Single Family
135 Oakside Drive
Active · Smithtown · Suffolk County, NY 11787
- Bedrooms
- 5 Beds
- Bathrooms
- 4 Baths
- Year built
- 1968
- Est. monthly taxes
- $1,810.56
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About this home
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.
Listing snapshot
- Days on site
- 59 days
- Listed on MLS
- Aug 21, 2026
- Full baths
- 3
- Half baths
- 1
- Annual property tax (MLS)
- $21,726.66
- Tax year
- 2026
- Area source (MLS)
- Measured
- Listing brokerage
- Century 21 Parisi Realty
- MLS ID
- KEY1041795
- Last updated
- Oct 21, 2026
General features
- Property type
- Single Family
- Property subtype
- Single Family Residence
- Year built
- 1968
- Garage
- Yes
- Garage spaces
- 2
- Total parking
- 6
- Parking
- Driveway, Garage, Garage Door Opener, Heated Garage, Off Street, Private
- Water source
- Public
- Sewer
- Cesspool
- Utilities
- Cable Available, Electricity Connected, Phone Available, Propane, Water Connected
Interior features
- Basement
- Walk-Out Access
- Heating
- Hot Air, Oil
- Cooling
- Central Air, Ductwork
- Interior
- 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, Natural Woodwork, Open Kitchen, Pantry, Primary Bathroom, Recessed Lighting, Soaking Tub, Stone Counters, Tray Ceiling(s), Walk-In Closet(s), Washer/Dryer Hookup
- Appliances
- Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Microwave, Refrigerator, Washer, Oil Water Heater
- Flooring
- Carpet, Ceramic Tile, Laminate, Tile
- Fireplace
- Yes
- Fireplaces
- 1
Exterior features
- Architectural style
- Chalet
- Construction materials
- Block, Frame, Stone, Wood Siding
- Private pool
- Yes
Schools (MLS)
- Elementary school
- Dogwood Elementary School
- Elementary school district
- Smithtown
- Middle school
- Accompsett Middle School
- Middle school district
- Smithtown
- High school
- Smithtown High School-West
- High school district
- Smithtown
School information is provided by the MLS. Confirm attendance eligibility with the school district.
Recent activity
- Listing updated from MLS
- Price changed to $1,298,970
- Price changed to $1,298,980
- Price changed to $1,298,990
- Price changed to $1,299,000
- Price changed to $1,325,000
- Price changed to $1,350,000
- Price changed to $1,399,000
- First seen on this site
- MLS status changed
Location
Estimate monthly payment
Estimated monthly principal & interest—
Monthly property taxNot provided
Monthly association / maintenance feesNot provided
Estimated monthly total of entered costs—
Listing data is supplied by the MLS and may change without notice.