# 135 Oakside Drive, Smithtown, NY 11787 > **TL;DR:** 5bd/4ba single family, $1,298,000 ($393/sqft), built 1968, 3,300 sqft. > Pool, Fireplace, A/C, 2-car garage. Est. $6,942/mo. Listed 67 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,298,000 | | Price/sqft | $393 | | Bedrooms | 5 | | Bathrooms | 3 full, 1 half | | Square Feet | 3,300 | | Year Built | 1968 | | Lot Size | 70,567 sqft (1.62 acres) | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 67 | ## Why This Home Stands Out - **Pool** - Patio, Deck ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $6,563 | | Estimated Insurance | $379 | | **Total** | **$6,942** | ## Nearby Schools - **Elementary:** Dogwood Elementary School - **Middle:** Accompsett Middle School - **High:** Smithtown High School-West ## Key Amenities - Pool - Fireplace - A/C - 2-car garage ## Property Highlights - Built in 1968 - 1.62 acre lot - 6 parking spaces - Private pool - Fireplace ## Description ### Agent 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.(With 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. ## Location - **Address:** 135 Oakside Drive, Smithtown, NY 11787 - **County:** Suffolk County - **Neighborhood:** NISSEAQUOGUE OVERLOOK - **Coordinates:** 40.882695, -73.19764 - **Google Maps:** https://www.google.com/maps?q=40.882695,-73.19764 ## Listing Agent - **Name:** Richard Parisi C2EX - **Brokerage:** Century 21 Parisi Realty - **Broker Phone:** (631) 669-3900 x19 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/135-Oakside-Dr_Smithtown_NY_11787_M45654-81413?f=listhub&s=MLSLINY&m=1041795&c=propsimple) ## Photos ![135 Oakside Drive - Photo 1](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f477126681r.jpg) ![135 Oakside Drive - Photo 2](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1191652305r.jpg) ![135 Oakside Drive - Photo 3](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1151551991r.jpg) ![135 Oakside Drive - Photo 4](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f2368333774r.jpg) ![135 Oakside Drive - Photo 5](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f65641171r.jpg) ![135 Oakside Drive - Photo 6](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f54477852r.jpg) ![135 Oakside Drive - Photo 7](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f3437562689r.jpg) ![135 Oakside Drive - Photo 8](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1782433171r.jpg) ![135 Oakside Drive - Photo 9](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f935168527r.jpg) ![135 Oakside Drive - Photo 10](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f705059538r.jpg) ![135 Oakside Drive - Photo 11](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1664784087r.jpg) ![135 Oakside Drive - Photo 12](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1284970662r.jpg) ![135 Oakside Drive - Photo 13](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f3515077243r.jpg) ![135 Oakside Drive - Photo 14](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f640441579r.jpg) ![135 Oakside Drive - 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Photo 25](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f610745103r.jpg) ![135 Oakside Drive - Photo 26](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1538420617r.jpg) ![135 Oakside Drive - Photo 27](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1698056457r.jpg) ![135 Oakside Drive - Photo 28](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f2662856611r.jpg) ![135 Oakside Drive - Photo 29](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f12639809r.jpg) ![135 Oakside Drive - Photo 30](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f3831807811r.jpg) ![135 Oakside Drive - Photo 31](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f177077969r.jpg) ![135 Oakside Drive - Photo 32](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f2548372641r.jpg) ![135 Oakside Drive - Photo 33](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1709199237r.jpg) ![135 Oakside Drive - Photo 34](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f2144585624r.jpg) ![135 Oakside Drive - Photo 35](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f137454073r.jpg) ![135 Oakside Drive - Photo 36](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f731490728r.jpg) ![135 Oakside Drive - Photo 37](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f652471r.jpg) ![135 Oakside Drive - Photo 38](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f731490728r.jpg) ![135 Oakside Drive - Photo 39](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1899554564r.jpg) ![135 Oakside Drive - Photo 40](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f194687921r.jpg) ![135 Oakside Drive - Photo 41](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f2944946326r.jpg) ![135 Oakside Drive - Photo 42](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1698757975r.jpg) ![135 Oakside Drive - Photo 43](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f808340850r.jpg) ![135 Oakside Drive - Photo 44](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f784849688r.jpg) ![135 Oakside Drive - Photo 45](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1709199237r.jpg) ![135 Oakside Drive - Photo 46](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f3956680842r.jpg) ![135 Oakside Drive - Photo 47](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f954777305r.jpg) ![135 Oakside Drive - Photo 48](http://lh.rdcpix.com/63a5e869db442e00f215a991fd65f1b7l-f1421483502r.jpg) --- **MLS#:** 1041795 | **Updated:** 2026-10-24 **Source:** listhub *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.* [View on PropertySimple](https://staging.propertysimple.ai/listing/135-oakside-drive-smithtown-ny-11787-de903c5ef5004f9f8efc78a6c121eadd) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/135-oakside-drive-smithtown-ny-11787-de903c5ef5004f9f8efc78a6c121eadd#listing", "url": "https://staging.propertysimple.ai/listing/135-oakside-drive-smithtown-ny-11787-de903c5ef5004f9f8efc78a6c121eadd", "name": "135 Oakside Drive, Smithtown, NY 11787", "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. 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