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Stephen Michalakos

propertiesbystephen@gmail.com +1(727) 601-8676

$ 14,750,000

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424 BOWDOIN CIR Sarasota, FL 34236

5 Beds

6 Baths

5,882 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 5,882 sqft

Price per Sqft $2,507

Subdivision Lido Shores

MLS Listing ID A4646393

Bedrooms 5

Full Baths 5

Half Baths 1

Construction Status Completed

HOA Fees $300/ann

HOA Y/N Yes

Annual Recurring Fee 300.0

Year Built 2023

Annual Tax Amount $131,498

Lot Size 0.390 Acres

Acres 0.39

Property Sub-Type Single Family Residence

Source Stellar MLS

Property Description

Set against Sarasota's coveted bayfront in Lido Shores, this extraordinary waterfront estate captures sweeping views of Sarasota Bay, the downtown skyline, Ringling Bridge, and City Island, offering an unparalleled luxury lifestyle with effortless access to boating, beaches, and downtown Sarasota. More than a residence, this is a statement property—an iconic example of West Indies–inspired architecture executed with exceptional craftsmanship and modern sophistication. A private gated entry introduces a home where over $1 million in enhancements and more than 2,000 hours of custom design are evident throughout. Advanced smart home automation allows seamless global control, blending innovation with refined living. The custom front door opens to a dramatic foyer and a great room defined by a coffered ceiling, media wall, linear fireplace, and expansive bay views. The dining space features a quartz-topped bar with wine storage and flows into a chef's kitchen appointed with Thermador appliances, a large floating island with quartz waterfall edges, and a walk-in pantry with an additional Bosch refrigerator. The primary suite is a tranquil sanctuary with floor-to-ceiling glass, sliders, and breathtaking water views. Two custom walk-in closets complement a spa-inspired bath featuring floating vanities, a soaking tub, a custom multi-head shower, and sliders leading to a private Zen garden with an outdoor shower. A sculptural staircase and glass-enclosed wine wall lead to an upper-level loft with a wet bar and waterfront terrace. A refined office with custom built-ins and four en-suite guest bedrooms, each with custom closets, projector screens, and private balconies, ensure comfort and privacy throughout. Outdoors, the estate transforms into a resort-style waterfront retreat. An infinity-edge pool with sun shelf, in-pool table, and cascading spa anchors the setting, surrounded by multiple seating areas, a firepit, and an outdoor shower. The fully equipped outdoor kitchen—featuring a smoker, grill, wok, and side burner—makes alfresco entertaining effortless, while a spiral staircase leads to an upper terrace with panoramic views. The newer deepwater dock is designed for serious boating, offering a 20,000-pound boat lift, jet ski lift, water and power, ambient lighting, and a dedicated fishing area. With direct access to Sarasota Bay just steps from the backyard, this property delivers exceptional boating and waterfront living. Additional features include a three-car garage, two laundry rooms, an elevator, a garage drop zone, and a hidden utility closet. The home is fully integrated with Control4 automation, security cameras, a 48-kilowatt generator, 20-kilowatt battery backup, high-end audio-visual systems, automated shades, circadian lighting, outdoor theater, app-controlled pool and irrigation, Wi-Fi-enabled appliances, EV charger prewiring, Starlink backup internet, motion-activated lighting, and voice control via Josh AI. Lido Shores is one of Sarasota's most sought-after and architecturally significant waterfront communities, offering residents exclusive access to the north end of Lido Beach and close proximity to St. Armands Circle, Longboat Key, City Island, and downtown Sarasota. This remarkable bayfront estate is an architectural triumph, designed for sophisticated entertaining, advanced living, and extraordinary waterfront luxury.

Location

State FL

County Sarasota

Community Lido Shores

Area 34236 - Sarasota

Zoning RSF2

Rooms

Other Rooms Bonus Room, Den/Library/Office, Family Room, Great Room

Interior

Interior Features Built-in Features, Ceiling Fans(s), Coffered Ceiling(s), Dry Bar, Eat-in Kitchen, Elevator, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Walk-In Closet(s), Window Treatments

Heating Central, Electric

Cooling Central Air, Zoned

Flooring Hardwood, Tile

Fireplaces Type Living Room, Outside

Fireplace true

Appliance Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Range Hood, Refrigerator, Washer

Laundry Laundry Room

Exterior

Exterior Feature Balcony, Lighting, Outdoor Kitchen, Outdoor Shower, Private Mailbox, Rain Gutters, Sliding Doors

Parking Features Driveway, Garage Door Opener, Garage Faces Side, Off Street

Garage Spaces 3.0

Pool Gunite, Heated, In Ground, Lighting, Salt Water

Community Features Deed Restrictions, Park

Utilities Available BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Sprinkler Well, Water Connected

Amenities Available Park

Waterfront Description Bay/Harbor

View Y/N Yes

Water Access Yes

Water Access Desc Bay/Harbor,Beach,Gulf/Ocean,Gulf/Ocean to Bay,Intracoastal Waterway

View City, Pool, Water

Roof Type Metal

Porch Covered, Deck, Rear Porch

Attached Garage true

Garage true

Private Pool Yes

Building

Lot Description Flood Insurance Required, FloodZone, City Limits, Landscaped, Paved

Story 2

Entry Level Two

Foundation Slab, Stem Wall

Lot Size Range 1/4 to less than 1/2

Sewer Public Sewer

Water Public, Well

Architectural Style Custom

Structure Type Block,Stucco

New Construction false

Construction Status Completed

Schools

Elementary Schools Southside Elementary

Middle Schools Booker Middle

High Schools Sarasota High

Others

Pets Allowed Yes

Senior Community No

Ownership Fee Simple

Monthly Total Fees $25

Acceptable Financing Cash, Conventional

Membership Fee Required Optional

Listing Terms Cash, Conventional

Special Listing Condition None

Virtual Tour https://my.matterport.com/show/?m=VHC8WcXZSd8

Listed by Joel Schemmel DOUGLAS ELLIMAN

Stephen Michalakos

Senior Real Estate Advisor | License ID: SL3408427

+1(727) 601-8676

Stephen Michalakos

424 BOWDOIN CIR Sarasota, FL 34236

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

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424 BOWDOIN CIR