Cocoanut Bayou Real Estate, Homes, Condos for Sale in Siesta Key, FL - Ed Grabowski

5 Beds ⋅ 6 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

Virtually Staged. Celebrated as one of SRQ Magazine’s “Home of the Year” in 2008 and born from the visionary imagination of acclaimed architect Mark Sultana and built by Voigt Construction, this extraordinary waterfront estate is not simply a home — it is a lifestyle. One of Siesta Key’s most iconic private residences, it stands as a living testament to the art of inspired modern design and the art of living beautifully. Deeply set on nearly one private acre along the tranquil Coconut Bayou, this gated 4-bedroom architectural masterpiece unfolds across multiple stories with absolute privacy, lush tropical splendor, and grounds generous enough for a pickleball court — all anchored by a fully separate guest house for family and friends who will never want to leave. From the moment the gates open, life here feels different. A breathtaking composition of glass, steel, and sculptural lines soars beneath dramatic ceilings, with natural light pouring through at every angle — whether that’s a lazy Sunday morning or a dinner party in full swing. Rise by private elevator or ascend the sweeping steel-and-glass staircase to the crown jewel of this residence: a 2,500 sq. ft. rooftop terrace, where the Siesta Key lifestyle reaches its absolute peak. Panoramic views sweep across Siesta Key, the downtown Sarasota skyline, and the shimmering waterways below — this is where memories are made. At the water’s edge, a brand-new dock on order, a double jet ski lift, and a dedicated kayak and paddleboard launch await — with direct, bridge-free access to the Intracoastal and the open Gulf beyond. This is the rare address that refuses to make you choose: the serenity of bayfront living, the thrill of open-water boating, and the privilege of private deeded beach access to the shores of Siesta Key — all from a single extraordinary estate. Designed with both beauty and resilience in mind, the residence sits impressively high and dry above the Bayou. Even through recent storms, the property remained untouched by flooding — including the pool area — offering a rare sense of peace of mind along Sarasota’s waterfront. The primary suite is a private world of its own — featuring a dedicated office/loft or exercise room, two custom walk-in closets, and a private balcony suspended above the Bayou. At the center of it all, an indulgent Champagne Jacuzzi infinity bathtub transforms every evening into a spa retreat. Downstairs, entertaining flows as naturally as conversation — from a dedicated movie theater room to tiered outdoor patios crowned by a spectacular summer kitchen, an open saltwater pool, and glowing fire bowl accents that keep the night alive. In the kitchen, Italian custom cabinetry, top-tier appliances, a service pantry, and a private wine cellar come together in a space as pleasurable to cook in as it is to gather around. Garage parking for five vehicles and separate guest quarters complete an offering with virtually nothing left to wish for. Minutes from The Out-of-Door Academy, Siesta Key Village, and Siesta Beach — this is not just an address. It is a life you’ll never want to leave.

4317 Midnight Pass Road, Sarasota

$7,500,000

4 Beds ⋅ 5 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

A timeless coastal estate with an air of refined European elegance, this gated waterfront residence on the protected deep waters of Cocoanut Bayou harmonizes classic architecture with thoughtful modern enhancements. Newly updated with wide-plank white oak engineered hardwood flooring and a gleaming white kitchen featuring new pearl quartz countertops and a Zellige tile backsplash, the home offers an elevated, move-in-ready experience for buyers seeking both luxury and serenity on Siesta Key. Step through custom arched double doors into a luminous grand foyer with 12-foot ceilings and beautifully crafted architectural details that introduce the home’s balance of scale, sophistication, and warmth. The soaring central living room, with its 24-foot ceilings, new hardwood floors, and expansive terrace, sets the tone for both intimate gatherings and grand entertaining. A sweeping 48-foot waterfront terrace extends the full width of the home, creating a captivating outdoor living space with room for dining, lounging, and enjoying breezy evenings by the stone fireplace. Inside, the newly refreshed gourmet kitchen shines with exceptional professional-grade appointments, including two Sub-Zero refrigerators, Wolf cooking equipment, two Miele dishwashers, Sub-Zero freezer drawers with ice maker, an oversized island, a casual dining area with French doors to the terrace, and an outdoor kitchen featuring a Wolf grill. The adjoining bar/butler’s pantry is well equipped with a 150-bottle, dual-temperature zoned Sub-Zero wine refrigerator and built-in Sub-Zero icemaker, along with additional glass-front cabinetry to display your treasured items. The kitchen flows effortlessly into a waterfront grand living room with five sets of French doors opening onto the terrace, for seamless indoor/outdoor living, and an elegant formal dining room for special occasions. On the opposite wing, you will find a handsome library/office, a home gym, and a large family room with serene water views and French doors to the terrace. A recently upgraded powder room and two large storage closets complete this level. The private second level, accessed by a sweeping staircase or the commercial-grade elevator, features four generous bedroom suites with walk-in closets, spa-inspired baths, and engineered hardwood flooring. The primary suite, a serene retreat, offers a gas fireplace, an expansive private terrace with bayou and bay views, the perfect spot to see incredible sunrises, and a luxurious marble bath with soaking tub, dual vanities, a large dual shower, and a built-in Sub-Zero mini-fridge. Spacious dual custom closets and a dressing area with a vanity complete the space. Boaters will appreciate the deep-water dock with direct access to Sarasota Bay and the Gulf of Mexico. Additional features include a second-floor laundry with a new Samsung washer and dryer, a 12-car garage, a whole-house sound system, impact-resistant windows and doors, concrete construction, state-of-the-art security, 4 HVAC units (one recently installed), and mature tropical landscaping that provides privacy and a true sense of retreat. A private community beach offers the rare opportunity to enjoy Siesta Key’s renowned white sands moments from home. Ideally located near Siesta Key Beach, Siesta Village, and vibrant downtown Sarasota, this exceptional estate combines architectural beauty, modern updates, and an enviable waterfront setting—offering a lifestyle entirely its own.

4205 Higel Avenue, Sarasota

$5,600,000

4 Beds ⋅ 4 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

This award-winning Modernist home was designed to provide privacy while maintaining direct tranquil water views framed by mature tropical landscaping. In the desired and private lot enclave of Cedar Park, one approaches the residence via a canopied private lane before entering the ideal spot for boaters, car enthusiasts, or those who just enjoy the serenity of the .6-acre grounds with plus/minus 350 feet of frontage on Cocoanut Bayou. The car enthusiast will appreciate the twin garages accommodating five cars, while boaters will be impressed by the water depth of plus/minus 4 feet, substantial IPE wood dock with 10,000-pound and 7,000-pound lifts, and immediate access to the Bay and Gulf. Designed with practicality and easy living in mind, the light-filled rooms feature high ceilings, wall-to-wall stacking glass doors, a chef’s kitchen with Miele appliances and Italian cabinetry, elevator, a generator, and an open concept plan that incorporates nearly 900 sq ft of non-conforming space in the most ingenious fashion, and transitions seamlessly between indoor and outdoor living spaces. Enjoy outdoor dining and relaxing on the expansive covered terrace, lounge by the private 40-foot saltwater pool with spa or just drink in the tranquility offered by this special property. The split plan with four bedrooms (one makes an ideal office) and 3½ baths allows for flexibility of use and manageable size. Private, gated beach access is available. This is the ideal home base to enjoy island lifestyle and for you and yours to take advantage of all Sarasota and Siesta offer. Set out by land or sea to enjoy the world-renowned sugar sand beaches, downtown cultural venues, museums, multiple restaurants and shopping. An exceptional opportunity for the discerning.

251 Cedar Park Circle, Sarasota

$7,200,000

5 Beds ⋅ 6 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

A truly exceptional waterfront retreat in one of Sarasota’s most coveted enclaves—Cedar Park Circle on North Siesta Key—this gated and private estate offers over 220 feet of prime bayfront with panoramic views of Cocoanut Bayou and Roberts Bay. Residents enjoy unrivaled boating access to the Gulf of Mexico and exclusive private deeded beach access. Spanning over 10,600 total square feet, including 6,500 square feet under air, this architectural masterpiece features 5 bedrooms, 5.5 bathrooms, and thoughtfully designed spaces across multiple expansive levels with an optional elevator if desired. Soaring ceilings, timeless finishes, and seamless indoor-outdoor living define the home’s coastal elegance. From the welcoming arbored front patio to the impressive wood-and-iron entry, every detail invites you in. Inside, the main living areas are designed for both comfort and grandeur. The foyer/sitting room opens to sweeping pool and bay views, while the massive great room impresses with an oversized stone gas fireplace, beamed ceilings, chandeliers, French doors, and a spacious dining area with custom built-ins. Around the corner, the newly renovated gourmet kitchen and den provide the perfect blend of everyday luxury and effortless entertaining. Here, you’ll find white-on-white custom cabinetry, quartz countertops, an 8-burner Wolf gas cooktop, dual SubZero refrigerator/freezers, a built-in Miele coffee system, and discreetly integrated conveniences like a second dishwasher and refrigerator. The adjoining den and breakfast nook boast tranquil water views, making this space an ideal private retreat. For the boating enthusiast, the property offers 150 feet of dockage, a 20,000-lb boat lift, two jet ski lifts, and a deep-water cut-in dock accommodating a 50’ vessel. After a day on the water, unwind on the expansive travertine-tiled back terrace with its teak summer kitchen, fire pit, multiple lounging and dining areas, and a saltwater infinity pool—all overlooking the bay. Hurricane-impact windows and doors, along with a new Dam Easy flood barrier, provide peace of mind. Private quarters are equally impressive. The luxurious master wing features his-and-her baths and closets, a dedicated exercise room or home office, and an outdoor tiled balcony—combining convenience, privacy, and resort-like amenities. On the opposite side of the home, three spacious guest suites each offer private balconies and baths. The ground floor grotto/media room with a full bar, wine room, steam bath, fifth bedroom, and two outdoor patios creates the ultimate guest haven. Additional features include dual laundry rooms (one on each wing), an oversized two-car garage with built-in storage, additional parking within the compound, and under-house storage. Designer landscape lighting, a four-zone heating/cooling system, and meticulous craftsmanship throughout ensure this residence is as functional as it is beautiful. This is a once-in-a-lifetime opportunity to own a one-of-a-kind sanctuary where private beach access, world-class boating, and timeless coastal luxury come together seamlessly at Cocoanut Bayou’s exclusive waterfront enclave.

265 Cedar Park Circle, Sarasota

$4,300,000

4 Beds ⋅ 4 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

Located in an exclusive enclave of multi-million-dollar homes, this custom residence offers a special combination of privacy, prestige, and move-in-ready waterfront living. Ideal for boating and car enthusiasts, this residence was completely updated in 2018 and is set on a beautifully landscaped 0.6-acre lot. Cedar Park owners can enjoy private beach access to a pristine beach overlooking Big Pass and the Gulf. Inside, an open and thoughtfully designed single-story layout maximizes water views and natural light. Elegant tray ceilings, a stacked-stone gas fireplace, and plank tile floors set a refined tone throughout the main living spaces. Sliding glass doors in the living area seamlessly connect the interior to the expansive outdoor space, delivering a true Florida indoor-outdoor lifestyle. The gourmet kitchen is appointed with custom cabinetry, quartz surfaces, high-end stainless appliances, a handy dumb waiter, and two islands, flowing naturally into the casual dining area and family room. The formal living and dining spaces provide flexibility for both entertaining and everyday living. The spacious primary suite enjoys pool and water views, direct access to the covered terrace, a luxurious spa-style bath with freestanding tub, and a spacious walk-in closet. Three additional bedrooms, a private office, a large laundry/hobby room and a butler’s pantry complete the interior footprint, offering flexibility and privacy for guests and everyday living needs. One of the best features of this home is the huge garage – there is room for all your toys, 6-8 vehicles, storage, a climate-controlled game room, and a workshop! Designed for effortless entertaining, the expansive covered lanai features retractable screens, multiple lounging and dining areas, and overlooks the resort-like heated pool and spa framed with lush tropical landscaping. Neatly manicured, thick mangroves protect the property and provide a gateway to a large Trex dock with a 10,000-lb boat lift and 4,500-lb lift for two jet skis. The calm, protected waters of Cocoanut Bayou offer quick access to the open waters of Sarasota Bay and the Gulf. Homeowners have access to 100 feet of private beachfront with a gated entry, tiki hut, a dog run, parking, and a set of multi-colored Adirondack chairs from which to enjoy the spectacular sunset skies. Additional features of the home include hurricane-impact windows and doors, central vac, circular brick driveway, a side parking pad, huge garage with workshop and game room fitted with Endura flood easy maintenance wall system, a pre-wired elevator shaft, and an outdoor shower. Block construction and built to hurricane code standards, this residence offers peace of mind and modern convenience. Located on the north end of the island, just 1.4 miles from Siesta Key Village and moments from downtown Sarasota - 244 Cedar Park Circle delivers a unique blend of privacy, boating lifestyle, and coastal elegance.

244 Cedar Park Circle, Sarasota

$10,350,000

5 Beds ⋅ 8 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

A True Island Estate…This picture perfect home is located in The Exclusive Cocoanut Bayou neighborhood. An intimate community with estate sized parcels, deep water docks, canopy lined streets and even a gated private beach. This home was redesigned by Clifford Schultz and could be featured in House Beautiful. The gated parcel is almost 2/3 of an acre, complete with mature tropical landscaping. The home features an oversized Chicago brick motor court with a 3 car side entry garage. The custom wood detailing throughout includes mahogany entry doors, crown moldings, cased impact windows, shiplap ceilings, wainscoting, custom built-ins and more. A gourmet kitchen with Campbell Custom Cabinetry featuring a butler’s pantry, a beverage station, Wolf appliances and an entertaining island complete with additional seating. The main house has a foyer gallery wall, soaring ceilings, picture perfect views, a Holiday sized living room, a coveted great room, a morning room, a private office, as well as a spectacular Owner’s suite…. all located on the first living level. The owner’s suite has a large sitting area, a spa inspired bathroom and 2 walk-in closets. The second floor has a hobby room, 3 ensuites and a flex room. The guest house above the garage has a kitchenette, a great room and an ensuite with private entrance in close proximity to the main home. The outdoor veranda is complete with kitchen, dining and living areas. The mesmerizing views of the Bayou are ever changing, a kaleidoscope of nature … you will see dolphin, manatee, area fish and seabirds, mangroves and much more. A resort style pool with travertine pavers, a separate spa, a large garden, and 2 boat docks complete this waterfront lifestyle. Cocoanut Bayou is minutes to Siesta village for shopping, dining and Siesta’s world-famous beach. You are close to downtown Sarasota which is known for its cultural significance. The opera, orchestra, ballet, symphony, performing arts center, art galleries are all at your disposal. Shop, dine or just enjoy the city that embraces it all. Sarasota County really has something for everyone. Selby Botanical Gardens, Mote Marine Aquarium, several nature parks, bike trails, water sports, Polo, sport venues, multiple Universities and the list goes on. Don’t wait to discover this unique opportunity … It will not last long.

241 Cedar Park Circle, Sarasota

$7,700,000

5 Beds ⋅ 6 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

OVER HALF A MILLION DOLLAR PRICE REDUCTION!! A stunningly beautiful custom home in the very best of locations in coveted Cedar Park Circle on north Siesta Key. A short walk or bike ride to famed Siesta Beach and fun, eclectic Siesta Village, minutes by car or boat to mainland Sarasota and the Gulf of Mexico. This fabulous property affords awe inspiring views of Cocoanut Bayou and Robert's Bay. A rare find, this very private, fenced and gated property boasts over 220 waterfront feet on the bay and includes 150 feet of dockage complete with a new 20k pound lift, 2 jet ski lifts, plus a cut-in sea-walled dock to accommodate a 50' vessel. Two expansive levels with soaring ceilings provide both formal and casual living spaces. The front entrance to the home features an arbored patio, ideal for welcoming guests with cocktails and hors d'oeuvres. Enter the stone-faced home through an impressive wood and iron door into the foyer/sitting room overlooking the pool and bay. Just to the right is a massive great room with oversized stone gas-fireplace, french doors, beamed ceilings, chandeliers, and the expansive dining room with custom built-ins just beyond. Around the corner, enter your newly and exquisitely renovated den/kitchen/nook area with views to the Bay/bayou. All of the best finishes and fixtures make this area your perfect private retreat. The gourmet kitchen features white on white cabinets and quartz countertops, an 8 burner Wolfe gas cooktop, two SubZero refrigerator/freezers, and a built-in Miele coffee system. The custom built-ins in the den area subtly contain a myriad of conveniences including second dishwasher and refrigerator. This home is a dream for entertaining. Virtually every room has an outdoor balcony. The expansive back terrace with newly tiled travertine features a summer kitchen, fire pit, reclining areas, covered dining area, and salt water infinity pool. Just steps away, board your boat or jet skis for a jaunt on the water. The home's private quarters provide infinite serenity. The exquisite master suite comes complete with separate his and her baths and closets. The exercise room, home office and outdoor tiled deck are just steps away in the private master wing. At the opposite side of the home, three sumptuous bedrooms with private balconies and baths provide a wonderful retreat for family and guests. The ground floor grotto/media room with full bar, wine room, 5th bedroom, steam bath, and two outdoor patios is the ideal guest haven. Two laundries - one on each wing of the home, an oversized two car garage with built-in storage, parking pad and abundant parking space within the compound, and under-house storage, all add to this incredible home. Additional appointments include designer outdoor landscape lighting, 4 zone heating/cooling, impact windows and doors, and so much more. This community affords beach access just across the street at the Cocoanut Bayou private beach!

265 Cedar Park Circle, Sarasota

$3,020,000

3 Beds ⋅ 3 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

Waterfront Pool Home with Private Dock and Beach Access. Conveniently located on the North side of Siesta Key and completely updated by Siebert Architects & Pat Ball Construction. This property contains a 2 bedroom/ 2 bath Main House, with open floor plan, custom solid cherry wood kitchen cabinets, stainless steel counters and appliances, Bonus workout room/office and 2 car tandem garage parking. The Spacious Primary Suite, has views of the water, large custom walk in closet, primary bath with walk in shower, separate large whirlpool style tub and plenty of storage. The living room has panoramic water views, TV viewing area, and custom cabinetry. The guest bedroom overlooks the pool area and has full bath with walk in shower. The Guest House: Contains 1 bedroom /1 bath, large living area, Kitchenette with marble countertop, stainless under counter refrigerator, sink, cooktop, full bath with walk in shower, and a large bedroom with garden and pool views. Common to Both Homes are tiled floors, impact windows and doors, on demand hot water, water purification systems, updated plumbing, metal roofs and new AC units. The Exterior of the property features: Gated entry with fully a fenced in yard, 40 ft dock with easy access to the Intracoastal waterway and out to the Gulf. Private screened in courtyard/lanai with a 30'x15' pool, Outdoor kitchen with custom concrete counter top, wood cabinets, stainless grill, and dining area. Expansive IPE wood deck overlooking Cocoanut Bayou, potting shed with stainless sink, storage shed, outdoor shower, large driveway, Private and nicely landscaped yard with outdoor lighting, fruit trees and waterside patio. This home is currently part of the Cocoanut Bayou Home Owners Association which is voluntary. If you choose to join the association, you must apply and members have access to the private beach located across the street on Higel Ave. If you are looking for that private waterfront home with a modernized mid-century feel that is simply beautiful, convenient to downtown Siesta Key and all that Sarasota has to offer, this home may be just right for you!

4165 Higel Avenue, Sarasota

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