Browse All Bay Oaks Estates Properties for Sale

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

$440,000

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

Dreaming of relaxing on your balcony in your chaise lounge, overlooking the pool, Listening to Jimmy Buffet and sipping a cold margarita? Sure, sounds perfect. Well, It’s here, and just a short walk to the crystal powdery sand beach and turquoise waters of Siesta Key Beach. This is the #1 beach in the US and # 4 in the world! The dream of owning at Siesta Key is still possible. This 2nd floor condo has elevators, covered parking and guest parking. The spacious condo has beachy décor, 2 large bedrooms, 2 baths, in unit washer dryer, stainless steel appliances, walk in closets. BAY OAKS complex has huge shade trees and mature landscaping and is located on the intercoastal on one side with a nice fishing pier and the beach on the other. This is your chance to own property for your family and use it as an investment property also. Siesta Key has beautiful sunsets, Sunday night drum circle, and close to restaurants, shopping and watersports. There is also a game room in the clubhouse, and a public laundry as well as free local taxis for a night out in the Village. Sarasota offers theatres, art galleries, museums, parks, Mote Marine, and Selby Gardens. So much, so close! Own a piece of Paradise. We have found out from the HOA that there could be an assesment coming. The seller is wiliing to put that in escrow for the buyer or reduce te price by that amount.

6157 Midnight Pass Road Unit E42, Sarasota

$470,000

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

Condo being sold Turn-Key! Welcome to Paradise on Siesta Key! This charming 2-bedroom, 2-bathroom condo offers 1,101 square feet of coastal living at its finest. Nestled in the heart of Siesta Key, this home is perfect for those seeking a relaxing island retreat or an ideal investment opportunity. Step inside to discover an open kitchen with granite countertops, a convenient breakfast bar, and sleek stainless steel appliances. The spacious layout includes a washer and dryer for your convenience, and the enclosed screened lanai is the perfect spot to unwind while overlooking the sparkling community pool. The lanai also features a handy storage closet—ideal for keeping your beach chairs and bicycles ready for your next adventure. Bay Oaks offers an array of amenities to enhance your island lifestyle, including tennis courts, a community pool, and a dock where you can relax and take in the breathtaking water views. For those who love to grill, the BBQ area is perfect for enjoying burgers and hotdogs with friends and family. Just down the road, you’ll find the world-renowned Siesta Key Beach, famous for its powdery white sand and crystal-clear waters. Siesta Key Village is also nearby, offering a vibrant mix of shops, restaurants, and nightlife. Don’t miss this incredible opportunity to own your slice of paradise on Siesta Key! Schedule your private showing today.

6157 Midnight Pass Road Unit E43, Sarasota

$700,000

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

Price Improvement! Don't miss out on the opportunity to own this spacious condominium in the rarely available Bay Oaks community on Siesta Key. This condo comes fully furnished and turnkey, making it perfect for personal use or as a lucrative investment with weekly rental potential with future bookings in place. Relish the Gulf breeze from one of your three balconies, each offering partial Intracoastal water views. The two bedrooms, each equipped with own private bathroom and walk-in closet, are located upstairs. The master bedroom boasts a private balcony with stunning water vistas, while an additional private balcony is nestled between the two bedrooms. The living room features a screened-in balcony with water views, thoughtfully updated with crown molding, new appliances, and delightful furnishings in excellent condition. Also provided is the convenience of in-unit laundry with additional storage space and a half bath on the lower level. The monthly fees are among the most affordable, covering water, sewer, roof maintenance, cable, pest control, exterior upkeep, and access to fantastic amenities like a heated pool, tennis courts, outdoor waterfront grilling, island shuttle bus services, and a fishing dock in a serene park-like environment. A short stroll away, you'll find the renowned white sandy beaches of Siesta Key and the vibrant Village, offering an array of dining and shopping options. This is your chance to own a slice of paradise!

6157 Midnight Pass Road Unit A52, Sarasota

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