Siesta Bayside Homes for Sale

Welcome to Siesta Bayside, a hidden gem nestled in the heart of Siesta Key, Florida, where coastal charm meets modern living. This delightful subdivision boasts a unique blend of tranquility and accessibility, making it an ideal haven for families, retirees, and anyone seeking a slice of paradise.

Siesta Bayside is renowned for its lush landscapes and picturesque surroundings, offering residents a serene atmosphere just moments away from the pristine beaches of Siesta Key. The community is characterized by its beautifully designed homes, many of which feature stunning waterfront views, spacious layouts, and modern amenities. Whether you’re looking for a cozy retreat or a luxurious family residence, Siesta Bayside has something for everyone.

Homes for sale in Siesta Bayside are truly a treasure trove for prospective buyers. With a variety of architectural styles, including charming coastal cottages and contemporary designs, each property reflects the laid-back elegance of the Florida lifestyle. Many homes come equipped with private docks, allowing for easy access to the sparkling waters of the Gulf of Mexico, perfect for boating enthusiasts or those who simply enjoy a day on the water.

Beyond the stunning homes, Siesta Bayside is conveniently located near local shops, gourmet restaurants, and vibrant cultural attractions, ensuring that residents can enjoy all that Siesta Key has to offer. With its perfect blend of natural beauty, community spirit, and access to modern conveniences, Siesta Bayside is more than just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this enchanting subdivision today!

Newest Siesta Bayside Homes for Sale

$2,395,000

3 Beds ⋅ 2 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code

The Fastest Open-Water Access Available on Siesta Key Under $2.5 Million Less than 3 minutes to Sarasota Bay, 95 feet of waterfront, and a 75 x 3 of dock designed for serious boating enthusiasts. If you’ve been searching for a waterfront home that prioritizes boating convenience over lengthy canal runs, this is one of the most compelling opportunities currently available on Siesta Key. Why spend 30–45 minutes idling through canals when you can be in Sarasota Bay in under 3 minutes? Positioned on one of Siesta Key’s premier deep-water canals, this exceptional waterfront residence offers the rare combination of protected dockage and near-immediate access to open water. For boaters who value time on the water, this location is difficult to replicate at any price point. Designed with larger vessels in mind, the property features approximately 95 feet of waterfront, a 75-foot dock, 200-amp dock service, and four 50-amp shore power connections. Whether you’re heading offshore, cruising the Intracoastal, or enjoying a sunset cruise across Sarasota Bay, this home delivers a level of boating convenience that few waterfront properties can match. Boater Highlights?• Less than 3 minutes to Sarasota Bay?• Approximately 95 feet of waterfront?• 75-foot dock?• Four 50-amp shore power connections?• 200-amp dock service?• Deep-water canal location?• Protected dockage with quick open-water access Inside, the home has been thoughtfully renovated with a clean coastal-modern design featuring designer tile flooring, an open-concept floor plan, Viking gas appliances, custom cabinetry, and expansive waterfront views. The spacious living areas flow seamlessly into the kitchen and entertaining spaces, creating an ideal environment for both everyday living and hosting guests. The private primary suite serves as a luxurious retreat, complete with an oversized walk-in closet, spa-inspired bathroom, glass-enclosed shower, and direct outdoor access. An additional flexible space offers the opportunity to create a fourth bedroom, private guest suite, office, or media room. Outdoor living is centered around the waterfront lifestyle. Enjoy a saltwater pool and spa, tropical landscaping, integrated lighting, retractable awning, propane fire pit, outdoor shower, and multiple seating and entertaining areas overlooking the canal. Additional features include a 13.5 kW generator, hurricane protection, epoxy-finished garage, updated HVAC system, newer water heater with circulation system, 250-gallon propane tank, and valuable dry storage space. Originally introduced at $2,690,000 and now offered at $2,450,000, this property represents one of the strongest values currently available for buyers seeking deep-water dockage, exceptional boating access, and luxury waterfront living on Siesta Key. Luxury yacht available separately.

4508 Woodside Road, Sarasota

$975,000

4 Beds ⋅ 2 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code

Virtually Staged. Nestled near the gentle waters of Roberts Bay, this enchanting Siesta Key home rests on a quiet cul de sac street where the only sounds are the whisper of palms and the laughter of neighbors walking by. T location captures the essence of island life — peaceful, private, and just moments from where the sun dips into the Gulf. A short stroll or quick bike or golf cart ride has you in the center of vibrant Siesta Key. This home is dependable and offers new hurricane impact-rated windows, garage door and sliders; re-lined plumbing lines as well as new pex water supply lines throughout; and a new HVAC system and water heater. Step inside, and you’ll feel the warmth of a home that’s been lovingly renewed. Every detail reflects care and comfort — from the four inviting bedrooms and two full baths to the light-filled kitchen adorned with stainless steel appliances and a captivating blue glass tile backsplash reminiscent of the Gulf waters just moments from your front door. The dining area invites long, easy meals, while two separate living spaces offer versatility for gathering, relaxing, or simply enjoying the rhythm of coastal living. Life is low maintenance and carefree with durable lvp flooring that looks modern and will compliment your coastal décor. Beyond the back door lies a spacious, fenced yard — a blank canvas waiting for your imagination. Picture a pool glimmering under the afternoon sun, a lush garden framed with tropical blooms, or a firepit where evenings stretch into starlit conversations. Here, you aren’t confined to someone else’s vision — you have the freedom to create your own perfect oasis suited to your tastes and dreamy outdoor vibe. The charming front porch welcomes your guests — a cheerful prelude to the life that awaits within. New hurricane-rated windows offer confidence and calm, while the spacious two-car garage with smart epoxy flooring and the generous, indoor laundry room offers convience. This is more than a house; it’s a fresh beginning on Siesta Key — a place where your coastal dream can take root.

630 Venice Lane, Sarasota

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