Bay Oaks Estates Homes with Community Pool type

Welcome to Bay Oaks Estates, a prestigious subdivision nestled in the heart of Siesta Key, Sarasota, FL. This exclusive community offers an unparalleled lifestyle with luxurious homes and top-notch amenities.

Homes in Bay Oaks Estates are designed to perfection, offering a blend of elegance and comfort. Residents can enjoy the true essence of Florida living with beautifully landscaped properties and spacious interiors. Whether you're looking for a cozy retreat or a spacious family home, Bay Oaks Estates has something for everyone.

One of the standout features of Bay Oaks Estates is the community pool, providing residents with a refreshing oasis right at their doorstep. Imagine spending sunny afternoons lounging by the pool, socializing with neighbors, and creating lasting memories with your loved ones.

Living in Bay Oaks Estates means enjoying the best of both worlds - a peaceful retreat away from the hustle and bustle, yet close to all the amenities and attractions that Sarasota has to offer. From pristine beaches to top-rated schools and dining options, everything you need is just a stone's throw away.

Come and experience the charm of Bay Oaks Estates for yourself. Discover the perfect blend of luxury, comfort, and community living in this sought-after subdivision in Siesta Key, FL.

Newest Bay Oaks Estates Homes with Community Pool type

$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

$340,000

2 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code ⋅ TB8482718 MLS ⋅ Active Status ⋅ A BLDG.

Looking for a vacation home that also produces income? This one is for you! A charming updated GROUND floor condo featuring 2 rentable bedrooms and 1 bathroom making this the LOWEST priced unit in the Bay Oaks complex. This unit comes completely furnished, allows short term 1 WEEK RENTALS and already has a high rating and excellent cash flow with VRBO #911238. The condo is equipped with a full kitchen and reserved covered parking, a water view from the lanai and is located in beautiful Siesta Key, Florida. This particular unit is located about 30 feet from the intracoastal waterway, so soak up pristine gulf views right from your own lanai! It is also a stone's throw away from the community's heated pool. The unit was refreshed with an updated bathroom, kitchen, lanai tile and added insulation for efficiency and sound dampening. The Bay Oaks community amenities include a heated pool, tennis court, dock on the bay, fishing pier, community barbecue grill, community billiard room, 1 parking space (and access to additional visitor space) and all common area and outdoor maintenance. Internet, water, and trash are also included in the fee. The community is on the Siesta Key trolley line with a stop right out front. Located near the vibrant Sarasota nightlife, upscale shops and dining options, there's always something to explore. Did I mention Siesta Key was named #1 beach in AMERICA and 4th in the WORLD? Its nearly 99% quartz-crystal powdered sand, dubbed the “world’s finest, whitest sand”, never gets hot under the Gulf Coast sun and tropical weather. The 2016 $20 million-dollar renovation added a new playground, two concession stands, more restrooms, a half-mile long esplanade, many shelters and pavilions, and a renovated Sarasota School of Architecture pavilion. With 950 free parking spaces, this venue provides the most parking for any public beach in Sarasota County. You will want to check this out for yourself. Book a week vacation and explore before you buy or book a single showing. Either way, you won't be disappointed.

6157 Midnight Pass Road Unit A51, 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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