1365 WINDSOR DRIVE, Clearwater, FL 33756
SOLD
MAY 21, 2026

$416,200

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,202 sqft

1365 WINDSOR DRIVE, Clearwater, FL 33756

Chesterfield Heights
Est. Refi. Payment $2,916/mo*
Refinance Your Home
Currently Off Market - Sold May 21, 2026 for $419,000

Home Value

Trulia Estimate
$416K
Since last month
Decreased$2K (-0.5%)
Since last year
Decreased$37K (-8.2%)
Since last sale
Decreased$3K (-0.6%)
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 +101% in the last 10 years
MonthEstimated value
2026
September 2026$416K
August 2026$416K
July 2026$418K
June 2026$419K
May 2026$419K
April 2026$409K
March 2026$450K
February 2026$447K
January 2026$436K
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
408 OCEAN COURT, Clearwater, FL
0.20
Single-Family Home
$366,000
05/28/26
2
2
1,406
1339 BUCKINGHAM DRIVE, Clearwater, FL
0.06
Single-Family Home
$505,000
04/06/26
3
2
1,460
1362 STRATFORD DRIVE, Clearwater, FL
0.10
Single-Family Home
$405,000
07/17/26
3
2
1,376
1324 CHESTERFIELD DRIVE, Clearwater, FL
0.13
Single-Family Home
$449,000
04/27/26
3
2
1,313
1729 KENILWORTH DRIVE, Clearwater, FL
0.14
Single-Family Home
$370,000
11/17/25
3
2
1,489
1478 CROYDON DRIVE, Clearwater, FL
0.31
Single-Family Home
$370,000
08/05/26
2
2
1,338
1354 BUCKINGHAM DR, Clearwater, FL
0.09
Single-Family Home
$326,000
04/07/26
3
2
1,527
1772 AVON LANE, Clearwater, FL
0.24
Single-Family Home
$330,000
07/28/26
2
1.5
984

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
1361 WINDSOR DRIVE, Clearwater, FL 33756
0.02
$472,800
3
2
1,285
Off Market
1354 CHESTERFIELD DRIVE, Clearwater, FL 33756
0.05
$504,300
4
2
1,846
Off Market
1350 CAMBRIDGE DRIVE, Clearwater, FL 33756
0.09
$370,000
3
2
1,525
Recently Sold
1348 CHESTERFIELD DRIVE, Clearwater, FL 33756
0.08
$437,700
3
2
1,422
Off Market
1341 BUCKINGHAM DRIVE, Clearwater, FL 33756
0.05
$523,300
4
2
1,640
Off Market
1347 BUCKINGHAM DRIVE, Clearwater, FL 33756
0.05
$330,000
2
1
1,192
For Sale
1340 WINDSOR DRIVE, Clearwater, FL 33756
0.07
$502,500
4
2
1,466
Off Market
1339 BUCKINGHAM DRIVE, Clearwater, FL 33756
0.06
$505,000
3
2
1,460
Recently Sold
1345 CAMBRIDGE DRIVE, Clearwater, FL 33756
0.11
$388,500
3
2
1,462
Off Market
1761 EATON DRIVE NE, Clearwater, FL 33756
0.12
$573,100
3
2
1,726
Off Market
1389 CHESTERFIELD DRIVE, Clearwater, FL 33756
0.09
$570,000
3
2
1,414
Recently Sold

Local Information

  • Map ViewExplore the area around 1365 WINDSOR DRIVE.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1963
1,202 sqft
$349/sqft
1 Car Garage

About this House

Welcome to this beautifully maintained 2-bedroom, 2-bath, single-story, solar-heated pool home that truly checks all the boxes! Nestled on a well-groomed, manicured lot in a quiet neighborhood surrounded by pride of ownership, this property offers the perfect blend of comfort, efficiency, and Florida lifestyle living. Step outside to your private screened-in in-ground pool, solar-heated when needed, featuring brand-new screening (2025), and a freshly painted pool deck (2025), all ideal for relaxing or entertaining year-round. The pool pump was replaced in 2022. Inside, the home continues to impress with thoughtful updates throughout. The kitchen has been refreshed with a new dishwasher and refrigerator (2025), while additional upgrades include newer attic insulation for improved energy efficiency (2020), an electric water heater replaced in 2023, and new ceiling fans installed in 2023 for added comfort. The fencing was partially replaced in 2023 and the yard provides privacy and space for pets or play. This home also features a long list of previous improvements including roof (2015), AC (2016), impact (hurricane) solar windows (2013), and paver driveway (2013). Paver driveway and front patio were just cleaned, re-sanded, and sealed in 2025. A convenient 8x10 shed with electricity offers additional storage or workspace. This is an extraordinary neighborhood with very very little traffic, almost no through traffic. Location is key, and this home delivers! It's just a short drive to beautiful beaches, shopping, dining, and the airport, making everyday living and weekend adventures a breeze. Don’t miss your opportunity to own this move-in ready Florida gem! Schedule your private tour today!
1365 WINDSOR DRIVE, Clearwater, FL 33756 is a 2 bedroom, 2 bathroom, 1,202 sqft single-family home in Chesterfield Heights, built in 1963. It last sold for the $419,000 asking price on May 21, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $416,200, with a rent estimate of $4,187/month.
Last check for updates: about 13 hours ago
Listed by Jeremy Mayer, (727) 900-6068
BLUE GECKO REALTY, LLC, (407) 709-6176
Bought with: Philip Hoover, (352) 713-9599, MAJESTIC OAKS REALTY, (352) 274-6224
Originating MLS: Suncoast Tampa
Source: Stellar MLS, MLS#TB8492554
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 1365 WINDSOR DRIVE

Interior Features

Interior Details
Number of Rooms: 4Types of Rooms: Primary Bedroom, Bedroom 2, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1202 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Fiber Optics, Public, Street Lights, Water ConnectedAppliances: Dishwasher, Electric Water Heater, Microwave, Range, RefrigeratorDishwasherLaundry: In GarageMicrowaveRefrigerator
Heating & Cooling
Heating: Central,Electric,Heat PumpHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: BlindsFlooring: Ceramic Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Ceramic Tile
View
No View
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Deck, Front Porch, Patio, ScreenedFencing: Fenced, Vinyl, WoodVegetation: Fruit TreesOther Structures: Shed(s)Exterior: Rain Gutters, Sidewalk, StorageFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: Driveway
Pool
Pool: Gunite, Heated, In Ground, Lighting, Pool Sweep, Solar HeatPool
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 19

Property Information

Year Built
Year Built: 1963
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, StuccoNot a New ConstructionNot Attached PropertyNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 272915150840001210

Price & Status

Price
List Price: $419,000Price Per Sqft: $349/sqft
Status Change & Dates
Off Market Date: Tue Apr 21 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Location

Direction & Address
City: CLEARWATERCommunity: CHESTERFIELD HEIGHTS

Building

Building Area
Building Area: 1745 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Suncoast TampaNo HOA

Lot Information

Lot Area: 10163 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: TB8492554Showing Advance Notice: 24Showing Considerations: No Sign, Pet(s) on PremisesShowing Requirements: 24 Hour Notice, Appointment Only, ShowingTimeUniversal Property Id: US-12103-N-272915150840001210-R-N

Price and Tax history

DateEventPrice
May 21, 2026
Source: Stellar MLS #TB8492554
Sold
$419,000
Apr 23, 2026
Source: Stellar MLS #TB8492554
Pending
$419,000
Apr 17, 2026
Source: Stellar MLS #TB8492554
PriceChange
$419,000
Price decreased by 2%
Apr 11, 2026
Source: Stellar MLS #TB8492554
PriceChange
$429,000
Price decreased by 2%
Apr 2, 2026
Source: Stellar MLS #TB8492554
Listed For Sale
$439,000

Market trends in Largo

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$346K
$333MoM
Sale-to-List Price
97.7%
Price per sq ft
$253
$0MoM
Available listings
534
37MoM

Around this home

Neighborhood Overview

Chesterfield Heights
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Chesterfield Heights

  • Mjbruneau52
    "Great and easy. Onto one area with a short school zone where you have to slow down but otherwise good."
    0
    Flag
  • Moreoddthaneven
    "I've lived in this area for 3 years now and have truly come to appreciate the location. We are close to Clearwater Beach, several parks, plenty of restaurants and grocery stores. Our neighborhood is safe and quiet. "
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LGBTQ Local Legal Protections

Frequently asked questions about 1365 WINDSOR DRIVE

  • What is 1365 WINDSOR DRIVE estimated to be worth?
    Trulia's estimated value for 1365 WINDSOR DRIVE in Clearwater, FL is $416,200.
  • What is the price history for 1365 WINDSOR DRIVE?
    1365 WINDSOR DRIVE in Clearwater, FL last sold for $419,000 in May 2026.
  • 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 $346K. That is up $333 from the prior month.
  • Does 1365 WINDSOR DRIVE have air conditioning?
    Yes, 1365 WINDSOR DRIVE in Clearwater, FL has air conditioning.
  • Does 1365 WINDSOR DRIVE have a pool?
    Yes, 1365 WINDSOR DRIVE in Clearwater, FL has a pool.

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