135 Oakside Drive, Smithtown, NY 11787
Property image
Property image
FOR SALE
1.62 ACRES

$1,350,000

Original price: $1,399,000
  • 4 Beds
  • 3.5 Baths
  • 3,000 sqft (on 1.62 acres)

135 Oakside Drive, Smithtown, NY 11787

Est. Mortgage $9,262/mo*
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Home Highlights

Single-Family Home
Built in 1968
1.62 acre lot
$450/sqft
Garage

Local Information

  • Map ViewExplore the area around 135 Oakside Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Spacious home on an equestrian estate (Horse property has small barn and tack room.) featuring handcrafted vaulted wood ceilings throughout and refined natural stone detailing. Guest suite with private bath, Situated within a private wooded landscape, surrounded by timeless natural beauty. Beautifully positioned windows frame breathtaking scenic views, with a private barn enjoying panoramic views. Three generous driveways and an impressive circular driveway enhance the estate-like setting. A truly exceptional property offering privacy, natural beauty, and timeless architectural character.
Last check for updates: about 3 hours ago
Listing by: Century 21 Parisi Realty, (631) 669-3900
Richard Parisi C2EX, (631) 669-3900
Source: OneKey® MLS as distributed by MLS GRID, MLS#1041795
Also Listed on OneKey® MLS as distributed by MLS GRID.

Home Details for 135 Oakside Drive

Interior Features

Interior Details
Basement: Walk-Out AccessNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3000 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Phone Available, Propane, Water ConnectedAppliances: Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Microwave, Refrigerator, Washer, Oil Water HeaterDishwasherDryerLaundry: Washer/Dryer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Air,OilHas CoolingAir Conditioning: Central Air,DuctworkHas HeatingHeating Fuel: Hot Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Masonry, Wood BurningHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Carpet, Ceramic Tile, Laminate, Tile
Levels, Entrance, & Accessibility
Levels: Tri-LevelFloors: Carpet, Ceramic Tile, Laminate, Tile
Security
Security: Security System

Exterior Features

Exterior Home Features
Patio / Porch: Covered, Deck, Patio, TerraceFencing: WoodOther Structures: Barn(s)Foundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 6Parking: Driveway,Garage,Garage Door Opener,Heated Garage,Off Street,Private
Pool
Pool: Fenced, Outdoor Pool, Pool Cover, Pool/Spa Combo, Solar CoverPool
Water & Sewer
Sewer: Cesspool
Farm & Range
Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 23Days on Market: 25

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Chalet
Building
Construction Materials: Block, Frame, Stone, Wood SidingNot Attached Property
Property Information
Condition: Updated/RemodeledParcel Number: 0800035000400025000

Price & Status

Price
List Price: $1,350,000Price Per Sqft: $450

Active Status

MLS Status: Active

Location

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

Agent Information

Listing Agent
Listing ID: 1041795

Building

Building Area
Building Area: 3000 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.62 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Agency

Miscellaneous

BasementMls Number: 1041795Attic: NoneAttribution Contact: 631-669-3900Showing Requirements: Call Owner

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

Market trends in Smithtown

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$828K
$14.33KMoM
Sale-to-List Price
103.0%
Price per sq ft
$411
$13MoM
Available listings
95
8MoM

Home Value

Trulia Estimate
$1.35M
Since last month
Increased$438K (+48%)
Since last year
Increased$369K (+37.6%)
Since last sale
Increased$1M (+316%)
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 +129% in the last 10 years
MonthEstimated value
2026
September 2026$1.35M
August 2026$1.51M
July 2026$914K
June 2026$908K
May 2026$889K
April 2026$853K
March 2026$896K
February 2026$901K
January 2026$854K
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
158 Landing Meadow Road, Smithtown, NY
0.53
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
144 Landing Meadow Road, Smithtown, NY
0.52
Single-Family Home
$1,225,000
08/11/26
5
4.5
3,937
277 River Road, Saint James, NY
0.69
Single-Family Home
$1,325,000
06/25/26
4
2.5
3,015
1 Valley Avenue, Smithtown, NY
0.71
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600
341 River Road, Saint James, NY
0.64
Single-Family Home
$954,000
06/18/26
4
2
2,360
1 Summit Trail, Nissequogue, NY
0.70
Single-Family Home
$1,350,000
04/08/26
4
4.5
3,900
270 Sachem Hill Place, Saint James, NY
0.79
Single-Family Home
$999,600
02/06/26
5
3.5
2,800
109 Oakside Drive, Smithtown, NY
0.38
Single-Family Home
$1,300,000
03/31/26
4
3.5
2,400
37 Bridle Path, Saint James, NY
0.76
Single-Family Home
$1,600,000
06/09/26
4
5
3,856
142 Landing Meadow Road, Smithtown, NY
0.56
Single-Family Home
$1,750,000
04/23/26
6
5
4,479

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
100 Riverview Terrace, Smithtown, NY 11787
0.08
$2,367,900
4
4
3,700
Off Market
2 Riverview Terrace, Smithtown, NY 11787
0.09
$2,599,000
6
6.5
3,946
For Sale
146 Oakside Drive, Smithtown, NY 11787
0.21
$3,076,300
6
5.5
7,200
Off Market
8 Riverview Terrace, Smithtown, NY 11787
0.16
$2,167,100
5
4
5,600
Off Market
148 Oakside Drive, Smithtown, NY 11787
0.24
$1,618,200
4
4
-
Off Market
10 Riverview Terrace, Smithtown, NY 11787
0.19
$2,846,000
5
4
6,798
Off Market
421 River Road, Saint James, NY 11780
0.21
$1,423,000
5
2.5
3,821
Off Market
428 River Road, Saint James, NY 11780
0.31
$1,324,700
4
2.5
3,300
Off Market
17 Wandering Way, Smithtown, NY 11787
0.31
$1,585,300
4
2.5
-
Off Market
410 River Road, Saint James, NY 11780
0.31
-
4
3.5
-
Off Market
326 Nissequogue River Road, Saint James, NY 11780
0.32
$3,499,000
6
6.5
6,000
For Sale

Price and Tax history

DateEventPrice
Sep 12, 2026
Source: OneKey® MLS as distributed by MLS GRID #1041795
PriceChange
$1,350,000
Price decreased by 4%
Sep 8, 2026
Source: OneKey® MLS as distributed by MLS GRID #1041795
PriceChange
$1,399,000
Price decreased by 7%
Aug 28, 2026
Source: OneKey® MLS as distributed by MLS GRID #1041795
PriceChange
$1,499,000
Price decreased by 14%
Aug 22, 2026
Source: OneKey® MLS as distributed by MLS GRID #1041795
Listed For Sale
$1,750,000
Jun 5, 2026
Source: Zillow Rentals
ListingRemoved
$2,600

LGBTQ Local Legal Protections

Richard Parisi C2EX, Century 21 Parisi Realty, (631) 669-3900
Agent Phone: (631) 669-3900
Based on information submitted to the MLS GRID as of 2026-09-16 01:38:13 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

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Frequently asked questions about 135 Oakside Drive

  • What is the estimated monthly payment for 135 Oakside Drive?
    Based on a $1,350,000 list price with 20% down at today's rates, the estimated monthly payment for 135 Oakside Drive in Smithtown, NY is approximately $9,421 (about $7,265 principal & interest, $2,081 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 135 Oakside Drive compare to homes in Smithtown?
    135 Oakside Drive in Smithtown, NY is listed at $1,350,000, about 63% above the $828K median sale price in Smithtown.
  • What do residents say about Smithtown?
    Residents describe Smithtown, NY as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Smithtown, NY.
  • What are the closest schools to 135 Oakside Drive?
    The closest schools to 135 Oakside Drive in Smithtown, NY are Accompsett Middle School (rated 7/10), Smithtown Elementary School (rated 7/10), Smithtown High School West (rated 10/10).
  • Does 135 Oakside Drive have air conditioning?
    Yes, 135 Oakside Drive in Smithtown, NY has air conditioning.
  • Does 135 Oakside Drive have a pool?
    Yes, 135 Oakside Drive in Smithtown, NY has a pool.
135 Oakside Drive, Smithtown, NY 11787 is a 4 bedroom, 4 bathroom, 3,000 sqft single-family home built in 1968. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Aug 22, 2026. The MLS # for this home is MLS# 1041795.