135 Oakside Drive, Smithtown, NY

$1,325,000

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4

Beds

4

Baths

3,000

Square feet

1.62

Acres

About 135 Oakside Drive

A Breathtaking Private Sanctuary Where Luxury Meets the Countryside ???? Set against a backdrop of  natural beauty, this expansive residence offers a rare convergence of architectural character, ultimate privacy, and premier equestrian living .As you approach via the impressive grand circular driveway—complemented by three generous additional driveways for effortless guest parking and trailer access—the estate-like scale of the property immediately unfolds. The Residence: Step inside to a dramatic, light-filled interior defined by soaring, handcrafted vaulted wood ceilings and refined natural stone detailing that anchors the home in organic elegance. Huge  covered brick patio Extensively positioned windows frame sweeping, cinematic 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 provides an ideal, secluded retreat for visitors or multi-generational living. The Equestrian Facilities: The property features a dedicated equestrian setup including an intimate,  functional small barn and an adjacent tack room with panoramic views of the rolling landscape, the barn brings convenience and beauty together in a healthy environment for your horse. This is more than a home; it is an exceptional legacy property offering  seclusion, natural splendor, and timeless craftsmanship.

Features of 135 Oakside Drive

MLS® # 1041795
Price $1,325,000
Bedrooms 4
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 3,000
Square Footage 70567
Acres 1.62
Year Built 1968
Type Residential
Sub-Type Single Family Residence
Style Chalet
Status Active

Community Information

Address 135 Oakside Drive
City Smithtown
County Suffolk County
State NY
Zip Code 11787

Amenities

Horse Property Yes
Utilities Cable Available, Electricity Connected, Phone Available, Propane, Water Connected
Parking Spaces 6
Parking Driveway, Garage, Garage Door Opener, Heated Garage, Off Street, Private
# of Garages 2
Is Waterfront No
Has Pool Yes
Pool Fenced, Outdoor Pool, Pool Cover, Pool/Spa Combo, Solar Cover

Interior

Interior Carpet, Ceramic Tile, Laminate, Tile
Interior Features First Floor Full Bath, Breakfast Bar, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, In-Law Floorplan, Open Kitchen, Pantry, Recessed Lighting, Soaking Tub, Walk-In Closet(s), Washer/Dryer Hookup
Appliances Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Microwave, Refrigerator, Washer, Oil Water Heater
Heating Hot Air, Oil
Cooling Central Air, Ductwork
Fireplace Yes
# of Fireplaces 1
Fireplaces Masonry, Wood Burning
Has Basement Yes
Basement Walk-Out Access

Exterior

Construction Block, Frame, Stone, Wood Siding

School Information

District Smithtown
Elementary Dogwood Elementary School
Middle Accompsett Middle School
High Smithtown High School-West

Additional Information

Date Listed August 21st, 2026
Days on Market 31
Taxes $21,727
Short Sale No
RE / Bank Owned No

Listing Details

OfficeCentury 21 Parisi Realty
Contact Info631-669-3900

Listing Map

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