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442 MIDWAY ISLAND, CLEARWATER BEACH, 33767

$3,495,000

5

Beds

4.5

Baths

4,039 ft2

Property Size

2008

Year Built

About The Property

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

Property Id: 106579
Price: $3,495,000
Property Size: 4,039 ft2
Property Lot Size: 0 ft2
Rooms: 12
Bedrooms: 5
Bathrooms: 4.5
ArchitecturalStyle: Elevated, Key West
BathroomsFull: 4
BathroomsHalf: 1
BuildingAreaTotal: 9004
ConstructionMaterials: Block, Cement Siding, Wood Frame
Cooling: Central Air
CoveredSpaces: 2
CumulativeDaysOnMarket: 410
DaysOnMarket: 410
DirectionFaces: South
Directions: 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.
Fencing: Other
Flooring: Porcelain Tile, Hardwood
Furnished: Negotiable
GarageSpaces: 2
Heating: Central, Electric, Exhaust Fan, Heat Pump
InternetAddressDisplayYN: 1
InternetEntireListingDisplayYN: 1
LaundryFeatures: Inside, Laundry Chute, Laundry Room
Levels: Three Or More
ListAOR: Orlando Regional
ListAgentFullName: Prudy Cole
ListOfficeName: CENTURY 21 BE3
ListingContractDate: 2025-06-23
ListingId: TB8399954
ListingTerms: Cash, Conventional, VA Loan
LivingAreaSource: Public Records
LivingAreaUnits: Square Feet
LotFeatures: Cul-De-Sac, City Lot, Irregular Lot, Landscaped, Oversized Lot, Street Dead-End
LotSizeArea: 11400
LotSizeDimensions: 113 x 120
LotSizeSquareFeet: 11400
LotSizeUnits: Square Feet
MLSAreaMajor: 33767 - Clearwater/Clearwater Beach
MlsStatus: Active
ModificationTimestamp: August 9, 2026 at 06:05pm
OnMarketDate: 2025-06-23
OriginalListPrice: 4250000
OriginatingSystemName: Stellar MLS
Ownership: Fee Simple
ParkingFeatures: Garage Door Opener
PatioAndPorchFeatures: Covered, Front Porch, Patio, Porch, Rear Porch, Side Porch, Wrap Around
PetsAllowed: Yes
PhotosChangeTimestamp: January 2, 2026 at 02:29pm
PhotosCount: 100
PostalCode: 33767
PropertyCondition: Completed
Roof: Metal
Sewer: Public Sewer
SpecialListingConditions: None
StateOrProvince: FL
StoriesTotal: 3
StreetName: MIDWAY
StreetNumber: 442
StreetSuffix: ISLAND
Utilities: Public, Street Lights
WaterSource: Public
WaterfrontFeatures: Intracoastal Waterway
YearBuilt: 2008

Amenities and Features

Outdoor Details
Garage Attached
Other Features
1
Balcony
Bar Fridge
Built-In Oven
Cathedral Ceiling(s)
Ceiling Fan(s)
Crown Molding
Dishwasher
Disposal
French Doors
Gas Water Heater
Has Cooling System
Has Garage
Has Heating System
Has Waterfront
High Ceilings
Irrigation System
Open Floorplan
Outdoor Shower
PrimaryBedroom Upstairs
Private Mailbox
Range
Range Hood
Solid Surface Counters
Solid Wood Cabinets
Sprinkler Metered
Stone Counters
Tankless Water Heater
Vaulted Ceiling(s)
Walk-In Closet(s)
Wet Bar
Wine Refrigerator

Map Location

Property Map

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Payment Calculator

$17,919.56
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 13,550.81

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Disclaimer

Property ID - | 106579

All listings featuring the Stellar MLS logo are provided by My Florida Regional MLS DBA Stellar MLS. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by MLS.

©2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved.

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Selinda Moore