Active
$17,650,000
Est. $110,256/mo

3799 Flamingo Ave, Sarasota, FL, 34242

$2,169/sqft·Bay Island

4 bd6 ba8,138 sqft8 car garageSingle Family
Listed by MICHAEL SAUNDERS & COMPANY· Last updated · MLS# A4699552

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Est. monthly payment
$110,256/mo
Down payment (20%)
$3,530,000
Property taxes
$9,379/mo
Rate assumed
6.8% · 30 yr
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At a glance

Single family
3 stories · 2016
Waterfront
Bay/Harbor
Private pool
Heated
8 car garage
Circular Driveway
1.40 acres
Lot size

About this home

Ceiling Fans(s)Central VaccumCoffered Ceiling(s)Crown MoldingEat-in KitchenElevatorHigh CeilingsLiving Room/Dining Room Combo

3799 Flamingo Ave is a 2016-built home in Bay Island, Sarasota. Inside you'll find 4 bedrooms, 6 bathrooms, and 8,138 square feet of living space. Listed at $17,650,000 (about $2,169/sqft), 33 days on market. Flood zone AE - confirm flood insurance requirements with your lender.

From the listing

Four Seasons Hotel in Bali or private estate? Set on more than an acre of coveted waterfront property along the prestigious north end of Siesta Key, this extraordinary Balinese-inspired estate is a rare sanctuary where timeless architecture, unparalleled craftsmanship, and the restorative beauty of nature exist in perfect harmony. Offered fully furnished, the residence has been curated to provide an effortless, move-in-ready lifestyle, where every detail has been thoughtfully considered and every space evokes a sense of calm, balance, and understated luxury. Spanning more than 8,000 square feet, the home embraces the philosophy of seamless indoor-outdoor living. Expansive walls of glass dissolve the boundaries between the interiors and the surrounding tropical landscape, filling the home with natural light, gentle coastal breezes, and mesmerizing waterfront views. Rich exotic woods, natural stone, tranquil water features, and handcrafted architectural elements create an atmosphere reminiscent of an exclusive Balinese resort, where every room serves as a peaceful retreat. Designed as a private wellness oasis, the grounds are nothing short of breathtaking. Lush tropical gardens, mature specimen palms, fragrant flowering plants, and winding pathways lead through a series of serene outdoor spaces that inspire quiet reflection and effortless entertaining. A tranquil koi pond, crossed by picturesque footbridges, gently meanders alongside the residence, filling the air with the soothing sound of flowing water and creating a Zen-inspired tranquility throughout the estate. The resort-caliber outdoor living spaces are exceptional. An infinity-edge pool appears to merge effortlessly with the sparkling bay beyond and features a swim-up bar, spa, expansive sun shelves, and multiple terraces for lounging in the Florida sunshine. A dramatic sunken fire pit provides the perfect setting for evening gatherings beneath the stars, while the outdoor kitchen, covered dining pavilion, and numerous seating areas invite unforgettable alfresco entertaining against a backdrop of spectacular sunsets and panoramic waterfront vistas. With more than 700 feet of waterfront frontage, the property offers an extraordinary connection to the water that is rarely found. Whether setting out for a morning paddle through calm mangrove-lined waters or enjoying effortless boating from the private dock, every day begins and ends immersed in Sarasota's extraordinary coastal beauty. A dedicated waterfront garage, newer seawall, and abundant shoreline further enhance this exceptional waterfront lifestyle. Inside, every space has been thoughtfully designed to nurture both relaxation and recreation. A private theater, game room, fitness studio, and dedicated meditation room create an environment centered around wellness, entertainment, and everyday enjoyment. An oversized garage accommodating more than eight vehicles provides ample space for collectors and enthusiasts alike. Modern technology complements the home's timeless design with Crestron smart home automation, a three-stop elevator, whole-house generator, reverse osmosis water filtration system, and numerous additional upgrades that deliver effortless comfort, security, and peace of mind. This one-of-a-kind estate represents one of Siesta Key's most extraordinary luxury offerings and an exceptionally rare opportunity to own a true legacy property.

The essentials

Built
2016
Price / sqft
$2,169
On market
42 days
Annual tax
$112,550
Flood zone
AE
Lot
60,968 sqft
Type
Single Family Residence

Location

3799 Flamingo Ave
Sarasota, FL, 34242·34242 - Sarasota/Crescent Beach/Siesta Key
Type
Single Family Residence
Year Built
2016
Lot
60,968 sqft
Cooling
Central Air, Zoned
Heating
Central, Zoned
Parking
Circular Driveway, Driveway, Garage Door Opener, Ground Level
Pool
Heated, In Ground, Infinity, Lap, Lighting, Salt Water
Waterfront
Bay/Harbor, Canal - Saltwater, Lagoon
Days on Market
42
Ceiling Fans(s)
Central Vaccum
Coffered Ceiling(s)
Crown Molding
Eat-in Kitchen
Elevator
High Ceilings
Living Room/Dining Room Combo
Open Floorplan
Primarybedroom Upstairs
Smart Home
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Vaulted Ceiling(s)
Walk-in Closet(s)
Wet Bar
Window Treatments
Balcony
Fire Pit
Lighting
Outdoor Kitchen
Outdoor Shower
Private Yard
Bar Fridge
Built-in Oven
Dishwasher
Disposal
Dryer
Ice Maker
Microwave
Range
Range Hood
Refrigerator
Washer
Wine Refrigerator

Elementary

Phillippi Shores Elementary

Middle

Brookside Middle

High

Sarasota High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on fileFlood Zone AE

Annual Tax (2025)

$112,550

Parcel #

2019150017

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision

Bay Island

County

Sarasota

MLS Area

34242 - Sarasota/Crescent Beach/Siesta Key

Lot Size

60,968 sqft

FloodZoneIrregular LotLandscapedOversized LotPrivatePaved
Date
Event
Price
7/31/2026
Listed for sale
Source: Stellar MLS #A4699552
$17,650,000
$2,169/sqft
Est. monthly payment$110,256/mo
Principal & interest$92,052
Property taxes$9,379
Insurance$8,825
Down payment20% · $3,530,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Offer Insights

Choose an offer strength

List price: $17,650,000
$16.77M – $17.65M
95% – 100% of listTops out right at the list price
80% of listList price
29 of the last 56 home closings in 34242 landed at this number or higher (52%). The median one sat 87 days before it went under contract, and this one is on day 42.

Sample: 56 closed home sales in 34242 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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