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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
    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.
    69 days
    on Zillow
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    2,062
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    118
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    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#: 877074MLS Logo
    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 109 Oakside Drive.

    Next available tour time:Today at 1:30pm

    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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