109 Oakside Drive, Smithtown, NY 11787
Local realty services provided by:Better Homes and Gardens Real Estate Safari Realty



Listed by:william r. zezelic
Office:signature premier properties
MLS#:877074
Source:One Key MLS
Price summary
- Price:$1,499,990
- Price per sq. ft.:$657.03
About this home
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.
Contact an agent
Home facts
- Year built:1960
- Listing Id #:877074
- Added:59 day(s) ago
- Updated:August 10, 2025 at 03:09 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:4
- Full bathrooms:4
- Living area:2,283 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Oil
Structure and exterior
- Year built:1960
- Building area:2,283 sq. ft.
- Lot area:2 Acres
Schools
- High school:Smithtown High School-West
- Middle school:Accompsett Middle School
- Elementary school:Accompsett Elementary School
Utilities
- Water:Public
- Sewer:Cesspool
Finances and disclosures
- Price:$1,499,990
- Price per sq. ft.:$657.03
- Tax amount:$29,360 (2025)
New listings near 109 Oakside Drive
- Open Sat, 12 to 2pmNew$829,000Active3 beds 2 baths
105 Lone Oak Path, Smithtown, NY 11787
MLS# 899629Listed by: DOUGLAS ELLIMAN REAL ESTATE - New$1,875,000Active5 beds 4 baths4,800 sq. ft.
48 River Heights Drive, Smithtown, NY 11787
MLS# 901347Listed by: LISTWITHFREEDOM.COM - Open Sat, 12 to 2pmNew$849,999Active4 beds 3 baths2,853 sq. ft.
98 Fifty Acre Road S, Smithtown, NY 11787
MLS# 900976Listed by: OVERSOUTH LLC - Open Sun, 12 to 1:30pmNew$2,199,000Active6 beds 5 baths5,000 sq. ft.
142 Landing Meadow Road, Smithtown, NY 11787
MLS# 900103Listed by: WALRUS REAL ESTATE CORP - Open Sat, 12 to 2pmNew$914,999Active4 beds 3 baths2,200 sq. ft.
49 Dorchester Road, Smithtown, NY 11787
MLS# 899794Listed by: SIGNATURE PREMIER PROPERTIES - New$825,000Active4 beds 4 baths3,000 sq. ft.
32 Hemlock Lane, Smithtown, NY 11787
MLS# 898604Listed by: PROPERTY PROFESSIONALS REALTY - Open Sat, 1 to 3pmNew$999,000Active4 beds 3 baths3,000 sq. ft.
24 River Heights Drive, Smithtown, NY 11787
MLS# 897793Listed by: DOUGLAS ELLIMAN REAL ESTATE - New$245,000Active1 beds 1 baths1,000 sq. ft.
365 Route 111 #Unit C-4, Smithtown, NY 11787
MLS# 897993Listed by: SIGNATURE PREMIER PROPERTIES - New$859,000Active5 beds 3 baths2,200 sq. ft.
90 Blydenburg Avenue, Smithtown, NY 11787
MLS# 897897Listed by: GREENE REALTY GROUP - Open Sat, 12am to 2pmNew$1,700,000Active5 beds 6 baths3,800 sq. ft.
74 Laurel Drive, Smithtown, NY 11787
MLS# 897287Listed by: DOUGLAS ELLIMAN REAL ESTATE