Siesta Key Homes with Sailboat Water Water Frontage

Welcome to Siesta Key, Florida – a slice of paradise nestled in Sarasota County, where the sun-kissed shores and stunning azure waters create an idyllic backdrop for your dream home. Renowned for its powdery white sand beaches, Siesta Key is not just a vacation hotspot; it’s a vibrant community that offers a unique blend of coastal living and laid-back charm.

Imagine waking up each morning to the gentle sound of waves lapping against your private dock, with sailboat water frontage right at your doorstep. Homes in Siesta Key with sailboat water access provide not only breathtaking views but also the ultimate gateway to the Gulf of Mexico. Whether you're an avid sailor or simply enjoy the tranquility of waterfront living, these properties offer unparalleled access to the open waters, making every day feel like a vacation.

In addition to its stunning waterfront homes, Siesta Key boasts a plethora of activities for residents and visitors alike. From delightful beachside dining and boutique shopping to vibrant nightlife and cultural events, there’s something for everyone. Enjoy a sunset stroll along the beach or indulge in water sports like paddleboarding and kayaking.

Siesta Key is more than just a location; it’s a lifestyle. With its friendly community atmosphere, top-rated schools, and easy access to nearby Sarasota’s attractions, it’s no wonder that so many people are eager to call this coastal gem home. Discover the allure of Siesta Key and explore the exceptional homes with sailboat water frontage that await you. Your dream waterfront retreat is just a visit away!

Newest Siesta Key Homes with Sailboat Water Water Frontage

3601 White Lane, Sarasota $7,900,000

Pre-Construction. To be built. ......YOU WILL BE IMPRESSED by this Permitted & Custom Designed Residence along Hansen Bayou---deep Sailboating Water with Immediate Access...

5 Beds
6 Baths
Siesta Rev 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

5855 Midnight Pass Road Unit 605, Sarasota image

5855 Midnight Pass Road Unit 605, Sarasota — Harbor Towers Y & R $719,000

Harbor Towers 605 represents a unique opportunity to live on a high floor in the building with the coveted south-facing views looking over the pool. Welcome to Harbor To...

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

4034 Roberts Point Road, Sarasota $7,900,000

A double waterfront, rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompa...

5 Beds
5 Baths
Elliot M A Property Siesta Key SubDv.
34242 Zip Code

732 Siesta Drive, Sarasota $2,550,000

Back on the market with a $445,000 price reduction, Rare and extraordinary waterfront offering on the coveted North end of Siesta Key, this premier Bay Island estate parc...

3 Beds
5 Baths
Bay Island Shores SubDv.
34242 Zip Code

1900 Cove Ii Place Unit 122, Sarasota image

1900 Cove Ii Place Unit 122, Sarasota — 1 $535,000

OPPORTUNITY KNOCKS - UNOBSTRUCTED WATER VIEWS!!! RARE OPPORTUNITY, INCREDIBLE PRICE - DIRECT INTRACOASTAL WATERFRONT | DEEDED BEACH ACCESS | 2 OVERSIZED BEDROOMS | WEEKLY...

2 Beds
2 Baths
Midnight Cove Ii SubDv.
34242 Zip Code

829 Idlewild Way, Sarasota $3,150,000

A boater’s paradise on Siesta Key! This sprawling single-story waterfront residence positioned on a half-acre home site adjacent to the Grand Canal comes with two lifts a...

4 Beds
4 Baths
Siesta Isles 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

3200 Higel Avenue, Sarasota $22,000,000

Virtually Staged. Pre-Construction. To be built. Welcome to 3200 Higel Avenue, an extraordinary new waterfront residence by Pham Development, nearing completion on one of...

4 Beds
7 Baths
Siesta Rev SubDv.
34242 Zip Code

3601 White Lane, Sarasota $2,900,000

INCREDIBLE LOCATION!....INCREDIBLE BOATING WATER!....INCREDIBLE SIZED LOT!.....Rarely Available EXPANSIVE 18,000+ square foot SAILBOAT WATERFRONT property with nearly 80'...

Siesta SubDv.
34242 Zip Code

9226 Midnight Pass Road Unit 3B, Sarasota image

9226 Midnight Pass Road Unit 3B, Sarasota — Castaway Cove $680,000 ▲

It's time to SIMPLIFY! Sun. Sand. Surf. Fantastic Opportunity and sure to impress! The last unit in this community sold for 800,000. Welcome to this completely renovated ...

2 Beds
2 Baths
Castaway Cove 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