Siesta Isles Homes with Upper Level Primary Interior

Welcome to Siesta Isles, an idyllic waterfront community nestled in the heart of Fort Myers Beach, Florida. This charming enclave is located in Lee County, where the sun-drenched beaches and vibrant local culture create a perfect backdrop for your dream home. Siesta Isles boasts a unique blend of tranquility and convenience, making it an ideal choice for both full-time residents and seasonal visitors.

The homes within Siesta Isles are designed with comfort and luxury in mind, featuring upper-level primary interiors that provide stunning views of the surrounding waterways and lush landscapes. Imagine waking up each morning to the gentle sounds of nature and breathtaking sunrises right from your bedroom. These thoughtfully designed residences offer spacious layouts, modern amenities, and an abundance of natural light, creating a warm and inviting atmosphere.

Beyond the beautiful homes, Siesta Isles is a stone’s throw away from the pristine beaches of Fort Myers, where you can soak up the sun, enjoy water sports, or take leisurely strolls along the shore. The community is also conveniently located near a variety of dining, shopping, and entertainment options, ensuring that you have everything you need just a short drive away.

Whether you’re looking for a serene retreat or a vibrant lifestyle, Siesta Isles offers the perfect blend of both. Come discover your piece of paradise in this enchanting community, where your dream home awaits!

Newest Siesta Isles Homes with Upper Level Primary Interior

$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 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

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