1008 Chester Drive, FL1008 Chester Drive, FL1008 Chester Drive, FL
Stellar MLS
1 / 21

$449,900

1008 Chester Drive

Clearwater, FL 33756

Listing updated: June 25, 2026 at 1:01 AM ET

Active
Stellar MLSListing courtesy of Jpt Realty Llc · Mabel Quevedo · MLS #TB8522980 · Active · 813-325-4177
4
Beds
2
Baths
1,273
Sq Ft
0.18
Acres
1955
Built
In-law suite$353/sqft360° tour
Single Family Residence

Property type

1955

Year built

8,028 sqft

Lot size

$353

Price / sq ft

No HOA

HOA dues

0

Days on market

1

Garage space

X

Flood zone

About this home

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.

Local Insight

At $353/sqft for a 1955 home in Clearwater, you're paying under market rate, but the 1,273 sqft layout is tight for four bedrooms—the in-law suite likely means one "bedroom" is cramped, so verify the actual living space feels functional before committing. The X flood zone is a major plus for this area, and no HOA keeps costs predictable, but a nearly 70-year-old home will need a thorough inspection to understand what deferred maintenance you're inheriting, especially on the roof and foundation.

AI-generated insight based on listing data and neighborhood context. Verify independently.

Estimated monthly payment

Principal & interest$2,275
Property taxes$498
Home insurance (est.)$206

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history0 days on market

  1. Status: Active
    Jun 24, 2026
  2. Listed$449,900
    Jun 24, 2026
  3. Price increased$449,900

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
0
Subdivision
Sirmons Heights 1st Add
County
Pinellas
Year built
1955
Living area
1,273 sq ft
Price/sq ft
$353
Building area
2,012 sq ft (Owner)
Lot size
8,028 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12103C0109J)
Garage
1 spaces
Annual taxes
$5,973 (2025)
Parcel #
15-29-15-82206-000-0700
MLS #
TB8522980

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Interior Details

Bedrooms
4
Full bathrooms
2
Flooring
Ceramic Tile
Appliances
Convection Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
Interior features
Ceiling Fans(s), Eat-in Kitchen, Solid Wood Cabinets
Laundry
Laundry Closet
Stories / Levels
One
Direction faces
North
In-law suite
Yes

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Garage spaces
1
Attached garage
Yes

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Min lease term
No Minimum
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No

Exterior & Construction

Exterior features
Private Entrance, Private Mailbox, Private Yard
Construction materials
Block
Roof
Shingle
Foundation
Slab
Road surface
Asphalt

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Electricity Connected, Sewer Connected, Water Connected

Room Details

RoomLevelDimensions
Primary BedroomFirst12x10
Living RoomFirst14x12
KitchenFirst10x10
Dining RoomFirst8x5

Listing Details

Listing date
2026-06-23
On market date
2026-06-24
Original list price
$449,900
Occupant type
Vacant
MLS area
33756 - Clearwater/Belleair
Listing AOR
Suncoast Tampa
Status changed
2026-06-24
Tax legal description
SIRMONS HEIGHTS 1ST ADD LOT 70

Flood risk

Minimal riskFEMA Zone XPanel 12103C0109J

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively 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.

Based on information submitted to the MLS GRID as of June 25, 2026 at 1:01 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA