Luxury Living & Exceptional Horse Property in the Heart of Smithtown
Set on 2 picturesque acres in a highly desirable Smithtown location, this 4-bedroom, 4-bath home offers the perfect blend of refined residential comfort and premium equestrian amenities - a rare and remarkable find.
Inside the home features an open floor plan that flows effortlessly for modern living. An updated eat-in kitchen with granite countertops and stainless steel appliances opens to a spacious family room centered around a striking stone fireplace, ideal for relaxing or entertaining. Refinished hardwood floors, recessed lighting, and custom moldings elevate the space, while the freshly painted interior and updated baths offer a move-in-ready experience.
The large main bedroom includes direct access to the backyard and deck - your own private retreat . A fully finished basement adds even more versatility to meet your lifestyle needs.
Step outside to an expansive Azek deck with an outdoor stone fireplace and tranquil waterfall, creating a peaceful backdrop for gatherings or quiet evening.
This is more than a property - it's a special, one-of-a-kind equestrian haven.
The meticulously maintained 4-stall barn is equipped with heat lamps on timers, a heated tack room with slop sink, and a hayloft for streamlined storage. PVC- fenced paddock is fully outfitted with lighting and irrigation, offering exceptional care and convenience for your horses.
A rare opportunity to own a turnkey home and horse property in a prime Smithtown setting - where luxury, lifestyle, and land come together beautifully.
For sale
Price cut: $299K (7/21)
$1,499,990
109 Oakside Drive, Smithtown, NY 11787
4beds
2,283sqft
Single Family Residence, Residential
Built in 1960
2 Acres Lot
$1,459,000 Zestimate®
$657/sqft
$-- HOA
What's special
Tranquil waterfallLarge main bedroomRecessed lightingOpen floor planExpansive azek deckStainless steel appliancesRefined residential comfort
- 69 days
- on Zillow |
- 2,062 |
- 118 |
Zillow last checked: 7 hours ago
Listing updated: August 09, 2025 at 10:39am
Listing by:
Signature Premier Properties 631-751-2111,
William R. Zezelic
Source: OneKey® MLS,MLS#: 877074

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 4
Heating
- Oil
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s)
- Laundry: Laundry Room
Features
- First Floor Bedroom, First Floor Full Bath, Crown Molding, Eat-in Kitchen, Formal Dining, Granite Counters, Primary Bathroom, Recessed Lighting
- Flooring: Ceramic Tile, Hardwood
- Basement: Finished,Full
- Attic: See Remarks
- Number of fireplaces: 1
- Fireplace features: Living Room
Interior area
- Total structure area: 2,283
- Total interior livable area: 2,283 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: One
- Patio & porch: Deck
Lot
- Size: 2 Acres
Details
- Additional structures: Barn(s)
- Parcel number: 0800035000400036000
- Special conditions: None
- Horses can be raised: Yes
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence, Residential
Materials
- Other, Vinyl Siding
- Foundation: Other
Condition
- Year built: 1960
Utilities & green energy
- Sewer: Cesspool
- Water: Public
- Utilities for property: See Remarks
Community & HOA
HOA
- Has HOA: No
Location
- Region: Smithtown
Financial & listing details
- Price per square foot: $657/sqft
- Tax assessed value: $1,308,372
- Annual tax amount: $29,359
- Date on market: 6/16/2025
- Listing agreement: Exclusive Right To Sell
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