105 Oakside Dr, Smithtown, NY 11787
OFF MARKET

105 Oakside Dr
Smithtown, NY 11787

  • 3 Beds
  • 3 Baths
  • 2,000 sqft (on 2.42 acres)

$1,016,200

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $6,679/mo*
Refinance Your Home

$1,016,200

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $6,679/mo*
Refinance Your Home
3 Beds
3 Baths
2,000 sqft
(on 2.42 acres)

Local Information

  • Map ViewExplore the area around 105 Oakside Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Lot Size
2.42 acres
Living Area
2,000 sqft
Price/Sqft
$508
Parking
Garage

Description

Custom Built Ranch Style Home In A Wonderful Location On 2.42 Acres Of Horse Property. Zoning For Up To Five(5) Horses, Custom Built Boulder I.G. Soaking Tub, Circular Front Driveway, Two (2) Car Attached Garage With Interior Stairs Leading To A Full Basement, Partly Finished With A Fireplace And Office, Possible Mother Daughter W/ Required Permits, Anderson Windows, #1 Grade Oak Floor, Living Room W/ Wood Burning Brick Fireplace, E.I.K W/Wood Fired Stove, Naturally Embraced Well Water.
105 Oakside Dr, Smithtown, NY 11787 is a 3 bedroom, 3 bathroom, 2,000 sqft single-family home built in 1965. It last sold for $624,000 on Aug 20, 2018. It is currently off market. The Trulia Estimate is $1,016,200, with a rent estimate of $4,624/month.

Home Details for 105 Oakside Dr

Interior Features

Heating & Cooling
Heating: OtherHeating Fuel: Other
Interior Details
Number of Rooms: 7

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Lot Information

Lot Area: 2.42 acres

Price History for 105 Oakside Dr

DatePriceEventSource
08/20/2018$624,000Sold
OneKey® MLS as distributed by MLS GRID #L3033383
06/23/2018$650,000PendingAgent Provided
05/19/2018$650,000Listed For SaleAgent Provided

Market trends in Smithtown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
122
29MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$747,000
Home facts updated by county records

Comparable Sales for 105 Oakside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
158 Landing Meadow Road, Smithtown, NY
0.16
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
4 Burham Court, Smithtown, NY
0.39
Single-Family Home
$950,000
12/22/25
3
2
1,918
368 Landing Avenue, Smithtown, NY
0.58
Single-Family Home
$850,000
03/20/26
4
2.5
2,000
1 Clark Street, Smithtown, NY
0.57
Single-Family Home
$850,000
02/20/26
3
2
1,958
56 Rose Street, Smithtown, NY
0.49
Single-Family Home
$680,000
01/22/26
4
2
2,300
109 Oakside Drive, Smithtown, NY
0.06
Single-Family Home
$1,300,000
03/31/26
4
3.5
2,400
11 Wandering Way, Smithtown, NY
0.20
Single-Family Home
$1,500,000
08/07/25
5
5
3,667
83 River Heights Drive, Smithtown, NY
0.66
Single-Family Home
$915,000
08/15/25
4
3
2,100
17 Thide Court, Smithtown, NY
0.45
Single-Family Home
$1,175,000
04/09/26
5
2.5
3,495
335 Landing Avenue, Smithtown, NY
0.65
Single-Family Home
$850,000
03/24/26
4
2.5
2,500

Nearby homes

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Assigned Schools

These are the assigned schools for 105 Oakside Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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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Explore by feature - Air Conditioning

6 rentals with air conditioning in Smithtown, NY

Homes for sale near 105 Oakside Dr

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Off Market Homes Near 105 Oakside Dr

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