David Ramirez
$4,500,000$4,900,0006 bd6 ba6,655 sqft$676 /sqft$29,240 /mo all-in ↓

5309 HIDDEN HARBOR ROAD, SARASOTA, FL, 34242

Active283 days on marketListed Oct 16, 2025MLS #A4668550

Reduced $400KWaterfrontPrivate poolSingle Family ResidenceHIDDEN HARBOR

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

Private poolWaterfrontFireplacePets allowed

Inside

FlooringBrick/Stone · Carpet · Ceramic Tile · Hardwood
AppliancesBar Fridge · Built-In Oven · Convection Oven · Dishwasher · Disposal · Dryer · Electric Water Heater · Exhaust Fan · Freezer · Ice Maker · Microwave · Range · Range Hood · Refrigerator · Washer · Wine Refrigerator
InteriorCeiling Fan(s) · Central Vacuum · Coffered Ceiling(s) · Crown Molding · High Ceilings · Kitchen/Family Room Combo · Living Room/Dining Room Combo · Primary Bedroom Main Floor · Solid Wood Cabinets · Stone Counters · Tray Ceiling(s) · Walk-In Closet(s) · Wet Bar · Window Treatments
LaundryInside · Laundry Room
CoolingCentral Air · Mini-Split Unit(s) · Zoned
HeatingCentral · Electric · Zoned

Outside & construction

RoofMetal
ConstructionBlock · HardiPlank Type · Wood Frame
FoundationSlab · Stem Wall
FacesSouth
ExteriorFrench Doors · Outdoor Grill · Rain Gutters · Sliding Doors

Community & fees

HOA fee$247/mo
Taxes (2023)$34,362/yr
PetsYes

Utilities & systems

UtilitiesBB/HS Internet Available · Cable Available · Electricity Connected · Public · Water Connected
WaterPublic

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%

Principal & interest$24,282
PMI (est., until 20% equity)$1,688
Property tax — 2023 actual bill$2,864
HOA fee — from the listing$247
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $450,000Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

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

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $450,000
Interest rate6.00%
Loan term

Estimated payment

$29,240/mo

Principal & interest$24,282
PMI (est., until 20% equity)$1,688
Property taxes (actual bill)$2,864
HOA / condo fee$247
Est. insurance$160

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

5
0 · this home
2
0
0
3
$173–439$439–705$705–971$971–1237$1237–1503$1503+

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

Map of 5309 HIDDEN HARBOR ROAD inside its neighborhood boundary

Drive times from this address

Downtown Tampa70 min

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

ElementaryPhillippi Shores Elementary School★★★★★
MiddleBrookside Middle School★★★★★
HighSarasota High School★★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Sarasota market

Seller’s marketBalanced6.0 months of inventoryBuyer’s 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

CurrentPrice reduced to $4,500,000 $400K
Oct 16, 2025Listed at $4,900,000 · 283 days on market since
2007Built · HIDDEN HARBOR

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.

2394 WINDWARD COVESold · Mar ’26

$690,000

2394 WINDWARD COVE · same community

5 bd · 4 ba · 4,920 sqft · $140/sqft · 209 DOM

2395 WINDWARD COVESold · Jun ’26

$545,000

2395 WINDWARD COVE · same community

4 bd · 3 ba · 3,621 sqft · $151/sqft · 55 DOM

5112 JUNGLE PLUM ROADSold · 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.

David Ramirez

Your agent

David Ramirez

Real Estate Agent · CENTURY 21 Edge

Tours, negotiation, and every question about 5309 HIDDEN HARBOR ROAD — start here.

Andrew Acosta

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.

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.

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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