3440 GULFMEAD DR, Sarasota, FL 34242
3440 GULFMEAD DR, Sarasota, FL 34242
3440 GULFMEAD DR, Sarasota, FL 34242
3440 GULFMEAD DR, Sarasota, FL 34242
3440 GULFMEAD DR, Sarasota, FL 34242
3440 GULFMEAD DR, Sarasota, FL 34242
REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your agent will contact you to discuss available opportunities.
In-PersonVirtual Tour
Griffin Cook

Griffin Cook

+1(513) 960-7448
$ 13,950,000
Est. payment | /mo

5 Beds

6 Baths

6,596 SqFt

Save
$ 13,950,000
Est. payment | /mo
Save

5 Beds

6 Baths

6,596 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 6,596 sqft

Price per Sqft $2,114

Subdivision Gulfmead Estates

MLS Listing ID A4679384

Bedrooms 5

Full Baths 4

Half Baths 2

Construction Status Completed

HOA Y/N No

Year Built 2008

Annual Tax Amount $58,420

Lot Size 0.720 Acres

Acres 0.72

Lot Dimensions 100x298

Property Sub-Type Single Family Residence

Source Stellar MLS

Property Description

Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key's most stunning and secluded waterfront sites — a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel's early 20th-century Higelhurst Hotel, the pioneering developer's beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner's meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler's pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef's kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home's focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted.

Location

State FL

County Sarasota

Community Gulfmead Estates

Area 34242 - Sarasota/Crescent Beach/Siesta Key

Zoning RSF1

Rooms

Other Rooms Attic, Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility, Interior In-Law Suite w/Private Entry, Storage Rooms

Interior

Interior Features Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Elevator, High Ceilings, Open Floorplan, PrimaryBedroom Upstairs, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments

Heating Central, Electric, Zoned

Cooling Central Air, Zoned

Flooring Brick, Other, Wood

Fireplaces Type Living Room, Wood Burning

Furnishings Unfurnished

Fireplace true

Appliance Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Kitchen Reverse Osmosis System, Microwave, Range, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine Refrigerator

Laundry Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup

Exterior

Exterior Feature French Doors, Lighting, Outdoor Shower, Rain Gutters

Parking Features Tandem, Workshop in Garage

Garage Spaces 6.0

Fence Fenced

Pool In Ground, Lap, Salt Water

Community Features Street Lights

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

Waterfront Description Gulf/Ocean

View Y/N Yes

Water Access Yes

Water Access Desc Gulf/Ocean to Bay

View Water, Gulf/Ocean - Full

Roof Type Metal

Porch Covered, Enclosed, Rear Porch, Screened, Side Porch, Wrap Around

Attached Garage true

Exposure East

Garage true

Private Pool Yes

Building

Lot Description FloodZone, City Limits, Landscaped, Street Dead-End, Paved

Story 3

Entry Level One

Foundation Stilt/On Piling

Lot Size Range 1/2 to less than 1

Builder Name ML Collingwood

Sewer Public Sewer

Water Public, Well

Architectural Style Custom, Florida

Structure Type Block,Concrete,Stucco

New Construction false

Construction Status Completed

Others

Pets Allowed Yes

Senior Community No

Ownership Fee Simple

Acceptable Financing Cash, Conventional

Listing Terms Cash, Conventional

Special Listing Condition None

Stellar MLS
© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved.
Listed by Jennifer Linehan MICHAEL SAUNDERS & COMPANY

AROUND THE AREA

Restaurants
Home Services
Health & Medical
Local Services
Shopping
Recreation
Arts & Entertainment
Food
Beauty
Nightlife
Event Planning & Services
Automotive
Religious Organizations
Financial Services
Professional Services
Travel
Education
Pets
Local Media
Local Events & Flavor

  • The Panini Place

    5204 Ocean Blvd, Siesta Key, FL 34242

    Sandwiches Phone: 941-346-7502

  • 3.14 Pi Craft Beer & Spirit

    5263 Ocean Blvd, Siesta Key, FL 34242

    Bars Phone: 941-346-1188

  • Lobster Pot Restaurant

    5157 Ocean Blvd, Sarasota, FL 34242

    Seafood Phone: 941-349-2323

  • Another Broken Egg Cafe

    140 Avenida Messina, Siesta Key, FL 34242

    Cafes Phone: 941-552-8320

  • Big Water Fish Market

    6641 Midnight Pass Rd, Siesta Key, FL 34242

    Seafood Phone: 941-554-8101

  • The Cottage

    153 A venida Messina, Siesta Key, FL 34242

    Tapas/Small Plates Phone: 941-312-9300

  • Bamboo Bistro

    5121 Ocean Blvd, Sarasota, FL 34242

    Phone: 941-552-8312

  • Aaron’s Fish Camp

    149 Avenida Messina, Sarasota, FL 34242

    Barbeque Phone: 941-346-0738

  • The Old Salty Dog

    5023 Ocean Blvd, Sarasota, FL 34242

    Seafood Phone: 941-349-0158

  • Subway

    5239 Ocean Blvd, Sarasota, FL 34242

    Fast Food Phone: 941-349-1955

  • Munchies on the Key

    6639 Midnight Pass Rd, Sarasota, FL 34242

    Pizza Phone: 941-346-2695

  • Turtle Beach Grill

    8865 Midnight Pass Rd, Sarasota, FL 34242

    Salad Phone: 941-349-2280

  • Captain Curt’s Crab & Oyster

    1200 Old Stickney Pt Rd, Sarasota, FL 34242

    Seafood Phone: 941-349-3885

  • Boardwalk Eats and Sweets

    217 Avenida Madera, Siesta Key, FL 34241

    Hot Dogs Phone: 941-346-3287

  • Daiquiri Deck Siesta Key

    5250 Ocean Blvd, Sarasota, FL 34242

    Seafood Phone: 941-349-8697

  • Village Cafe

    5133 Ocean Blvd, Sarasota, FL 34242

    American (Traditional) Phone: 941-349-2822

  • Siesta Key Oyster Bar

    5238 Ocean Blvd, Sarasota, FL 34242

    Seafood Phone: 941-346-5443

  • Napoli’s Italian Restaurant & Pizzeria

    5200 Ocean Blvd, Sarasota, FL 34242

    Italian Phone: 941-346-2452

  • Flavops Italian Resturant

    Beach Rd, Siesta Key, FL 34242

    Italian

  • Bonjour Frenchcafe

    5214 Ocean Blvd, Siesta Key, FL 34242

    Cafes Phone: 941-346-0600

  • Gilligan’s Island Bar & Grill

    5253 Ocean Blvd, Siesta Key, FL 34242

    Music Venues Phone: 941-346-8122

  • Siesta Key Deli

    5263 Ocean Blvd, Siesta Key, FL 34242

    Delis

  • A Taste Of Germany

    6575 Midnight Pass Rd, Sarasota, FL 34242

    German Phone: 941-346-1800

  • Lelu Coffee Lounge

    5251 Ocean Blvd, Sarasota, FL 34242

    Coffee & Tea Phone: 941-346-5358

  • Senor Siesta Restaurant

    5110 Ocean Blvd, Siesta Key, FL 34242

    Spanish Phone: 941-349-0818

  • Subway

    1250 Stickney Point Rd, Sarasota, FL 34242

    Sandwiches Phone: 941-349-3035

READY TO VIEW THIS HOME?

3440 GULFMEAD DR

FEATURED LISTINGS

More

#TCGELEVATINGLIFESTYLES

Griffin Cook
Griffin Cook

Luxury Realtor

+1(513) 960-7448 | thecookgrouptcg@gmail.com

Name
Phone*
Message

By checking this box, I agree by electronic signature to the Electronic Disclosure Consent Agreement; to receive recurring marketing communication from or on behalf of Griffin Cook, including auto-dialed calls, texts, and artificial/prerecorded voice messages (message frequency varies; data rates may apply; reply "STOP" to opt-out of texts or "HELP" for assistance); and to the Terms of Service and Privacy Policy of this website. Consent not required to make a purchase. I understand that I can call to obtain direct assistance.