Active
$449,900
Est. $3,069/mo

1008 Chester Dr, Clearwater, FL, 33756

$353/sqft·Sirmons Heights 1st

4 bd2 ba1,273 sqft1 car garageSingle Family
Listed by JPT REALTY LLC· Last updated · MLS# TB8522980

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Est. monthly payment
$3,069/mo
Down payment (20%)
$89,980
Property taxes
$498/mo
Rate assumed
6.8% · 30 yr
View full breakdown

At a glance

Single family
Built 1955
1 car garage
8,028 sqft lot
Lot size
1,273 sqft
Living area

About this home

Ceiling Fans(s)Eat-in KitchenSolid Wood CabinetsPrivate EntrancePrivate MailboxPrivate YardConvection OvenCooktop

1008 Chester Dr is a 1955-built home in Sirmons Heights 1st Add, Clearwater. Inside you'll find 4 bedrooms, 2 bathrooms, and 1,273 square feet of living space. Listed at $449,900 (about $353/sqft), 1 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

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.

The essentials

Built
1955
Price / sqft
$353
On market
79 days
Annual tax
$5,973
Flood zone
X · Low risk
Lot
8,028 sqft
Type
Single Family Residence

Location

1008 Chester Dr
Clearwater, FL, 33756·33756 - Clearwater/Belleair
Type
Single Family Residence
Year Built
1955
Lot
8,028 sqft
Cooling
Central Air
Heating
Central
Parking
-
Days on Market
79
Ceiling Fans(s)
Eat-in Kitchen
Solid Wood Cabinets
Private Entrance
Private Mailbox
Private Yard
Convection Oven
Cooktop
Dishwasher
Dryer
Electric Water Heater
Microwave
Refrigerator
Washer
Flood Zone X

Annual Tax (2025)

$5,973

Parcel #

15-29-15-82206-000-0700

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision

Sirmons Heights 1st Add

County

Pinellas

MLS Area

33756 - Clearwater/Belleair

Lot Size

8,028 sqft

Date
Event
Price
6/24/2026
Listed for sale
Source: Stellar MLS #TB8522980
$449,900+19.7%
$353/sqft
6/1/2022
Sold
Source: Pinellas County Public Record
$376,000
$295/sqft
Est. monthly payment$3,069/mo
Principal & interest$2,346
Property taxes$498
Insurance$225
Down payment20% · $89,980
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Offer Insights

Choose an offer strength

List price: $449,900
$445,000 – $449,900
98.6% – 100% of listTops out right at the list price
80% of listList price
52 of the last 102 home closings in 33756 landed at this number or higher (51%). The median one sat 26 days before it went under contract, and this one is on day 79.

Sample: 102 closed home sales in 33756 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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