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60 Winston DriveSmithtown, NY 11787

For Sale

$1,795,000

Smart Buyer Rebate $17,950

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 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.

Listed by Derek J. Greene

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Greene Realty Group

·

860-560-1006

Last updated June 14, 2026

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Source: OneKey #1012725

Listing Facts

  • TypeSingle-family
  • NeighborhoodSmithtown
  • Bedrooms7
  • Bathrooms6
  • Days on Prevu3
  • Taxes$24,377/year
  • Size6,087 sqft
  • Price per sqft$295

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

06/13/2026
Listed by Greene Realty Group
$1,795,000

Property Details for 60 Winston Drive

Exterior

Construction

  • Property Condition: Updated/Remodeled
  • Window Features: Bay Window(s), Blinds, Casement, Double Pane Windows, Insulated Windows, Oversized Windows, Screens, Skylight(s), Wall Of Windows
  • Year Built: 1963
  • Architectural Style: Contemporary, Estate
  • Construction Materials: Vinyl Siding
  • Exterior Features: Balcony, Lighting, Mailbox, Rain Gutters, Tennis Court(s)

Features

  • Direction Faces: East
  • Fencing: Back Yard, Chain Link, Fenced, Full, Vinyl, Wood
  • Patio And Porch Features: Deck
  • Pool Features: Diving Board, Fenced, In Ground, Outdoor Pool, Pool Cover, Vinyl
  • Pool Private: Yes

Measurements

  • Building Area Units: Square Feet
  • Lot Features: Back Yard, Cleared, Front Yard, Landscaped, Level, Near School, Near Shops, Private, Sprinklers In Front, Sprinklers In Rear, Views
  • Lot Size Acres: 1.06
  • Lot Size Square Feet: 46,174

Financial

Taxes

  • Parcel Number: 0800-123-00-04-00-017-000
  • Tax Annual Amount: $24,377.00
  • Tax Assessed Value: $11,460.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Exhaust Fan, Freezer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
  • Fireplace Features: Gas, Living Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Carpet, Ceramic Tile, Hardwood, Tile, Wood
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chandelier, Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, In-Law Floorplan, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Pantry, Primary Bathroom, Storage, Tile Counters, Walk Through Kitchen, Walk-In Closet(s), Washer/Dryer Hookup

Measurements

  • Living Area: 6,087
  • Living Area Source: Appraiser

Rooms

  • Bathrooms Full: 5
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 6
  • Bedrooms Total: 7
  • Rooms Total: 17

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes
  • Parking Features: Driveway, Garage, Garage Door Opener
  • Parking Total: 9

Schools

Elementary School

  • Elementary School: Pines Elementary School
  • Elementary School District: Hauppauge

High School

  • High School: Hauppauge High School
  • High School District: Hauppauge

Middle or Junior School

  • Middle Or Junior School: Hauppauge Middle School
  • Middle Or Junior School District: Hauppauge

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Baseboard, Hot Water, Oil
  • Laundry Features: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
  • Other Equipment: Irrigation Equipment, Pool Equip/Cover
  • Sewer: Cesspool
  • Utilities: Cable Available, Electricity Connected, Phone Connected, Trash Collection Public, Water Connected
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 7 bedrooms and 6 bathrooms in this single-family home at 60 Winston Drive.

What schools are nearby to 60 Winston Drive?

Nearby schools include the Pines Elementary School, Hauppauge Middle School, and Hauppauge High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 60 Winston Drive.

What are the annual taxes for 60 Winston Drive?

Annual taxes for this single-family home are estimated at $24,377.

How does 60 Winston Drive compare to other single-family homes in Smithtown?

This single-family home is listed 46% above the average price for single-family homes in Smithtown and has been on the market for 49 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 6,087 sqft.

60 Winston Drive is a 7-bedroom, 6-bath single-family home for sale in Smithtown NY 11787. Available on Prevu for 3 days at $1,795,000. This property features 6,087 square feet of living space, located in Smithtown. The median listing price for single-family homes in this area is $889,000. Nearby schools include Pines Elementary School, Hauppauge Middle School, and Hauppauge High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. Explore more single-family home listings in Suffolk County.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey™ MLS. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. Information Copyright 2026, OneKey™ MLS. All Rights Reserved.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.