Siesta Key Homes with Sidewalks Community Features

Welcome to Siesta Key, Florida, a stunning barrier island located in Sarasota County that boasts some of the most beautiful beaches in the United States. Known for its powdery white sand and crystal-clear turquoise waters, Siesta Key is not just a beach lover’s paradise; it’s also a vibrant community filled with charm and character.

Siesta Key offers a unique blend of laid-back island living and modern conveniences. Residents and visitors alike enjoy a variety of dining, shopping, and entertainment options, making it a lively destination year-round. The island is home to an array of outdoor activities, from kayaking and paddleboarding to biking along scenic paths. With its tropical climate, Siesta Key is perfect for enjoying the great outdoors, whether you’re lounging on the beach or exploring local parks.

One of the standout features of this community is its commitment to walkability. Homes with sidewalks are prevalent throughout Siesta Key, encouraging residents to stroll through the picturesque neighborhoods. Imagine starting your day with a leisurely walk along tree-lined streets, greeting friendly neighbors, and soaking in the beautiful surroundings. These pedestrian-friendly pathways not only enhance the sense of community but also promote an active lifestyle.

With its blend of natural beauty, vibrant culture, and welcoming atmosphere, Siesta Key is more than just a destination; it’s a place to call home. Whether you’re seeking a vacation retreat or a permanent residence, this enchanting island offers an idyllic setting for a life well-lived. Come discover the charm of Siesta Key, where every day feels like a vacation!

Newest Siesta Key Homes with Sidewalks Community Features

8302 Midnight Pass Road, Sarasota $1,400,000

WELCOME TO THE SIDE OF SIESTA KEY YOU NEVER WANT TO LEAVE. Glistening Heron Lagoon stretches peacefully behind this beautifully restored and renovated income producing si...

4 Beds
2 Baths
Ocean View SubDv.
34242 Zip Code

5673 Midnight Pass Road Unit 202, Sarasota image

5673 Midnight Pass Road Unit 202, Sarasota $479,999

Welcome to Paradise! White Sands Village is great property that is located directly across from the world- famous beautiful Siesta Key beach! It is a great investment or ...

2 Beds
2 Baths
White Sands Village SubDv.
34242 Zip Code

6144 Midnight Pass Road Unit 4N, Sarasota image

6144 Midnight Pass Road Unit 4N, Sarasota — 6144 $1,495,000

Welcome to effortless beachfront living at Island House on iconic Siesta Key, where spectacular Gulf views, a premier location, and relaxed coastal style come together be...

2 Beds
2 Baths
Island House SubDv.
34242 Zip Code

9393 Midnight Pass Road Unit 302, Sarasota image

9393 Midnight Pass Road Unit 302, Sarasota — B $675,000

If you seek incredible views, look no further. Surrounded by water on three sides, enjoy the panoramic vistas on the southernmost end of Siesta Key. Look from the lanai t...

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

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

1035 Seaside Drive Unit 502, Sarasota image

1035 Seaside Drive Unit 502, Sarasota — Ten35 Seaside $3,995,000

Welcome to Ten35 Seaside Drive, a newer mid-rise community at the south end of world-renowned Siesta Key Beach, where turquoise Gulf waters meet pristine quartz sand. Ten...

4 Beds
3 Baths
Ten35 Seaside SubDv.
34242 Zip Code

8977 Midnight Pass Road Unit 219, Sarasota image

8977 Midnight Pass Road Unit 219, Sarasota — 8977 $529,000

Experience true waterfront living at Sunrise Cove with spectacular Intracoastal Waterway views, breathtaking sunrises each morning, and beautiful moonrises each evening....

2 Beds
2 Baths
Sunrise Cove SubDv.
34242 Zip Code

915 Seaside Dr Unit 405, WEEKS 22-23, Sarasota image

915 Seaside Dr Unit 405, WEEKS 22-23, Sarasota — 405 $45,000

Fractional Ownership. FRACTIONAL OWNERSHIP **GUARANTEED GULF FRONT DELUXE UNIT** Imagine a perfect family retreat every year for Memorial Weekend on world famous Siest...

4 Beds
3 Baths
Siesta Key Beach Residences SubDv.
34242 Zip Code

1900 Cove Ii Place Unit 127, Sarasota image

1900 Cove Ii Place Unit 127, Sarasota — Bldg 1 $575,000

Welcome to this gorgeous WATER FRONT condo in desirable Midnight Cove II on beautiful Siesta Key! This coastal designed, TURNKEY furnished 2 bedroom beauty is move-in rea...

2 Beds
2 Baths
Midnight Cove Ii 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

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