5 bedroom Single Family Residence at 442 MIDWAY ISLAND, ISLAND ESTATES OF CLEARWATER, CLEARWATER BEACH — photo 1Front elevation
347 days on market Single Family Residence
$3,495,000

442 MIDWAY ISLAND, CLEARWATER BEACH, FL 33767

Single Family Residence in ISLAND ESTATES OF CLEARWATER, CLEARWATER BEACH · No CDD · FEMA Zone X
ISLAND ESTATES OF CLEARWATER · CLEARWATER BEACH, FL 33767 · Pinellas
Listing data updated July 8, 2026 · refreshed twice daily
5Bedrooms
4.5Bathrooms
4,039Sq Ft
2008Year Built
$865Per Sq Ft
Waterfront2-car garageNo CDDFEMA Zone X5 bedrooms
Highlights
  • No CDD assessment on record
  • FEMA Zone X — flood insurance generally not federally required
  • Built 2008 · 18 yrs
  • 4,039 sq ft of living area
  • 2-car garage
  • $865/sq ft — compared with the displayed median of $532 from recent nearby sales
  • Listed at $3,495,000 — recent neighborhood median sale price ~$1,912,000 (nearby sales; deemed reliable, not an appraisal)
  • 347 days on market
  • HOA ~$50/mo (estimate; confirm)

This listing is shown at $3,495,000, with 5 bedrooms and 4.5 bathrooms, and 4,039 square feet. The page displays an estimated monthly payment, FEMA flood-zone information, estimated ownership costs, a source-tagged Momentum Fact Check, and recent comparable-sale data where available. All estimates should be independently verified.

Momentum Snapshot

The whole picture, at a glance

Property

Bedrooms5
Bathrooms4.5
Living area4,039 sq ft
Year built2008
Property typeSingle Family Residence

Financial

Est. monthly payment$22,694
Est. taxes / yr~$36,698
Est. insurance / yr~$16,294
HOA$50/mo
CDDNone on record
Price / sq ft$865

Risk

Flood zoneZone X · minimal hazard (FEMA)
Ground elevation~20 ft
Wind exposureCoastal — obtain a quote
Insurance (est.)~$16,294/yr

Market

Days on market347
Neighborhood median DOM99
Active listings (area)22
Months of supply16.5
Comparable-sales median$1,912,000

Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.

Visual snapshot

The numbers, at a glance

Flood risk
Zone X
Minimal hazard, outside the SFHA per FEMA
Est. insurance
~$16,294/yr
Estimated homeowners premium; get a real quote.
Months of supply
16.5 mo
Under 3 months typically favors sellers; 3–6 is balanced; over 6 favors buyers.
Market activity
1/100
Slower market — from supply, under-contract share, and days on market.

Estimated monthly payment

$22,694/mo
  • Principal & interest $18,228/mo 80%
  • Taxes $3,058/mo 13%
  • Insurance $1,358/mo 6%
  • HOA $50/mo 0%

Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.

Momentum Scores

Momentum Property Score

30/100
Strongest on: Flood safety (95), Insurance cost (74)

A rules-based composite of the objective indicators below — each computed from listing facts, public records, and recent nearby sales, not opinion.

How to read it: a higher score means more of these objective measures line up in a buyer’s favor — for example, priced competitively against recent nearby sales, lower carrying costs, or lower flood risk. A lower score means fewer do. It reflects only the indicators below — not the home’s quality, condition, or desirability, and nothing about who should live there.

Price vs area0
This home $865/sq ft vs area median $532/sq ft from recent nearby sales.
Affordability0
List price $3,495,000 vs area median $1,912,000. Not a measure of personal affordability.
Flood safety95
FEMA Zone X, ~20 ft elevation. Verify the parcel with FEMA.
Insurance cost74
From FEMA Zone X and a 2008 build. Obtain a property-specific quote.
Market liquidity15
Area median 99 days on market, ~16.5 months of supply.
Investment metrics7
Objective supply and demand metrics for the area - not investment advice.
Renovation upside20
From a 2008 build and $865/sq ft vs area $532/sq ft. Not a condition assessment.

Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent nearby sales. They are not appraisals, valuations, investment advice, or judgments about a neighborhood or who should live there. Verify independently.

Listing facts & disclosures
$3,495,000
List price
As listed in the MLS
5 / 4.5
Bed / bath
Per the listing
4,039
Living area
Sq ft (approx.)
$865
Price / sq ft
List ÷ living area

The home

Year built2008
Per public record.
Property typeSingle Family Residence
Per the listing.

Costs

HOA$50/mo
Disclosure — confirm exact dues and inclusions.
CDD assessmentNone on record
Estimate/disclosure — confirm the parcel's actual CDD with the county.
Est. first-year tax~$36,698/yr
Opinion/estimate at typical county millage — your assessed bill will differ. Do not rely on this.

Site & risk

FEMA flood zoneZone X · minimal hazard (FEMA)
From the FEMA flood map; verify the parcel.
Ground elevation~20 ft
Approximate parcel elevation (USGS).
WindstormLow
Coastal exposure varies; obtain an insurer quote.

Please note. Figures such as estimated taxes, insurance, CDD/HOA amounts, payments, and any market or comparable-sales summary are opinions and estimates for general information only, may be inaccurate, are not appraisals or advice, and should not be relied upon. Verify everything independently before making any decision.

Listing courtesy of CENTURY 21 BE3 · Listing agent: Prudy Cole · 727-596-1811Provided via the Stellar MLS Internet Data Exchange, as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID. · deemed reliable but not guaranteedIDX 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 by the MLS to be accurate.
Price benchmark

Pricing & market trend in ISLAND ESTATES OF CLEARWATER

How this home's list $/sq ft compares with recent nearby closed sales, and how prices in the community have moved. Public-record reference only — not an appraisal or a statement of value.

This home's $/sq ft vs. nearby sales

Price per sq ft · this home vs. recent nearby sales333 MIDWAY ISLAND333 MIDWAY ISLAND: $331/sq ft$331301 MIDWAY ISLAND301 MIDWAY ISLAND: $527/sq ft$527514 WINDWARD PASSAGE514 WINDWARD PASSAGE: $538/sq ft$538511 WINDWARD PASSAGE511 WINDWARD PASSAGE: $580/sq ft$580This homeThis home: $865/sq ft$865Median $532

Recent sold prices in this community

$900,000$2,197,500$3,495,000Oct 2025: $1,300,000Nov 2025: $1,275,000Jan 2026: $1,500,000Mar 2026: $900,000Apr 2026: $2,199,000Apr 2026: $1,390,000Jun 2026: $2,905,000Jun 2026: $1,625,000This home (list price): $3,495,000This homeOct 2025Jun 2026
The Messtimate™

The Messtimate: $1,890,252 – $2,407,244

This is a deliberately dumb estimate — living area times a range of recent neighborhood $/sq ft, and nothing else. It is not an appraisal, not market value, and not a valuation of this home. Even a tight range from comparable sales can’t price a specific home — here’s why.

$1,890,252the mess$2,407,244

Actual list price: $3,495,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.

A 27% spread on the same house — and that gap is exactly what an automated guess can't see:

  • Condition & updates — a renovated kitchen, new roof, or older interior finishes can swing value six figures. Sq ft can't see it.
  • The lot — a premium waterfront, conservation, or cul-de-sac lot vs. a road-facing one: same sq ft, very different price.
  • Outliers skew it — one flip or one distressed sale in the comps drags the whole $/sq ft up or down.
  • Layout & beds/baths — two homes at 2,000 sq ft with 3/2 vs. 4/3 don't sell for the same number.
  • Views & orientation — golf, water, or preserve views aren't in the square footage.
  • Upgrades & systems — solar, pool, impact windows, new HVAC: real money, invisible to a calculator.
  • Unpermitted or mismeasured sq ft — public records are often wrong, and unpermitted additions don't count.
  • Carrying costs — CDD bonds, HOA dues, and flood-zone insurance change what a buyer will actually pay.
  • Timing & concessions — the market moves monthly, and seller-paid rate buydowns hide the true price.
  • School zoning & micro-location — one street over can mean a different school, and a different price.

And here's what the live market is doing — which the number above ignores entirely:

  • This home: 347 days on market vs. a ~99-day neighborhood median
  • 22 active listings competing in ISLAND ESTATES OF CLEARWATER
  • 1 under contract now
  • 4% of for-sale inventory is currently under contract (under contract + pending, as a share of all for-sale inventory)
  • 16.5 months of supply (one market-context metric; should not be used alone)
  • 7 new-construction homes competing
  • 16 closed here in the last 12 months

For reference, this home is listed at $3,495,000 ($865/sq ft) — a number set with analysis a Messtimate can't do.

Want a property-specific review from a licensed agent? A Momentum Realty agent will do a real, free comparative market analysis — walking the home, the lot, the condition, and the live market. That's the difference between a Messtimate and a valuation.

Selling your own home? Try the Messtimate on your address →

Methodology: 4,039 sq ft × $468–$596/sq ft from recent nearby closed sales (public records). Estimate for general information only; not an appraisal, valuation, or offer. Updated July 8, 2026.

Property timeline

This home’s history

  • 2008BuiltPer public record
  • NowActiveCurrently for sale

Build year is from public record. Listing milestones reflect movewithmomentum.com’s own observations since we began tracking this listing and are not the MLS listing history; dates and prices are deemed reliable but not guaranteed.

If you rent it out

Investment snapshot

Objective rental and cash-flow estimates for a buyer weighing this as an investment. Rough figures for general information only — not a guarantee of rent, an appraisal, or investment advice. Verify independently.

Estimated rent$16,019 – $23,300/moa rough gross-rent-yield range on list price (comp-based estimate coming).
Estimated cap rate4.5%Net operating income ÷ list price; excludes financing.
Est. monthly cash flow−$7,137 – −$585At 25% down, 30-yr; after a 10% vacancy/maintenance/management reserve.
Momentum Fact Check

Every number, sourced

We separate what is listing data, what comes from public records, what we calculate or estimate, and what a buyer should verify. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.

Listing facts MLS

List price$3,495,000
Bed / bath5 / 4.5
Living area4,039 sq ft
Year built2008
Property typeSingle Family Residence
MLS #TB8399954
Listing status347 days on market
Days on market347

Public records & third-party data

FEMA flood zoneZone X
Ground elevation~20 ft
CountyPinellas
Estimated first-year tax~$36,698/yr
CDD assessmentNone on record
HOA (estimate)$50/mo

Calculated estimates

Price per sq ft$865
Estimated monthly payment$22,694
Estimated insurance~$16,294/yr
Messtimate rangeNot available on this page
Comparable-sales median$1,912,000

Buyer should verify Buyer verify

Exact HOA dues, fees, and restrictionsRoof age and conditionHVAC age and conditionA property-specific insurance quoteSurvey and lot boundariesPermit historyFlood-insurance requirementsSchool zoning (confirm with the district)Property taxes after sale (homestead reset)CDD / community assessmentsSquare footage and room dimensions
No surprises at closing

Estimate a monthly payment

A tool to estimate a monthly payment. All values are editable estimates, not a loan offer or a statement about this property. Property tax, insurance, CDD, and HOA figures are approximations — verify each independently.

Estimated monthly payment
$22,694
Principal & interest$18,228
Property tax$3,058
Insurance$1,358
CDD assessment$0
HOA$50
PMI$0

Down payment $699,000 · Loan $2,796,000. Estimate only — not a loan offer. We'll connect you with a local lender for an exact quote.

Estimated ownership costs

Estimated costs & disclosures

Estimates and disclosures for general information only. These are opinions/approximations, not guarantees, and should not be relied upon — confirm every figure with the county, your lender, and an insurer.

Property tax reset
~$36,698/yr

The seller likely pays less due to the homestead cap. At a $3,495,000 purchase, expect your first full-year Pinellas bill near $36,698 before exemptions.

CDD assessment
None

No CDD assessment on record for this community.

Insurance
~$16,294/yr

Estimate for a 2008 build in Pinellas. Newer construction and wind-mitigation features lower premiums. Flood not mandated (Zone X).

HOA
$50/mo

Covers the master association & common areas. Confirm exact dues and what they include.

Environmental data

Flood zone & elevation

Sourced environmental data for the parcel. Confirm with FEMA and your insurer.

FEMA flood zone
Zone X

From the FEMA National Flood Hazard Layer. In this zone lender-required flood insurance is generally not mandated; confirm for the parcel.

Ground elevation
~20 ft

Approximate parcel elevation from USGS. Run --online for a live reading.

Windstorm / insurance
Obtain a quote

This is a coastal Florida county. Premiums and coverage vary by home; obtain a quote from a licensed insurer.

Market data · public records

Recent sales activity in ISLAND ESTATES OF CLEARWATER

Recent comparable closed sales near this home, from public records. Summary figures are for general reference only and are not a valuation of this property. See the ISLAND ESTATES OF CLEARWATER neighborhood guide for more.

Comparable sales found
4

Recent nearby closings in the data set.

Median sale price (set)
$1,912,000

Median closed price of the comparable set. Reference only.

Median $/sq ft (set)
$532

Median $/sq ft of the comparable set. Reference only.

This home $/sq ft
$865

List price divided by living area. Provided as data, not a value judgment.

Go deeper on ISLAND ESTATES OF CLEARWATER

See schools, amenities, builders, HOA/CDD detail, and every active & sold home in the community — the single biggest advantage of buying here over a portal.

Assigned schools

Assigned schools

Schools currently assigned to this address in Pinellas County, provided as neutral factual data. Assignments can change — confirm current zoning with the school district. This is not a statement about the home's suitability for any person or family.

School zoningThis address is in the Pinellas County School District. Specific elementary, middle, and high-school assignments vary by street and can change. Confirm current zoning with the district before relying on it.
How it stacks up

Comparable recent sales

Recent closed sales nearby, with photos, so you can compare. Sold prices are public record, deemed reliable but not guaranteed.

Median of the set: $532/sq ft. Shown for general reference only — this is not an appraisal or a statement of this home's value. Sold prices are public record and deemed reliable but not guaranteed.

Keep looking

Similar homes for sale near ISLAND ESTATES OF CLEARWATER

Active listings nearby at a comparable size and price. Listings held by brokerages other than Momentum Realty are marked with the listing broker. Deemed reliable but not guaranteed.

Before you decide

Buyer research checklist

A neutral list of items to confirm for any home. This is general guidance, not advice about this specific property.

  • Confirm roof age and condition during inspection.
  • Confirm HVAC age and condition during inspection.
  • Request current HOA documents before relying on dues or restrictions.
  • Obtain an insurance quote for this specific property.
  • Confirm school zoning directly with the district.
  • Order a survey to confirm lot boundaries.
  • Review permit history with the county.
  • Confirm whether flood insurance is required for this parcel.
  • Confirm square footage and room dimensions independently.
  • Ask the county how property taxes may change after a sale.
Listing description

About this home

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.

Description provided by CENTURY 21 BE3 and reproduced from the MLS; not independently verified.

The full spec sheet

Property details & features

Interior

  • Bedrooms5
  • Bathrooms4.5
  • Living area4,039 sq ft

Exterior & lot

  • TypeSingle Family Residence

Systems

  • Year built2008
  • Age18 yrs

Listing

  • MLS #TB8399954
  • StatusActive
  • Days on market347
Nearby & commute

Approximate distances

Approximate drive times for general reference only.

Connectivity

Internet & broadband

Fiber
Check availability

AT&T Fiber covers much of NE Florida. Run --online or confirm at the address.

Cable
Likely

Xfinity/Spectrum cable broadband is widely available.

5G Home
Backup

T-Mobile / Verizon fixed-wireless as a backup option.

Transparency

Price & listing history

Listed for $3,495,000Momentum Realty · on market 347 days
Public records

Building permits

Permit history not yet linkedAdd county permit records via overrides
Answered before you ask

Frequently asked questions

Why might my property taxes differ from the current owner's?

Florida's Save Our Homes rule caps annual assessment increases for homesteaded owners, and the assessment can be re-set after a sale. As a result a new owner's bill may differ from the seller's. Any tax figure shown here is an estimate, not the actual bill — confirm with the county property appraiser and tax collector.

Where does the flood-zone information come from?

The flood designation shown (Zone X) comes from the FEMA flood map and is provided for general information. Confirm the parcel's status with FEMA and your insurer.

Can I rely on the figures on this page?

No. Estimated taxes, insurance, payments, and any market or comparable-sales summary are opinions and estimates for general information only and should not be relied upon. Verify all information independently before making any decision.

Ready when you are

See 442 MIDWAY ISLAND in person

Private tours available 7 days a week, in person or by live video walkthrough. Request a tour or send a question and a licensed Momentum Realty agent will follow up.

Momentum Realty · licensed in FL & GA

Opinion & estimate — do not rely on this page. Any figure on this page that is not a verbatim fact from the listing or a public record — including estimated property taxes, insurance, CDD/HOA amounts, mortgage payments, comparable-sales summaries, and market statistics — is an opinion and estimate provided for general informational purposes only. These figures may be inaccurate or out of date, are not appraisals, valuations, or financial, legal, tax, or investment advice, and should not be relied upon. Do not make any purchase, offer, financing, or other decision based on this page. Independently verify everything — price, square footage, lot size, year built, taxes, CDD/HOA, flood status, school assignments, permits, and community rules — with the listing broker, the county, your lender, a licensed inspector, an insurer, and your own advisors before acting.

Estimate methodology. Tax estimates apply a typical county millage rate to the list price and will differ from the actual assessed bill. Cost and market figures are derived from available data and simple calculations, not a professional appraisal. We make no representation that any estimate reflects fair market value.

Equal Housing Opportunity. Content on this page is compiled from public records, MLS data, and automated sources and may contain errors or be out of date. It is general information only, not a representation about any specific property, community, builder, or association. Verify information independently before relying on it. Momentum Realty supports the Fair Housing Act and does not discriminate on the basis of race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity. Information about schools, distances, and amenities is provided as neutral factual data to help you research the property and is not a statement about who should or should not live here or the suitability of the home or neighborhood for any person or group. School data may change — confirm current assignments with the school district.

Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email and we will review and correct or remove it promptly.

Automated content. Some summaries, distances, and estimates on this page are generated automatically from public and proprietary data sources and may contain errors or omissions. We strive for accuracy but cannot guarantee the completeness or accuracy of any information. Verify anything important independently.

MLS / IDX. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Stellar MLS Internet Data Exchange, as distributed by MLS GRID. Real estate listings held by brokerage firms other than Momentum Realty are marked with the listing broker's name and include the name of the listing agent. Data provided is deemed reliable but is not guaranteed by the MLS to be accurate. The information being provided is 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. Source: Stellar MLS, as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. All rights reserved.

Listing data is deemed reliable but is not guaranteed and is subject to change or withdrawal without notice. Square footage and lot size are approximate. Real estate brokerage services provided by Momentum Realty, licensed in Florida and Georgia. © 2026 Move With Momentum LLC.