442 MIDWAY ISLAND CLEARWATER BEACH FL 33767 MLS #TB8399954

442 MIDWAY ISLAND
CLEARWATER BEACH, FL, 33767
$3,950,000
5 Beds
4.5 Baths
4,039 SqFt
0.26 Acres
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MLS #TB8399954 image #0
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.

Property Details

Price:
$3,950,000
MLS #:
TB8399954
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLAND ESTATES OF CLEARWATER
Neighborhood:
33767clearwaterclearwaterbeach
Listed Date:
Jun 23, 2025
Finished Sq Ft:
4,039
Total Sq Ft:
9,004
Lot Size:
11,400 sqft / 0.26 acres (approx)
Year Built:
2008
Waterfront33767 – Clearwater/clearwater Beach33767clearwaterclearwaterbeachIsland Estates Of ClearwaterTo Be Verified.1 MonthPets Allowed

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Schools

Interior

Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Gas Water Heater, Range, Range Hood, Tankless Water Heater, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Porcelain Tile, Hardwood
Heating
Central, Electric, Exhaust Fan, Heat Pump
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, High Ceilings, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
Laundry Features
Inside, Laundry Chute, Laundry Room
Levels
Three Or More

Exterior

Architectural Style
Elevated, Key West
Attached Garage YN
1
Construction Materials
Block, Cement Siding, Wood Frame
Covered Spaces
2
Direction Faces
South
Exterior Features
Balcony, French Doors, Irrigation System, Outdoor Shower, Private Mailbox, Sprinkler Metered
Fencing
Other
Garage Spaces
2
Lot Features
Cul-De-Sac, City Lot, Irregular Lot, Landscaped, Oversized Lot, Street Dead-End
Parking Features
Garage Door Opener
Patio And Porch Features
Covered, Front Porch, Patio, Porch, Rear Porch, Side Porch, Wrap Around
Roof
Metal
Waterfront Features
Intracoastal Waterway
Window Features
Storm Window(s)

Financial

Tax Year
2024
Taxes
$19,718

Map

Community

Subdivisions in CLEARWATER BEACH

Market Summary

Current real estate data for Single Family in CLEARWATER BEACH as of May 05, 2026
100
Single Family Listed
327
Avg DOM
898
Avg $ / SqFt
$1,835,181
Avg List Price

Property Summary

    Located in the ISLAND ESTATES OF CLEARWATER subdivision, 442 MIDWAY ISLAND CLEARWATER BEACH FL is a Single Family for sale in CLEARWATER BEACH, FL, 33767. It is listed for $3,950,000 and features 5 beds, 5 baths, and has approximately 4,039 square feet of living space, and was originally constructed in 2008. The current price per square foot is $978. The average price per square foot for Single Family listings in CLEARWATER BEACH is $898. The average listing price for Single Family in CLEARWATER BEACH is $1,835,181. To schedule a showing of MLS#tb8399954 at 442 MIDWAY ISLAND in CLEARWATER BEACH, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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