109 Oakside Drive, Smithtown, NY 11787
SOLD
MAR 31, 2026

$1,331,600

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,400 sqft (on 200 acres)

109 Oakside Drive, Smithtown, NY 11787

Est. Refi. Payment $8,903/mo*
Refinance Your Home
Currently Off Market - Sold Mar 31, 2026 for $1,300,000 (10% below list price)

Home Value

Trulia Estimate
$1.33M
Since last month
Increased$8K (+0.6%)
Since last year
Decreased$123K (-8.4%)
Since last sale
Increased$35K (+2.7%)
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 +77% in the last 10 years
MonthEstimated value
2026
August 2026$1.33M
August 2026$1.33M
July 2026$1.33M
June 2026$1.31M
May 2026$1.32M
April 2026$1.31M
March 2026$1.39M
February 2026$1.39M
January 2026$1.38M
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
41 Landing Meadow Road, Smithtown, NY
0.58
Single-Family Home
$1,380,000
07/09/26
4
4.5
3,149
158 Landing Meadow Road, Smithtown, NY
0.18
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
1 Valley Avenue, Smithtown, NY
0.34
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600
144 Landing Meadow Road, Smithtown, NY
0.33
Single-Family Home
$1,225,000
08/11/26
5
4.5
3,937
17 Thide Court, Smithtown, NY
0.50
Single-Family Home
$1,175,000
04/09/26
5
2.5
3,495
56 Rose Street, Smithtown, NY
0.54
Single-Family Home
$680,000
01/22/26
4
2
2,300
54 Branglebrink Road, Saint James, NY
1.24
Single-Family Home
$1,480,000
09/04/26
4
2.5
3,485
368 Landing Avenue, Smithtown, NY
0.62
Single-Family Home
$850,000
03/20/26
4
2.5
2,000
335 Landing Avenue, Smithtown, NY
0.68
Single-Family Home
$850,000
03/24/26
4
2.5
2,500

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
173 Oakside Drive, Smithtown, NY 11787
0.13
$1,019,400
3
2
-
Off Market
17 Wandering Way, Smithtown, NY 11787
0.13
$1,590,600
4
2.5
-
Off Market
11 Wandering Way, Smithtown, NY 11787
0.16
$1,588,900
5
5
3,667
Off Market
152 Landing Meadow Road, Smithtown, NY 11787
0.17
$1,941,100
5
4
-
Off Market
156 Landing Meadow Road, Smithtown, NY 11787
0.18
$1,059,100
4
3
-
Off Market
158 Landing Meadow Road, Smithtown, NY 11787
0.18
$1,495,000
4
3.5
3,634
Recently Sold
445 Landing Avenue, Smithtown, NY 11787
0.27
$853,800
3
1.5
2,500
Off Market
146 Landing Meadow Road, Smithtown, NY 11787
0.25
$1,343,000
4
2.5
43,560
Off Market
467 Landing Avenue, Smithtown, NY 11787
0.28
$850,600
4
2.5
-
Off Market
3 Tree Top Terrace, Smithtown, NY 11787
0.28
$1,211,500
4
2.5
3,000
Off Market
20 Stony Hill Path, Smithtown, NY 11787
0.28
$2,083,700
5
4.5
7,123
Off Market

Local Information

  • Map ViewExplore the area around 109 Oakside Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1960
200 acre lot
2,400 sqft
$542/sqft
Garage

About this House

Welcome to 109 Oakside Dr., your dream equestrian retreat, set on 2 scenic acres in the heart of Smithtown. This updated 4-bed, 3.5-bath ranch blends easy single-level living with true equestrian amenities. An eat-in kitchen with granite counters and stainless appliances opens to a spacious family room anchored by a stone fireplace. Throughout the home you’ll find hardwood floors, custom millwork, and recessed lighting.

The private main bedroom offers direct access to a low-maintenance Azek deck overlooking a serene backyard with outdoor fireplace, waterfall, and koi pond. A finished basement adds flexible recreation/storage space.

For horse enthusiasts: a meticulously maintained barn with 4 heated stalls, tack room, washroom, and hayloft; plus a PVC-fenced paddock with lighting and irrigation for year-round care.

Move-in ready and thoughtfully appointed—an exceptional property where comfort, convenience, and equestrian living come together.
109 Oakside Drive, Smithtown, NY 11787 is a 4 bedroom, 4 bathroom, 2,400 sqft single-family home built in 1960. It last sold for $1,300,000 on Mar 31, 2026 (10% below the $1,450,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,331,600, with a rent estimate of $6,044/month.
Last check for updates: about 15 hours ago
Listed by George C. McKnight
George Mcknight REALTORS Inc, (631) 269-6666
Bought with: Betty Anne Smith, (516) 658-8228, Howard Hanna Coach, (631) 757-4000
Source: OneKey® MLS as distributed by MLS GRID, MLS#915379

Home Details for 109 Oakside Drive

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 7
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2400 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Trash Collection Public, Water ConnectedAppliances: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Microwave, RefrigeratorDishwasherDryerMicrowaveRefrigerator
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Gas & Electric
Has Electric on Property

Exterior Features

Exterior Home Features
Fencing: Back Yard, VinylOther Structures: Arena, Barn(s), Corral(s), Stable(s)No Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 2Parking: Garage
Water & Sewer
Sewer: Cesspool
Farm & Range
Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 238

Property Information

Year Built
Year Built: 1960
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Ranch
Building
Construction Materials: Vinyl SidingNot Attached Property
Property Information
Parcel Number: 0800035000400036000

Price & Status

Price
List Price: $1,450,000Price Per Sqft: $542/sqft
Status Change & Dates
Off Market Date: Mon Feb 09 2026

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: 2400 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 200 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 915379Attic: Full, UnfinishedAttribution Contact: 631-269-6666Showing Requirements: Appointment Only, Call Listing Agent

Price and Tax history

DateEventPrice
Mar 31, 2026
Source: OneKey® MLS as distributed by MLS GRID #915379
Sold
$1,300,000
Feb 9, 2026
Source: OneKey® MLS as distributed by MLS GRID #915379
Pending
$1,450,000
Oct 26, 2025
Source: OneKey® MLS as distributed by MLS GRID #915379
PriceChange
$1,450,000
Price decreased by 3%
Sep 20, 2025
Source: OneKey® MLS as distributed by MLS GRID #915379
Listed For Sale
$1,499,990
Sep 20, 2025
Source: OneKey® MLS as distributed by MLS GRID #877074
ListingRemoved
$1,499,990

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 2026-09-09 11:43:18 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 109 Oakside Drive

  • What is 109 Oakside Drive estimated to be worth?
    Trulia's estimated value for 109 Oakside Drive in Smithtown, NY is $1,331,600.
  • What is the price history for 109 Oakside Drive?
    109 Oakside Drive in Smithtown, NY last sold for $1,300,000 in March 2026.
  • 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 109 Oakside Drive have air conditioning?
    Yes, 109 Oakside Drive in Smithtown, NY has air conditioning.
  • Does 109 Oakside Drive have laundry facilities?
    Yes, 109 Oakside Drive in Smithtown, NY has laundry facilities.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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11 rentals with a washer/dryer in Smithtown, NY

Apartments for Rent

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Off Market Homes Near 109 Oakside Drive

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