2 Windward Is, Clearwater, FL 33767
Property image
Property image
OFF MARKET

2 Windward Is
Clearwater, FL 33767

Island Estate
  • 4 Beds
  • 4 Baths
  • 3,488 sqft

$2,275,800

Trulia Estimate
as of Jul 26, 2026
Est. Refi. Payment $15,172/mo*
Refinance Your Home

$2,275,800

Trulia Estimate
as of Jul 26, 2026
Est. Refi. Payment $15,172/mo*
Refinance Your Home
4 Beds
4 Baths
3,488 sqft

Local Information

  • Map ViewExplore the area around 2 Windward Is.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Living Area
3,488 sqft
Price/Sqft
$652

About this House

A rare and rarefied culmination of a Wow factor interior with walls of windows and soaring ceilings, an open southside orientation, sweeping views, an enviable private lot, deep boating water, and a grandfathered boathouse all within a cul-de-sac location on Windward Island. As you enter this home you will find an open, airy and sunny predisposition conducive for year round entertaining. An integrated kitchen with volume great room, master with ensuite and den/study plus two more bedrooms flow seamlessly throughout 3,480 + square feet. This wide view, open water home is structurally enhanced with a new seawall, windows and sliders, new roof and air conditioning. Island Estates has long been regarded as a community which offers self contained amenities and features including it's very own grocery, convenience store, several banks, pubs, Island Way Grill, gas station, pharmacy etc...
 This exceptional property is ideal as year round residence or perfect as a second home offering a playground for boating, jet skiing, and a casual Island Estates lifestyle.
2 Windward Is, Clearwater, FL 33767 is a 4 bedroom, 4 bathroom, 3,488 sqft single-family home in Island Estate, built in 1965. It last sold for $1,090,000 on Aug 4, 2016. It is currently off market. The Trulia Estimate is $2,275,800, with a rent estimate of $7,926/month.

Home Details for 2 Windward Is

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: StuccoFoundation Type: FootingPatio
Pool
Pool

Property Information

Year Built
Year Built: 1965Year Updated: 1992
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 6098 sqft

Price History for 2 Windward Is

DatePriceEventSource
08/04/2016$1,090,000Sold
N/A
04/09/2010$850,000Sold
N/A
02/03/2009$1,695,000ListingRemovedAgent Provided
06/06/2008$1,695,000Listed For SaleAgent Provided
12/21/2005$1,800,000Sold
N/A
10/04/2000$36,000Sold
N/A
08/03/2000$454,900Sold
N/A
02/10/2000$462,900Sold
N/A
09/24/1999$459,900Sold
N/A
07/22/1999$449,900Sold
N/A
04/09/1999$300,000Sold
N/A
12/31/1998$365,000Sold
N/A
08/27/1998$310,000Sold
N/A
05/22/1998$297,500Sold
N/A
10/09/1997$286,000Sold
N/A

Market trends in Clearwater

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$357K
$10KMoM
Sale-to-List Price
96.9%
0.4%MoM
Price per sq ft
$260
$4MoM
Available listings
1453
46MoM
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Property Tax and Assessment

Year2024
Tax$21,037
Assessment$2,063,490
Home facts updated by county records

Comparable Sales for 2 Windward Is

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
106 Midway Is, Clearwater, FL
0.30
Single-Family Home
$1,625,000
09/26/25
3
3.5
2,821
74 Windward Is, Clearwater, FL
0.19
Single-Family Home
$1,300,000
10/10/25
3
2
2,563
514 Windward Psge, Clearwater, FL
0.27
Single-Family Home
$1,625,000
06/26/26
5
4
3,022
13 Windward Is, Clearwater, FL
0.04
Single-Family Home
$1,500,000
01/02/26
3
2
1,667
333 Midway Is, Clearwater, FL
0.55
Single-Family Home
$1,390,000
04/10/26
4
3.5
4,198
301 Midway Is, Clearwater, FL
0.48
Single-Family Home
$2,199,000
04/10/26
4
3
4,176
511 Windward Psge, Clearwater, FL
0.23
Single-Family Home
$2,905,000
06/24/26
5
5.5
5,006
230 Midway Is, Clearwater, FL
0.46
Single-Family Home
$1,275,000
11/17/25
3
2
1,740
223 Palm Is SW, Clearwater, FL
0.81
Single-Family Home
$2,395,000
03/19/26
4
3
3,297
295 Bayside Dr, Clearwater Beach, FL
0.56
Single-Family Home
$4,550,000
04/02/26
5
4.5
5,051

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Windward Is.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Island Estate
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Island Estate

At least 35 Trulia users voted on each feature.

  • 95 % Say there are sidewalks

  • 95 % Say it's dog friendly

  • 95 % Say it's walkable to grocery stores

  • 89 % Say streets are well-lit

  • 81 % Say parking is easy

  • 81 % Say it's quiet

  • 79 % Say people would walk alone at night

  • 76 % Say it's walkable to restaurants

  • 66 % Say they plan to stay for at least 5 years

  • 63 % Say there's holiday spirit

  • 58 % Say neighbors are friendly

  • 51 % Say there are community events

  • 43 % Say yards are well-kept

  • 43 % Say car is needed

  • 39 % Say kids play outside

  • 18 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "I love the area but slightly expensive. looking for affordable housing near or in Clearwater. I love the beach and restaurants"
    0
    Flag
  • Ajsimpso
    "This is mostly an area for retirees. But it would be a nice place to raise kids. Very safe and there is a park and the aquarium of course."
    3
    Flag
  • Mariaeberta
    "Nice neighborhood but sometimes it takes many hours to get home because of the traffic. Our grocery store is super nice and everyone that works their are nice. "
    3
    Flag
  • Katherine A.
    "Very proactive dog neighborhood. Pet events are held as well. There are many dog walking families. "
    16
    Flag
  • paula d. w.
    "We've been here almost 2 years. We love it. So convenient to everything. Everyone is so Friendly. Also Free Ride and the Trolleys are Wonderful."
    1
    Flag
  • Mariaeberta
    "Is like a town of its own, clothing store, grocery store, gas station, restaurant, salon, wine bar, ups store, almost everyone is friendly. safe to walk around and the views are speculators. "
    0
    Flag
  • Amber D.
    "Florida is a warm friendly place to vacation or live year round. Those big bugs are a fact of life in a tropical climate so don't let a bug bug you or make you think it is not clean. As we move forward into the next year old and worn down is being replaced by new and innovative places to play and stay. Beautiful beaches and friendly residents await. Try us again. You'll be glad you did! Amber"
    1
    Flag

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Homes for sale near 2 Windward Is

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Off Market Homes Near 2 Windward Is

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