Bay Oaks Estates Homes with Tennis Court(s) Community Features

Welcome to Bay Oaks Estates, a hidden gem nestled in the picturesque Siesta Key, Florida. This charming subdivision is not just a place to live; it’s a lifestyle that embraces the best of coastal living. Known for its stunning beaches, vibrant community, and laid-back atmosphere, Siesta Key offers an idyllic setting for families, retirees, and everyone in between.

Bay Oaks Estates is particularly appealing for those who appreciate an active lifestyle. The community features homes with tennis courts, providing residents with the perfect opportunity to engage in friendly matches or refine their skills while soaking up the Florida sun. Imagine stepping out of your beautifully appointed home and onto the court, with the sound of waves gently crashing in the background—a daily routine that feels like a vacation!

Each residence in Bay Oaks Estates is thoughtfully designed, featuring spacious layouts, modern amenities, and lush landscaping that complements the natural beauty of the area. With a strong sense of community, neighbors often gather for social events, fostering friendships and creating lasting memories.

Beyond the tennis courts, residents can explore the nearby pristine beaches, indulge in local dining hotspots, or partake in water sports and outdoor activities. Whether you’re enjoying a sunset stroll along the shore or hosting a barbecue in your backyard, Bay Oaks Estates is the perfect backdrop for a fulfilling life.

Discover the charm of Bay Oaks Estates, where your dream home awaits in the heart of Siesta Key, and embrace a lifestyle filled with sunshine, community, and endless possibilities.

Newest Bay Oaks Estates Homes with Tennis Court(s) Community Features

$499,000

2 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code ⋅ A4698724 MLS ⋅ Active Status ⋅ E BLDG.

New Listing Photos now attached! Weekly rentals, prime Siesta Key location, and immediate income potential—this is the beach investment opportunity buyers wait for. Welcome to Bay Oaks, where island living meets exceptional rental flexibility in one of the most desirable communities on Siesta Key. This beautifully updated 2-bedroom, 2-bath condo is being offered fully turn-key furnished, making ownership effortless from day one. Even better, future rental bookings are already in place, allowing you to start generating income immediately—no waiting, no setup, no downtime. Just close and collect. Since its last listing, the home has been enhanced with a newly renovated kitchen, featuring stylish modern finishes that elevate both form and function. The bright, open-concept layout creates an inviting coastal feel, with seamless flow between the kitchen, dining, and living spaces—perfect for relaxing after a day at the beach or entertaining guests. Enjoy peaceful mornings on your private balcony surrounded by lush tropical landscaping, while both spacious bedrooms provide comfortable retreats filled with natural light. Bay Oaks is beloved for its unbeatable location and resort-style amenities. Situated on the bayside of Siesta Key and just moments from the powdery sands of world-famous Siesta Key Beach, residents and guests enjoy access to a sparkling pool, private fishing pier, tennis courts, shuffleboard, and beautifully maintained grounds. Hop on the free trolley for quick access to the restaurants, boutiques, and nightlife of Siesta Key Village. For investors, the biggest advantage is Bay Oaks’ highly desirable weekly rental policy—a rare and valuable feature on Siesta Key that opens the door to strong vacation rental demand and attractive income potential. Whether you're searching for a personal beach getaway, a savvy investment property, or the perfect combination of both, this Bay Oaks condo delivers. Flip-flops encouraged. **Updated Listing Photos Now Attached!**

6157 Midnight Pass Road Unit E12, Siesta Key

$529,900

2 Beds ⋅ 3 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code ⋅ A4692762 MLS ⋅ Active Status ⋅ Na BLDG.

This property is a rare find, featuring two master suites upstairs, each with its own private balcony. The home is tastefully decorated and is being sold Turnkey, making it an excellent opportunity for immediate use or investment. Notably, the property already has a strong track record of rental income with several future bookings already in place. The Bay Oaks community offers a serene setting with mature landscaping and a wide array of amenities, including a heated pool, tennis courts, recreation room and a fishing pier. It also provides the convenience of on-site management and a picnic area with Barbeques for your enjoyment. Located less than a mile from Crescent Beach, the property offers easy access to the world-renowned powdery, quartz sand of Siesta Key, recently ranked as the #4 beach in the world by Tripadvisor in 2025. The area is a premier destination spot. Additionally, the trolley stops directly in front of the complex providing easy transportation to the various dining, shopping and nightlife options Siesta Key is famous for.

6157 Midnight Pass Road Unit F22, Siesta Key

$474,000

1 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code ⋅ A4663201 MLS ⋅ Active Status ⋅ Building E BLDG.

Elevated Living on the 4th Floor! Discover this well appointed 1-bedroom, 1-bath condo just minutes from the world-renowned Siesta Key Beach. This TURN KEY residence offers the ideal blend of relaxed Florida living and exceptional value. Step into a bright and airy space where natural light pours into the east-facing screened balcony, overlooking lush tropical landscaping. The interior features ceramic tile flooring throughout the kitchen, dining, and living areas, creating a clean and cohesive look. The kitchen is equipped with stainless steel appliances, including a range and dishwasher, and boasts a generous walk-in pantry for all your storage needs. A separate large closet provides ample space for beach and pool gear. Residents and guests enjoy access to a host of amenities including a community pool, tennis courts, social room, and fishing pier. Recent updates include a brand-new water heater and a newer A/C system for added peace of mind. Best of all, this gem allows for weekly rentals, offering a fantastic opportunity to offset ownership costs. Gross rental income ranging from $30,000 to $40,000 annually. Great place to vacation when you can...and rent when you can't! The unit includes one assigned covered parking space, plus plenty of guest parking. Don’t miss out—schedule your showing today!

6157 Midnight Pass Road Unit E24, Siesta Key

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