Land with Home for Sale in Smithtown, New York
135 Oakside Dr, Smithtown, NY 11787
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.
Location
- Street address
- 135 Oakside Dr
- County
- Suffolk County
- Zip code
- 11787
- Community
- Nisseaquogue Overlook
- School district
- Smithtown
- Elevation
- 106 feet
Property details
- Acreage
- 1.62 acres70,567 sq ft
- MLS #
- MLSLI 1041795
- Posted
Property taxes
- 2026
- $21,727
Parcels
- 0800-035-00-04-00-025-000
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
- Franchise
- Century 21 Real Estate
Exterior
- Parking Spaces
- 6
- Parking
- Driveway, Garage, Off Street, Open
- Pool
- Deck, Patio
Structure
- Basement
- Walk-Out Access
- Water
- Public
- Sewer
- Cesspool
- Heating
- Oil
- Cooling
- Central Air
- Materials
- Block, Frame, Stone, Wood Siding
- Windows
- Double Pane Windows, ENERGY STAR Qualified W Indows, Screens, Skylight(s)
Interior
- Room Count
- 10
- Rooms
- Basement, Bathroom x 4, Bedroom x 5, Dining Room
- Flooring
- Carpet, Laminate, Tile, Tile-Ceramic
- Fireplaces
- Yes
- Appliances
- Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Microwave, Oil Water Heater, Refrigerator, Washer
- Security
- Security System
- Features
- Breakfast Bar, Built-In Features, Cathedral Ceiling(s), Ceiling Fan(s), Double Vanity, Eat-In Kitchen, Entrance Foyer, First Floor Full Bath, 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
Nearby schools
| Name | Type | District |
|---|---|---|
| Dogwood Elementary School | Elementary | Smithtown |
| Accompsett Middle School | Middle | Smithtown |
| Smithtown High School-West | High | Smithtown |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Oct 16, 2026 | Price drop | $1,298,000 | $970 -0.07% | MLSLI |
| Oct 13, 2026 | Price drop | $1,298,970 | $10 0% | MLSLI |
| Oct 9, 2026 | Price drop | $1,298,980 | $10 0% | MLSLI |
| Oct 7, 2026 | Price drop | $1,298,990 | $10 0% | MLSLI |
| Sept 25, 2026 | Price drop | $1,299,000 | $26,000 -2% | MLSLI |
| Sept 21, 2026 | Price drop | $1,325,000 | $25,000 -1.9% | MLSLI |
| Sept 13, 2026 | Price drop | $1,350,000 | $49,000 -3.5% | MLSLI |
| Sept 8, 2026 | Price drop | $1,399,000 | $100,000 -6.7% | MLSLI |
| Aug 28, 2026 | Price drop | $1,499,000 | $251,000 -14.3% | MLSLI |
| Aug 22, 2026 | New listing | $1,750,000 | — | MLSLI |