For Sale

Listed by Derek Greene from Greene Realty Group

Source: OneKey #1012725

60 Winston Drive, Smithtown, NY, 11787

$1,795,000

7
6
9
6087 sq. ft.
46174 sq. ft.

SingleFam

1 day on the market

What's around 60 Winston Drive

About this property

At $295 per square foot, this impressive contemporary is the best value in the Smithtown Pines! Set on a beautifully landscaped level 1.06-acre property in the desirable Hamlet of Smithtown Pines, this expansive 6,087 square foot, 17-room contemporary offers an exceptional blend of space, elegance and resort-style living. Featuring 7 bedrooms, 5.5 bathrooms, and a dedicated study, this home is thoughtfully designed to accommodate both everyday comfort and grand entertaining, including ideal accommodations for extended or multi-generational living. Inside you will find 5 inch red oak plank hardwood floors with a custom medallion, complemented by custom moldings and 7 inch baseboards throughout, as well as a mix of carpet and ceramic tile. The home boasts dual staircases and two luxurious primary bedroom suites, each with its own private bath. The magnificent living room features a custom marble gas fireplace, custom wainscoting, and oversized picture windows that flood the space with natural light. Additionally, there are 133 high hats, 3 skylights, and 9 ceiling fans that ensure the home is bright and comfortable all year-round. A grand eat-in kitchen with stainless steel appliances showcases striking Uba Tuba granite with a full 6 inch backsplash and ample cabinetry ideal for both everyday living and entertaining. The banquet-sized dining room offers panoramic views of the country club-style backyard, where you’ll find a 50 foot custom L-shaped vinyl in-ground pool, an oversized tennis court with a dedicated viewing deck, underground sprinklers and a serene rock pond with a built-in waterfall creating your own private retreat. Additional highlights include 58 double-pane Andersen windows, 3 Andersen sliding glass doors leading to multi-level decks, plus 3 exterior doors that enhance seamless indoor-outdoor flow. The lower level offers a separate 1,000 square foot guest wing with its own private entrance with a designated parking area that provides excellent flexibility for extended family, guests or potential home office use. With 16 closets, storage is abundant throughout and the home’s generous layout offers endless possibilities for customization. Brand new oil tank. Located in the award-winning Hauppauge School District and set within the highly sought- after Smithtown Pines, this custom home offers access to top-tier education while benefiting from Smithtown-area amenities and comparatively lower taxes. Conveniently situated near the Long Island Expressway and Northern State Parkway, this property combines privacy with accessibility giving the best of both worlds. This one-of-a-kind property delivers luxury living, unbeatable value and exceptional versatility in one extraordinary offering. Perfect for entertaining, extended family living, or creating your own private estate compound, this is a rare find and must be seen to be appreciated.

Looking for more information on 60 Winston Drive?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties for sale nearby

For Sale
$999,000
80 Mt Pleasant Rd
Smithtown NY 11787
7
3
2
Single-Family
Listing courtesy of Homes By Mara
For Sale
$5,899,000
Landing Meadow Rd
Smithtown NY 11787
7
6
4
Single-Family
Listing courtesy of Greene Realty Group

Other properties for sale by Greene Realty Group

For Sale
$1,999,999
124 Glenlawn Ave
Sea Cliff NY 11579
4
4
4
Single-Family
Listing courtesy of Greene Realty Group
For Sale
$2,175,000
589 Plank Road
Mount Tremper NY 12457
9
5
10
Duplex
Listing courtesy of Greene Realty Group
For Sale
$1,499,000
62-40 Cromwell Crescent
New York NY 11374
4
3
2
Single-Family
Listing courtesy of Greene Realty Group

Browse properties sold in nearby areas

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent