About This Home

This 5-bedroom, 4-bathroom single family at 135 Oakside Drive in Smithtown, NY is listed for $1,298,000 ($393 per sqft). Built in 1968, the home offers 3,300 sqft of living space on a 1.62 acres lot.

Key Features

  • Built in 1968
  • 1.62 acre lot
  • 6 parking spaces
  • Private pool
  • Fireplace

Property Details

3 full, 1 half
2-car garage
1968

Amenities

PoolFireplaceA/C
Listing Description

North Smithtown, Nisseaquogue Overlook Section 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.

Step inside to a light-filled interior defined by handcrafted vaulted wood ceilings and natural stone. The Anderson windows frame sweeping, 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 for multi-generational living.(Wi

th Mother daughter permit from the town) 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.

Monthly Cost Estimate

$6,942/mo

20% down · 6.5% · 30 years

Principal$939
Interest$5,625
Insurance$379

Estimates only. Actual payments may vary.

Location

135 Oakside Drive

Smithtown, NY 11787

NISSEAQUOGUE OVERLOOK

Features & Amenities

Interior Features

First Floor Full BathBreakfast BarBuilt-in FeaturesCathedral Ceiling(s)Ceiling Fan(s)Double VanityEat-in KitchenEntrance FoyerFormal DiningGranite CountersHigh CeilingsIn-Law FloorplanNatural WoodworkOpen KitchenPantryPrimary BathroomRecessed LightingSoaking TubStone CountersTray Ceiling(s)Walk-In Closet(s)Washer/Dryer Hookup

Property Details

Flooring

Tile - CeramicCarpetLaminateTile

Construction

Block Frame Stone Wood Siding

Pool Features

Pool

Outdoor Features

PatioDeck

Parking

OpenGarageDrivewayOff Street

Heating

Oil

Cooling

Central Air

Appliances

Convection OvenDishwasherDryerElectric CooktopElectric OvenElectric RangeMicrowaveRefrigeratorWasherOil Water Heater

Questions & Answers

This 5-bedroom, 4-bathroom single family at 135 Oakside Drive is listed at $1,298,000 ($393/sqft). The estimated monthly payment is $6,942 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1968, 1.62 acre lot, 6 parking spaces, Private pool, Fireplace. Interior Features: First Floor Full Bath, Breakfast Bar, Built-in Features.

This property is listed by Richard Parisi C2EX.

RC

Richard Parisi C2EX

Agent at Century 21 Parisi Realty

Listed by Century 21 Parisi Realty · Broker phone: (631) 669-3900 x19 · View on Broker Site · Broker website

MLS# 1041795· Source: OneKey MLS· 66 days on PropertySimple

Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

135 Oakside Drive, Smithtown, NY 11787

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