1365 Windsor Dr, Clearwater, FL 33756
SOLD
MAY 21, 2026

1365 Windsor Dr
Clearwater, FL 33756

Chesterfield Heights
  • 2 Beds
  • 2 Baths
  • 1,202 sqft

$419,000

Last Sold: May 21, 2026
$349/sqft
Est. Refi. Payment $2,199/mo*
Refinance Your Home

$419,000

Last Sold: May 21, 2026
$349/sqft
Est. Refi. Payment $2,199/mo*
Refinance Your Home
2 Beds
2 Baths
1,202 sqft

Local Information

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

Description

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 Dr, 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. It is currently off market. The Trulia Estimate is $419,000, with a rent estimate of $2,843/month.

Home Highlights

Parking
1 Car Garage
Outdoor
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
$349/sqft
Listed
97 days ago

Home Details for 1365 Windsor Dr

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
Last check for updates: 1 day 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

Price History for 1365 Windsor Dr

DatePriceEventSource
05/21/2026$419,000Sold
Stellar MLS #TB8492554
04/23/2026$419,000PendingStellar MLS #TB8492554
04/17/2026$419,000PriceChange
Stellar MLS #TB8492554
04/11/2026$429,000PriceChange
Stellar MLS #TB8492554
04/02/2026$439,000Listed For SaleStellar MLS #TB8492554
03/24/2021ListingRemovedN/A
12/06/2017$240,000ListingRemovedN/A
12/06/2017$240,000Listed For SaleN/A
11/29/2017$238,000Sold
N/A
11/02/2017$240,000PendingN/A
10/29/2017$240,000Listed For SaleN/A
08/26/2017$245,000ListingRemovedN/A
08/17/2017$245,000Listed For SaleN/A
07/29/2016$205,000Sold
Stellar MLS #U7781521
07/25/2016$195,000PendingAgent Provided
06/17/2016$195,000Listed For SaleAgent Provided
03/30/2005$155,000Sold
N/A

Market trends in Largo

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$327K
$10.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$246
$6MoM
Available listings
604
8MoM
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Property Tax and Assessment

Year2024
Tax$3,267
Assessment$398,716
Home facts updated by county records

Comparable Sales for 1365 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1413 Croydon Dr, Clearwater, FL
0.15
Single-Family Home
$410,000
09/16/25
2
2
1,040
408 Ocean Ct, Clearwater, FL
0.20
Single-Family Home
$366,000
05/28/26
2
2
1,406
1339 Buckingham Dr, Clearwater, FL
0.06
Single-Family Home
$505,000
04/06/26
3
2
1,460
1324 Chesterfield Dr, Clearwater, FL
0.13
Single-Family Home
$449,000
04/27/26
3
2
1,313
1729 Kenilworth Dr, Clearwater, FL
0.14
Single-Family Home
$370,000
11/17/25
3
2
1,489
1354 Buckingham Dr, Clearwater, FL
0.09
Single-Family Home
$326,000
04/07/26
3
2
1,527
1379 Ponce De Leon Blvd, Clearwater, FL
0.11
Single-Family Home
$410,000
09/02/25
3
2
1,630

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Assigned Schools

These are the assigned schools for 1365 Windsor Dr.
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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

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."
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  • 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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