Skip main navigation
For sale
$3,495,000
5beds
4,039sqft

442 MIDWAY ISLAND, CLEARWATER BEACH, FL 33767

5beds
4,039sqft
Single Family Residence
Built in 2008
0.26 Acres Lot
$865/sqft

What's special

Private balconyDesigner finishesWrap-around verandaThree additional bedroomsElevated key west-style homeWalls of windowsVaulted cathedral ceilings

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.

474 days
819
58
Source: Stellar MLS,MLS#: TB8399954MLS LogoOriginating MLS: Orlando Regional
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Prudy Cole 863-397-7305,

CENTURY 21 BE3 727-596-1811

Source: Stellar MLS,MLS#: TB8399954MLS LogoOriginating MLS: Orlando Regional

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 5
  • Bathrooms: 5
  • Full bathrooms: 4
  • 1/2 bathrooms: 1
Rooms
  • Room types: Den/Library/Office, Dining Room, Living Room, Great Room, Utility Room, Storage Rooms
Primary bedroom
  • Features: Walk-In Closet(s)
  • Level: Third
  • Area: 258.42 Square Feet
  • Dimensions: 14.6x17.7
Bedroom 2
  • Features: En Suite Bathroom, Built-in Closet
  • Level: Second
  • Area: 172.84 Square Feet
  • Dimensions: 14.9x11.6
Bedroom 3
  • Features: Jack & Jill Bathroom, Built-in Closet
  • Level: Third
  • Area: 153.69 Square Feet
  • Dimensions: 14.1x10.9
Bedroom 4
  • Features: Jack & Jill Bathroom, Built-in Closet
  • Level: Third
  • Area: 147.66 Square Feet
  • Dimensions: 13.8x10.7
Bedroom 5
  • Features: En Suite Bathroom, Built-in Closet
  • Level: Third
  • Area: 162.41 Square Feet
  • Dimensions: 14.9x10.9
Dining room
  • Level: Second
  • Area: 239.36 Square Feet
  • Dimensions: 17.6x13.6
Foyer
  • Level: Second
  • Area: 209.25 Square Feet
  • Dimensions: 15.5x13.5
Great room
  • Level: Second
  • Area: 474.72 Square Feet
  • Dimensions: 27.6x17.2
Kitchen
  • Features: Granite Counters
  • Level: Second
  • Area: 239.4 Square Feet
  • Dimensions: 12.6x19
Laundry
  • Level: Second
  • Area: 76.95 Square Feet
  • Dimensions: 9.5x8.1
Living room
  • Level: Second
  • Area: 143.19 Square Feet
  • Dimensions: 12.9x11.1
Office
  • Level: Third
  • Area: 123.21 Square Feet
  • Dimensions: 11.1x11.1
Heating
  • Central, Electric, Exhaust Fan, Heat Pump
Cooling
  • Central Air
Appliances
  • Included: Bar Fridge, Oven, Dishwasher, Disposal, Gas Water Heater, Range, Range Hood, Tankless Water Heater, Wine Refrigerator
  • Laundry: Inside, Laundry Chute, Laundry Room
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
  • Flooring: Porcelain Tile, Hardwood
  • Doors: French Doors, Outdoor Shower
  • Has fireplace: No
Interior area
  • Total structure area: 9,004
  • Total interior livable area: 4,039 sqft
Video & virtual tour

Property

Parking
  • Total spaces: 2
  • Parking features: Garage Door Opener
  • Attached garage spaces: 2
Features
  • Levels: Three Or More
  • Stories: 3
  • Patio & porch: Covered, Front Porch, Patio, Porch, Rear Porch, Side Porch, Wrap Around
  • Exterior features: Balcony, Irrigation System, Outdoor Shower, Private Mailbox, Sprinkler Metered
  • Fencing: Other
  • Has view: Yes
  • View description: Intracoastal Waterway
  • Has water view: Yes
  • Water view: Intracoastal Waterway
  • Waterfront features: Intracoastal Waterway, Intracoastal Waterway Access, No Wake Zone, Sailboat Water, Seawall
Lot
  • Size: 0.26 Acres
  • Dimensions: 113 x 120
  • Features: Cul-De-Sac, City Lot, Irregular Lot, Landscaped, Oversized Lot, Street Dead-End
  • Residential vegetation: Trees/Landscaped
Details
  • Parcel number: 082915433440000600
  • Special conditions: None

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Elevated,Key West
  • Property subtype: Single Family Residence
Materials
  • Block, Cement Siding, Wood Frame
  • Foundation: Slab, Raised
  • Roof: Metal
Condition
  • Completed
  • New construction: No
  • Year built: 2008

Utilities & green energy

  • Sewer: Public Sewer
  • Water: Public
  • Utilities for property: Public, Street Lights

Community & HOA

Community
  • Pet fee: $0 monthly
  • Subdivision: ISLAND ESTATES OF CLEARWATER
HOA
  • Has HOA: No
Location
  • Region: Clearwater

Financial & listing details

  • Price per square foot: $865/sqft
  • Tax assessed value: $2,676,571
  • Annual tax amount: $19,718
  • Date on market: 6/23/2025
  • Cumulative days on market: 473 days
  • Listing terms: Cash,Conventional,VA Loan
  • Ownership: Fee Simple
  • Total actual rent: 0
  • Road surface type: Asphalt

Price history

DateEventPrice
5/28/2026Price change$3,495,000-11.5%$865/sqft
Source: Stellar MLS #TB8399954 Report a problem
2/13/2026Listed for sale$3,950,000-7.1%$978/sqft
Source: Stellar MLS #TB8399954 Report a problem
6/23/2025Listed for sale$4,250,000+1417.9%$1,052/sqft
Source: Stellar MLS #TB8399954 Report a problem
11/2/1995Sold$280,000$69/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$20,745 +5.2%$1,114,353 +2.9%
2024$19,718 +1.4%$1,082,948 +3%
2023$19,452 +2.5%$1,051,406 +3%
2022$18,975 -1.6%$1,020,783 +3%
2021$19,282 +0.2%$991,051 +1.4%
2020$19,252 +1.5%$977,368 +2.3%
2019$18,965 $955,753 +1.9%
2018$18,965 +1.2%$937,932 +2.1%
2017$18,740 +5.3%$918,641 +2.1%
2016$17,791 -1.5%$899,746 +0.7%
2015$18,053 +0.4%$893,492 +0.8%
2014$17,978 +0.4%$886,401 +1.5%
2013$17,898 +1.8%$873,301 +1.7%
2012$17,578 $858,703 -1.2%
2011-- $869,061 +1.1%
2010-- $859,794 +1.3%
2009-- $849,179 +206.9%
2008$4,817 $276,695 +3%
2007-- $268,636 -66.7%
2005-- $806,200 +15.6%
2004$6,078 +1.6%$697,500 +23%
2003$5,984 +5.2%$567,300 +13.4%
2002$5,687 $500,200 +10.2%
2001$5,687 +3.8%$453,900 +54.1%
2000$5,479 $294,600
Find assessor info on the county website

Monthly payment

Est. payment
$24,703/mo
Principal & interest
$19431
Property taxes
$5272
More affordability toolsChevron Right

Estimated market value

Not available

Estimated sales range

Not available

Not available

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: Island Estate

Nearby schools

Sandy Lane Elementary School
Grades PK-5 • 2 miles
8/10
GreatSchools® Rating
Test Score Rating
7/10
Student Progress Rating
9/10
Dunedin Highland Middle School
Grades 6-8 • 2.5 miles
9/10
GreatSchools® Rating
Test Score Rating
8/10
Student Progress Rating
10/10
Clearwater High School
Grades 9-12 • 3.8 miles
5/10
GreatSchools® Rating
Test Score Rating
4/10
College Readiness Rating
7/10
Student Progress Rating
3/10