New Listing - 06/13/2026 Price Reduced 8.36%

$1,645,000 ($270.25 per sqft)

Est. Mortgage $7,996/mo *

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Price History

$1,795,000
6/13/2026

$1,645,000
6/19/2026


60 Winston Drive, Smithtown, NY, 11787

60 Winston Drive, Smithtown, NY, 11787

17 rooms

7 beds

5 Full / 1 Half baths

1963

Contemporary, Estate

6,087 sqft

FSBO. At $270 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 under roof, 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.


Status:

Active

Type:

Single-family residential

Laundry Remarks:

Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup

Garage:

2-car

Heating:

Baseboard, Hot Water, Oil

Cooling:

Central Air

Parking:

9-car, Driveway, Garage, Garage Door Opener

Acreage:

1.06

Est. Taxes:

$24,377

Assessment

$11,460

Construction

Vinyl Siding

Utilities

Cable Available, Electricity Connected, Phone Connected, Trash Collection Public, Water Connected

Lot Description:

Back Yard, Cleared, Front Yard, Landscaped, Level, Near School, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear, Views

Elementary School:

Pines Elementary School

Middle School:

Hauppauge Middle School

High School:

Hauppauge High School

School District:

Hauppauge

Days on Market:

6

Appliances:

Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Exhaust Fan, Freezer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer

Pool:

Diving Board, Fenced, In Ground, Outdoor Pool, Pool Cover, Vinyl

MLS #:

1012725


Community Info

School Info

Walk Score

Mass Transit

Yelp



Listing courtesy of Greene Realty Group 860-560-1006