Siesta Isles Real Estate

Siesta Isles Real Estate

Welcome to Siesta Isles, an enchanting waterfront community nestled in the heart of Fort Myers Beach, Florida. This hidden gem in Lee County offers a perfect blend of serene coastal living and vibrant community life, making it an ideal destination for families, retirees, and anyone looking to embrace the Florida lifestyle.

Siesta Isles boasts a unique array of charming homes, many of which feature stunning views of the shimmering waters of the Gulf of Mexico. With a variety of architectural styles, from quaint beach cottages to modern waterfront estates, there’s something for everyone in this idyllic neighborhood. Residents enjoy easy access to private docks, making it a paradise for boating enthusiasts and fishing aficionados alike.

The community’s prime location means you’re just moments away from the soft sands of Fort Myers Beach, where you can soak up the sun, explore local shops, or savor delicious seafood at nearby restaurants. Siesta Isles is also conveniently situated near the bustling heart of Fort Myers Beach, offering a plethora of entertainment options, from beachside festivals to live music events.

Nature lovers will appreciate the proximity to beautiful parks and nature preserves, where you can hike, bike, or simply enjoy the breathtaking scenery. With year-round sunshine and a welcoming atmosphere, Siesta Isles is not just a place to live; it’s a lifestyle. Whether you’re seeking a tranquil retreat or an active community, Siesta Isles invites you to experience the best of Florida living. Discover your dream home in this picturesque paradise today!

Newest Listings in Siesta Isles

$700,000
2026035277 MLS
Rare opportunity to own a premier waterfront lot on a wide, deep-water canal with quick, unobstructed access to Fort Myers Beach and the sparkling Gulf of Mexico. This is boating at its finest—wide enough for effortless navigation, deep enough for serious vessels, and positioned for some of the best boating Southwest Florida has to offer. Whether you're chasing snook and tarpon, cruising to sunset dinners on the water, or paddling a kayak through quiet mangrove backwaters, this location delivers it all right from your own backyard. The lot is cleared, giving you a clean slate to design and construct the custom home you've always envisioned. The previous home has been removed, saving you time and expense, so you can move straight into planning your new build without delay. Set in a highly desirable neighborhood undergoing a wave of exciting redevelopment, this street is lined with spectacular new construction homes alongside classic properties being torn down and rebuilt to modern luxury standards. Buying here means joining a community on the rise, where property values are climbing alongside the caliber of homes being built around you. Location is everything, and this lot delivers a lifestyle few can match: minutes to Fort Myers Beach's sugar-sand shores, Direct Gulf access for world-class offshore and inshore fishing, nearby championship golf courses and a growing number of pickleball courts, Kayaking, paddleboarding, and every water sport right off your dock! Year-round sunshine and that unmistakable Florida waterfront way of life. This is more than a lot—it's a launching point for the waterfront home and lifestyle you've been searching for. Bring your builder, bring your vision, and start living the boating dream you deserve.

18291 Cutlass Drive, Fort Myers Beach
$1,699,000
4 Beds ⋅ 4 Baths ⋅ 2026016415 MLS
Exceptional boating and incredible value in one of the best waterfront locations in the entire region! Situated on a quiet cul-de-sac in desirable Siesta Isles, this 3,049 sq ft fully furnished home offers direct sailboat access and sits on one of the deepest and widest canals in the area, approximately 160 feet wide, making it an outstanding setup for larger vessels and serious boaters. The run to open Gulf waters is among the shortest in the region, while allowing you to enjoy minutes to the beach without island traffic, bridges, or premium island pricing. And it's not just the boating that's exceptional—this remarkable location also provides a front-row seat to numerous dolphins, manatees, snook, and a wide variety of marine life that frequently visit these waters. What truly sets this home apart is the way it blends indoor and outdoor living across three levels. The property opens to a series of generous outdoor spaces including a massive pool deck and multiple balconies, creating a natural extension of the living areas and a seamless coastal flow throughout the home. Designed for both entertaining and everyday coastal living, the home features 3 stories of interior living space, an oversized garage, abundant parking, and strong connection to the water from nearly every level. Enjoy a heated pool, included spa, a large second floor balcony, and an additional private balcony off the upper living level with beautiful sunset views over the canal. The wide waterway also provides an added sense of privacy rarely found in waterfront settings. Inside, you’ll find soaring vaulted ceilings in the main living area, skylights, real hardwood flooring throughout much of the home, and flexible living spaces designed for both comfort and entertaining. The upper level includes the primary suite with an adjoining loft, while the first floor offers an additional bonus room complete with a large TV area and impressive bar right off the pool. Major updates have already been completed, including a new standing seam metal roof (June 2025) and nearly $100,000 of new windows and doors installed in 2023. The seller has even listed the home at a $100,000 discount to generously account for the older kitchen, creating immediate value and clear upside for the next owner. With only a voluntary HOA of just $250 per year and no restrictive HOA limitations, plus nearby new construction currently asking millions more, this is a rare opportunity to secure a well-positioned waterfront property in a location that continues to grow in desirability. Be sure to view the virtual tour for larger photos, detailed floorplans, and a full 3D walkthrough of this impressive waterfront home. Easy to see!

18260 Deep Passage Lane, Fort Myers Beach
$699,000
2026009406 MLS
Looking for that unique boating community, with deep water direct access out to the the Gulf of America and minutes to the beaches, well you just found it. The seller put in a new seawall, new dock, new electricity with two 50 amp and 30 amp services. Metered city water. There is currently one new pier, with boat slips on either side and you have the option of adding another pier to create two more boat slips for a total of 4 boat slips. (with Lee County Approval). An added bonus, directly across the street is a large vacant multi family lot ready to build on. There was a structure on this lot at one time which was scraped many years ago. You can build your multi family structure, rent out the other half or rent out the entire building and have your four boat slips right out your front door. The multi family lot and boats slips are sold as one property, one strap number. Can you imagine renting out the entire building and renting out all four boat slips, that could potentially be 6 income streams at one property. This is a unique property with the perfect set up for the avid boater, minutes out to the Gulf of America, beaches and barrier islands..

12110/12112 Siesta Drive, Fort Myers Beach
$689,000
2025026328 MLS
Rare opportunity to own a duplex-zoned waterfront lot in the highly desirable Siesta Isles boating community, which allows non-restricted vacation rentals. There is no HOA, allowing you the freedom to enjoy your property to the fullest without restrictive rules or fees. Enjoy quick access to Fort Myers Beach by land or reach the Gulf of Mexico by boat in minutes. Siesta Isles offers deep-water, unrestricted boating with no bridges, making it ideal for serious boaters. The property features a newly constructed 80’ finger pier dock with nearly 200’ of total dockage. Dock amenities include two power pedestals with 50/30/20 amp service and water. Bonus the dock is currently income producing, there are three vessels that are currently leasing the dock. A pre-approved building permit for a duplex is in place, with building plans and pro forma included in the sale and available upon request. This is an exceptional opportunity for development, short-term rental income, or a waterfront investment in one of the area’s most sought-after neighborhoods.

12070 Siesta Drive, Fort Myers Beach
$799,000
2026000479 MLS
Located in the sought-after boating community of Siesta Isles, this cleared waterfront lot offers direct Gulf access with no bridges and quick, easy access to open water. Ideally positioned just before the bridge to Fort Myers Beach, the location allows you to enjoy boating and beach life while avoiding heavy island traffic. The property features new floating docks and a new bulkhead, providing a solid foundation for your future home. The seller has already invested in professional home renderings and is willing to include them with the sale—a valuable bonus for a buyer ready to build. Enjoy a short bike ride to Fort Myers Beach, along with nearby restaurants, bars, and live music. Seller financing is available, making this an excellent opportunity to build in one of the area’s most desirable waterfront neighborhoods.

18164 Cutlass Drive, Fort Myers Beach
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