181 Oakside Dr, Smithtown, NY 11787
OFF MARKET

181 Oakside Dr
Smithtown, NY 11787

  • 4 Beds
  • 4.5 Baths
  • 2,711 sqft (on 2 acres)

$1,157,300

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $7,548/mo*
Refinance Your Home

$1,157,300

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $7,548/mo*
Refinance Your Home
4 Beds
4.5 Baths
2,711 sqft
(on 2 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Custom Built Home W/Huge Granite Eik,Gas/Wood Fp, Center Island,Large Wine Refrigerator & Radiant Heat,Fdr W/Wall Of Glass, Hw Floors,Flr W/Fp,Beautiful Sunroom,Office,Suana & Gym In Basement,Roof-(50 Yr Arch Roof New With Warranty, New Hot Water Heater, New Cesspool, Updated 400 Amp Elec. Igs, Igp (New Looploc Cover),Cabana & Hottub! Fully Fenced Yard For Dogs- Set On 2 Acres Of Gorgeous- Flat Horse Property With A Beautiful Center Aisle Barn, Riding Arena And Sep Pony Area With Run In Shed.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 181 Oakside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Workshop, Sun RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, Other, Radiant, Oil, Other, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: VinylLawnPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Building

Pool
Sauna

Price History for 181 Oakside Dr

DatePriceEventSource
05/24/2019$678,000Sold
OneKey® MLS as distributed by MLS GRID #L3097376
03/03/2019$699,000PriceChange
Agent Provided
01/30/2019$749,000Listed For SaleAgent Provided
04/15/2014$649,000Sold
OneKey® MLS as distributed by MLS GRID #L2640170
11/11/2013$649,000PriceChange
Agent Provided
07/31/2013$679,000PriceChange
Agent Provided
07/18/2013$719,000Listed For SaleAgent Provided
02/10/1995$34,500,000Sold
N/A

Market trends in Smithtown

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
65
14MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$986,750
Home facts updated by county records

Comparable Sales for 181 Oakside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
158 Landing Meadow Road, Smithtown, NY
0.24
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
56 Rose Street, Smithtown, NY
0.34
Single-Family Home
$680,000
01/22/26
4
2
2,300
11 Wandering Way, Smithtown, NY
0.36
Single-Family Home
$1,500,000
08/07/25
5
5
3,667
83 Oakside Road, Smithtown, NY
0.23
Single-Family Home
$830,000
06/26/25
4
3
2,103
467 Landing Avenue, Smithtown, NY
0.07
Single-Family Home
$800,000
07/09/25
4
2.5
-
368 Landing Avenue, Smithtown, NY
0.58
Single-Family Home
$850,000
03/20/26
4
2.5
2,000
109 Oakside Drive, Smithtown, NY
0.22
Single-Family Home
$1,300,000
03/31/26
4
3.5
2,400
17 Thide Court, Smithtown, NY
0.41
Single-Family Home
$1,175,000
04/09/26
5
2.5
3,495
60 Oak Street, Smithtown, NY
0.53
Single-Family Home
$869,000
01/22/26
4
2.5
2,660
41 Stony Hill Path, Smithtown, NY
0.41
Single-Family Home
$1,875,000
06/13/25
4
4
4,884

Nearby homes

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Assigned Schools

These are the assigned schools for 181 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 231 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. "
    1
    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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181 Oakside Dr, Smithtown, NY 11787 is a 4 bedroom, 5 bathroom, 2,711 sqft single-family home built in 1961. This property is not currently available for sale. 181 Oakside Dr was last sold on May 24, 2019 for $678,000. The current Trulia Estimate for 181 Oakside Dr is $1,157,300.