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$4,250,000
New Listing

442 MIDWAY ISLAND
CLEARWATER BEACH, FL 33767

For Sale|Single Family Residence|Active
5
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
4,039
SqFt
$1,052
/SqFt
2008
Built
Subdivision:
ISLAND ESTATES OF CLEARWATER
County:
Pinellas
Call Now: (561) 935-3331
Is this the listing for you? We can help make it yours.
(561) 935-3331
442 MIDWAY ISLAND442 MIDWAY ISLAND442 MIDWAY ISLAND442 MIDWAY ISLAND
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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.

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Listing Snapshot
Price 
$4,250,000
Days On Site 
0 Days
Bedrooms 
5
Inside Area (SqFt) 
4,039 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
0.26 Acres
Year Built 
2008
MLS® Number 
TB8399954
Status 
Active
Property Tax 
$19,718
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
2 hours agoListing updated with changes from the MLS®
18 hours agoListing first seen on site
General Features
Acres 
0.26
Attached Garage 
Yes
Direction Faces 
South
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Number Of Stories 
3
Parking 
Garage Door OpenerAttached
Pets 
Yes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
9004
Stories 
Three Or More
Style 
ElevatedKey West
Water Source 
Public
Interior Features
Appliances 
Bar FridgeDishwasherDisposalGas Water HeaterRangeRange HoodTankless Water HeaterWine Refrigerator
Cooling 
Central Air
Flooring 
TileWood
Furnished 
Negotiable
Heating 
CentralElectricExhaust FanHeat Pump
Interior 
Cathedral Ceiling(s)Crown MoldingHigh CeilingsOpen FloorplanStone CountersVaulted Ceiling(s)Walk-In Closet(s)Wet Bar
Laundry Features 
InsideLaundry ChuteLaundry Room
Window Features 
Storm Window(s)
Bedroom 2 
Dimensions - 14.9x11.6Level - Second
Bedroom 3 
Dimensions - 14.1x10.9Level - Third
Bedroom 4 
Dimensions - 13.8x10.7Level - Third
Bedroom 5 
Dimensions - 14.9x10.9Level - Third
Dining Room 
Dimensions - 17.6x13.6Level - Second
Foyer 
Dimensions - 15.5x13.5Level - Second
Great Room 
Dimensions - 27.6x17.2Level - Second
Kitchen 
Dimensions - 12.6x19Level - SecondFeatures - Granite Counters
Laundry 
Dimensions - 9.5x8.1Level - Second
Living Room 
Dimensions - 12.9x11.1Level - Second
Master Bedroom 
Dimensions - 14.6x17.7Level - Third
Office 
Dimensions - 11.1x11.1Level - Third
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Exterior Features
Construction Details 
BlockCement SidingFrame
Exterior 
BalconyOutdoor ShowerDock
Fencing 
Other
Lot Features 
Cul-De-SacIrregular LotLandscapedWaterfront
Patio And Porch 
CoveredFront PorchPatioPorchRear PorchSide PorchWrap Around
Roof 
Metal
View 
Water
Waterfront 
Yes
Waterview 
Water
Windows/Doors 
Storm Window(s)
Community Features
Community Features 
Street Lights
Financing Terms Available 
CashConventionalVA Loan
MLS Area 
33767 - Clearwater/Clearwater Beach
Roads 
Asphalt
Township 
29
Listing courtesy of CENTURY 21 BE3 8633977305



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2025, Stellar MLS.
Last checked: 2025-06-24 08:41 AM EDT

Neighborhood & Commute
Source: Walkscore
Community information and market data Powered by ATTOM Data Solutions. Copyright ©2019 ATTOM Data Solutions. Information is deemed reliable but not guaranteed.
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