
5309 HIDDEN HARBOR ROAD, SARASOTA, FL, 34242
Active283 days on marketListed Oct 16, 2025MLS #A4668550
About this home
5309 HIDDEN HARBOR ROAD
Majestic waterfront home nestled in one of Siesta Key's most exclusive neighborhoods. Prime waterfront location with direct access to the inter-coastal (no bridges) and features a 16,000 pound vertical lift and a jet ski lift. This Waterfront home features wraparound decks on multiple levels composed of Brazilian Ipe decking, wood ceilings, a private grill area with a dramatic view up the canal and a resort like swimming pool and spa featuring a rock waterfall and paver patio to fill your sun filled afternoons. Upon entering the home, you will see the amount of detail and craftsmanship that was put into this home. Hand-scraped wood flooring, coffered tongue-n-groove ceilings, huge baseboard and crown molding throughout. Expansive windows let the natural light in and an aquarium glass wall in the kitchen/family room overlooks your lower deck, swimming pool, spa and water view. The home has well over 6000 square feet of living area with the master suite occupying the first-floor level. This home affords 6 bedrooms, 5 full baths, 2 half baths, a private office with built-in cabinetry, 2 wet bars one on each level, 2 laundries with one on each level, a Sports room/ man cave with a built-in entertainment center. Upstairs has 4 bedrooms, two of which are suites, a second family room/playroom, theater/entertainment room which connects to your second level deck. The main level of the home incorporates your kitchen, family room, pantry, wet bar, dining room, private office, master suite and laundry. The kitchen features a huge walk-in pantry with entry door, a huge center island with a granite top, Subzero refrigerator, a Wolf 6 burner/griddle stove, a Wolf warming drawer, a Wolf microwave, 2 drawer Fisher Paykel dishwasher and a second Miele dishwasher for all your entertainment needs. Each level has a wet bar with the lower level having a subzero wine refrigerator and a drink refrigerator and the upstairs level has a Fisher Paykel dishwasher, an ice-maker, microwave, and a refrigerator. For the car enthusiast you have two 2 car garages with separate drives which provides additional parking as well. This spectacular home is hard to match, and you won't be disappointed. The home has an elevation of 15 feet and also has a home generator to provide comfort and a sense of security during any power outages that may occur. Schedule an appointment to see your future home!
Facts & features
The home at a glance
6
Bedrooms
6
Bathrooms
6,655
Sqft
0.42 ac
Lot size
4
Garage
2007
Year built
Two
Levels
$676
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 and the real association fee — not generic estimates.
$29,240 /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
$29,240/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 HIDDEN HARBOR
$676 vs $821
Days on market
283 vs 58 typical
Where $676/sqft sits among the 10 homes for sale in HIDDEN HARBOR
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 Hidden Harbor
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Hidden Harbor — neighborhood snapshot
Population
193
Median age
64
Median income
$178,493
Median home value
$910,200
Avg household
2
Households w/ children
4%
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)
2 of 10
HIDDEN HARBOR have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 801% above the SARASOTA 34242 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 5309 HIDDEN HARBOR ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$690,000
2394 WINDWARD COVE · same community
5 bd · 4 ba · 4,920 sqft · $140/sqft · 209 DOM
Sold · Jun ’26$545,000
2395 WINDWARD COVE · same community
4 bd · 3 ba · 3,621 sqft · $151/sqft · 55 DOM
Sold · Jan ’26$1,600,000
5112 JUNGLE PLUM ROAD · same community
2 bd · 2.5 ba · 3,074 sqft · $520/sqft · 321 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 5309 HIDDEN HARBOR ROAD — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5309 HIDDEN HARBOR ROAD — 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
5309 HIDDEN HARBOR ROAD FAQs
What would the monthly payment be for 5309 HIDDEN HARBOR ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $29,240/mo — principal and interest, the actual property-tax bill, the $247/mo association fee 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.
How much are the HOA fees at 5309 HIDDEN HARBOR ROAD?+
The association fee works out to $247 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5309 HIDDEN HARBOR ROAD?+
The most recent tax bill on record (2023) was $34,362. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5309 HIDDEN HARBOR ROAD?+
The listing reports pets: 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 $4,500,000, this home is listed about 689% above the Sarasota median of $570,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5309 HIDDEN HARBOR ROAD?+
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
01Positioned at the premium end
$4,500,000 runs 801% above the SARASOTA 34242 median — but at 6,655 sqft it's also nearly 4 times the size of the typical Sarasota listing.
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
283 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 $4,900,000, now $4,500,000 — a $400K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of WATERSIDE REALTY LLC · Brian Livesey. MLS #A4668550.
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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