$875,000
143 Oakside Drive Smithtown, NY 11787
- 3 Beds
- 1.5 Baths
Listing courtesy of Jessica L. Stanco AHWD PSA, Howard Hanna Coach
NY · Long Island
15 closed sales, median $457,500, typically 29 days on market.
also Hauppauge
a year, median of the homes for sale
median of the homes for sale
since 2014, $116,000 to $970,000
School districts, taxes and year built describe the homes for sale in Smithtown today; taxes and year built are medians. Data courtesy of OneKey MLS as distributed by MLS GRID as of November 8, 2026.
Overview
Smithtown is an unincorporated hamlet in the Town of Smithtown, in Suffolk County. It borders Nissequogue and Head of the Harbor to the northeast and Village of the Branch to the east. The nearest station is Smithtown, on the Port Jefferson Branch, about one mile from the center. Direct weekday morning trains reach Penn Station in 79 to 82 minutes of scheduled time on board.
The 8,235 homes counted in Smithtown CDP are overwhelmingly detached, with about nine in ten single-family houses. Most were built between 1950 and 1969. Four-bedroom houses make up the largest size category, and about half of homes have four or more bedrooms. About nine in ten are owner occupied.
Caleb Smith State Park sits about 0.7 miles from the center, and Millers Pond County Park is also nearby. FEMA's mapped flood zones place about one in twenty of Smithtown CDP in a high-risk flood area, where flood insurance is required on federally backed mortgages. Less than one percent falls into a moderate-risk zone.
As an unincorporated hamlet, Smithtown has no government of its own. The Town of Smithtown handles zoning, permits and roads, and its Building Department issues permits and the certificate of occupancy. Addresses fall in the Smithtown Central School District or the Hauppauge Union Free School District, with the district set by the property's tax bill. PSEG Long Island provides electricity, National Grid supplies gas, and water comes from the Smithtown Water District in parts of the hamlet or directly from the Suffolk County Water Authority.
Sources: U.S. Census Bureau place boundaries and OpenStreetMap contributors, as of September 17, 2026 ; MTA Long Island Rail Road schedule data (GTFS) and OpenStreetMap contributors, as of September 17, 2026 ; U.S. Census Bureau, American Community Survey 5-year estimates, as of December 1, 2025 ; National Center for Education Statistics (EDGE, Common Core of Data) and New York State Education Department, as of June 1, 2025 ; OpenStreetMap contributors, as of September 17, 2026 ; FEMA National Flood Hazard Layer, as of September 17, 2026 ; Official town, village, county and utility websites, as of September 17, 2026 .
Homes for sale in Smithtown today have a median asking price of $965,000. Three-bedroom homes are asking a median of $809,999, four-bedroom homes $965,000 and homes with five or more bedrooms $1,250,000.
Data courtesy of OneKey MLS as distributed by MLS GRID as of November 8, 2026. These are asking prices, not sold prices.
Stephanie Calinoff, a Licensed Associate Real Estate Broker and Realtor with Signature Premier Properties, has closed 16 sales in Smithtown since 2014, from $116,000 to $970,000.
On the market today
What sellers in Smithtown are asking on November 8, 2026, and how the asking prices are spread. These are the homes on the market, not homes that have sold.
Based on 47 listings.
Half have been listed longer than this. Based on 47 listings.
Based on the 46 of 47 listings that state a size.
Came on the market in the past 7 days, 3 of 47 listings.
Bands are set from this town’s own quartiles, rounded. Based on 47 listings.
Based on 7 listings.
Based on 25 listings.
Based on 14 listings.
A bedroom count with fewer than three homes for sale is left out.
Every figure above is a median or a share of the asking prices of homes for sale in Smithtown on November 8, 2026. Asking prices are what sellers want, not what homes have sold for. Data courtesy of OneKey MLS as distributed by MLS GRID as of November 8, 2026.
47 on the market
$875,000
Listing courtesy of Jessica L. Stanco AHWD PSA, Howard Hanna Coach
$945,000 2 days on market
Listing courtesy of Patrice E. Silvestri, Coldwell Banker American Homes
$849,000 1 days on market
Listing courtesy of Christopher Galluzzo, Compass Greater NY LLC
$819,999 1 days on market
Listing courtesy of Donna Cupaiolo CBR, Signature Premier Properties
$869,900 6 days on market
Listing courtesy of Michael J. Carroll, RE/MAX Best
$798,000 7 days on market
Listing courtesy of Rohit Garg, Island Edge Homes
$2,599,000 1 days on market
Listing courtesy of Jamie Marcantonio, Signature Premier Properties
$1,199,999 1 days on market
Listing courtesy of Lisa A. Kass, Coldwell Banker American Homes
$799,999
Listing courtesy of Christopher White, Compass Greater NY LLC
$809,999 15 days on market
Listing courtesy of John A. Reade, John A Reade
$749,999 1 days on market
Listing courtesy of Sheryl R. Hecht, Douglas Elliman Real Estate
$965,000 2 days on market
Listing courtesy of Gina Davino Concolino ABR SRES, Exit Realty Achieve
$875,000 1 days on market
Listing courtesy of Robert Daddino, Coldwell Banker American Homes
$869,000 20 days on market
Listing courtesy of Lori Zamore CBR SRES, Signature Premier Properties
$1,395,000 17 days on market
Listing courtesy of Derek Eisenberg, Continental Real Estate Group
$1,149,999 19 days on market
Listing courtesy of Deborah Lettieri, Signature Premier Properties
$759,999 17 days on market
Listing courtesy of Domenic Brocco, Real Broker NY LLC
$1,599,999 17 days on market
Listing courtesy of Albert Bongiorno, Nest Seekers International LLC
$999,999 32 days on market
Listing courtesy of Patrice E. Silvestri, Coldwell Banker American Homes
$899,999 2 days on market
Listing courtesy of Robert Scaccia, Signature Premier Properties
$1,195,000 32 days on market
Listing courtesy of Lynn J. Sabatelle, Daniel Gale Sothebys Intl Rlty
$1,299,000 35 days on market
Listing courtesy of Elena M. Galluzzo, Compass Greater NY LLC
$1,349,000 34 days on market
Listing courtesy of Geris Hernandez, Signature Premier Properties
$838,000 47 days on market
Listing courtesy of Roody Casseus, OneSpace Realty Group LLC
Closed sales
16 closed sales in Smithtown since 2014, $116,000 to $970,000.
Figures are from Stephanie Calinoff's own closed transactions, data courtesy of OneKey MLS as distributed by MLS GRID, covering June 2014 to October 2026.
Boundaries are the Census Bureau 2023 cartographic place boundaries, which are drawn for statistics and need not match the postal town or a school district. Map data © OpenStreetMap contributors.
Source: U.S. Census Bureau place boundaries and OpenStreetMap contributors, as of 17 September 2026.
Train times are the scheduled minutes on board and do not include getting to the station, parking or waiting. Road names from OpenStreetMap, © OpenStreetMap contributors.
American Community Survey figures are survey estimates, not counts. They cover Smithtown CDP as the Census Bureau draws it, which need not match the postal town.
Source: U.S. Census Bureau, American Community Survey 5-year estimates, 2020 to 2024.
District lines are drawn independently of hamlet and ZIP code lines, so two houses with the same mailing address can sit in different districts.
Distances are straight-line from the centre of the town, not driving distance. Many town beaches, marinas and ramps require a resident permit. Check with the town before you go. Map data © OpenStreetMap contributors.
Source: OpenStreetMap contributors, as of 17 September 2026.
These are area estimates from FEMA's mapped flood zones, sampled across the Census place boundary. They describe the area, not any one property, and mapped zones can change.
Source: FEMA National Flood Hazard Layer, as of 17 September 2026.
Service areas can differ street by street. Confirm providers for a specific address.
Source: Official town, village, county and utility websites, as of 17 September 2026.
The median sale price in Smithtown was $830,000 in October 2026, across 28 closed sales. The median price per square foot was $450.
Median days on market in Smithtown was 37 in October 2026.
Just over half are. In October 2026, 16 of 28 Smithtown sales closed at or above asking, and the median sale to list ratio was 100.4 percent.
Around the $830,000 median, six of the 28 October 2026 sales fell between $800,000 and $899,999. Below that, eight sales closed between $700,000 and $799,999 and four between $600,000 and $699,999. Nothing sold below $600,000 that month.
Twenty nine new listings came on the market in October 2026.
Yes. Six of the 28 Smithtown sales in October 2026 closed at $1,000,000 or over, and another four fell between $900,000 and $999,999.
Stephanie Calinoff, Licensed Associate Real Estate Broker, Signature Premier Properties, as of October 31, 2026.
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Stephanie CalinoffLicensed Associate Real Estate Broker, Signature Premier Properties