421 Windward Psge, Clearwater, FL 33767
Property image
Property image
OFF MARKET

$2,173,300

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,680 sqft (on 0.34 acres)

421 Windward Psge, Clearwater, FL 33767

Island Estate
Est. Refi. Payment $14,641/mo*
Refinance Your Home
Currently Off Market - Sold Mar 6, 2023 for $2,000,000

Home Value

Trulia Estimate
$2.17M
Since last month
Decreased$21K (-1%)
Since last year
Decreased$77K (-3.4%)
Since last sale
Increased$179K (+8.9%)
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 +84% in the last 10 years
MonthEstimated value
2026
August 2026$2.18M
August 2026$2.17M
July 2026$2.2M
June 2026$2.28M
May 2026$2.28M
April 2026$2.28M
March 2026$2.27M
February 2026$2.3M
January 2026$2.25M
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
514 WINDWARD PASSAGE, Clearwater, FL
0.12
Single-Family Home
$1,625,000
06/26/26
5
4
3,022
106 MIDWAY ISLAND, Clearwater, FL
0.06
Single-Family Home
$1,625,000
09/26/25
3
3.5
2,821
511 WINDWARD PASSAGE, Clearwater, FL
0.08
Single-Family Home
$2,905,000
06/24/26
5
5.5
5,006
301 MIDWAY ISLAND, Clearwater, FL
0.24
Single-Family Home
$2,199,000
04/10/26
4
3
4,176
333 MIDWAY ISLAND, Clearwater, FL
0.31
Single-Family Home
$1,390,000
04/10/26
4
3.5
4,198
74 WINDWARD ISLAND, Clearwater, FL
0.14
Single-Family Home
$1,300,000
10/10/25
3
2
2,563
223 PALM ISLAND SW, Clearwater, FL
0.56
Single-Family Home
$2,395,000
03/19/26
4
3
3,297
511 ISLAND WAY, Clearwater, FL
0.67
Single-Family Home
$1,700,000
01/12/26
4
3
2,876
624 SNUG ISLAND, Clearwater, FL
0.76
Single-Family Home
$1,925,000
05/05/26
4
4
2,538
475 ISLAND WAY, Clearwater, FL
0.56
Single-Family Home
$1,425,000
07/30/26
4
4
2,509

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
431 WINDWARD PASSAGE, Clearwater, FL 33767
0.02
$684,200
3
2
1,607
Off Market
411 WINDWARD PASSAGE, Clearwater, FL 33767
0.03
$2,463,800
5
3.5
3,724
Off Market
106 MIDWAY ISLAND, Clearwater, FL 33767
0.06
$1,588,300
3
3.5
2,821
Off Market
511 WINDWARD PASSAGE, Clearwater, FL 33767
0.08
$2,905,000
5
5.5
5,006
Recently Sold
54 MIDWAY ISLAND, Clearwater, FL 33767
0.07
$1,307,200
4
2
2,007
Off Market
31 LEEWARD ISLAND, Clearwater, FL 33767
0.07
$1,403,800
3
2
2,339
Off Market
380 WINDWARD PASSAGE, Clearwater, FL 33767
0.09
$1,271,600
3
3
2,311
Off Market
44 LEEWARD ISLAND, Clearwater, FL 33767
0.09
$1,349,600
3
3
2,325
Off Market
42 MIDWAY ISLAND, Clearwater, FL 33767
0.09
$3,099,000
4
3.5
4,944
For Sale
106 LEEWARD ISLAND, Clearwater, FL 33767
0.11
$2,365,100
4
3
3,786
Off Market
514 WINDWARD PASSAGE, Clearwater, FL 33767
0.12
$1,625,000
5
4
3,022
Recently Sold
19 LEEWARD ISLAND, Clearwater, FL 33767
0.10
$1,891,900
4
3
2,924
Off Market

Local Information

  • Map ViewExplore the area around 421 Windward Psge.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1962
0.34 acre lot
3,680 sqft
$591/sqft
Garage

About this House

BACK UPS REQUESTED.......Island Estates Waterfront Beauty! This sprawling 2-story luxury estate Waterfront home has everything on your list: Close to the famous white sands of Clearwater Beach? Check, Pool & spa? Check, A private dock with boat lift plus a deck to soak up the year-round Florida sun and a renovated interior? Check, check & check! This 3600+ Square Foot estate with 4 bedrooms, 4 full baths & 20 x 30 bonus room is a project-free paradise -- meaning nearly every room & system has been upgraded to make sure you can move in & start enjoying the Florida beach lifestyle! It has a new metal roof [2018], hurricane shutters on all of the windows & a newer water heater. No expense was spared to update, automate & expand all your exterior amenities. The meticulous landscaping includes tropical plants, many mature palm trees & multicolored LED lighting throughout the property. The pull-through driveway has high-end pavers & the pool area was given a spectacular facelift. Off the living room & kitchen you will enjoy a large enclosed pool area which offers plenty of covered space for dining and relaxing, a gorgeous pool, a new spill over spa, travertine tile laid in a French pattern, spectacular views of the waterways and surrounded by one of the larger yards in Island Estates. The home's renovated interior matches all those outdoor upgrades, with a modern open-concept floor plan and water views from almost every room. The main living area features luxury Shaw hardwood floors and vaulted ceilings. The massive kitchen includes stainless steel appliances, tons of cabinet space and a stunning granite slab backsplash to match the countertops. You can serve snacks to the crowd gathered around the center island while enjoying your guests in the large family room too. The ground floor owners suite is located at one end of the home, has plenty of natural light, beautiful water views straight down the canal, a private door to the pool/hot tub & a large walk-in closet with built ins. The owners ensuite includes a dual-head glass shower, double sinks and a separate claw foot soaking tub. At the opposite end of the home, down a hallway you will find 3 guest bedrooms & a guest bath which doubles as a pool bath. The bedroom at the end of the hall is spacious & would make a perfect in-law suite with its own private bath, sitting area and glass sliders out to the pool. Upstairs, there's a bonus space with full bath that could be used as a 5th bedroom, a rec room or man cave the possibilities are endless. This great bonus room also has its own private sun deck which is perfect to enjoy sunsets & some of the best fireworks during annual celebrations in Clearwater Beach. Need more reasons to spend time outside? How about a Covered dock with lift, davits & 163 Feet of Seawall! You will love all of the outdoor space where you have room to store another boat, RV or golf cart on a pavered pad on the side of the home behind a fence. All that storage space, plus 2 Tuff Shed storage units in addition to a 2-car garage that includes built-in roll-up overhead storage & durable epoxy flooring. This waterfront home will not last long! It's close to shopping, dining [forget about traffic-- just hop in your boat or jet skis!] & the airport. Island Estates is a very active community and is just a few min walk to the White Sands of Clearwater Beach & features top restaurants, a Brand New Publix Grocery Store, playground, banks & so much more! This is a must see!
421 Windward Psge, Clearwater, FL 33767 is a 4 bedroom, 4 bathroom, 3,680 sqft single-family home in Island Estate, built in 1962. It last sold for $2,000,000 on Mar 6, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,173,300.

Home Details for 421 Windward Psge

Interior Features

Heating & Cooling
Heating: Forced Air, Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Number of Rooms: 6Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: MetalExterior: StuccoFoundation Type: FootingPatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1962Year Updated: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price and Tax history

DateEventPrice
Mar 6, 2023
Source: N/A
Sold
$2,000,000
Dec 23, 2022
Source: Stellar MLS #U8168128
Pending
$2,425,000
Nov 20, 2022
Source: Stellar MLS #U8168128
PriceChange
$2,425,000
Price decreased by 5%
Oct 20, 2022
Source: Stellar MLS #U8168128
PriceChange
$2,560,000
Price decreased by 5%
Sep 14, 2022
Source: Stellar MLS #U8168128
Listed For Sale
$2,700,000

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 421 Windward Psge

  • What is 421 Windward Psge estimated to be worth?
    Trulia's estimated value for 421 Windward Psge in Clearwater, FL is $2,173,300.
  • What is the price history for 421 Windward Psge?
    421 Windward Psge in Clearwater, FL last sold for $2,000,000 in March 2023.
  • 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 421 Windward Psge have air conditioning?
    Yes, 421 Windward Psge in Clearwater, FL has air conditioning.
  • Does 421 Windward Psge have a pool?
    Yes, 421 Windward Psge in Clearwater, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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