Siesta Key Homes with Gated Amenities

Welcome to Siesta Key, Florida—a slice of paradise nestled in Sarasota County, renowned for its stunning beaches, vibrant culture, and luxurious living. This enchanting barrier island is not just a dream destination for vacationers; it’s a thriving community that offers an exceptional lifestyle for those seeking a permanent residence or a serene getaway.

Siesta Key is celebrated for its powdery white sands and crystal-clear waters, consistently ranked among the best beaches in the United States. Imagine waking up to the soothing sounds of the ocean and the gentle breeze wafting through your windows. Here, outdoor enthusiasts can indulge in a variety of activities, from paddleboarding and kayaking to biking along scenic trails. The island is also home to a lively village atmosphere, featuring boutique shops, exquisite dining options, and vibrant nightlife.

For those seeking a touch of exclusivity and security, Siesta Key offers homes with gated amenities that elevate your living experience. These luxurious properties provide not only privacy but also access to a range of upscale features such as swimming pools, fitness centers, and beautifully landscaped grounds. Whether you’re looking for a contemporary condo with breathtaking ocean views or a sprawling estate surrounded by lush greenery, Siesta Key has something to suit every taste and lifestyle.

In this idyllic coastal community, you can enjoy the best of both worlds: a tranquil retreat with easy access to the cultural and recreational offerings of Sarasota. Discover your dream home in Siesta Key today, and embrace the enchanting lifestyle that awaits you in this coastal gem!

Newest Siesta Key Homes with Gated Amenities

9393 Midnight Pass Road Unit 205, Sarasota image

9393 Midnight Pass Road Unit 205, Sarasota — North $650,000

This beautifully renovated 2-bedroom, 2-bath condominium overlooking the bay was freshly painted on 9/8/2026 and is truly move-in ready. Turnkey furnished with an open ki...

2 Beds
2 Baths
Pointe On Midnight Pass SubDv.
34242 Zip Code

7740 Sanderling Road, Sarasota $22,000,000

Pre-Construction. To be built. Architectural Rendering Of What Could Be Built Are For Planning Purposes Only. An Extraordinary Gulf-Front Estate Opportunity! There ...

6 Beds
8 Baths
Siesta Properties Inc SubDv.
34242 Zip Code

6300 Midnight Pass Road Unit 809, Sarasota image

6300 Midnight Pass Road Unit 809, Sarasota — Crystal Sands $1,795,000

From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renown...

2 Beds
2 Baths
Crystal Sands SubDv.
34242 Zip Code

5855 Midnight Pass Road Unit 222, Sarasota image

5855 Midnight Pass Road Unit 222, Sarasota — 5855 $625,000

Turnkey and ready for its next chapter, this spacious residence in the curve of Harbor Towers Yacht & Racquet Club is one of the largest floor plans in the building, feat...

2 Beds
2 Baths
Harbor Towers Y & R SubDv.
34242 Zip Code

1001 Point Of Rocks Road Unit 310, Sarasota image

1001 Point Of Rocks Road Unit 310, Sarasota — Siesta Sands Resort $798,000

Located directly on Siesta Key Beach, Unit 310 at Siesta Sands is situated on the third floor and features a private balcony with sweeping Gulf views, tropical breezes, a...

1 Beds
1 Baths
Siesta Sands Resort (Timeshare) SubDv.
34242 Zip Code

1141 W Peppertree Drive Unit 1141, Sarasota image

1141 W Peppertree Drive Unit 1141, Sarasota — 36 $669,000

Discover effortless Siesta Key living in this beautifully updated and fully furnished 2-bedroom, 2-bath condo in the highly desirable Peppertree Bay community. Located on...

2 Beds
2 Baths
Peppertree Bay SubDv.
34242 Zip Code

5770 Midnight Pass Road Unit 301, Sarasota image

5770 Midnight Pass Road Unit 301, Sarasota — 5770 $1,099,000

Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium complex. If you are looking for a great investment or the perfect place to call home, look no further. Loca...

2 Beds
2 Baths
Gulf & Bay Club SubDv.
34242 Zip Code

5400 Ocean Boulevard Unit 15 1-4, Sarasota image

5400 Ocean Boulevard Unit 15 1-4, Sarasota — The Terrace $4,000,000

Perched 15 floors above the Gulf of Mexico within The Terrace—Frank Folsom Smith's iconic beach-front landmark on Siesta Key—two corner residences were combined to create...

2 Beds
3 Baths
Terrace SubDv.
34242 Zip Code

1280 Dolphin Bay Way Unit 402, Sarasota image

1280 Dolphin Bay Way Unit 402, Sarasota — 1280 $1,589,000

Welcome to Dolphin Bay, one of Siesta Key's premier waterfront communities, where luxury coastal living meets breathtaking scenery. This beautifully maintained 2-bedroom,...

2 Beds
2 Baths
Dolphin Bay-Siesta Key SubDv.
34242 Zip Code

6020 Midnight Pass Road Unit 49, Sarasota image

6020 Midnight Pass Road Unit 49, Sarasota — Aloha Kai #49 $625,000

Turn-Key Furnished Villa in Aloha Kai – One of Siesta Key's Premier Beachfront Communities! Just steps from world-famous Siesta Key Beach, this beautifully updated 2-bedr...

2 Beds
2 Baths
Aloha Kai Apts SubDv.
34242 Zip Code

5400 Ocean Boulevard Unit 17-04, Sarasota image

5400 Ocean Boulevard Unit 17-04, Sarasota — The Terrace $1,559,000

The iconic Terrace building is a masterpiece designed by renowned architect Frank Folsom Smith. This modernist building, built of poured concrete exudes strength and dura...

2 Beds
2 Baths
Terrace SubDv.
34242 Zip Code

1001 Point Of Rocks Road Unit 208, Sarasota image

1001 Point Of Rocks Road Unit 208, Sarasota — Siesta Sands $1,195,000

Gulf view condominium at the Siesta Sands Resort, at the southern tip of world-famous Crescent Beach on Siesta Key. This second-floor end unit, featuring two bedrooms, tw...

2 Beds
2 Baths
Siesta Sands Resort (Timeshare) SubDv.
34242 Zip Code