109 Oakside Drive Smithtown, NY $ 1,450,000
109 Oakside Drive
$ 1,450,000
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109 Oakside Drive

Smithtown, NY, 11787
$ 1,450,000
Bedrooms4 Baths3.1 Sq 2,400

Monthly Estimate*

$ 9,046

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Single Family Home for sale in Smithtown, NY

for $1,450,000 with 4 bedrooms and 3 full baths, 1 half bath. This 2,400 square foot home was built in 1960 on a lot size of 2.

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.

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Single Family Active

Price

$ 1,450,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 29,386

Style

Ranch

Lot Size

2

Year Built

1960

Town/City

Smithtown

County/Region

Suffolk

MLS | Web ID

915379

Features
Interior
Interior Amenities First Floor Bedroom First Floor Full Bath Eat-in Kitchen Entrance Foyer Formal Dining Granite Counters
Basement Finished
Basement Features Finished
Basement (Y/N) Y
Half Baths 1
Total Bedrooms 4
Total Baths 4
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General
Sewer Cesspool
Heating Hot Water Oil
Cooling Central Air
Utilities Cable Available Electricity Connected Trash Collection Public Water Connected
Appliances Dishwasher Dryer Electric Cooktop Electric Oven Microwave Refrigerator
Garage Spaces 2
Architectural Style Ranch
Construction Materials Vinyl Siding
Year Built 1960
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 0800-035-00-04-00-036-000
County Suffolk County
Property Type Residential
HOA N
Garage Y/N Y
Other Structures Arena Barn(s) Corral(s) Shed(s) Stable(s)
Total Rooms 7
Full Baths 3
Directions Landing Avenue to Oakside Drive
High School Smithtown High School-West
City Smithtown
Senior Community Y/N N
High School District Smithtown
Carport Y/N N
Elementary School Accompsett Elementary School
Property Attached Y/N N
Tax Annual Amount 29386
Middle/Junior High School Accompsett Middle School
Virtual Tour https://show.tours/e/mdFzfQB https://show.tours/e/mdFzfQB
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Smithtown
Elementary School District Smithtown
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Exterior
Fencing Back Yard Vinyl
Water Source Public
Waterfront Y/N N
Horse Y/N Y
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Internal Only
Street Number 1 109
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* Excluded Features
List By
George C. McKnight

Listing Agent

George Mcknight Realtors Inc

Broker

631-269-6666

Contact

Affordability Calculator

$11,495
Per Month
79%
21%
0%
Monthly Principal & Interest
$9,046
Monthly Property Taxes
$2,449
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4099909 Elementary School
4100218 Middle School
Smithtown High School-West High School
Pricing History
DatePricePrice ChangeDescription
10/26/2025$1,450,000 -3.33% Price Down
9/20/2025$1,499,990 Listed Price

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109 Oakside Drive, Smithtown, NY, 11787 is a Single Family Home for sale at $1,450,000 with 2,400 sqft and a lot size of 2. 109 Oakside Drive has 4 bedrooms, 3.1 baths, and was built in 1960. The property's zip code is 11787 which is in Smithtown, NY