dr

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