55 Windward Is, Clearwater, FL 33767
OFF MARKET

$1,430,000

Trulia Estimate
  • Studio
  • 2 Baths
  • 1,907 sqft (on 0.25 acres)

55 Windward Is, Clearwater, FL 33767

Island Estate
Est. Refi. Payment $9,858/mo*
Refinance Your Home

Home Value

Trulia Estimate
$1.43M
Since last month
Increased$2K (+0.2%)
Since last year
Increased$63K (+4.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +47% in the last 10 years
MonthEstimated value
2026
September 2026$1.42M
August 2026$1.43M
July 2026$1.42M
June 2026$1.49M
May 2026$1.44M
April 2026$1.43M
March 2026$1.45M
February 2026$1.45M
January 2026$1.41M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
74 WINDWARD ISLAND, Clearwater, FL
0.04
Single-Family Home
$1,300,000
10/10/25
3
2
2,563
13 WINDWARD ISLAND, Clearwater, FL
0.12
Single-Family Home
$1,500,000
01/02/26
3
2
1,667
230 MIDWAY ISLAND, Clearwater, FL
0.33
Single-Family Home
$1,275,000
11/17/25
3
2
1,740
106 MIDWAY ISLAND, Clearwater, FL
0.19
Single-Family Home
$1,625,000
09/26/25
3
3.5
2,821
514 WINDWARD PASSAGE, Clearwater, FL
0.13
Single-Family Home
$1,625,000
06/26/26
5
4
3,022
301 MIDWAY ISLAND, Clearwater, FL
0.34
Single-Family Home
$2,199,000
04/10/26
4
3
4,176
511 WINDWARD PASSAGE, Clearwater, FL
0.11
Single-Family Home
$2,905,000
06/24/26
5
5.5
5,006
441 PALM ISLAND NE, Clearwater, FL
0.74
Single-Family Home
$1,250,000
08/31/26
3
2
2,167
411 PALM ISLAND NE, Clearwater, FL
0.74
Single-Family Home
$1,100,000
07/27/26
3
2
1,512
333 MIDWAY ISLAND, Clearwater, FL
0.42
Single-Family Home
$1,390,000
04/10/26
4
3.5
4,198

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
74 WINDWARD ISLAND, Clearwater, FL 33767
0.04
$1,272,300
3
2
2,563
Off Market
89 WINDWARD ISLAND, Clearwater, FL 33767
0.09
$1,592,000
3
2
2,020
Off Market
41 WINDWARD ISLAND, Clearwater, FL 33767
0.04
$1,523,900
4
3
2,517
Off Market
511 WINDWARD PASSAGE, Clearwater, FL 33767
0.11
$2,905,000
5
5.5
5,006
Recently Sold
514 WINDWARD PASSAGE, Clearwater, FL 33767
0.13
$1,625,000
5
4
3,022
Recently Sold
54 MIDWAY ISLAND, Clearwater, FL 33767
0.13
$1,307,200
4
2
2,007
Off Market
42 MIDWAY ISLAND, Clearwater, FL 33767
0.13
$3,099,000
4
3.5
4,944
For Sale
431 WINDWARD PASSAGE, Clearwater, FL 33767
0.15
$684,200
3
2
1,607
Off Market
112 WINDWARD ISLAND, Clearwater, FL 33767
0.16
$1,095,400
4
3
2,098
Off Market
113 WINDWARD ISLAND, Clearwater, FL 33767
0.15
$1,737,000
3
2
2,259
Off Market
118 WINDWARD ISLAND, Clearwater, FL 33767
0.17
$1,347,300
3
2
2,364
Off Market
13 WINDWARD ISLAND, Clearwater, FL 33767
0.12
$1,500,000
3
2
1,667
Recently Sold

Local Information

  • Map ViewExplore the area around 55 Windward Is.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1964
0.25 acre lot
1,907 sqft
$750/sqft
Garage

About this House

This single-family home is located at 55 Windward Is, Clearwater, FL. 55 Windward Is is in the Island Estate neighborhood in Clearwater, FL and in ZIP code 33767. This property has 2 bathrooms and approximately 1,907 sqft of floor space. This property has a lot size of 0.25 acres and was built in 1964.
55 Windward Is, Clearwater, FL 33767 is a studio, 2 bathroom, 1,907 sqft single-family home in Island Estate, built in 1964. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,430,000, with a rent estimate of $6,178/month.

Home Details for 55 Windward Is

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Linoleum Vinyl
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoFoundation Type: FootingPatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1964Year Updated: 1978
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.25 acres

Price and Tax history

YearProperty taxTax assessment
2025
$24,251
$1,253,135
Home facts updated by county records

Market trends in Clearwater

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$368K
$10KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$261
$0MoM
Available listings
1417
24MoM

Around this home

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

LGBTQ Local Legal Protections

Frequently asked questions about 55 Windward Is

  • What is 55 Windward Is estimated to be worth?
    Trulia's estimated value for 55 Windward Is in Clearwater, FL is $1,430,000.
  • Is Clearwater a buyer's or seller's market?
    Clearwater is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Clearwater?
    The median sale price in Clearwater is $368K. That is up $10K from the prior month.
  • What do residents say about the Island Estate neighborhood?
    Residents describe the Island Estate neighborhood in Clearwater, FL as pedestrian-friendly, dog-friendly, and walkable to grocery stores. See recently sold homes in Island Estate, Clearwater.
  • Does 55 Windward Is have air conditioning?
    Yes, 55 Windward Is in Clearwater, FL has air conditioning.
  • Does 55 Windward Is have a pool?
    Yes, 55 Windward Is in Clearwater, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

96 rentals with an outdoor space in Clearwater, FL

Apartments for Rent

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Off Market Homes Near 55 Windward Is

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