Siesta Isles Homes with Boating Community Type

Welcome to Siesta Isles, a hidden gem nestled in the heart of Fort Myers Beach, Florida. This charming neighborhood is a paradise for boating enthusiasts and those seeking a vibrant coastal lifestyle. With its serene waterways and direct access to the Gulf of Mexico, Siesta Isles offers an idyllic setting for families, retirees, and anyone looking to embrace the beauty of waterfront living.

The community is characterized by its picturesque homes, many of which boast private docks, making it easy for residents to embark on their boating adventures at a moment's notice. Imagine waking up to the gentle sound of lapping waves and stepping outside to your boat, ready for a day of fishing, island hopping, or simply enjoying the stunning sunsets that grace the skies over the water.

Siesta Isles is not just about the homes; it's about the lifestyle. The neighborhood fosters a strong sense of community, where neighbors become friends and gather to enjoy the beautiful Florida weather. From casual strolls along the waterfront to lively gatherings at local parks, there’s always something happening in this vibrant enclave.

Conveniently located near the bustling Fort Myers Beach, residents can easily access a variety of dining, shopping, and entertainment options. Whether you’re in the mood for fresh seafood, boutique shopping, or a night out, everything you need is just a short drive away.

Discover the enchanting lifestyle of Siesta Isles, where every day feels like a vacation, and the joys of boating and beach living await you. Come and experience the magic of this exceptional community!

Newest Siesta Isles Homes with Boating Community Type

$725,000

2026033557 MLS

Deep Water Direct Access Boating community Siesta Isles. If you are thinking about building your dream home, this lot and neighborhood has to be an option. Approximately 80x135 lot, newer seawall and cap. Fantastic boating Deep Water Direct NO bridges access to Gulf of Mexico 1 mile and 5 or 6 homes to the Gulf Of America. Western facing lot you can build your dream home. No Impact fees with this lot as there was a home formerly built on. This is an easy one.

18196 Cutlass DR, Fort Myers Beach

$1,488,000

2 Beds ⋅ 2 Baths ⋅ 2026018870 MLS

Stepping into this home, you’re immediately welcomed by a bright, open living space designed for both comfort and entertainment. The expansive great room flows seamlessly into the chef’s kitchen, with exotic Brazilian Quartzite countertops, a large center island with generous seating, Bosch double ovens, cooktop, and dishwasher, LG refrigerator makes dual ice, Sharp Pull-out drawer Microwave, A pot-filler and Kraus sink create a true culinary experience. A full bar with matching Brazilian Quartzite, beverage cooler and icemaker opens to the living area complete with a fireplace, making the entire space ideal for gatherings. 2024 updates include all new kitchen cabinetry, new porcelain 3x3 tile floors throughout the entire first floor. Impact windows and doors throughout, with the exception of one upstairs slider equipped with manual hurricane shutters. A flex room is off the living area. The first floor also offers a large bedroom, a bathroom with double vanity with leather granite and walk in shower. A large laundry room with cabinets, granite countertops and utility sink. Large sliders open to offer indoor/outdoor living. Stepping out, you’re greeted by the ultimate waterfront lifestyle. Relax by the pool while watching dolphins and manatees glide through the wide, deep-water canal. With 80-foot frontage on a true DEEP waterway canal, this property is yacht ready and can accommodate substantial vessels. Your boating options are endless with quick access to the Gulf from your private dock. The outdoor living areas include a covered seating space, screened lanai around the pool, and a large open pavered sun deck overlooking the canal. A vinyl louvered privacy fence provides privacy and the circular driveway adds ample parking. A metal roof and Certainteed Cedar Shingles for maintenance free living Back inside, the spiral staircase leads to a loft with a Murphy bed adding flexible sleeping or workspace options with windows overlooking the water. The oversized primary suite provides a private retreat with a sitting area. The primary bath offers a large walk in shower, a jetted tub, double vanities and double sinks. The impact French doors from primary suite lead to an upper deck and cat walk with Brazilian wood railing. Enjoy the sunrise from the back deck and sunsets from the front deck. Being sold furnished, this home offers perfect waterfront living. Minutes to Fort Myers Beach by boat or car. One of the best opportunities in Siesta Isles and SW Florida!!

18323 Cutlass DR, 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 LN, 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 DR, 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 DR, 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 DR, Fort Myers Beach

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