Active
135 Oakside Drive
Smithtown, NY, 11787
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AN INTRODUCTION
A closer look.
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.
Property overview
- Property type
- Single Family Residence
- Architecture
- Chalet
- Condition
- Updated/Remodeled
- Year built
- 1968
- Lot size (sq ft)
- 70,567
- Status
- Active
- Listed
- 2026-08-21
- MLS number
- KEY1041795
Interior & comfort
- 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
- Basement
- Walk-Out Access
- Fireplaces
- 1
Outdoors & amenities
- Parking
- Driveway, Garage, Garage Door Opener, Heated Garage, Off Street, Private
- Garage spaces
- 2
- Pool
- Fenced, Outdoor Pool, Pool Cover, Pool/Spa Combo, Solar Cover
Schools & location
- Postal town
- Smithtown
- County
- Suffolk County
- School district
- Smithtown
- Elementary school
- Dogwood Elementary School
- Middle school
- Accompsett Middle School
- High school
- Smithtown High School-West
Taxes & utilities
- Annual property taxes
- $21,727
- Tax year
- 2026
- Association
- No
- Water
- Public
- Sewer
- Cesspool
Listing courtesy of Century 21 Parisi Realty · 631-669-3900
MLS #KEY1041795 · Active

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