1008 CHESTER DRIVE, CLEARWATER, FL, 33756
Active30 days on marketListed Jun 24, 2026MLS #TB8522980
About this home
1008 CHESTER DRIVE
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.
Facts & features
The home at a glance
4
Bedrooms
2
Bathrooms
1,273
Sqft
0.18 ac
Lot size
1
Garage
1955
Year built
One
Levels
$353
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,505 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,505/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+25%
$/sqft vs Clearwater actives
$353 vs $219
Days on market
30 vs 47 typical
Where $353/sqft sits among the 400 Clearwater actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Clearwater
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Clearwater. See the full Clearwater guide →
CLEARWATER 33756 — neighborhood snapshot
Population
32,928
Median age
45
Median income
$63,990
Median home value
$335,800
Avg household
2.46
Households w/ children
2,867
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Clearwater market
$332K → $335K
Clearwater median sold, yr/yr
95.8%
Sale-to-list ratio (12 mo)
215 of 400
Clearwater actives have cut their price
Median sold price, Clearwater, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 32% above the CLEARWATER 33756 median. See the full Clearwater market guide →
Paper trail
This home's history
Reality check
What actually sold near 1008 CHESTER DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$475,000
905 S BETTY LANE · same community
3 bd · 2 ba · 1,268 sqft · $375/sqft · 2 DOM
Sold · Sep ’25$342,000
1557 S MARTIN LUTHER KING JR AVENUE
3 bd · 2 ba · 1,272 sqft · $269/sqft · 25 DOM
Sold · Mar ’26$247,000
1621 S JEFFERSON AVENUE
3 bd · 1 ba · 1,260 sqft · $196/sqft · 3 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Eric Chery
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1008 CHESTER DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1008 CHESTER DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Eric's phone and CRM.
Straight answers
1008 CHESTER DRIVE FAQs
What would the monthly payment be for 1008 CHESTER DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,505/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 1008 CHESTER DRIVE?+
The most recent tax bill on record (2025) was $5,973. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Clearwater?+
At $449,900, this home is listed about 64% above the Clearwater median of $275,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1008 CHESTER DRIVE?+
Plumb Elementary School (elementary), Clearwater High School (high), Oak Grove Middle School (middle) — Pinellas County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of JPT REALTY LLC · Mabel Quevedo. MLS #TB8522980.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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