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135 Oakside Drive Smithtown, NY $ 1,298,000
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$ 1,298,000 Get more info
135 Oakside Drive
$ 1,298,000
Back to search
Share Save

135 Oakside Drive

Smithtown, NY, 11787
$ 1,298,000
Bedrooms5 Baths3.1 Sq 3,300

Monthly Estimate*

$ 8,965

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Single Family Home for sale in Smithtown, NY

for $1,298,000 with 5 bedrooms and 3 full baths, 1 half bath. This 3,300 square foot home was built in 1968 on a lot size of 1.62.

North Smithtown, Nisseaquogue Overlook Section As you approach via the impressive circular driveway—complemented by three generous additional driveways for effortless guest parking and trailer access—the estate-like scale of the property immediately unfolds. Step inside to a light-filled interior defined by handcrafted vaulted wood ceilings and natural stone. The Anderson windows frame sweeping, views of the surrounding woodlands at every turn, combining sophisticated indoor living and the serene outdoors A private, self-contained guest suite complete with its own bath for multi-generational living.(With Mother daughter permit from the town) The Horse Facilities: The property features a dedicated equestrian setup including an intimate functional small barn and an adjacent tack room with views of the Nissequogue River landscape. This is more than a home; it is an exceptional legacy property offering, seclusion, natural splendor, and timeless craftsmanship. Arrange a showing today.

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Single Family Active

Price

$ 1,298,000

Bedrooms

5

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 21,726

Style

Chalet

Lot Size

1.62

Year Built

1968

Town/City

Smithtown

County/Region

Suffolk

MLS | Web ID

1041795
Features
Interior
Interior Amenities First Floor Full Bath Breakfast Bar Built-in Features Cathedral Ceiling(s) Ceiling Fan(s) Double Vanity Eat-in Kitchen Entrance Foyer Formal Dining Granite Counters High Ceilings In-Law Floorplan Nat
Basement Walk-Out Access
Flooring Carpet Ceramic Tile Laminate Tile
Total Fireplaces 1
Fireplace Features Masonry Wood Burning
Basement Features Walk-Out Access
Basement (Y/N) Y
Window Features Double Pane Windows ENERGY STAR Qualified Windows New Windows Oversized Windows Screens Skylight(s) Wall of Windows
Fireplace Y/N Y
Half Baths 1
Total Bedrooms 5
Total Baths 4
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General
Sewer Cesspool
Heating Hot Air Oil
Cooling Central Air Ductwork
Utilities Cable Available Electricity Connected Phone Available Propane Water Connected
Appliances Convection Oven Dishwasher Dryer Electric Cooktop Electric Oven Electric Range Microwave Refrigerator Washer Oil Water Heater
Garage Spaces 2
Patio/Porch Features Covered Deck Patio Terrace
Architectural Style Chalet
Pool Features Fenced Outdoor Pool Pool Cover Pool/Spa Combo Solar Cover
Security Features Security System
Construction Materials Block Frame Stone Wood Siding
Year Built 1968
Property Subtype Single Family Residence
Tax Year 2026
Parcel Number 0800-035-00-04-00-025-000
County Suffolk County
Property Type Residential
HOA N
Subdivision Name NISSEAQUOGUE OVERLOOK
Garage Y/N Y
Other Structures Barn(s)
Total Rooms 10
Full Baths 3
High School Smithtown High School-West
City Smithtown
Senior Community Y/N N
High School District Smithtown
Carport Y/N N
Spa Features Bath
Elementary School Dogwood Elementary School
Property Attached Y/N N
Tax Annual Amount 21726.66
Middle/Junior High School Accompsett Middle School
Property Condition Actual Updated/Remodeled
Additional Parcels Y/N N
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Smithtown
Elementary School District Smithtown
Tax Assessed Value 7935
Year Built Effective 2004
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Exterior
Fencing Wood
Parking Features Driveway Garage Garage Door Opener Heated Garage Off Street Private Driveway Garage Garage Door Opener Heated Garage Off Street Private
Water Source Public
Total Parking 6
Parking Spaces 6
Foundation Details Concrete Perimeter
Spa N
Building Area Total 3300
Waterfront Y/N N
Horse Y/N Y
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Internal Only
Street Number 1 135
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* Excluded Features
List By
Richard Parisi C2EX

Listing Agent

Century 21 Parisi Realty

Broker

631-669-3900

Contact

Affordability Calculator

$10,775
Per Month
83%
17%
0%
Monthly Principal & Interest
$8,965
Monthly Property Taxes
$1,811
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.
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Nearby
4099366 Elementary School
4100218 Middle School
Smithtown High School-West High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
10/15/2026$1,298,000 -0.07% Price Down
10/13/2026$1,298,970 0.00% Price Down
10/9/2026$1,298,980 0.00% Price Down
10/7/2026$1,298,990 0.00% Price Down
9/25/2026$1,299,000 -1.96% Price Down
9/21/2026$1,325,000 -1.85% Price Down
9/12/2026$1,350,000 -3.50% Price Down
9/8/2026$1,399,000 -6.67% Price Down
8/28/2026$1,499,000 -14.34% Price Down
8/22/2026$1,750,000 Listed Price

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135 Oakside Drive, Smithtown, NY, 11787 is a Single Family Home for sale at $1,298,000 with 3,300 sqft and a lot size of 1.62. 135 Oakside Drive has 5 bedrooms, 3.1 baths, and was built in 1968. The property's zip code is 11787 which is in Smithtown, NY

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