5577 CONTENTO DRIVE, SARASOTA, FL, 34242
Active836 days on marketListed Apr 16, 2024MLS #A4607468
About this home
5577 CONTENTO DRIVE
This is a short term (weekly) rental. Listing reflects off season rate. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates throughout, from the brand-new kitchen to the spa-like bathrooms. You'll find a designated office space off the kitchen, perfect for remote work. The first bedroom features a king bed, and the second bedroom features a queen bed. Outside, soak up the Florida sunshine by the sparkling saltwater pool. With direct canal access, cast a line for some fishing, or launch a paddle board and explore the tranquil canals, where you're likely to spot local manatees and other fascinating wildlife. After exploring the canals, take a leisurely walk of just a few minutes to the world-famous Siesta Key Beach. Feel the soft, powdery quartz sand between your toes and bask in the beauty of the Gulf. Then, it's back to your private oasis where, as the sun begins its descent, it's 'tini time! Mix your favorite martini and savor it while watching the spectacular sunset paint the sky over the canal, beautifully highlighting silhouetted palm trees. It's truly an unforgettable end to a perfect day! Bikini Tini Time offers the perfect blend of tranquility and convenience, just moments from Siesta Key Village's vibrant shops and restaurants. Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,424
Sqft
0.26 ac
Lot size
1969
Year built
One
Levels
$4
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$196 /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
$196/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; 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 SIESTA ISLES
$4 vs $974
Days on market
836 vs 58 typical
Where $4/sqft sits among the 6 homes for sale in SIESTA ISLES
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 Sarasota Beach
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Sarasota Beach — neighborhood snapshot
Population
1,618
Median age
66
Median income
$128,627
Median home value
$1,096,296
Avg household
2
Households w/ children
91%
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Sarasota market
$470K → $470K
Sarasota median sold, yr/yr
95.1%
Sale-to-list ratio (12 mo)
3 of 6
SIESTA ISLES have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 99% below the SARASOTA 34242 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 5577 CONTENTO DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$700,000
5223 SHADOW LAWN DRIVE · same community
3 bd · 2 ba · 1,459 sqft · $480/sqft · 161 DOM
Sold · Oct ’25$640,000
5369 SHADOW LAWN DRIVE · same community
2 bd · 2 ba · 1,348 sqft · $475/sqft · 55 DOM
Sold · Jun ’26$933,000
5353 SHADOW LAWN DRIVE · same community
3 bd · 2 ba · 1,596 sqft · $585/sqft · 1 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5577 CONTENTO DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5577 CONTENTO DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
5577 CONTENTO DRIVE FAQs
What would the monthly payment be for 5577 CONTENTO DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $196/mo — principal and interest, estimated property taxes 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.
Are pets allowed at 5577 CONTENTO DRIVE?+
The listing reports pets: Breed Restrictions, Number Limit, Size Limit, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Sarasota?+
At $5,000, this home is listed about 99% below the Sarasota median of $570,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5577 CONTENTO DRIVE?+
Phillippi Shores Elementary School (elementary), Brookside Middle School (middle), Sarasota High School (high) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Under the SARASOTA 34242 market on paper
$5,000 is 99% below the SARASOTA 34242 median of $495,000, and at $4/sqft it sits under the Sarasota average of $496.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
836 days on market against a Sarasota median of 58 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Phillippi Shores Elementary School, Brookside Middle School, Sarasota High School — Phillippi Shores Elementary School rates 5 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $6,500, now $5,000 — a $2K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of ASCENDIA REAL ESTATE · Beth Dilley. MLS #A4607468.
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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