
Residential Land with Home for Sale in Smithtown, New York
109 Oakside Dr, Smithtown, NY 11787
Welcome to 109 Oakside Dr., your dream equestrian retreat, set on 2 scenic acres in the heart of Smithtown. This updated 4-bed, 3.5-bath ranch blends easy single-level living with true equestrian amenities. An eat-in kitchen with granite counters and stainless appliances opens to a spacious family room anchored by a stone fireplace. Throughout the home you'll find hardwood floors, custom millwork, and recessed lighting. The private main bedroom offers direct access to a low-maintenance Azek deck overlooking a serene backyard with outdoor fireplace, waterfall, and koi pond. A finished basement adds flexible recreation/storage space. For horse enthusiasts: a meticulously maintained barn with 4 heated stalls, tack room, washroom, and hayloft; plus a PVC-fenced paddock with lighting and irrigation for year-round care. Move-in ready and thoughtfully appointed-an exceptional property where comfort, convenience, and equestrian living come together.
Location
- Street address
- 109 Oakside Dr
- County
- Suffolk County
- School district
- Smithtown
- Elevation
- 142 feet
Directions
Landing Avenue to Oakside Drive
Property details
- Acreage
- 2 acres
- MLS #
- MLSLI 915379
- Posted
Property taxes
- 2025
- $29,386
Parcels
- 0800-035-00-04-00-036-000
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
- Franchise
- Century 21 Real Estate
Exterior
- Structures
- Arena
Structure
- Style
- Ranch
- Basement
- Finished
- Water
- Public
- Sewer
- Cesspool
- Heating
- Hot Water, Oil
- Cooling
- Central Air
- Materials
- Vinyl Siding
Interior
- Room Count
- 7
- Rooms
- Basement, Bathroom x 4, Bedroom x 4, Dining Room
- Appliances
- Dishwasher, Dryer, Electric Cooktop, Electric Oven, Microwave, Refrigerator
- Features
- Eat-In Kitchen, Entrance Foyer, First Floor Bedroom, First Floor Full Bath, Formal Dining, Granite Counters
Nearby schools
| Name | Level | District | Description |
|---|---|---|---|
| Accompsett Elementary School | Elementary | Smithtown | — |
| Accompsett Middle School | Middle | Smithtown | — |
| Smithtown High School-West | High | Smithtown | — |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Oct 26, 2025 | Price drop | $1,450,000 | $49,990 -3.3% | MLSLI |
| Sept 21, 2025 | New listing | $1,499,990 | — | MLSLI |











































