60 Winston Drive, Smithtown, NY 11787

$1,795,000

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… Read More 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. Read Less

Listing Courtesy of Greene Realty Group, 860-560-1006.

Listing Snapshot

Days Online

Last Updated

Jun 14, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

6,087

Year Built

1963

Property Tax

$24,377

MLS Number

1012725

30 Days Snapshot Of 11787

$713k

-30%

(avg) sold price

-6%

homes sold

-25%

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

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

Building

Area: 6087, Architecture: "Contemporary", "Estate", Construction Materials: "Vinyl Siding", Levels: "Two", Year Built: 1963, Effective Year built: 2010

Cooling

Details: "Central Air"

Exterior Features

Features: "Balcony", "Lighting", "Mailbox", "Rain Gutters", "Tennis Court(s)", Patio Features: "Deck"

Fence

Description: "Back Yard", "Chain Link", "Fenced", "Full", "Vinyl", "Wood"

Fireplaces

Total Fireplaces: 1

Floors

Flooring: "Carpet", "Ceramic Tile", "Hardwood", "Tile", "Wood"

Garage

Garage Spaces: 2

Heating

Heating: "Baseboard", "Hot Water", "Oil"

Laundry

Description: "Electric Dryer Hookup", "Inside", "Laundry Room", "Washer Hookup"

Lot

Features: "Back Yard", "Cleared", "Front Yard", "Landscaped", "Level", "Near School", "Near Shops", "Private", "Sprinklers In Front", "Sprinklers In Rear", "Views", Acres: 1.06

Parking

Parking Total: 9

Property

Description: "Irrigation Equipment", "Pool Equip/Cover"

Pool

Features: "Diving Board", "Fenced", "In Ground", "Outdoor Pool", "Pool Cover", "Vinyl", Private Pool

Utilities

Sewer: "Cesspool", Water Source: "Public", Utilities: "Cable Available", "Electricity Connected", "Phone Connected", "Trash Collection Public", "Water Connected"

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Debra A Chiappetta, Real Estate Broker

Debra A Chiappetta, Real Estate Broker