• $3,950,000List Price
  • ActiveStatus
  • 100Number of Photos
  • 27.983239Latitude
  • 442 Midway IslandAddress
  • Midway IslandStreet
  • Clearwater BeachTown
  • FLState
  • 33767Zip
  • PinellasCounty
  • ResidentialProperty Type
  • TB8399954MLS Number
  • 5Bedrooms
  • 4Full Bath
  • 1Half Baths
  • 4,039Square Feet
  • 2008Year Built
  • 0.26Acreage

Listing Tools

One-of-a-Kind Island Estates Waterfront Masterpiece Welcome to an extraordinary waterfront retreat in the prestigious and highly sought-after community of Island Estates. Perfectly positioned at the end of the island on deep, open water, this exceptional residence offers 150 feet of pristine water frontage, providing the ultimate haven for boating enthusiasts - with space to accommodate any size vessel you desire. From the moment you arrive, the home's curb appeal is undeniable. A welcoming driveway, beautifully manicured landscaping, and graceful palm trees create a peaceful, tropical setting. Thoughtfully constructed with superior craftsmanship, this elevated Key West-style home rests atop nearly 50 reinforced pilings, offering lasting strength, security, and peace of mind against Florida's coastal storms. Spanning over 9,000 total square feet (4,000 square feet under air) across three thoughtfully designed levels, this property offers versatility, luxury, and space in abundance. The ground level includes two separate garages and an enormous storage area - ideal for multiple uses such as a gym, workshop, hobby space, or simply an incredible amount of storage for all your toys and gear. On the main living level, a wrap-around veranda welcomes you to relax and take in the endless water views. Step inside to soaring 20-foot ceilings, walls of windows (nearly 100 in total!) and gleaming Brazilian cherry wood floors that create warmth and elegance throughout the space. Wherever you stand, you're greeted by breathtaking water vistas - it's impossible not to be inspired by the beauty surrounding you. The heart of the home is the expansive, open-concept great room and gourmet kitchen, designed for both entertaining and everyday living. A beautifully appointed wet bar makes hosting friends and family effortless. For more formal gatherings, enjoy the elegant dining room or unwind in the charming sitting room/parlor. A private guest suite with its own en-suite bath completes this level, offering comfort and privacy for visitors. Upstairs, the primary suite is a true retreat - complete with vaulted cathedral ceilings, a private balcony overlooking the water, and a recently renovated, spa-inspired en-suite bathroom featuring luxurious finishes, an oversized walk-in shower, soaking tub, and dual vanities. The custom wrap-around closet offers exceptional storage and organization. Three additional bedrooms, each with either an en-suite or Jack-and-Jill bathroom, ensure that every family member or guest has their own private haven- and each has a balcony with captivating water views. And for the grand finale - ascend to the one-of-a-kind rooftop sun deck, thoughtfully engineered to support a hot tub if desired. From this exclusive perch, enjoy unmatched 360-degree views of Island Estates, the Intracoastal Waterway, and Clearwater Beach - truly the best view in town. Whether savoring sunsets, hosting gatherings, or simply soaking in the peaceful surroundings, this private rooftop escape is unforgettable. With deep water access, robust construction, designer finishes, endless storage potential, and panoramic views from every corner of the home, this Island Estates masterpiece is a rare and exceptional offering - where luxury, comfort, and coastal living come together in perfect harmony.

Location

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of May 16, 2026 3:31 PM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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