Active
$3,495,000
Est. $21,619/mo

442 Midway Is, Clearwater Beach, FL, 33767

$865/sqft·Island Estates Of Clearwater

5 bd5 ba4,039 sqft2 car garageSingle Family
Listed by CENTURY 21 BE3· Last updated · MLS# TB8399954

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Est. monthly payment
$21,619/mo
Down payment (20%)
$699,000
Property taxes
$1,643/mo
Rate assumed
6.8% · 30 yr
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At a glance

Single family
3 stories · 2008
Waterfront
Intracoastal Waterway
2 car garage
Garage Door Opener
0.26 acres
Lot size
4,039 sqft
Living area

About this home

Cathedral Ceiling(s)Ceiling Fans(s)Crown MoldingHigh CeilingsOpen FloorplanPrimarybedroom UpstairsSolid Surface CountersSolid Wood Cabinets

442 Midway Is is a 2008-built home in Island Estates Of Clearwater, Clearwater Beach. Inside you'll find 5 bedrooms, 5 bathrooms, and 4,039 square feet of living space. Listed at $3,495,000 (about $865/sqft), 428 days on market. Flood zone AE - confirm flood insurance requirements with your lender.

From the listing

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.

The essentials

Built
2008
Price / sqft
$865
On market
445 days
Annual tax
$19,718
Flood zone
AE
Lot
11,400 sqft
Type
Single Family Residence

Location

442 Midway Is
Clearwater Beach, FL, 33767·33767 - Clearwater/Clearwater Beach
Type
Single Family Residence
Year Built
2008
Lot
11,400 sqft
Cooling
Central Air
Heating
Central, Electric, Exhaust Fan, Heat Pump
Parking
Garage Door Opener
Waterfront
Intracoastal Waterway
Days on Market
445
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
Balcony
Outdoor Shower
Private Mailbox
Sprinkler Metered
Street Lights
Bar Fridge
Built-in Oven
Dishwasher
Disposal
Gas Water Heater
Range
Range Hood
Tankless Water Heater
Wine Refrigerator
Homestead exemption on fileFlood Zone AE

Annual Tax (2024)

$19,718

Parcel #

08-29-15-43344-000-0600

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision

Island Estates Of Clearwater

County

Pinellas

MLS Area

33767 - Clearwater/Clearwater Beach

Lot Size

11,400 sqft

Cul-De-SacCity LimitsIrregular LotLandscapedOversized LotStreet Dead-End
Date
Event
Price
5/28/2026
Price change
Source: Stellar MLS #TB8399954
$3,495,000-11.5%
$865/sqft
Price change
Source: Stellar MLS #TB8399954
$3,950,000-7.1%
$978/sqft
6/23/2025
Listed for sale
Source: Stellar MLS #TB8399954
$4,250,000
$1,052/sqft
Est. monthly payment$21,618/mo
Principal & interest$18,228
Property taxes$1,643
Insurance$1,748
Down payment20% · $699,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Offer Insights

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List price: $3,495,000
$3.20M – $3.50M
91.7% – 100% of listTops out right at the list price
80% of listList price
12 of the last 22 home closings in 33767 landed at this number or higher (55%). The median one sat 49 days before it went under contract, and this one is on day 445 after a $755,000 cut.

Sample: 22 closed home sales in 33767 over the last 8 months, Stellar MLS. A small sample in a thin market. A starting point, not a guarantee.

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