442 MIDWAY ISLAND

$ 3,495,000

Overview

  • Updated On:
  • August 9, 2026
  • 5 Bedrooms
  • 4.5 Bathrooms
  • 4,039 ft2 Area Size
  • TB8399954 MLS ID

Description

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.

Listing updated: August 9, 2026 at 06:05pm

Listed by Realtor: Prudy Cole

Listed by office:  CENTURY 21 BE3

Source: Stellar MLS

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

Property Address

Address: 442 MIDWAY ISLAND
State/County:
Zip: 33767
Country: US

Property Details

Property Id: 1972250
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
ContractStatusChangeDate: 2025-06-23
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
FoundationDetails: Slab,Stilt/On Piling
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
ListAgentAOR: Suncoast Tampa
ListAgentEmail: prudycole@c21be.com
ListAgentFullName: Prudy Cole
ListAgentKey: 6c5bc068d757f5abc06f73632f90436b
ListAgentMlsId: 265579133
ListAgentPreferredPhone: 863-397-7305
ListOfficeKey: 3f18f10f1ec34ba24bc47e1715fc9529
ListOfficeMlsId: 261017922
ListOfficeName: CENTURY 21 BE3
ListOfficePhone: 727-596-1811
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
Last Modified: August 9, 2026 at 06:05pm
OnMarketDate: 2025-06-23
OriginalEntryTimestamp: June 23, 2025 at 07:16pm
OriginalListPrice: 4250000
OriginatingSystemKey: stellar
OriginatingSystemName: Stellar MLS
Ownership: Fee Simple
ParcelNumber: 082915433440000600
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
PriceChangeTimestamp: May 28, 2026 at 05:27pm
PropertyCondition: Completed
RoadFrontageType: Street Dead-End
RoadSurfaceType: Asphalt
Roof: Metal
Sewer: Public Sewer
SourceSystemKey: 762864906
SpecialListingConditions: None
StateOrProvince: FL
StatusChangeTimestamp: January 2, 2026 at 02:26pm
StoriesTotal: 3
StreetName: MIDWAY
StreetNumber: 442
StreetNumberNumeric: 442
StreetSuffix: ISLAND
TaxAnnualAmount: 19718
TaxBookNumber: 47-62
TaxLegalDescription: ISLAND ESTATES OF CLEARWATER UNIT 3 LOT 60
TaxLot: 60
TaxYear: 2024
Utilities: Public,Street Lights
WaterSource: Public
WaterfrontFeatures: Intracoastal Waterway
WindowFeatures: Storm Window(s)
YearBuilt: 2008

Virtual Tour

Payment Calculator

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

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