Bay Oaks Estates Homes with Golf Carts OK Community Features

Welcome to Bay Oaks Estates, a hidden gem nestled in the heart of Siesta Key, Florida. This charming subdivision offers a unique blend of coastal living and community spirit, making it the perfect destination for those seeking a vibrant lifestyle in one of the Sunshine State's most desirable locales.

Bay Oaks Estates is renowned for its picturesque surroundings, where lush landscapes meet the serene waters of the Gulf. The community is designed with the outdoor enthusiast in mind, featuring scenic walking paths, lush greenery, and easy access to some of the finest beaches in the country. Residents enjoy the convenience of a golf cart-friendly environment, allowing for leisurely rides to nearby shops, restaurants, and, of course, the stunning shoreline.

The homes in Bay Oaks Estates are as inviting as the community itself. With a variety of architectural styles, from charming beach cottages to modern coastal retreats, there’s something to suit every taste. Many residences boast spacious layouts, private outdoor spaces, and the latest amenities, making it easy to entertain friends and family or relax in your own tranquil haven.

Community features are abundant, with friendly neighbors and a welcoming atmosphere that fosters a sense of belonging. Whether you're taking a stroll through the neighborhood, enjoying a sunset at the beach, or participating in local events, Bay Oaks Estates offers a lifestyle that celebrates the best of Siesta Key living.

Come discover your perfect slice of paradise at Bay Oaks Estates, where every day feels like a vacation!

Newest Bay Oaks Estates Homes with Golf Carts OK 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

$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

Start Your Search

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,