442 MIDWAY ISLAND | Clearwater Beach

$4,250,000 | 5 Beds | 5 Baths (4 Full, 1 Half) | 4,039 Sq. Ft.

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. StellarMLS TB8399954

Directions to property: Hwy 60 follow toward Clearwater Beach turn right onto Island Way then turn right onto Windward Passage and left onto Midway Island home is at the end of the cul de sac.

MLS Listing ID: 
StellarMLS TB8399954
Basic Property Information
Fields containing basic information about the property.
Property Type: 
Residential
Property Sub Type: 
Single Family Residence
Primary Market Area: 
Clearwater Beach
Address: 
442 MIDWAY ISLAND, Clearwater Beach, FL 33767, US
County: 
Pinellas
Community Information
Subdivision: 
ISLAND ESTATES OF CLEARWATER
Building Details
Details about the building on a property.
Architectural Style: 
Elevated
Year Built: 
2008
New Construction: 
0
Living Area: 
4,039
Interior: 
Cathedral Ceiling(s), Crown Molding, Open Floorplan, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
Construction
Construction Materials: 
Block, Cement Siding, Wood Frame
Foundation Details: 
Slab, Stilt/On Piling
Roof: 
Metal
Exterior Features: 
Balcony, French Doors, Irrigation System, Outdoor Shower, Sprinkler Metered
Porch: 
Covered, Front Porch, Patio, Porch, Rear Porch, Side Porch, Wrap Around
Room Details
Details about the rooms in the building.
Total Rooms: 
12
Total Bedrooms: 
5
Total Bathrooms: 
5
Total Full-Bathrooms: 
4
Total Half-Bathrooms: 
1
Utilities
Information about utilities available on the property.
Heating System: 
Central, Electric, Heat Pump
Cooling System: 
Central Air
Water Source: 
Public
Sewer: 
Public Sewer
Lot/Land Details
Details about the lots and land features included on the property.
Acres: 
0.26
Lot Size (Area): 
11,400
Lot Size (Dimensions): 
113 x 120
Waterfront: 
1
Water Body Category: 
Other
Lot Features
Parking Type: 
Garage Door Opener
Fence: 
Other
Public Record
Parcel Number: 
082915433440000600
Annual Tax: 
$19,718.00
Listing Dates
Dates involved in the transaction.
Listing Entry Date/Time: 
6/23/2025
Listing Participants
Participants (agents, offices, etc.) in the transaction.
Listing Agent Name: 
Prudy Cole
Listing Office Name: 
CENTURY 21 BE3