Niles Harrison Pfeiffer

Niles Harrison Pfeiffer Central Florida REALTOR®

$4,250,000.00
442 MIDWAY ISLAND, CLEARWATER BEACH, FL - 33767
5 beds
4.5 baths
4,039 sqft
$4,250,000.00
442 MIDWAY ISLAND, CLEARWATER BEACH, FL - 33767
Niles Harrison Pfeiffer
$4,250,000.00
5 beds
4.5 baths
4,039 sqft
442 MIDWAY ISLAND, CLEARWATER BEACH, FL - 33767
For Sale
Photo 1
  • Built in 2008
  • 2 garage spaces
  • $1,052.24/sqft
  • Lot size: 11,400 sqft
  • 191 days on market

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.

  • 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.
  • County: Pinellas
  • Geo subdivision: ISLAND ESTATES OF CLEARWATER

Features

Financial

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Niles Harrison Pfeiffer

Niles Harrison Pfeiffer

Central Florida REALTOR®

See also

For Sale
306 HARBOR DRIVE, INDIAN ROCKS BEACH, FL - 33785
$3,900,000.00
5 bds
4 ba
4,571 sqft
306 HARBOR DRIVE, INDIAN ROCKS BEACH, FL - 33785
For Sale
829 BRUCE AVENUE, CLEARWATER BEACH, FL - 33767
$4,200,000.00
5 bds
5.0 ba
7,261 sqft
829 BRUCE AVENUE, CLEARWATER BEACH, FL - 33767
For Sale
124 LEEWARD ISLAND, CLEARWATER BEACH, FL - 33767
$3,899,999.00
5 bds
4 ba
5,798 sqft
124 LEEWARD ISLAND, CLEARWATER BEACH, FL - 33767
Stellar MLS
  • Source: Stellar MLS
  • MLS #: TB8399954
Listing updated: January 2, 2026 at 2:29PM
Listing provided by: Prudy Cole, CENTURY 21 BE3
Last checked 1 hour ago
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