For Sale
3D Tour3D Tour
Single family home for sale at 442 Midway Is, Clearwater Beach, FL 33767 | MLS# TB8399954 | Listing updated on 2026-10-17
Photo 1 of Single family home for sale at 442 Midway Is, Clearwater Beach, FL 33767 | MLS# TB8399954 | Listing updated on 2026-10-17
Photo 2 of Single family home for sale at 442 Midway Is, Clearwater Beach, FL 33767 | MLS# TB8399954 | Listing updated on 2026-10-17
Photo 3 of Single family home for sale at 442 Midway Is, Clearwater Beach, FL 33767 | MLS# TB8399954 | Listing updated on 2026-10-17
Photo 4 of Single family home for sale at 442 Midway Is, Clearwater Beach, FL 33767 | MLS# TB8399954 | Listing updated on 2026-10-17
96+
Beds Icon

Virtual Tour

Beds Icon

Street View

$3,495,000

Monthly Est:$17,396

  • Beds Icon5 Beds
  • Beds Icon
    5 Baths
  • Beds Icon4,039sqft

442 Midway Is, Clearwater Beach, FL 33767

$17,396/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2008

  • $-- HOA

  • 11,400 sqft lot

  • $865/sq.ft

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.

  • Houzeo last checked: 13 minutes ago
  • Listing updated: October 17, 2026 at 5:05 pm
  • Listing Provided by: Prudy Cole (863) 397-7305 | CENTURY 21 BE3 (727) 596-1811
  • Source: Stellar MLS-FL as distributed by MLS GRID | MLS#: TB8399954 Stellar MLS-FL as distributed by MLS GRID

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    3

  • County

    Pinellas County

  • City

    Clearwater

  • Neighborhood

    Clearwater Beach

  • Year Built

    2008

  • HOA Fees

    -

  • Finished Area

    4,039 sqft

  • Lot Size

    11,400 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    TB8399954

  • MLS Status

    Active

  • Days on Market

    504

  • Cumulative Days on Market

    479

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 5

  • Kitchen

    Level: Second

    Area: 239.40 Square Feet

    Dimensions: 12.6x19

  • Great Room

    Level: Second

    Area: 474.72 Square Feet

    Dimensions: 27.6x17.2

  • Primary Bedroom

    Level: Third

    Area: 258.42 Square Feet

    Dimensions: 14.6x17.7

  • Foyer

    Level: Second

    Area: 209.25 Square Feet

    Dimensions: 15.5x13.5

  • Dining Room

    Level: Second

    Area: 239.36 Square Feet

    Dimensions: 17.6x13.6

  • Living Room

    Level: Second

    Area: 143.19 Square Feet

    Dimensions: 12.9x11.1

  • Laundry

    Level: Second

    Area: 76.95 Square Feet

    Dimensions: 9.5x8.1

  • Bedroom 2

    Level: Second

    Area: 172.84 Square Feet

    Dimensions: 14.9x11.6

  • Bedroom 3

    Level: Third

    Area: 153.69 Square Feet

    Dimensions: 14.1x10.9

  • Bedroom 4

    Level: Third

    Area: 147.66 Square Feet

    Dimensions: 13.8x10.7

  • Bedroom 5

    Level: Third

    Area: 162.41 Square Feet

    Dimensions: 14.9x10.9

  • Office

    Level: Third

    Area: 123.21 Square Feet

    Dimensions: 11.1x11.1

Interior

  • Window Features

    Storm Window(s)

  • Flooring

    Tile, Wood

  • Heating

    Central, Electric, Exhaust Fan, Heat Pump

  • Cooling

    Central Air

  • Sewer

    Public Sewer

  • Appliances

    Bar Fridge, Built In Oven, Dishwasher, Disposal, Gas Water Heater, Range, Range Hood, Tankless Water Heater, Wine Refrigerator

  • Exterior Features

    Balcony, Outdoor Shower, Private Mailbox, Sprinkler Metered

  • Interior Features

    Cathedral Ceiling(s), Ceiling Fans(s), Crown Molding, High Ceilings, Open Floorplan, Primary Bedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk In Closet(s), Wet Bar

Construction

  • Year Built

    Year Built: 2008

  • Home type

    Single Family Residence

  • Roof

    Metal

  • Property Condition

    Completed

  • Foundation Details

    Slab, Stilt/on Piling

  • Construction Materials

    Block, Cement Siding, Frame

  • Architectural Style

    Elevated, Key West

Utilities & Energy

  • Parking Features

    Garage Door Opener

  • Laundry Features

    Inside, Laundry Chute, Laundry Room

  • Utilities

    Public

  • Water Source

    Public

Other Features

  • Subdivision Name

    Island Estates Of Clearwater

  • Lot Features

    Cul De Sac, City Limits, Irregular Lot, Landscaped, Oversized Lot, Street Dead End

  • Patio And Porch Features

    Covered, Front Porch, Patio, Porch, Rear Porch, Side Porch, Wrap Around

  • Community Features

    Street Lights

  • Vegetation

    Trees/landscaped

Price History

DateEventPrice

05/28/2026

Source: mls_logoStellar MLS-FL #MFRTB8399954

Price Decreased

$3,495,000 -11.52%

$865/sqft

01/02/2026

Source: mls_logoStellar MLS-FL #MFRTB8399954

Listed for Sale

$3,950,000 -7.06%

$978/sqft

01/01/2026

Source: mls_logoStellar MLS-FL #MFRTB8399954

Listing Removed

$4,250,000

$1,052/sqft

06/23/2025

Source: mls_logoStellar MLS-FL #MFRTB8399954

Listed for Sale

$4,250,000

$1,052/sqft

Clearwater Beach Ranks #9 in Clearwater, FL

Homes for sale
127

Homes

Rental prices
$3,501

Rental Prices

Median Home Price
$570K

Median Home Price

Clearwater Beach, Clearwater, FL neighborhood guide

Nearby Homes

Based on information from Stellar MLS® through Nov 10, 2026, 08:30AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

Advertising Broker: Fred McGill | Simple Showing, Inc

Skip to Main Content