
1109 CHARLES STREET, CLEARWATER, FL, 33755
Active131 days on marketListed Mar 22, 2026MLS #TB8489075
About this home
1109 CHARLES STREET
One or more photo(s) has been virtually staged. This is a rare opportunity to own a truly one-of-a-kind legacy property designed for coastal living in one of Pinellas County's most sought-after locations. Situated on a tropical double lot just blocks from St. Joseph’s Sound and minutes from Downtown Dunedin, this exceptional property offers a combination of land, flexibility, charm, and income potential that is increasingly difficult to find. Perhaps the most valuable feature of this property is its rare grandfathered multifamily designation within a residential zoning district, allowing it to function as either a single-family residence or an income-producing duplex with an additional ADU. Owners have the unique ability to live comfortably in one residence while generating income from the others, creating exceptional income opportunities. Thoughtfully renovated from the studs out by a renowned local builder, the property preserves the timeless character and “Old Florida” charm of the original structures while seamlessly incorporating modern luxury, craftsmanship, and convenience throughout. High-end finishes, thoughtful design, and flexible living spaces create a property that feels both elevated and inviting. The oversized double lot offers endless possibilities for expansion, outdoor entertaining, RV or boat parking, and private resort-style living. Surrounded by tropical landscaping, the outdoor setting is anchored by a brand-new pool with elegant paver decking, creating a private coastal retreat perfect for relaxing, entertaining, and enjoying Florida living year-round. Despite being located just minutes from the waterfront, the property sits outside the flood zone, eliminating the need for flood insurance. The Pinellas Trail is located at the end of the block and provides direct biking/walking access to downtown Dunedin’s acclaimed restaurants, breweries, bars, live music venues, boutique shopping, marinas, award-winning Gulf beaches, and Major League Baseball spring training facilities. The staged renderings showcase the incredible versatility of the property and highlight the many ways the spaces can be customized to fit your vision—whether as a private retreat, multigenerational compound, luxury seasonal residence, or high-performing investment property. Properties offering this level of location, flexibility, land value, and coastal character rarely come to market! This property is listed below appraised value and priced to sell!
Facts & features
The home at a glance
3
Bedrooms
3
Bathrooms
1,833
Sqft
0.27 ac
Lot size
2
Garage
1936
Year built
Two
Levels
$490
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.
$5,924 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
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
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$5,924/mo
Includes estimated PMI — it drops off once you reach 20% equity. 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.
$/sqft vs Clearwater actives
$490 vs $218
Days on market
131 vs 47 typical
Where $490/sqft sits among the 399 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 33755 — neighborhood snapshot
Population
28,057
Median age
41.3
Median income
$59,613
Median home value
$300,200
Avg household
2.46
Households w/ children
2,788
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)
223 of 399
Clearwater actives have cut their price
Median sold price, Clearwater, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 150% above the CLEARWATER 33755 median. See the full Clearwater market guide →
Paper trail
This home's history
Reality check
What actually sold near 1109 CHARLES STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$765,000
1144 CHARLES STREET · same community
3 bd · 2 ba · 1,283 sqft · $596/sqft · 3 DOM
Sold · Jul ’26$843,000
920 N OSCEOLA AVENUE UNIT 603
2 bd · 2 ba · 1,865 sqft · $452/sqft · 1 DOM
Sold · Feb ’26$825,000
920 N OSCEOLA AVENUE UNIT 402
2 bd · 2 ba · 1,800 sqft · $458/sqft · 0 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 1109 CHARLES STREET — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1109 CHARLES STREET — 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
1109 CHARLES STREET FAQs
What would the monthly payment be for 1109 CHARLES STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,924/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 1109 CHARLES STREET?+
The most recent tax bill on record (2025) was $6,914. 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 $899,000, this home is listed about 227% above the Clearwater median of $275,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1109 CHARLES STREET?+
Skycrest Elementary School (elementary), Clearwater High School (high), Dunedin Highland Middle School (middle) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$899,000 runs 150% above the CLEARWATER 33755 median — but at 1,833 sqft it's also 46% larger than the typical Clearwater listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Time on market is leverage
131 days on market against a Clearwater median of 47 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Skycrest Elementary School, Clearwater High School, Dunedin Highland Middle School — Dunedin Highland Middle School rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $999,000, now $899,000 — a $100K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of CHARLES RUTENBERG REALTY INC · Elena Kapetaneas. MLS #TB8489075.
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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