CLEARWATER, FL 33756 1008 CHESTER DRIVE

1008 CHESTER DRIVE CLEARWATER, FL - Image 11008 CHESTER DRIVE CLEARWATER, FL - Image 21008 CHESTER DRIVE CLEARWATER, FL - Image 3
16 more
1008 CHESTER DRIVE CLEARWATER, FL - Image 41008 CHESTER DRIVE CLEARWATER, FL - Image 51008 CHESTER DRIVE CLEARWATER, FL - Image 61008 CHESTER DRIVE CLEARWATER, FL - Image 71008 CHESTER DRIVE CLEARWATER, FL - Image 81008 CHESTER DRIVE CLEARWATER, FL - Image 91008 CHESTER DRIVE CLEARWATER, FL - Image 101008 CHESTER DRIVE CLEARWATER, FL - Image 111008 CHESTER DRIVE CLEARWATER, FL - Image 121008 CHESTER DRIVE CLEARWATER, FL - Image 131008 CHESTER DRIVE CLEARWATER, FL - Image 141008 CHESTER DRIVE CLEARWATER, FL - Image 151008 CHESTER DRIVE CLEARWATER, FL - Image 161008 CHESTER DRIVE CLEARWATER, FL - Image 171008 CHESTER DRIVE CLEARWATER, FL - Image 181008 CHESTER DRIVE CLEARWATER, FL - Image 191008 CHESTER DRIVE CLEARWATER, FL - Image 20
Presented By: with . - 813-325-4177
  • MLS# TB8522980
  • 06/23/2026
  • Request Tour
  • Request Info
Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 4
  • Baths • 2
  • SQFT • 1,273
  • Garage • 1

Home Details

Welcome to this beautifully full remodeled 4 bedroom, 2 bathroom home located in the desirable city of Clearwater. This property offers a perfect blend comfort, funtionality, and investment potential. One of the standout features is a converted garage that serves as a private in-law suite, complete with its own separate entrance and kitchenette, ideal for guests, extended family, or as an income producing rental opportunity. The home has been thoughfully updated throughout, featuring modern finishes, upgraded fixtures, and a fresh contemporary design. Whether you are looking for a primary residence or an investment property, this home offers versatility to meet your needs. Conveniently located near beaches, shopping, dining, and major roadways, this move in ready property is a must see.
Presented By: with . - 813-325-4177

Interior Features for 1008 CHESTER DRIVE

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths0
Total Baths2

Other Interior Features

LivingAreaSourceOwner
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringCeramic Tile
Furnished Y/NPartially
Heating Y/NYes
Interior AmenitiesCeiling Fan(s), Eating Space In Kitchen, Solid Wood Cabinets
Laundry FeaturesLaundry Closet

General for 1008 CHESTER DRIVE

Additional Parcels Y/NNo
AppliancesConvection Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityCLEARWATER
Construction MaterialsBlock
CoolingCentral Air
CountyPinellas
DirectionsFrom Gulf to Bay BLV, head south on S Hillcrest Ave, turn right onto Druid RD, make the second left onto Chester DR. The Property will be on the right.
DockY/NNo
Facing DirectionNorth
Flood Zone CodeX
Flood Zone Code XY
Full Baths2
Garage Spaces1
Garage Y/NYes
HeatingCentral
In Law Suite Description1 Bathroom, 1 Bedroom, Kitchenette, Private Entrance
In Law Suite YNYes
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionSIRMONS HEIGHTS 1ST ADD LOT 70
LevelsOne
Listing TermsCash, Conventional, FHA, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet8028
Lot Size UnitsSquare Feet
MLS Area33756 - Clearwater/Belleair
Minimum LeaseNo Minimum
New ConstructionNo
Occupancy TypeVacant
OwnershipFee Simple
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameSIRMONS HEIGHTS 1ST ADD
Tax Annual Amount5973
Tax Lot70
Tax Year2025
Total Rooms4
UtilitiesElectricity Connected, Sewer Connected, Water Connected
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1955

Exterior for 1008 CHESTER DRIVE

Building Area Total2012
Covered Spaces1
Exterior AmenitiesPrivate Entrance, Private Mailbox, Private Yard
Foundation DetailsSlab
Lot Size Acres0.18
Lot Size Area8028
Private PoolNo
Road Surface TypeAsphalt
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Schools

High School Hubert H Humphrey Middle School
Middle School N/A
Elementary School Big Hollow Elementary School

Steven Pugh

Broker Associate | Team Leader
Price $449,900
MLS#TB8522980
List Date 06/23/2026
Property Type Single Family
Request Tour
Request Info
Visit My Website

Similar Properties to 1008 CHESTER DRIVE

MLS® Disclaimer

MLS Logo Copyright © MFRMLS.com All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of MFR MLS. All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

33. Required DMCA Notice

DMCA Disclaimer

The Digital Millennium Copyright Act of 1998, 17 U.S.C. §512, the DMCA, provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owners behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.