$449,900
1008 Chester Drive
Clearwater, FL 33756
Listing updated: June 25, 2026 at 1:01 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage space
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
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
- Status: ActiveJun 24, 2026
- Listed$449,900Jun 24, 2026
- 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
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | 12x10 |
| Living Room | First | 14x12 |
| Kitchen | First | 10x10 |
| Dining Room | First | 8x5 |
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-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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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.
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