43 Oakside Road, Smithtown, NY 11787
OFF MARKET

$1,035,100

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 2,500 sqft (on 0.61 acres)

43 Oakside Road, Smithtown, NY 11787

Est. Refi. Payment $7,003/mo*
Refinance Your Home
Currently Off Market - Sold Dec 5, 2023 for $830,000

Home Value

Trulia Estimate
$1.03M
Since last month
Decreased$3K (-0.3%)
Since last year
Increased$54K (+5.5%)
Since last sale
Increased$205K (+24.7%)
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 +78% in the last 10 years
MonthEstimated value
2026
August 2026$1.04M
August 2026$1.03M
July 2026$1.04M
June 2026$1.04M
May 2026$1.03M
April 2026$1M
March 2026$998K
February 2026$980K
January 2026$969K
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
17 Thide Court, Smithtown, NY
0.12
Single-Family Home
$1,175,000
04/09/26
5
2.5
3,495
4 Burham Court, Smithtown, NY
0.11
Single-Family Home
$950,000
12/22/25
3
2
1,918
335 Landing Avenue, Smithtown, NY
0.47
Single-Family Home
$850,000
03/24/26
4
2.5
2,500
368 Landing Avenue, Smithtown, NY
0.31
Single-Family Home
$850,000
03/20/26
4
2.5
2,000
6 Nowick Lane, Smithtown, NY
0.29
Single-Family Home
$780,000
02/20/26
4
3
2,488
3 Bradley Court, Smithtown, NY
0.19
Single-Family Home
$800,000
08/20/26
4
2
1,844
56 Rose Street, Smithtown, NY
0.49
Single-Family Home
$680,000
01/22/26
4
2
2,300
24 River Heights Drive, Smithtown, NY
0.52
Single-Family Home
$1,071,000
03/09/26
4
2.5
3,000
16 Ursular Court, Smithtown, NY
0.51
Single-Family Home
$1,035,000
08/14/26
4
3
2,074
1 Valley Avenue, Smithtown, NY
0.23
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600

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
41 Neil Drive, Smithtown, NY 11787
0.05
$980,200
5
2.5
-
Off Market
10 Burham Drive, Smithtown, NY 11787
0.08
$1,250,000
6
3.5
4,061
For Sale
48 Oakside Road, Smithtown, NY 11787
0.08
$1,048,500
4
3
3,500
Off Market
38 Neil Drive, Smithtown, NY 11787
0.09
$1,100,300
4
2.5
-
Off Market
4 Burham Court, Smithtown, NY 11787
0.11
$950,000
3
2
1,918
Recently Sold
37 Nowick Lane, Smithtown, NY 11787
0.12
$766,600
4
2
2,000
Off Market
16 Burham Drive, Smithtown, NY 11787
0.14
$902,200
3
2
2,350
Off Market
17 Thide Court, Smithtown, NY 11787
0.12
$1,175,000
5
2.5
3,495
Recently Sold
32 High Gate Drive, Smithtown, NY 11787
0.14
$1,071,700
5
2.5
-
Off Market
19 Burham Drive, Smithtown, NY 11787
0.16
$947,300
3
2
1,886
Off Market
9 Bradley Court, Smithtown, NY 11787
0.16
-
4
2
-
Off Market

Local Information

  • Map ViewExplore the area around 43 Oakside Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1962
Lot Size
0.61 acres
Living Area
2,500 sqft
Price/Sqft
$414

About this House

This colonial home in the desirable Legend Woods of Smithtown features five bedrooms and two full baths and two half bathrooms. The unfinished basement provides ample storage and bonus space. The kitchen has been updated with all new stainless steel appliances, as well as granite countertops and a brand new roof and fencing around property. Situated on a corner lot and the garage that has been converted into a home office. All of these features make this house perfect for anyone looking for a large home., Additional information: Appearance:Excellent,Separate Hotwater Heater:Yes
43 Oakside Road, Smithtown, NY 11787 is a 5 bedroom, 4 bathroom, 2,500 sqft single-family home built in 1962. It last sold for $830,000 on Dec 5, 2023 (1% above the $819,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,035,100, with a rent estimate of $5,401/month.
Last check for updates: about 20 hours ago
Listed by Stacy L. McFadden SRS, (917) 613-9604
Signature Premier Properties, (631) 422-3100
Bought with: Brian Montross, (631) 672-0132, EXP Realty, (888) 276-0630
Source: OneKey® MLS as distributed by MLS GRID, MLS#L3475055

Home Details for 43 Oakside Road

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 13
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 2500 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, ENERGY STAR Qualified Appliances, Microwave, Refrigerator, Washer, Oil Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Central Air,DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Window: ScreensFlooring: Hardwood
Levels, Entrance, & Accessibility
Levels: Three Or MoreFloors: Hardwood
Security
Security: Security System, Video Cameras

Exterior Features

Exterior Home Features
Patio / Porch: Deck, Patio, PorchFencing: FencedHas a Private Pool
Parking & Garage
No CarportNo GarageParking: Private
Pool
Pool: Above GroundPool
Water & Sewer
Sewer: Cesspool

Property Information

Year Built
Year Built: 1962
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: Cedar, Vinyl SidingNot Attached Property
Property Information
Parcel Number: 0800050000400041000

Price & Status

Price
List Price: $819,000
Status Change & Dates
Off Market Date: Wed May 24 2023

Active Status

MLS Status: Sold

Location

Direction & Address
City: Smithtown
School Information
Elementary School: Accompsett Elementary SchoolJr High / Middle School: Accompsett Middle SchoolHigh School: Smithtown High School-WestHigh School District: Smithtown

Building

Building Area
Building Area: 2500 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.61 acres

Offer

Listing Agreement Type: Exclusive Right To Lease

Miscellaneous

BasementMls Number: L3475055Attic: Full, ScuttleShowing Requirements: Showing Service

Price and Tax history

DateEventPrice
Dec 5, 2023
Source: N/A
Sold
$830,000
Jul 25, 2023
Source: OneKey® MLS as distributed by MLS GRID #L3475055
Sold
$830,000
May 24, 2023
Source: OneKey® MLS as distributed by MLS GRID #3475055
Pending
$819,000
May 2, 2023
Source: OneKey® MLS as distributed by MLS GRID #3475055
Listed For Sale
$819,000
Sep 15, 2017
Source: OneKey® MLS as distributed by MLS GRID #L2926552
Sold
$540,000

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

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

Based on information submitted to the MLS GRID as of 2026-09-02 12:08:00 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information

Frequently asked questions about 43 Oakside Road

  • What is 43 Oakside Road estimated to be worth?
    Trulia's estimated value for 43 Oakside Road in Smithtown, NY is $1,035,100.
  • What is the price history for 43 Oakside Road?
    43 Oakside Road in Smithtown, NY last sold for $830,000 in December 2023.
  • 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 43 Oakside Road have air conditioning?
    Yes, 43 Oakside Road in Smithtown, NY has air conditioning.
  • Does 43 Oakside Road have a pool?
    Yes, 43 Oakside Road in Smithtown, NY has a pool.

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