Siesta Bayside Real Estate

Welcome to Siesta Bayside, an enchanting subdivision nestled in the heart of Siesta Key, Florida. Known for its stunning beaches and vibrant community, Siesta Bayside offers an idyllic coastal lifestyle that perfectly blends relaxation with adventure. This charming enclave is situated within Sarasota County, just moments away from the world-renowned Siesta Beach, celebrated for its powdery white sands and crystal-clear waters.

Siesta Bayside is characterized by its picturesque waterfront properties, many of which boast breathtaking views of the bay and direct access to serene boating channels. The neighborhood is designed for those who appreciate both tranquility and a sense of community. With beautifully landscaped grounds and well-maintained homes, residents take pride in their surroundings, creating a welcoming atmosphere for families and retirees alike.

Living in Siesta Bayside means embracing the quintessential Florida lifestyle. Spend your days basking in the sun, exploring local boutiques, or indulging in fresh seafood at nearby restaurants. For outdoor enthusiasts, the area offers numerous recreational activities, including kayaking, paddleboarding, and fishing, ensuring that there’s never a dull moment.

The subdivision is also conveniently located near top-rated schools, healthcare facilities, and vibrant cultural attractions in Sarasota, making it an ideal choice for families and professionals. Whether you’re seeking a vacation home or a permanent residence, Siesta Bayside is a hidden gem that invites you to experience the best of coastal living. Come discover your slice of paradise in this charming Siesta Key community!

Newest Listings in Siesta Bayside

$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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