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.
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.
Property Details
Price:
$3,950,000
MLS #:
TB8399954
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLAND ESTATES OF CLEARWATER
Neighborhood:
33767clearwaterclearwaterbeach
Listed Date:
Jun 23, 2025
Finished Sq Ft:
4,039
Total Sq Ft:
9,004
Lot Size:
11,400 sqft / 0.26 acres (approx)
Year Built:
2008
See this Listing
Schools
Interior
Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Gas Water Heater, Range, Range Hood, Tankless Water Heater, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Porcelain Tile, Hardwood
Heating
Central, Electric, Exhaust Fan, Heat Pump
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
Laundry Features
Inside, Laundry Chute, Laundry Room
Levels
Three Or More
Exterior
Architectural Style
Elevated, Key West
Attached Garage YN
1
Construction Materials
Block, Cement Siding, Wood Frame
Covered Spaces
2
Direction Faces
South
Exterior Features
Balcony, French Doors, Irrigation System, Outdoor Shower, Private Mailbox, Sprinkler Metered
Fencing
Other
Garage Spaces
2
Lot Features
Cul-De-Sac, City Lot, Irregular Lot, Landscaped, Oversized Lot, Street Dead-End
Parking Features
Garage Door Opener
Patio And Porch Features
Covered, Front Porch, Patio, Porch, Rear Porch, Side Porch, Wrap Around
Roof
Metal
Waterfront Features
Intracoastal Waterway
Window Features
Storm Window(s)
Financial
Tax Year
2024
Taxes
$19,718
Map
Community
- Address442 MIDWAY ISLAND CLEARWATER BEACH FL
- SubdivisionISLAND ESTATES OF CLEARWATER
- CityCLEARWATER BEACH
- CountyPinellas
- Zip Code33767
Subdivisions in CLEARWATER BEACH
- 440 WEST CONDO
- 51 ISLAND WAY CONDO
- 610 ISLAND WAY CONDO
- 650 ISLAND WAY CONDO
- 700 ISLAND WAY I CONDO
- 736 ISLAND WAY CONDO
- AQUALEA RESIDENCES CONDO
- AVALON CLUB RESORT CONDO
- AZURE CONDO
- BARBOUR-MORROW SUB
- BAY ISLAND CONDO ISLAND ESTATES
- BAYSIDE CONDO
- BAYSIDE SUB
- BAYSIDE SUB 2
- BAYSIDE SUB 4
- BAYWAY SHORES CONDO
- BELLE AQUA VILLAS
- BELLE HARBOR CONDO
- BRIGHTWATER COVE 2
- BRIGHTWATER TWNHMS
- CABANA CLUB CONDO
- CARLOUEL SUB
- CHATEAUS ON WHITE
- CLEARWATER BEACH REV
- CLEARWATER POINT
- CLEARWATER POINT 1
- CLEARWATER POINT 2
- CLEARWATER POINT 3
- CLEARWATER POINT 5
- CLEARWATER POINT 7 TENNIS
- CLEARWATER POINT 8 TENNIS
- CLEARWATER POINT NO. 8 CONDO SAILMASTER BLDG, UNIT
- CLEARWATER POINT TENNIS
- CLEARWATER SAND KEY
- CLEARWATER SAND KEY CLUB
- CONTINENTAL TOWERS INC CONDO
- CORAL MOTEL CONDO
- CRESCENT BEACH CLUB
- CRESCENT BEACH CLUB CONDO
- CRESCENT BEACH CLUB ONE CONDO
- CRESCENT BEACH CLUB TWO CONDO
- CUTTER COVE CONDO
- CW RESORT
- DANS ISLAND ON SAND KEY CONDO
- DIAMOND ISLE CONDO
- DOCKSIDE CONDO
- DOLPHIN COVE CLEARWATER
- DOLPHIN HARBOUR CONDO
- ENCHANTMENT CLEARWATER BEACH HOTEL CONDO
- ENCHANTMENT CLEARWATER BEACH HOTEL CONDOMINIUM
- FINALE AT SAND KEY CONDO
- GRANDE ON SAND KEY
- GRANDE ON SAND KEY CONDO
- HARBORAGE CONDO
- HARBORAGE CONDO BELLEAIR BEACH
- HARBORAGE CONDO CLEARWATER
- HARBORSIDE TWNHMS
- HARBORVIEW GRANDE CONDO
- HARBOUR LIGHT TOWERS CONDO
- HARBOUR THE CONDO
- HORIZON HOUSE CO-OP
- ISLAND ESTATE OF CLEARWATER UNITS 6D 7A 7C
- ISLAND ESTATES OF CLEARWATER
- ISLAND ESTATES OF CLEARWATER UNIT 6-A
- ISLAND ESTATES OF CLEARWATER UNIT 6-B
- ISLAND ESTATES OF CLEARWATER UNIT 7B
- ISLAND ESTATES OF CLEARWATER UNITS 6D 7A 7C
- ISLAND MOORINGS CONDO
- ISLAND POINT 1 CONDO
- ISLAND POINT NO. 1 CONDO
- ISLAND TWNHMS CLEARWATER
- ISLAND VIEW CONDO
- ISLAND WALK CONDO
- ISLAND WAY TOWERS CONDO
- ISLAND YACHT CLUB CONDO
- ISLANDER THE CONDO
- ISLE OF SAND KEY 1 CONDO
- LA BRISA DEL MAR CONDO
- LA BRISA DEL MAR CONDO UNIT 202
- LANDMARK TOWERS
- LIGHTHOUSE TOWERS CONDO
- M B R CONDO
- MAJESTIC POINT CONDO
- MANDALAY BEACH CLUB
- MANDALAY BEACH CLUB CONDO
- MANDALAY POINT SUB
- MANDALAY SUB
- MANDALAY UNIT 5 REP
- MARINA DEL REY AT SAND KEY
- MERIDIAN ON SAND KEY CONDO
- MOORINGS OF SAND KEY THE
- PELICAN POINTE ON
- PELICAN POINTE ON CLEARWATER BEACH CONDO
- PURA VIDA RESIDENCES
- PURA VIDA RESIDENCES CONDO
- REGATTA BEACH CLUB CONDO
- RESIDENCES AT SANDPEARL RESORT CONDO
- RESIDENCES AT WINDWARD PASSAGE CONDO
- ROYAL CAMELOT RESORT CONDO
- SAND KEY CONDO-BAYSIDE GARDENS II
- SAND KEY CONDO-BAYSIDE GARDENS III
- SAND KEY CONDO-BAYSIDE GARDENS IV
- SAND KEY CONDO-SOUTH BAY
- SAND KEY CONDO-SOUTH BEACH
- SAND KEY CONDO-SOUTH BEACH 1
- SAND KEY CONDO-SOUTH BEACH 1460
- SAND KEY CONDO-SOUTH BEACH 2
- SANDPIPERS COVE CONDO
- SEA ISLAND APTS 1 CONDO
- SEA ISLAND NORTH 3 CONDO
- SEA ISLAND SOUTH 4 CONDO
- SKIFF HARBOUR TWNHS CONDO
- STARBOARD TOWER
- SUITES AT SANDPEARL RESORT CONDO THE
- SUN WEST PALMS CONDO
- ULTIMAR ONE CONDO
- ULTIMAR THREE CONDO
- ULTIMAR TWO CONDO
- UTOPIA CONDO
- VILLAGE ON ISLAND ESTATES
- VILLAS OF CLEARWATER BEACH CONDO
Market Summary
Current real estate data for Single Family in CLEARWATER BEACH as of May 05, 2026
100
Single Family Listed
327
Avg DOM
898
Avg $ / SqFt
$1,835,181
Avg List Price
Property Summary
- Located in the ISLAND ESTATES OF CLEARWATER subdivision, 442 MIDWAY ISLAND CLEARWATER BEACH FL is a Single Family for sale in CLEARWATER BEACH, FL, 33767. It is listed for $3,950,000 and features 5 beds, 5 baths, and has approximately 4,039 square feet of living space, and was originally constructed in 2008. The current price per square foot is $978. The average price per square foot for Single Family listings in CLEARWATER BEACH is $898. The average listing price for Single Family in CLEARWATER BEACH is $1,835,181. To schedule a showing of MLS#tb8399954 at 442 MIDWAY ISLAND in CLEARWATER BEACH, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of CENTURY 21 BE3. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 442 MIDWAY ISLAND
CLEARWATER BEACH, FL
