1365 Windsor Drive, CLEARWATER, FL 33756
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  • MLS#: TB8492554 ( Residential )
  • Street Address: 1365 Windsor Drive
  • Viewed: 3
  • Price: $439,000
  • Price sqft: $252
  • Waterfront: No
  • Year Built: 1963
  • Bldg sqft: 1745
  • Bedrooms: 2
  • Total Baths: 2
  • Full Baths: 2
  • Garage / Parking Spaces: 1
  • Days On Market: 6
  • Additional Information
  • Geolocation: 27.9333 / -82.7803
  • County: PINELLAS
  • City: CLEARWATER
  • Zipcode: 33756
  • Subdivision: Chesterfield Heights
  • Provided by: BLUE GECKO REALTY, LLC
  • Contact: Jeremy Mayer
  • 407-709-6176
  • mfrmls
  • DMCA Notice
  • 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. Dont miss your opportunity to own this move in ready Florida gem! Schedule your private tour today!
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Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Rain Gutters, Sidewalk, Storage
  • Fencing: Fenced, Vinyl, Wood
  • Flooring: Ceramic Tile
  • Living Area: 1202.00
  • Other Structures: Shed(s)
  • Roof: Shingle
Garage and Parking
  • Garage Spaces: 1.00
  • Open Parking Spaces: 0.00
  • Parking Features: Driveway
Eco-Communities
  • Pool Features: Gunite, Heated, In Ground, Lighting, Pool Sweep, Solar Heat
  • Water Source: Public, Well
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air
  • Heating: Central, Electric, Heat Pump
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Connected, Fiber Optics, Public, Water Connected
Finance and Tax Information
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2025
Other Features
  • Appliances: Dishwasher, Electric Water Heater, Microwave, Range, Refrigerator
  • Country: US
  • Furnished: Unfurnished
  • Interior Features: Ceiling Fans(s)
  • Legal Description: CHESTERFIELD HEIGHTS LOT 121
  • Levels: One
  • Area Major: 33756 - Clearwater/Belleair
  • Occupant Type: Owner
  • Parcel Number: 27-29-15-15084-000-1210
  • Possession: Close Of Escrow
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Headshot for Associate Sara Oquendo
  1. Sara Oquendo, REALTOR ®
  2. Tropic Shores Realty
  3. Mobile: 352.428.8657
  4. saraoquendo1972@gmail.com