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442 MIDWAY ISLAND

House For Sale
$3,495,000

BTC: 54.60937500

ETH: 2,001.71821306

-$755K (2026/05/28)
345 days
Waterfront
5 bds
4 ba
4,039 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Garage Door Opener
Year Built:
2008
Lot:
0.26 Acres
Heating:
Central / Electric / Exhaust Fan / Heat Pump
Price/sqft:
$865
Cooling:
Central Air
HOA:
No Data

Valuation

Our model vs. what's actually selling nearby.
Estimate
$2,100,000
$885K – $4.3M
Confidence Low
List vs. estimate
$1.4M above estimate
List $3,495,000 · +66.4%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$865
+40.0% vs. city median $617
Based on
7 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$19,718
2024
Waterfront
Intracoastal Waterway
Garage
2 car garage
Furnished
Negotiable
Pets
Allowed
All facts and features
  • Flooring

    • Porcelain Tile

    • Hardwood

    Heating

    • Central

    • Electric

    • Exhaust Fan

    • Heat Pump

    Cooling

    • Central Air

    Appliances

    • Bar Fridge

    • Built-In Oven

    • Dishwasher

    • Disposal

    • Gas Water Heater

    • Range

    • Range Hood

    • Tankless Water Heater

    • Wine Refrigerator

    Other interior features

    • Cathedral 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

    Bedrooms and bathrooms

    • Bedrooms: 5

    • Bathrooms: 1

    • Full bathrooms: 4

  • Parking

    • Garage Door Opener

    Property

    • Levels: Three Or More

    • Exterior Features: Balcony / French Doors / Irrigation System / Outdoor Shower / Private Mailbox / Sprinkler Metered

    Lot

    • Lot: 0.26 Acres

    Other Property Information

    • Parcel Number: 082915433440000600

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • Public

    • Street Lights

  • Other financial information

    • Annual tax amount: $19,718

  • Source details

    • MLS ID: TB8399954

    Other facts

    • Construction Materials: Block / Cement Siding / Wood Frame

    • Foundation Details: Slab / Stilt/On Piling

    • Laundry Features: Inside / Laundry Chute / Laundry Room

    • Lot Features: Cul-De-Sac / City Lot / Irregular Lot / Landscaped / Oversized Lot / Street Dead-End

    • Patio And Porch Features: Covered / Front Porch / Patio / Porch / Rear Porch / Side Porch / Wrap Around

    • Window Features: Storm Window(s)

    • Direction Faces: South

    • Architectural Style: Elevated / Key West

    • Waterfront: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 4039

    • Water Source: Public

    • Lot Size Dimensions: 113 x 120

    • Subdivision Name: ISLAND ESTATES OF CLEARWATER

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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: CENTURY 21 BE3