156 SIESTA DRIVE, SARASOTA, FL, 34242
Active360 days on marketListed Aug 13, 2025MLS #A4661717
About this home
156 SIESTA DRIVE
Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer’s haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.
Facts & features
The home at a glance
5
Bedrooms
3
Bathrooms
2,901
Sqft
0.25 ac
Lot size
2
Garage
1977
Year built
Three Or More
Levels
$568
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.
$11,261 /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
$11,261/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.
vs edgeAI estimate
−21.4%
$/sqft vs Sarasota actives
$568 vs $345
Days on market
360 vs 61 typical
Where $568/sqft sits among the 400 Sarasota 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 Bay Island
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Bay Island — neighborhood snapshot
Population
531
Median age
61
Median income
$151,850
Median home value
$2,000,000
Avg household
2
Households w/ children
31%
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
$475K → $493K
Sarasota median sold, yr/yr
95.2%
Sale-to-list ratio (12 mo)
162 of 400
Sarasota actives have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 262% above the SARASOTA 34242 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 156 SIESTA DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$1,550,000
185 FAUBEL STREET · same community
5 bd · 4 ba · 3,783 sqft · $410/sqft · 9 DOM
Sold · Feb ’26$1,490,000
3615 FLORES AVENUE
4 bd · 3 ba · 2,889 sqft · $516/sqft · 7 DOM
Sold · May ’26$2,220,000
4013 RED ROCK LANE
4 bd · 3.5 ba · 2,844 sqft · $781/sqft · 385 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
Erwin Vazquez
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 156 SIESTA DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 156 SIESTA DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Erwin's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
156 SIESTA DRIVE FAQs
What would the monthly payment be for 156 SIESTA DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $11,261/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 156 SIESTA DRIVE?+
The most recent tax bill on record (2024) was $19,016. 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 Sarasota?+
At $1,649,000, this home is listed about 190% above the Sarasota median of $569,000. The market section on this page shows how the area is trending.
Which schools are assigned to 156 SIESTA DRIVE?+
Brookside Middle School (middle), Phillippi Shores Elementary School (elementary), 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
01Positioned at the premium end
$1,649,000 runs 262% above the SARASOTA 34242 median — but at 2,901 sqft it's also 72% larger than the typical Sarasota 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
360 days on market against a Sarasota median of 61 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Brookside Middle School, Phillippi Shores Elementary 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 $1,730,000, now $1,649,000 — a $81K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KW COASTAL LIVING III · Curt Ware. MLS #A4661717.
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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