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, an enchanting subdivision nestled in the heart of Siesta Key, Florida, within the picturesque Sarasota County. This exclusive community offers a unique blend of coastal charm and modern conveniences, making it an ideal place for those who seek a serene lifestyle with easy access to the vibrant culture of the nearby city.

Bay Oaks Estates is renowned for its stunning homes that boast exquisite architectural designs and lush landscaping. Many of these properties feature private tennis courts, providing residents with the perfect opportunity to enjoy an active lifestyle right at home. Whether you are a seasoned player or just looking to pick up a racket for some fun, the tennis courts are a fantastic addition to the community’s offerings.

Living in Bay Oaks Estates means embracing the best of both worlds: the tranquility of a close-knit neighborhood and the excitement of Siesta Key’s world-famous beaches and local attractions. Spend your days basking in the sun on powdery white sands, indulging in fresh seafood at local eateries, or exploring the eclectic shops and art galleries that define this vibrant area.

In addition to the tennis courts, Bay Oaks Estates features well-maintained common areas that enhance community spirit and encourage social interactions among neighbors. With its idyllic setting and luxurious amenities, Bay Oaks Estates is not just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this remarkable subdivision and experience the best that Siesta Key has to offer!

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

$399,000
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
$499,000
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
$529,900
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
Start Your Search