Bay Oaks Estates Homes with Brookside Middle Middle school

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 suburban tranquility, making it an ideal destination for families and individuals alike. With its picturesque streets lined with mature trees and lush landscaping, Bay Oaks Estates exudes a warm and inviting atmosphere that feels like home from the moment you arrive.

The homes in Bay Oaks Estates are thoughtfully designed, featuring a variety of architectural styles that cater to diverse tastes. From modern beach cottages to spacious family residences, each property boasts ample outdoor space, perfect for enjoying Florida’s sunshine. Many homes come equipped with private pools, expansive patios, and easy access to the stunning beaches that Siesta Key is renowned for.

Families will appreciate the community’s proximity to Brookside Middle School, known for its excellent educational programs and dedicated staff. This makes Bay Oaks Estates an ideal choice for families looking to provide their children with a quality education while enjoying the laid-back lifestyle that the area offers.

Beyond the homes and schools, residents of Bay Oaks Estates can indulge in the vibrant local culture of Siesta Key, with its eclectic shops, delightful dining options, and, of course, the world-famous Siesta Beach. Whether you’re looking to relax by the shore, explore the local parks, or enjoy a night out, Bay Oaks Estates places you at the center of it all.

Discover the charm and convenience of Bay Oaks Estates—your perfect slice of paradise awaits!

Newest Bay Oaks Estates Homes with Brookside Middle Middle school

$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

$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