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

Bay Oaks Estates Homes with Tennis Court(s) 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 luxury and leisure, making it the perfect place for those seeking a vibrant community lifestyle. Located in Sarasota County, Bay Oaks Estates is just moments away from the stunning beaches and crystal-clear waters that Siesta Key is famous for.

The homes in Bay Oaks Estates are designed with both comfort and elegance in mind. Many properties feature spacious layouts, modern amenities, and lush landscaping, creating an inviting atmosphere for families and individuals alike. One of the standout features of this community is its exclusive access to tennis courts, providing residents with the perfect opportunity to stay active and socialize with neighbors. Whether you’re a seasoned player or just starting out, the tennis courts are a fantastic way to enjoy the Florida sunshine while engaging in friendly competition.

In addition to tennis, Bay Oaks Estates boasts a close-knit community feel, where residents often come together for social gatherings and events. The nearby Siesta Key Village offers an array of dining, shopping, and entertainment options, ensuring that you’ll never run out of things to do. With its prime location, luxurious homes, and exceptional amenities, Bay Oaks Estates is more than just a place to live; it’s a lifestyle. Discover the charm of this remarkable community and make it your new home in paradise!

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

2 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code

Enjoy easy island living in this beautifully maintained first-floor condominium at Bay Oaks on Siesta Key. With your assigned carport just steps from the front door, there's no need to wait for elevators, making everyday living and guest arrivals effortless. This versatile one-bedroom residence features a converted den that functions as a second bedroom, allowing the property to be successfully marketed and rented as a two-bedroom vacation rental. A favorite among returning guests, this turnkey-furnished unit offers an excellent opportunity for personal enjoyment or investment income. Inside, ceramic tile flooring flows throughout the living and dining areas, while the flexible floor plan comfortably accommodates family and visitors. Step outside to a private patio surrounded by mature trees, providing a peaceful retreat and convenient rear access to the community's resort-style amenities. Residents and guests enjoy Bay Oaks' impressive amenities, including a heated pool, tennis courts, fishing dock, social room, and outdoor grilling areas. Located directly on the free Siesta Key trolley route, you'll have easy access to world-famous Siesta Beach and the shops, dining, and entertainment of Siesta Key Village. Bay Oaks permits one-week rentals, making this a highly desirable and consistently popular rental property. Sold turnkey furnished, this island getaway is ready for immediate enjoyment or rental income from day one.

6157 Midnight Pass Road Unit G11, Sarasota

2 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code

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, Sarasota

2 Beds ⋅ 3 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code

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, Sarasota

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Bill Kilpatrick

Bill Kilpatrick is a licensed Florida Realtor® and real estate broker with more than 20 years of experience serving buyers, sellers, and investors throughout Lakeland, Tampa Bay, Winter Haven, and the greater Central Florida area. Since becoming licensed in 2002, he has built a reputation for strong negotiation skills, market expertise, and delivering exceptional service to hundreds of families across Florida. As the Managing Broker for the Keller Williams Realty Tampa Central office and the Keller Williams Realty Smart One office, Bill oversees more than 400 real estate agents and helps support offices that collectively generate billions of dollars in annual real estate sales volume. Bill also leads The Bill Kilpatrick Team at Keller Williams Realty, where his team has helped more than 800 families buy and sell homes throughout Central Florida. His experience spans luxury homes, residential sales, relocation, investment properties, and strategic pricing and marketing. Before real estate, Bill managed his family’s convenience store and gas station business, where he developed the customer service and leadership foundation that still drives his business today. Outside of real estate, Bill enjoys spending time with his wife Tiffany, his son Sebastian, and stepchildren Elle and Chase. He also enjoys boating, fishing, tennis, and snow skiing.

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