442 MIDWAY ISLAND, Clearwater Beach, Pinellas, Residential

442 MIDWAY ISLAND

MLS# TB8399954478 days on marketUpdated October 16, 2026 2:10 pm

$ 865 / sqft

$ 3,495,000

Reduced from $ 4,250,000

Overview

UpdatedOctober 16, 2026 2:10 pm
MLS #TB8399954
Bedrooms5
Bathrooms4.5
Size4,039 ft²
Year Built2008
Garage2

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.

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Interior

  • AppliancesBar Fridge, Built-In Oven, Dishwasher, Disposal, Gas Water Heater, Range, Range Hood, Tankless Water Heater, Wine Refrigerator
  • Bathrooms Full4
  • Bathrooms Half1
  • Bathrooms Total Integer5
  • Bedrooms Total5
  • CoolingCentral Air
  • CoolingYes
  • FlooringPorcelain Tile, Hardwood
  • FurnishedNegotiable
  • HeatingCentral, Electric, Exhaust Fan, Heat Pump
  • HeatingYes
  • Interior FeaturesCathedral 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 FeaturesInside, Laundry Chute, Laundry Room
  • LevelsThree Or More
  • Living Area4,039
  • Living Area SourcePublic Records
  • Living Area UnitsSquare Feet
  • Rooms Total12
  • Window FeaturesStorm Window(s)

Exterior

  • Attached GarageYes
  • Covered Spaces2
  • Direction FacesSouth
  • Exterior FeaturesBalcony, French Doors, Irrigation System, Outdoor Shower, Private Mailbox, Sprinkler Metered
  • FencingOther
  • Garage Spaces2
  • GarageYes
  • Lot FeaturesCul-De-Sac, City Lot, Irregular Lot, Landscaped, Oversized Lot, Street Dead-End
  • Lot Size Acres0
  • Lot Size Area11,400
  • Lot Size Dimensions113 x 120
  • Lot Size Square Feet11,400
  • Lot Size UnitsSquare Feet
  • Parking FeaturesGarage Door Opener
  • Patio And Porch FeaturesCovered, Front Porch, Patio, Porch, Rear Porch, Side Porch, Wrap Around
  • Road Frontage TypeStreet Dead-End
  • Road Surface TypeAsphalt
  • RoofMetal
  • Waterfront FeaturesIntracoastal Waterway

Structure

  • Architectural StyleElevated, Key West
  • Building Area Total9,004
  • Construction MaterialsBlock, Cement Siding, Wood Frame
  • Foundation DetailsSlab, Stilt/On Piling
  • Property ConditionCompleted
  • Stories Total3
  • Year Built2008

Utilities

  • SewerPublic Sewer
  • UtilitiesPublic, Street Lights
  • Water SourcePublic

Financial

  • Parcel Number082915433440000600
  • Pets AllowedYes
  • Tax Annual Amount19,718
  • Tax Block0
  • Tax Book Number47-62
  • Tax Legal DescriptionISLAND ESTATES OF CLEARWATER UNIT 3 LOT 60
  • Tax Lot60
  • Tax Year2024

Location

  • CountryUnited States
  • County Or ParishPinellas
  • DirectionsHwy 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.
  • Latitude28
  • Longitude-83
  • MLS Area Major33767 - Clearwater/Clearwater Beach
  • Postal Code33767
  • Street NameMIDWAY
  • Street Number442
  • Street Number Numeric442
  • Street SuffixISLAND
  • Subdivision NameISLAND ESTATES OF CLEARWATER
  • Unparsed Address442 MIDWAY ISLAND

Listing Info

  • Contract Status Change DateJune 23, 2025
  • Cumulative Days On Market478
  • Days On Market478
  • Lease ConsideredYes
  • List AOROrlando Regional
  • List Agent AORSuncoast Tampa
  • List Agent Emailprudycole@c21be.com
  • List Agent Full NamePrudy Cole
  • List Agent Key6c5bc068d757f5abc06f73632f90436b
  • List Agent MLS ID265579133
  • List Agent Preferred Phone863-397-7305
  • List Office Key3f18f10f1ec34ba24bc47e1715fc9529
  • List Office MLS ID261017922
  • List Office NameCENTURY 21 BE3
  • List Office Phone727-596-1811
  • List Price3,495,000
  • Listing Contract DateJune 23, 2025
  • Listing IDTB8399954
  • Listing Key16096b37c34d7a4861bc3819fd5f49bf
  • Listing TermsCash, Conventional, VA Loan
  • MLS StatusActive
  • Modification TimestampOctober 16, 2026
  • On Market DateJune 23, 2025
  • Original Entry TimestampJune 23, 2025
  • Original List Price4,250,000
  • Originating System Keystellar
  • Originating System NameStellar MLS
  • OwnershipFee Simple
  • Photos Change TimestampJanuary 2, 2026
  • Photos Count100
  • Price Change TimestampMay 28, 2026
  • Source System Key762864906
  • Special Listing ConditionsNone
  • Status Change TimestampJanuary 2, 2026

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