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$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

$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

$1,275,000
2 Beds 2 Baths Gulf & Bay Club SubDv. 34242 Zip Code
Welcome to your Siesta Key beachfront retreat, situated on one of the most globally desirable shorelines. This exclusive, gated Gulf & Bay Club residence offers an incredibly beautiful lifestyle right on the Gulf of Mexico. Savor sweeping views of the Gulf of Mexico waters and pristine sugar sand from this beautifully updated 1,335sqft open concept condo. Starting in the kitchen with stone countertops and stainless-steel appliances to the updated flooring through to the spacious lanai for additional space to entertain. With 2-bedrooms, 2 updated bathrooms, recessed lighting, and a primary suite with dual sinks to enhance the luxurious living experience. Immerse yourself in resort-style amenities, including 3 heated pools, 8 tennis courts, a fitness center with spa and dry sauna, an expansive clubhouse, racquetball and basketball courts, and multiple barbecue areas with Tiki-style picnic tables. Gulf & Bay Club is situated on 32 acres of manicured tropical landscaping, with a gate and guard, 800 feet of private beach, walking trails, and an engaging social calendar. With conveniences like in-unit laundry and a recently renovated covered carport, this residence at the Gulf & Bay Club on Siesta Key offers quintessential and elevated island life. This unit has not previously been used as a rental.

5750 Midnight Pass Road Unit 607E, Sarasota

$1,400,000
2 Beds 2 Baths Gulf & Bay Club SubDv. 34242 Zip Code
Exquisite, fully updated, turnkey furnished, 2-bedroom, 2-bath beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring high end detailed finishes and interiors professionally crafted to perfection. This unit is a rare find in the highly sought-after E Building with direct beach access just steps away from your front door. Enjoy breath taking sunsets from your personal balcony. The sandy white powder stretches 800 feet across this pristine 32-acre meticulously cared for tropical community. Enjoy the comfort of 24-hour gated security, heated pools, fitness center, dry saunas, hot tub, tennis courts, racquetball and pickleball courts. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The clubhouse has a library, bar, pool table and TVs for your enjoyment. Electric car charging stations and on-site car wash. You are moments away from Siesta Village to enjoy outdoor dining with live music, specialty shopping and more! Take a short trip to downtown and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.

5750 Midnight Pass Road Unit 309, Sarasota

$1,200,000
2 Beds 2 Baths Gulf & Bay Club SubDv. 34242 Zip Code
Brilliant views of the sparkling waters of the Gulf of Mexico captivate from this third floor unit in the exquisite Gulf & Bay Club on Siesta Key. Located in the coveted building E with southern exposure, this end unit offers additional windows that allow the warm Florida sunshine to flood your light and bright living space. This unit has been tastefully updated with ample recessed lighting and charming plantation shutters throughout. Create your favorite fare for family and friends in the kitchen with bright white cabinets contrasted by the stunning black granite countertops. Stay organized or work from home in your complete office alcove just off the kitchen. With 1,335 square feet of living space, an open concept from kitchen through to the spacious lanai, providing an additional 136 square feet, offers great space for entertaining, including countertop seating and dining space that comfortably seats 6. The comfort continues to the owner’s suite and guest quarters, both offering nicely appointed baths featuring walk in showers. Situated on 32 acres of perfectly manicured tropical landscaping, the gated and guarded Gulf & Bay Club offers an enviable lifestyle with 800 feet of private beach; three heated swimming pools; two clubhouses; tennis, pickleball, racquetball and basketball courts; walking trails amongst the lush landscape; media and library facilities and much, much more. Conveniences are endless with in unit laundry, a recently renovated covered car port, electric car charging stations, along with an engaging social calendar with organized events, games and cultural outings. Venture away from Siesta Key for a day and explore the spectacular arts and culture of Florida’s vibrant gulf coast communities. The quintessential and elevated island life can be yours at the Gulf & Bay Club on Siesta Key.

5750 Midnight Pass Road Unit 301, Sarasota