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

$1,768,700

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,762 sqft

20 Windward Is, Clearwater, FL 33767

Island Estate
Est. Refi. Payment $11,780/mo*
Refinance Your Home
Currently Off Market - Sold Jul 10, 2015 for $1,100,000

Home Value

Trulia Estimate
$1.77M
Since last month
Decreased$21K (-1.1%)
Since last year
Decreased$134K (-7.1%)
Since last sale
Increased$668K (+60.8%)
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 +46% in the last 10 years
MonthEstimated value
2026
August 2026$1.77M
August 2026$1.76M
July 2026$1.79M
June 2026$2.01M
May 2026$1.97M
April 2026$1.96M
March 2026$1.94M
February 2026$1.93M
January 2026$1.87M
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
0.12
Single-Family Home
$1,300,000
10/10/25
3
2
2,563
13 WINDWARD ISLAND, Clearwater, FL
0.04
Single-Family Home
$1,500,000
01/02/26
3
2
1,667
106 MIDWAY ISLAND, Clearwater, FL
0.25
Single-Family Home
$1,625,000
09/26/25
3
3.5
2,821
514 WINDWARD PASSAGE, Clearwater, FL
0.20
Single-Family Home
$1,625,000
06/26/26
5
4
3,022
301 MIDWAY ISLAND, Clearwater, FL
0.42
Single-Family Home
$2,199,000
04/10/26
4
3
4,176
333 MIDWAY ISLAND, Clearwater, FL
0.49
Single-Family Home
$1,390,000
04/10/26
4
3.5
4,198
230 MIDWAY ISLAND, Clearwater, FL
0.41
Single-Family Home
$1,275,000
11/17/25
3
2
1,740
511 WINDWARD PASSAGE, Clearwater, FL
0.18
Single-Family Home
$2,905,000
06/24/26
5
5.5
5,006
475 ISLAND WAY, Clearwater, FL
0.77
Single-Family Home
$1,425,000
07/30/26
4
4
2,509
223 PALM ISLAND SW, Clearwater, FL
0.77
Single-Family Home
$2,395,000
03/19/26
4
3
3,297

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
13 WINDWARD ISLAND, Clearwater, FL 33767
0.04
$1,500,000
3
2
1,667
Recently Sold
41 WINDWARD ISLAND, Clearwater, FL 33767
0.05
$1,523,900
4
3
2,517
Off Market
74 WINDWARD ISLAND, Clearwater, FL 33767
0.12
$1,272,300
3
2
2,563
Off Market
42 MIDWAY ISLAND, Clearwater, FL 33767
0.14
$3,099,000
4
3.5
4,944
For Sale
54 MIDWAY ISLAND, Clearwater, FL 33767
0.16
$1,307,200
4
2
2,007
Off Market
89 WINDWARD ISLAND, Clearwater, FL 33767
0.17
$1,592,000
3
2
2,020
Off Market
511 WINDWARD PASSAGE, Clearwater, FL 33767
0.18
$2,905,000
5
5.5
5,006
Recently Sold
19 LEEWARD ISLAND, Clearwater, FL 33767
0.21
$1,891,900
4
3
2,924
Off Market
431 WINDWARD PASSAGE, Clearwater, FL 33767
0.20
$684,200
3
2
1,607
Off Market
514 WINDWARD PASSAGE, Clearwater, FL 33767
0.20
$1,625,000
5
4
3,022
Recently Sold
31 LEEWARD ISLAND, Clearwater, FL 33767
0.23
$1,403,800
3
2
2,339
Off Market
411 WINDWARD PASSAGE, Clearwater, FL 33767
0.24
$2,463,800
5
3.5
3,724
Off Market

Local Information

  • Map ViewExplore the area around 20 Windward Is.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1960
2,762 sqft
$640/sqft
Garage

About this House

AWC - Taking Backup Offers SELLER TAKING BACK-UP OFFERS - BEST VALUE IN ISLAND ESTATES & MOVE IN READY !! Enjoy Florida's finest resort style and gracious living in this fabulous 4 bedroom - 3 bath waterfront home.
This home was "roof off" renovated in 2005. Open floor plan is ideal for a large family or entertaining.
Enormous great room with built-ins, opens to a incredible kitchen that features endless maple cabinets, center island w/cooktop, double ovens and a drop down stainless cooktop hood. Built in desk area, granite counters and granite breakfast island. Gorgeous hard wood flooring throughout, travertine tile in kitchen, foyer and baths. Unbelievable 2nd floor master suite w/kitchenette, gorgeous water front views through French doors opening to the private balcony. Elegant master bath that includes a jetted tub, double sinks, large glass block walk-in shower. The covered lani features Saltillio tiles, huge granite custom bar over looking a magnificent pool that was installed in 2009 including a wrap-around paver deck. The 9 year old dock features a covered boathouse with a metal roof and a 6 ton boat lift, double jet ski lift. This amazing property also includes argon gas filled windows, hurricane shutters throughout, top of the Line Trane A/C system with newer duct work, central vac system, crown molding throughout. 150 MPH rated insulated garage door, pavered driveway, travertine entry, 3 baths w/high end bath fixtures and a ductless a/c system in the garage with finished floors.
20 Windward Is, Clearwater, FL 33767 is a 4 bedroom, 3 bathroom, 2,762 sqft single-family home in Island Estate, built in 1960. It last sold for $1,100,000 on Jul 10, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,768,700.

Home Details for 20 Windward Is

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 4
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: TileExterior: Other, StuccoFoundation Type: Footing
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1960Year Updated: 1993
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 9526 sqft

Price and Tax history

DateEventPrice
Jul 10, 2015
Source: N/A
Sold
$1,100,000
Jul 6, 2015
Source: Agent Provided
PendingToActive
$1,200,000
Jul 6, 2015
Source: Agent Provided
Pending
$1,200,000
Jul 2, 2015
Source: Agent Provided
PendingToActive
$1,200,000
May 29, 2015
Source: Agent Provided
Pending
$1,200,000

Market trends in Clearwater

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$356K
$250MoM
Sale-to-List Price
97.2%
0.2%MoM
Price per sq ft
$261
$1MoM
Available listings
1439
17MoM

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 20 Windward Is

  • What is 20 Windward Is estimated to be worth?
    Trulia's estimated value for 20 Windward Is in Clearwater, FL is $1,768,700.
  • What is the price history for 20 Windward Is?
    20 Windward Is in Clearwater, FL last sold for $1,100,000 in July 2015.
  • 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 $356K. That is down $250 from the prior month.
  • Does 20 Windward Is have air conditioning?
    Yes, 20 Windward Is in Clearwater, FL has air conditioning.
  • Does 20 Windward Is have a pool?
    Yes, 20 Windward Is in Clearwater, FL has a pool.

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