
442 MIDWAY ISLAND, CLEARWATER BEACH, FL, 33767
Active404 days on marketListed Jun 23, 2025MLS #TB8399954
About this home
442 MIDWAY ISLAND
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.
Facts & features
The home at a glance
5
Bedrooms
4.5
Bathrooms
4,039
Sqft
0.26 ac
Lot size
2
Garage
2008
Year built
Three Or More
Levels
$865
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$21,973 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$21,973/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs ISLAND ESTATES OF CLEARWATER
$865 vs $750
Days on market
404 vs 84 typical
Where $865/sqft sits among the 8 homes for sale in ISLAND ESTATES OF CLEARWATER
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Island Estate
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Clearwater Beach. See the full Clearwater Beach guide →
Island Estate — neighborhood snapshot
Population
2,783
Median age
62
Median income
$108,222
Median home value
$631,400
Avg household
2
Households w/ children
223
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Clearwater Beach market
$535K → $916K
Clearwater Beach median sold, yr/yr
93.9%
Sale-to-list ratio (12 mo)
5 of 8
ISLAND ESTATES OF CLEARWATER have cut their price
Median sold price, Clearwater Beach, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 530% above the CLEARWATER BEACH 33767 median. See the full Clearwater Beach market guide →
Paper trail
This home's history
Reality check
What actually sold near 442 MIDWAY ISLAND
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$2,199,000
301 MIDWAY ISLAND · same community
4 bd · 3 ba · 4,176 sqft · $527/sqft · 186 DOM
Sold · Apr ’26$1,390,000
333 MIDWAY ISLAND · same community
4 bd · 3.5 ba · 4,198 sqft · $331/sqft · 263 DOM
Sold · Jun ’26$2,905,000
511 WINDWARD PASSAGE · same community
5 bd · 5.5 ba · 5,006 sqft · $580/sqft · 93 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 442 MIDWAY ISLAND — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 442 MIDWAY ISLAND — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
442 MIDWAY ISLAND FAQs
What would the monthly payment be for 442 MIDWAY ISLAND?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $21,973/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 442 MIDWAY ISLAND?+
The most recent tax bill on record (2024) was $19,718. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 442 MIDWAY ISLAND?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Clearwater Beach?+
At $3,495,000, this home is listed about 332% above the Clearwater Beach median of $808,600. The market section on this page shows how the area is trending.
Which schools are assigned to 442 MIDWAY ISLAND?+
Sandy Lane Elementary School (elementary), Dunedin Highland Middle School (middle), Clearwater High School (high) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$3,495,000 runs 530% above the CLEARWATER BEACH 33767 median — but at 4,039 sqft it's also nearly 3 times the size of the typical Clearwater Beach listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
404 days on market against a Clearwater Beach median of 84 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Sandy Lane Elementary School, Dunedin Highland Middle School, Clearwater High School — Dunedin Highland Middle School rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $4,250,000, now $3,495,000 — a $755K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of CENTURY 21 BE3 · Prudy Cole. MLS #TB8399954.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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