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$449,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,273 Sq. Ft.
  • Updated 5 days ago
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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.

Full Property Details for 1008 Chester Dr

General

  • Price: $449,900
  • Taxes: $5,973 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: TB8522980
  • Updated: 6/25/2026
  • Added to Site: 6 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 4
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Solid Wood Cabinets
  • Appliances: Convection Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
  • Furnishings: Partially
  • Flooring: Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Closet

Exterior

  • Exterior Features: Private Entrance, Private Mailbox, Private Yard

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 1
  • Covered Spaces: 1

Location

  • Area: 33756 - Clearwater/Belleair
  • County: Pinellas
  • Development Name: 33756 - Clearwater/Belleair
  • Subdivision: SIRMONS HEIGHTS 1ST ADD
  • Driving Directions: From 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.
  • Direction Faces: North

Community

  • Community Name: 33756 - Clearwater/Belleair

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Block
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,273
  • Sq. Ft. Source: Owner
  • Year Built: 1955

Lot Features

  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 8,028
  • Lot Size: 8028
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Tax Amount: $5,973
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: SIRMONS HEIGHTS 1ST ADD LOT 70
  • Flood Zone Info: X
  • APN: 152915822060000700
  • Property ID: 152915822060000700
  • Block/Lot/Section: 26400

Listed by Jpt Realty Llc

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Listing agent

— 1008 Chester Dr —

  • Jpt Realty Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1008 Chester Dr

School District:Pinellas County School District
NameGradesDistance
Plumb Elementary School
1920 Lakeview Road, Clearwater, FL 33764
PK-51.5 mi
Oak Grove Middle School
1370 South Belcher Road, Clearwater, FL 33764
6-82.1 mi
Clearwater High School
540 South Hercules Avenue, Clearwater, FL 33764
9-121.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1008 Chester Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/24/2026
Listed
$449,900
136.17%
MLS
6/11/2018
Sold
$190,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1008 Chester Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,973
6%
$350,982
3%
2024
$5,661
-7%
$341,090
8%
2023
$6,101
126%
$316,501
81%
2021
$2,703
1%
$175,215
-3%
2022
$2,679
-1%
$180,471
4%
2021
$2,703
3%
$172,796
2%
2019
$2,633
302%
$168,911
143%
2018
$655
3%
$69,569
2%
2017
$638
—
$68,138
2%
2016
$641
-41%
$66,737
-27%
2015
$1,078
-40%
$91,725
7%
2014
$1,784
5%
$85,713
—
2013
$1,700
—
$85,349
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Jpt Realty Llc

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1008 Chester Drive, Clearwater, FL 33756 (MLS# TB8522980) is a Single Family property with 4 bedrooms and 2 full bathrooms. 1008 Chester Drive is currently listed for $449,900 and was received on June 24, 2026. Want to learn more about 1008 Chester Drive? Do you have questions about finding other Single Family real estate for sale in Clearwater? You can browse all Clearwater real estate or contact a Coldwell Banker agent to request more information.

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