143 Oakside Drive Smithtown, NY $ 875,000
143 Oakside Drive
$ 875,000
Share Save

143 Oakside Drive

Smithtown, NY, 11787
$ 875,000
Bedrooms3 Baths1.1

Monthly Estimate*

$ 6,043

143 Oakside Drive, Smithtown, NY 11787 - Image 1
143 Oakside Drive, Smithtown, NY 11787 - Image 2

Single Family Home for sale in Smithtown, NY

for $875,000 with 3 bedrooms and 1 full bath, 1 half bath. This home was built in 1848 on a lot size of 1.

Historic charm meets modern farmhouse living in a tranquil setting with a view of the Nissequogue River. Perched on a full acre, this special property offers a peaceful connection to nature, with deer, wild turkeys, and other wildlife making frequent appearances. Built in the late 19th century as a servants’ cottage for the Kenyon Estate, the home blends its distinctive past with extensive updates completed within the last two years. A fabulous farmhouse kitchen offers abundant counter space and opens to the dining area, while two beautifully renovated bathrooms carry the modern farmhouse style throughout. A unique third bedroom, also ideal as a separate home office, awaits finishing, with materials included in the sale. Extensive improvements include all-new plumbing, two-zone heating and central air, new 200-amp electric service, roof, and Andersen windows. A renovated inground pool adds to the outdoor enjoyment. This special location affords homeowners a peaceful retreat with everyday conveniences close by. Enjoy beach rights to multiple Town of Smithtown beaches, boat ramp access, and nearby hiking trails, parks, nature preserves, and golf courses. Main Street’s restaurants and shops are just moments away, with convenient access to the LIRR and parkways. A rare opportunity to own a piece of history in a setting that feels like a retreat. ** PROFESSIONAL PHOTOS COMING SOON**

See more

Single Family Coming Soon

Price

$ 875,000

Bedrooms

3

Full Bath

1

Half Bath

1

Property Type

Single Family

Taxes

$ 14,136

Style

Colonial

Lot Size

1

Year Built

1848

Town/City

Smithtown

County/Region

Suffolk

MLS | Web ID

1070587

Features
Interior
Interior Amenities Eat-in Kitchen Open Kitchen Quartz/Quartzite Counters Recessed Lighting Walk-In Closet(s) Washer/Dryer Hookup
Basement Storage Space Unfinished
Flooring Laminate
Basement Features Storage Space Unfinished
Basement (Y/N) Y
Window Features New Windows Skylight(s) Wood Frames
Fireplace Y/N N
Half Baths 1
Total Bedrooms 3
Total Baths 2
See more
General
Sewer Septic Tank
Heating Forced Air Oil
Cooling Central Air
Utilities Cable Available Electricity Connected Phone Available Trash Collection Public Water Connected
Appliances Dishwasher Dryer Electric Range Electric Water Heater Refrigerator Stainless Steel Appliance(s) Washer
Patio/Porch Features Patio Porch
Architectural Style Colonial
Pool Features Fenced In Ground Pool Cover
Security Features Security System Smoke Detector(s) Video Cameras
Construction Materials Clapboard Frame
Year Built 1848
View River
Property Subtype Single Family Residence
Tax Year 2026
Parcel Number 0800-035-00-04-00-020-000
County Suffolk County
Property Type Residential
HOA N
Facing Direction North
Garage Y/N N
Other Structures Barn(s) Outbuilding Shed(s)
Total Rooms 6
Full Baths 1
Directions Edgewood Ave north on Landing Ave right on 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 Smithtown Elementary School
Property Attached Y/N N
Tax Annual Amount 14136
Middle/Junior High School Accompsett Middle School
Property Condition Updated/Remodeled
Building Area Units Square Feet
Standard Status Coming Soon
Middle/Junior School District Smithtown
Elementary School District Smithtown
Tax Assessed Value 5090
Tax Lot 020.000
Year Built Effective 2024
See more
Exterior
Exterior Amenities Mailbox
Fencing Chain Link
Parking Features Driveway Driveway
Water Source Public
Spa N
Waterfront Y/N N
Road Frontage Type Municipal
Other Equipment Pool Equip/Cover
Road Responsibility Public Maintained Road
Horse Y/N N
See more
Internal Only
Street Number 1 143
See more
* Excluded Features
List By
Jessica L. Stanco AHWD PSA

Listing Agent

Howard Hanna Coach

Broker

631-757-4000

Contact

Affordability Calculator

$7,221
Per Month
84%
16%
0%
Monthly Principal & Interest
$6,043
Monthly Property Taxes
$1,178
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% 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.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
4099196 Elementary School
4100218 Middle School
Smithtown High School-West High School
Pricing History
DatePricePrice ChangeDescription
11/6/2026$875,000 Listed Price

Map


See all

143 Oakside Drive, Smithtown, NY, 11787 is a Single Family Home for sale at $875,000 with a lot size of 1. 143 Oakside Drive has 3 bedrooms, 1.1 baths, and was built in 1848. The property's zip code is 11787 which is in Smithtown, NY