$3,495,000
442 Midway Island
Clearwater Beach, FL 33767
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history337 days on market
- Status: ActiveJan 2, 2026
- Listed$4,250,000Jun 23, 2025
- Price reduced$3,495,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 337
- Subdivision
- Island Estates Of Clearwater
- County
- Pinellas
- Year built
- 2008
- Living area
- 4,039 sq ft
- Price/sq ft
- $865
- Building area
- 9,004 sq ft (Public Records)
- Lot size
- 11,400 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- AE (12103C0102H)
- Garage
- 2 spaces
- Annual taxes
- $19,718 (2024)
- Parcel #
- 08-29-15-43344-000-0600
- MLS #
- TB8399954
Interior Details
- Bedrooms
- 5
- Full bathrooms
- 4
- Half bathrooms
- 1
- Flooring
- Tile, Wood
- Appliances
- Bar Fridge, Built-In Oven, Dishwasher, Disposal, Gas Water Heater, Range, Range Hood, Tankless Water Heater, Wine Refrigerator
- Interior features
- Cathedral Ceiling(s), Ceiling Fans(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
- Inside, Laundry Chute, Laundry Room
- Stories / Levels
- Three Or More
- Direction faces
- South
Heating & Cooling
- Heating
- Central, Electric, Exhaust Fan, Heat Pump
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Garage Door Opener
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1 Month
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- To be verified.
- Approval process
- To be verified.
Exterior & Construction
- Exterior features
- Balcony, French Doors, Outdoor Shower, Private Mailbox, Sprinkler Metered
- Construction materials
- Block, Cement Siding, Frame
- Roof
- Metal
- Foundation
- Slab, Stilt/On Piling
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Public
Community
- Pets allowed
- Yes
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | Second | 12.6x19 |
| Great Room | Second | 27.6x17.2 |
| Primary Bedroom | Third | 14.6x17.7 |
| Foyer | Second | 15.5x13.5 |
| Dining Room | Second | 17.6x13.6 |
| Living Room | Second | 12.9x11.1 |
| Laundry | Second | 9.5x8.1 |
| Bedroom 2 | Second | 14.9x11.6 |
| Bedroom 3 | Third | 14.1x10.9 |
| Bedroom 4 | Third | 13.8x10.7 |
| Bedroom 5 | Third | 14.9x10.9 |
| Office | Third | 11.1x11.1 |
Listing Details
- Listing date
- 2025-06-23
- On market date
- 2025-06-23
- Original list price
- $4,250,000
- Occupant type
- Owner
- MLS area
- 33767 - Clearwater/Clearwater Beach
- Listing AOR
- Orlando Regional
- Status changed
- 2026-01-02
- Tax legal description
- ISLAND ESTATES OF CLEARWATER UNIT 3 LOT 60
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of May 28, 2026 at 1:28 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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