135 Oakside Drive, Smithtown, NY

$1,298,990

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4

Beds

4

Baths

3,000

Square feet

1.62

Acres

About 135 Oakside Drive

North Smithtown, Nisseaquogue Overlook Private Sanctuary Where Luxury Meets the Countryside Set against a backdrop of natural beauty, this unique residence offers architectural character, privacy, and equestrian capability. .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 dramatic, light-filled interior defined by soaring, handcrafted vaulted wood ceilings and refined natural stone. The 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.

Features of 135 Oakside Drive

MLS® # 1041795
Price $1,298,990
Bedrooms 4
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 3,000
Acres 1.62
Taxes $21,727
Year Built 1968
Type Residential
Sub-Type Single Family Residence
Style Chalet
Status Active

Community Information

Address 135 Oakside Drive
Subdivision NISSEAQUOGUE OVERLOOK
City Smithtown
County Suffolk County
State NY
Zip Code 11787
Adult 55+ Community No

Amenities

Utilities Cable Available, Electricity Connected, Phone Available, Propane, Water Connected
Parking Spaces 6
Parking Driveway, Garage, Garage Door Opener, Heated Garage, Off Street, Private
# of Garages 2
Is Waterfront No
Has Pool Yes
Pool Fenced, Outdoor Pool, Pool Cover, Pool/Spa Combo, Solar Cover

Interior

Interior Carpet, Ceramic Tile, Laminate, Tile
Interior Features First Floor Full Bath, Breakfast Bar, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, In-Law Floorplan, Open Kitchen, Pantry, Recessed Lighting, Soaking Tub, Walk-In Closet(s), Washer/Dryer Hookup
Appliances Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Microwave, Refrigerator, Washer, Oil Water Heater
Heating Hot Air, Oil
Cooling Central Air, Ductwork
Has Basement Yes
Basement Walk-Out Access
Fireplace Yes
# of Fireplaces 1
Fireplaces Masonry, Wood Burning

Exterior

Exterior Block, Frame, Stone, Wood Siding

School Information

District Smithtown
Elementary Dogwood Elementary School
Middle Accompsett Middle School
High Smithtown High School-West

Additional Information

Date Listed August 21st, 2026
Days on Market 49
Short Sale No
RE / Bank Owned No
Levels Tri-Level

Listing Details

OfficeCentury 21 Parisi Realty
Contact Info631-669-3900

Listing Map

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