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For Sale

135 Oakside Drive Smithtown, NY 11787

$1,325,000

Listed August 21, 2026, 33 days ago

Listing courtesy of Richard Parisi C2EX, Century 21 Parisi Realty MLS #KEY1041795

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  • 4Bedrooms
  • 3.5Bathrooms
  • 3,000Square feet
  • $442Per square foot
  • 1968Year built

About this home

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 equestrian living .As you approach via the impressive 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, views of the surrounding  woodlands at every turn, combining sophisticated indoor living and the serene outdoors.  A private, self-contained 3 room maid or guest suite complete with its own bath for visitors or multi-generational living. The Horse Facilities: The property features a dedicated equestrian setup including an intimate,  functional small barn and an adjacent tack room with views of the Nissequogue River landscape. This is more than a home; it is an exceptional legacy property offering  seclusion, natural splendor, and timeless craftsmanship. Arrange a showing today.

Description supplied by the listing broker.

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)

Property details

Interior

Additional rooms
Home Office,Library/Den
Flooring
Carpet, Ceramic Tile, Laminate, Tile
Levels
Tri-Level
Fireplace
Yes
Fireplaces
1
Appliances
Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Microwave, Refrigerator, Washer, Oil Water Heater

Systems and utilities

Heating
Hot Air, Oil
Cooling
Central Air, Ductwork
Utilities
Cable Available, Electricity Connected, Phone Available, Propane, Water Connected
Water
Public

Exterior and lot

Construction
Block, Frame, Stone, Wood Siding
Architectural style
Chalet
Condition
Updated/Remodeled
Parking
Driveway, Garage, Garage Door Opener, Heated Garage, Off Street, Private
Private pool
Yes
Pool
Fenced, Outdoor Pool, Pool Cover, Pool/Spa Combo, Solar Cover
Fencing
Wood
Patio and porch
Covered, Deck, Patio, Terrace
Horse property
Yes

Tax and legal

Parcel number
0800-035-00-04-00-025-000
Listing agreement
Exclusive Agency

Property details supplied by the listing broker through OneKey MLS, as of September 23, 2026. Fields not shown were not supplied and should not be read as absent from the property.

This listing

  1. September 21, 2026 Reduced to $1,325,000 from $1,350,000
  2. September 12, 2026 Reduced to $1,350,000 from $1,399,000
  3. September 8, 2026 Reduced to $1,399,000 from $1,499,000
  4. August 28, 2026 Reduced to $1,499,000 from $1,750,000

Location

135 Oakside Drive, Smithtown, NY 11787

About Smithtown

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