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$1,450,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2 Car Garage

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 1/17 1:00 PM - 3:00 PM

109 Oakside Drive,Smithtown, NY 11787

109 Oakside DriveSmithtownNY11787

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Join us at 109 Oakside Drive on:

  • Open House: 1:00 PM - 3:00 PM

    Sunday 1/18 1:00 PM - 3:00 PM

    109 Oakside Drive,Smithtown, NY 11787
    109 Oakside DriveSmithtownNY11787
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See This Home
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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.

Full Property Details for 109 Oakside Dr

General

  • Price: $1,450,000
  • Taxes: $29,386
  • Status: Active
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 915379
  • Updated: 10/26/2025
  • Added to Site: 119 day(s) ago

Interior

  • Number of Rooms: 7
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters
  • Appliances: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Microwave, Refrigerator

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Parking

  • Garage: Yes
  • Garage Spaces: 2

Location

  • County: Suffolk County
  • Cross Streets: Landing Avenue
  • Driving Directions: Landing Avenue to Oakside Drive

School Information

  • High School District: Smithtown
  • Elementary School: Accompsett Elementary School
  • Middle School: Accompsett Middle School
  • High School: Smithtown High School-West

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Hot Water, Oil

Utilities

  • Sewer: Cesspool
  • Water: Public
  • Utility Description: Cable Available, Electricity Connected, Trash Collection Public, Water Connected

Structural Information

  • Architectural Style: Ranch
  • Detached/Attached: Detached
  • Construction: Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Finished
  • Unfinished Attic: Yes
  • Sq. Ft. Source: Other
  • Year Built: 1960

Additional Structures

  • Other Structures: Arena, Barn(s), Corral(s), Shed(s), Stable(s)

Lot Features

  • Lot Size (Acres): 2
  • Lot Size (Sq. Ft.): 8,712,000
  • Fence: Yes
  • Fencing (Description): Back Yard, Vinyl

Financial Considerations

  • Tax Amount: $29,386

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 0800-035-00-04-00-036-000

Listed by George Mcknight REALTORS Inc

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Listing agent

— 109 Oakside Dr —

  • George Mcknight REALTORS Inc

631-269-6666

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 109 Oakside Dr

School District:Smithtown Central School District
NameGradesDistance
Smithtown Elementary School
51 Lawrence Avenue, Smithtown, NY 11787
K-51.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 109 Oakside Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/26/2025
Price Reduced
$1,450,000
-3.33%
MLS
9/20/2025
Listed
$1,499,990
156.41%
MLS
8/22/2011
Sold
$585,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 109 Oakside Dr

Year
Property Taxes
Change
Tax Assessment
Change
2020
100%
$11,252
—
2022
-100%
$11,252
—
2016
$24,796
-9%
$11,252
—
2020
$27,357
3%
$11,252
—
2018
$26,612
4%
$11,252
—
2017
$25,672
-4%
$11,252
-5%
2016
$26,681
-2%
$11,850
—
2015
$27,179
4%
$11,850
—
2015
$26,113
7%
$11,850
—
2014
$24,453
28%
$11,850
22%
2013
$19,169
—
$9,705
—
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Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by George Mcknight REALTORS Inc

109 Oakside Drive, Smithtown, NY 11787 (MLS# 915379) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 109 Oakside Drive is currently listed for $1,450,000 and was received on September 20, 2025. Want to learn more about 109 Oakside Drive? Do you have questions about finding other Single Family real estate for sale in Smithtown? You can browse all Smithtown real estate or contact a Coldwell Banker agent to request more information.

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