Bay Island Shores Real Estate, Homes, Condos for Sale in Siesta Key, FL - Ed Grabowski

4 Beds ⋅ 5 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides exceptional convenience to the bridge, mainland, and all that the island has to offer. The home features 4 bedrooms and 4.5 bathrooms, with the upper level remaining intact and in great condition. The ground level experienced flooding during the recent hurricanes; however, the seller has already completed professional remediation, providing a clean slate for updates and renovations to suit your vision. Situated on a protected deep-water basin, the property is ideal for boating and waterfront living, complete with a private dock, no fixed bridges, and direct access just minutes to the Gulf. The home also features a pool, offering the perfect foundation to create a true coastal retreat. This is a unique opportunity to secure a well-located waterfront property and finish it to your exact specifications in one of Siesta Key’s most desirable communities.

847 Freeling Drive, Sarasota

$750,000

4 Beds ⋅ 2 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Investor Special!!Welcome to your next amazing project! Known damage with full or partial rehab. Excellent renovation opportunity on an oversized lot in a highly desirable Siesta Key area. Sold AS-IS with significant upside potential.

749 Siesta Drive, Sarasota

$5,825,000

4 Beds ⋅ 5 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Under Construction. The exterior presentation of this spectacular waterfront residence is most impressive with its blend of modern architecture and refined luxury. With superior elevation high above the water’s edge on Siesta Key’s prestigious Bay Island, this new to-be-built 4,310 sq. ft. residence is an unparalleled oasis of tranquility in a breathtaking setting. A place where architectural elegance and natural beauty converge in perfect harmony with elaborate artisanal work, functional design, and top-tier amenities. For boaters, the location is ideal with a new seawall and a private dock allowing quick access to the bay and gulf beyond. Built with intention and quality, large windows flood the space with natural light illuminating the graceful enhancements within. When entering the home through the 4-car garage, an elevator takes you to the first and second living levels. An elegant foyer entry with double-height ceiling and sleek iron-railed staircase usher you into the spacious interiors where every detail, from the fluid layout to the custom finishes, is thoughtfully curated. Adding a distinctive touch to the stunning great room are 20-foot ceilings and a two-story entertainment wall flanked by artistic display niches. A wall of glass sliders sets a dramatic tone, framing water views and uniting indoor-outdoor living. Designed for effortless entertaining and timeless family gatherings, the outdoor area overlooks the water to create a tranquil setting that feels both secluded and well-connected. With nearly 500 sq. ft. of covered lanai, an outdoor cook center and a heated pool/spa, there’s ample opportunity for hosting special gatherings or simply enjoying the quiet beauty laid before you. Lovely landscaping, lush greenery and outdoor spaces add to the home's overall aesthetic appeal. A remarkable gourmet kitchen is designed for functionality and style, equipped with high-end finishes, top-tier appliances, a large island and a butler’s pantry with additional refrigerator and dishwasher. An adjoining dining room comfortably seats 8-10 and offers wonderful water views while dining. The primary wing is remarkable with an exquisite spa bath, enlarged customized wardrobe room, and direct access to the laundry facilities. The first level also includes a den suite ideal for remote work or creative pursuits and a completely private guest bedroom with its own full bath. Upstairs, there’s an overlook to the great room below, 2 bedrooms, 2 full baths, and an amazingly-sized bonus room with private balcony. The award-winning and talented team of professionals at Allegra Homes has thoughtfully and expertly created a residence offering a secure, exclusive lifestyle in one of Sarasota's most sought-after and high-value areas. The construction quality is of the highest standard, ensuring that the home is both beautiful and built to last. Just minutes to the mainland, downtown’s cultural mecca, world-class dining and shopping venues, gorgeous area beaches and a top-ranked school system coveted by families for generations, the prized waterfront location couldn’t be better. Showcasing extraordinary craftsmanship throughout, this never-lived-in showplace is the ultimate vision for those who value the very best of coastal Florida living. There’s still time to make your own personal choices for creating the perfect custom home tailored to your family’s taste and style.

527 Freeling Drive, Sarasota

$4,000,000

4 Beds ⋅ 4 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Coastal Elegance on the Northern tip of Siesta Key. Discover timeless luxury in this waterfront estate nestled in the exclusive Bay Island enclave on Siesta Key's coveted North end. With panoramic views of Roberts Bay and the Intracoastal Waterway, this home captures the essence of Florida lifestyle- elegant, relaxed and designed for seamless indoor/outdoor living. Step inside to find all new engineered hardwood flooring, a gourmet kitchen with all new top of the line appliances featuring a Sub-Zero refrigerator, Bosch dishwasher, a Jenn Air Oven/Microwave combination, a 5-burner gas cooktop, a warming drawer and all new custom-made wood cabinetry. It also has a double door pantry for all your kitchen supplies and a built-in desk for all your recipes or a workstation for the family. The rear of the home has a wall of sliders across the back which gives you expansive views out to the bay. This level has 3 bedrooms and 3 baths, two of them are bedroom suites and there is a large laundry room with new washer/dryer and a wall of shelving for any storage or folding needs. The second level encompasses your main bedroom suite and two expansive screened-in porches/lanais for incredible southern and northern views. The all-new main bath has a soaking tub, a walk-in shower all new cabinetry and a walk-in closet. Stepping outside embrace the outdoors with an open-air pool, and an outdoor shower. Boating enthusiasts will appreciate the three docks, featuring a 16,000-pound boat lift, a 10,000-pound lift for an accessory boat or jet ski, and mooring for a 35-foot boat. The property offers direct sailboat access to the Gulf of Mexico, making it a boater's paradise. The property features a complete newer seawall installed in 2018 with a new wall and cap. The northern tip offers the convenient access to the gulf and easy-on/off the island for shopping, restaurants and access to downtown Sarasota. Freeling Drive is renowned for its pristine waters. From your backyard, watch dolphins play and kayakers glide by. Catch fresh stone crabs and blue crabs right off your dock. You're just minutes away from Siesta Key Beach, Shell Beach, downtown Sarasota, shopping, and the arts.

878 Freeling Drive, Sarasota

$4,700,000

4 Beds ⋅ 5 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Welcome to Casa Della Fontana — The Fountain House. Nestled on the tranquil north end of Siesta Key, this gated waterfront estate is a blend of seaside serenity, architectural distinction, and lifestyle luxury. Perched on a deep, sailboat-accessible bayou that connects to the Intracoastal Waterway, the almost half acre lot provides generous room for outdoor living, boat docking, and privacy. Built by Magnum Builders, this residence was recently transformed through a multi-year, high-end renovation to blend modern amenities with timeless character. The home is engineered with concrete footings, steel pilings, and reinforced concrete/rebar, designed for storm resilience. A Spanish barrel tile roof (2024), hurricane-rated garage doors and a whole-house generator round out the safety and durability features. This residence spans 6,827? square feet of air-conditioned living space offering 4 bedrooms, 4 full baths, and 1 half bath. At the heart of the home is the great room, soaring to 20-foot ceilings, commanding sweeping water views, and anchored by a two-story library wall. A gallery and loft overlook the formal dining space, and elegant iron railings and hand-hewn wood trestles bring an artisanal, Old World feel. A hidden wood-paneled staircase adds a dramatic, secretive touch. The gourmet kitchen is outfitted with Wolf, Sub-Zero, and Miele appliances, quartzite countertops, a coffered ceiling, a waterfront breakfast nook, and a walk-in pantry. Hand-hewn beams extend throughout the kitchen and lanai, harmonizing the interior and exterior aesthetic. The primary suite is a sanctuary: two private balconies, dual bathrooms, a central walk-in shower with dual entry, and twin walk-in closets. The guest wing, with three bedrooms and three baths, provides privacy and independent access to the driveway. Additional interior amenities include a media/game room, office/library, elevator, high ceilings, built-in features, central vacuum, and smart home automation. Designed for entertaining and coastal living, the property features a heated/in-ground gunite pool with spa, a sizable lanai with kitchen and multiple alfresco seating areas. For boating enthusiasts, the dock features three lifts and docking for large vessels. Living here means effortless access to both island leisure and Sarasota urban life. You’re just minutes from Siesta Beach’s famed white sand, Siesta Key Village’s shops and restaurants, and the art, culture, dining, and amenities of downtown Sarasota. The home’s deep-water location makes boat outings to the Gulf a delight. Casa Della Fontana is more than a house — it’s a waterfront masterpiece built for those who demand beauty, durability, and lifestyle in equal measure. With its structural reinforcements, state-of-the-art systems, and sophisticated design, it offers both peace of mind and the romance of island water front living.

749 Freeling Drive, Sarasota

$2,995,000

3 Beds ⋅ 5 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Rare and extraordinary waterfront offering on the coveted North end of Siesta Key, this premier Bay Island estate parcel presents the ultimate canvas for creating a world-class coastal retreat. Set on nearly half an acre, the property commands sweeping waterway views and offers 90 feet of protected sailboat-water frontage, complete with an existing 73-foot composite and tile dock—an exceptional amenity for the discerning boating enthusiast. To seamlessly bring your vision to life, fully customizable luxury home plans, as well as projected expenditure framework are available for review from Salt Wave Construction thus significantly expediting the design-build process. The seller has also committed to demolition of the existing structure, allowing for a smooth and efficient transition to new construction. The proposed residence spans approximately 6,366 square feet, including over 4,000 square feet of refined, air-conditioned living space, thoughtfully designed to maximize waterfront exposure and elevate indoor-outdoor living. Multiple entertaining spaces, expansive terraces, and view-oriented decks create the perfect setting for both grand gatherings and intimate moments, all framed by captivating water vistas. Ideally located for effortless access on and off Siesta Key and just minutes from the culture, dining, and sophistication of Downtown Sarasota, this exceptional property offers the rare combination of privacy, prestige, and proximity. An unparalleled opportunity to craft a legacy waterfront estate in one of Sarasota’s most sought-after enclaves.

732 Siesta Drive, Sarasota

$1,701,000

3 Beds ⋅ 3 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Dreaming of waterfront living on Siesta Key? This rare and exclusive Bay Island property is your chance to create the home of your dreams while basking in one of Sarasota's most prized locations. With an impressive 70 feet of seawall and sailboat water, this oversized 12,900-square-foot lot is as exceptional as it gets. Enjoy direct access to Sarasota Bay with quick entry to Big Pass and the Gulf of Mexico—ideal for boat lovers who crave effortless days on the water. Nestled on the north end of Siesta Key, this lot offers a premier address that provides a perfect balance of privacy and connectivity. You'll find yourself just minutes from the vibrant shops and restaurants of Siesta Key Village and the world-famous Siesta Key Beach, with its powdery quartz sands that attract visitors from all over the globe. When you're craving a cultural escape, downtown Sarasota is just a short drive away, offering galleries, theater, and fine dining. This coveted neighborhood on Bay Island is surrounded by some of Siesta Key's most admired homes, known for the exclusivity and ease of lifestyle it offers. The existing home is being removed, and the pool is being filled, leaving you with a blank canvas to design and build a custom waterfront masterpiece perfectly suited to your vision. Opportunities like this are rarely available, making this property a true gem for anyone seeking premier waterfront living. Reach out today—this is your chance to own a piece of paradise on Siesta Key.

527 Freeling Drive, Sarasota

$2,400,000

3 Beds ⋅ 3 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. Experience the ultimate in coastal living with this two-story residence in the highly desirable Bay Island Shores on the world-renowned Siesta Key. Located in a prime waterfront setting, this all-concrete block home boasts a new tile roof in 2016 and offers unparalleled access to deep water and sailboat-friendly waters, making it the perfect haven for boating enthusiasts. The property, set on over a .35-acre lot, is nestled in a protected basin and features a newer dock with composite decking, complete with two boat lifts (12,000 and 4,500 pounds), installed in 2018—truly a boater’s paradise.The home’s elevated design places all living spaces on the second floor, ensuring captivating water views and privacy. A secure, walled gated entrance leads to a spacious garage area of nearly 3,000 square feet, offering abundant storage for vehicles, watercraft, outdoor equipment, just off the pool and spa. With room for multiple cars, golf carts, motorcycles, and kayaks, this area can also be transformed into a game room, home theater, fitness space, or sauna—catering to a variety of lifestyles and interests.Perfectly suited for both relaxation and entertaining, the home features high ceilings, crown molding, an elevator, and expansive living areas that flow effortlessly into the outdoors. A wraparound balcony, accessible from nearly every room, allows you to enjoy the island breeze and scenic surroundings, while multiple indoor and outdoor spaces provide plenty of room to host family and friends.Located on the desirable north end of Siesta Key, this property is just moments from the renowned Siesta Key Beach and the vibrant downtown Sarasota area. Additionally, being within the city of Sarasota, the property offers the flexibility of weekly rentals, making it an excellent investment opportunity. This exceptional home combines the best of island living with modern amenities—your coastal dream awaits.

508 Siesta Drive, Sarasota

$3,000,000

Bay Island Shores SubDv. ⋅ 34242 Zip Code

Now is the perfect opportunity to build your dream home on the highly sought-after north end of Siesta Key! This prime property boasts wide, breathtaking water views and deep-water, ideal for boating enthusiasts. The expansive lot spans over 1/3 acre, offering plenty of space to create a custom retreat. The home is gated with a paver courtyard, beautifully landscaped and includes an outdoor kitchen and entertainment bar off the inviting pool. Crafted for boating aficionados, the home features two docks/lifts—one rated for a 20,000 lb boat and the other for your run-about bay boat. For the serious boater looking for wide deep waters and quick access to the Gulf of Mexico, this is the perfect place to call home. Enjoy the ultimate combination of location and convenience, with easy access off the island and just moments to the beach. Don’t miss out on this rare opportunity to own a prime piece of Siesta Key paradise!

864 Siesta Drive, Sarasota

$3,000,000

4 Beds ⋅ 5 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Now is the perfect opportunity to build your dream home or renovate on the highly sought-after north end of Siesta Key! This prime property boasts wide, breathtaking water views and deep-water access, ideal for boating enthusiasts. The expansive lot spans over 1/3 acre, offering ample space to create a custom retreat. Currently, the first floor of the home needs renovation, as it took on water from recent storms. The second floor, however, remains unaffected. Although being sold for land value, buyers have the option to renovate the existing structure. Inside, the home features an open floor plan with a wall of glass sliders that stretch the length of the home and showcase the stunning water views and seamlessly connect indoor and outdoor spaces. The main level includes three spacious bedrooms, each with its own ensuite bathroom for maximum convenience and privacy and washer dryer hookups. The second floor offers a large private master suite with a walk-in closet, washer and dryer, dual sinks, soaking tub and beautiful walk-in shower. Off the bedroom is a spacious balcony, perfect for enjoying morning coffee while taking in the expansive bay views. The home is gated with a paver courtyard, beautifully landscaped and includes an outdoor kitchen and entertainment bar off the inviting pool. Crafted for boating aficionados, the home features two docks/lifts—one rated for a 20,000 lb boat and the other for your run-about bay boat. For serious boaters seeking wide, deep waters and quick access to the Gulf of Mexico, this is the perfect place to call home. Enjoy the ultimate combination of location and convenience, with easy access off the island and just moments from the beach. Don’t miss out on this rare chance to own a prime piece of Siesta Key paradise!

864 Siesta Drive, Sarasota

$4,127,000

4 Beds ⋅ 4 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

**Be sure to view the immersive 3D floor plan by visiting our state-of-the art virtual tour.** A MODERN SIESTA KEY HOME ON DEEP SAILBOAT WATER! This luxurious residence, revitalized to meet today’s standards, beckons to those yearning for their own waterfront paradise. The custom multi-level home offers 4 full bedrms, & 3.5 baths. A convenient elevator accesses all four levels. Expansive water views set the stage in the main living area w/ its own balcony, 2-story ceilings, & clerestory windows. The upgraded tile flooring flows elegantly into the eating space w/ an attached covered & screened veranda, the perfect place for al fresco dining. Adjacent a contemporary kitchen has been remodeled w/ new coastal inspired furniture quality cabinetry, stone counter tops, a vegetable sink, a breakfast bar, a planning center, & high-end stainless-steel appliances; a Sub Zero refrigerator, Fisher Paykel dishwashers, a trash compactor, a GE Café double convection wall oven w/ a warming drawer, built-in wine refrigeration & a microwave. The 6-foot cooking island has matched cabinetry & twofold cascading stone surfaces & a Wolf brand gas cooktop w/ a stainless-steel hood. A large walk-in pantry has additional storage space. Nearby are a lavish powder rm w/ Onyx for guests & a fully equipped laundry rm. The formal dining rm has an open wall & flexibility of use. Hardwood flooring flows gracefully from this rm into the den/study or family rm. Handcrafted built-in shelving surrounds the gas fireplace here w/ vaulted ceilings & a front overlook balcony. The penthouse floor is comprised of only the Owner’s Suite. Serenity envelops the private chambers & includes a waterside balcony w/ views. 2 facing California-style walk-ins connect the spa-inspired personal bath. Retreat & rejuvenate in the jetted tub encased w/ soft lighting. The glass enclosed walk-in shower has both an overhead rainfall nozzle & secondary faucet. Separate vanities each have their own hammered copper basins, & LED lighted mirrors. A water closet, stone tiles, a skylight, & recessed linear LED lighting add the fishing touches. 2 full bedrms w/ a middle bath can be found at the entry level of the home. Bonus millwork includes crown moldings & wainscoting. Elevating the interior entertainment amenities are a ground level bedrm suite (w/ a pool bath entrance), a large walk-in closet, & a recreation rm. Sliding glass doors open to extend the living space onto the covered patio overlooking the saltwater pool & spa. Brick pavers have been laid by hand poolside all the way down to the water’s edge. 'Custom Dock & Davit' reconstructed the dock that accommodates 2 vessels w/ a boat lift for a 25-foot vessel & will house another boat up to 38-FT. W/ great water depth (8-foot in channel at low tide), there are no fixed bridges from the protected waterway directly to the ICW, Big Pass & or the Gulf of Mexico. All decking has been upgraded to Trex composite boards. A climate controlled 3-car garage w/ an insulated door & an extra storage rm enters from the side via an extended paver brick drive. Improved w/ a whole house generator, four zoned a/c units, impact rated doors & windows w/ remote controlled treatments. A new standing seam metal roof, lush tropical foliage & walled privacy further enhance the island lifestyle afforded by this North Siesta Key home. Please note that security cameras are in use. Room Feature: Linen Closet In Bath (Bedroom 2). Room Feature: Linen Closet In Bath (Bedroom 3). Bedroom Closet Type: Walk-in Closet (Primary Bedroom). Room Feature: Linen Closet In Bath (Bedroom 4).

722 Siesta Drive, Sarasota

$2,750,000

6 Beds ⋅ 4 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

New price - $650,000 reduction! An exceptional location for serious boaters who value deep sailboat water and quick access to Sarasota Bay, Big Pass and the Gulf of Mexico. Experience the best of waterfront living and the Siesta Key lifestyle on Bay Island, the coveted northern tip of Siesta Key. For investors, this large six-bedroom home is in an area with impressive vacation rental potential in one of the finest boating locations in the area. Gated and walled, this estate is the ultimate for privacy and living the saltwater island life. Enter an oasis canopied by mature, lush landscaping with mango and avocado trees to the expansive paver motor courtyard which offers parking for numerous cars and toys. With spectacular harbor views from the front door, the home's bright, open floor plan offers soaring beamed ceilings anchored by a wood-burning fireplace in the large dining room. A wall of glass spans the adjoining waterfront great room. An island kitchen, breakfast room, media room, guest suite and one-and-half baths complete the main living level. Two separate second-floor living areas flank this spacious home and are connected by a rooftop deck with an additional observation deck overlooking the pool and large waterfront yard, offering spectacular views of the deep-water boating harbor. The waterfront master suite offers a full bath and office; the upstairs guest wing offers three bedrooms and a full bath. Outdoors, relax in the sun by the oversized waterfront pool. Boasting 90 feet of waterfront, the large dock and 15,000-pound boat lift with water and electric offer an array of outdoor fun – just minutes to the bay and Gulf to savor fabulous Siesta Key sunsets or fish, paddleboard and kayak from your own dock; you'll enjoy colorful sunrises and amazing marine life, including dolphin and manatee. Plans are included for a two-story, guesthouse/multi-bay expansion of the air-conditioned two-car garage. Natural gas-powered generator and underground lines. Conveniently located, the famous white quartz Siesta Beach sand and azure Gulf water are minutes away. Sarasota’s vibrant downtown with restaurants, shopping, entertainment, and cultural events is a short 10 minutes by auto over the Siesta Drive Bridge.

746 Siesta Drive, Sarasota

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