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Siesta Isles Fort Myers Beach Florida Homes for Sale

Naples Florida Real Estate

Siesta Isles Fort Myers Beach Real EstateSiesta Isles Fort Myers Beach

Homes For Sale5$800K - $5.9M
Land For Sale1$725K
Sold ( Past 6 Months )6$799K - $3.5M
Last updated at 10:00pm 09/23/2025

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$5,915,500
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$580K
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Siesta Isles

18230 Old Pelican Bay Dr, Fort Myers Beach, FL 33931

Homes - 3,945 ft² / 7,916 ft² - 4 Car Garage

4 Bed / 4 Baths / 2 Half / Pool / Spa

Built 2026
Siesta Isles Fort Myers Beach Homes for Sale: The Eden Model is a brand new floor plan being offered for the first time by Claussen Residential Communities. The well thought out flow of the home will give the new owners a very comfortable live style with rooms for guests on the second floor which includes a separate laundry and gathering room. The elevator services all three levels of the residence. Located on a premium lot with water in front and a canal behind. Boat Dock included. Direct access to the Gulf of Mexico only being minutes away. Lot 4 is one of 24 new lots available in this phase of development. The home is a to be built.



$2,260,000
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Siesta Isles

18468 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 3,114 ft² / 3,799 ft² - 2 Car Garage

5 Bed / 4 Baths / Pool / Spa

Built 1961
Siesta Isles Fort Myers Beach Homes for Sale: A True Boater’s Paradise – WITH UNMATCHED HURRICANE WATER SURGE PROTECTION! Minutes from Fort Myers Beach and Sanibel Island, this stunning waterfront home sits in Siesta Isles—voted one of Southwest Florida’s premier boating communities. Enjoy deep-water, sailboat Gulf access with no miserable mile, surrounded by multi-million-dollar estates that define luxury coastal living. A FIRST IN SW FLORIDA We’ve just invested over $50,000 IN CUSTOM-ENGINEERED FLOOD BARRIERS—40" high, precision-fit for every door and window, including the massive 23' x 12'-- 90° sliders in the lanai. Designed to protect against storm surge, these barriers offer peace of mind and unparalleled property protection. WATERFRONT PERFECTION! • 101 ft. of shoreline with a new 14,000-lb boat lift & canopy (fits 28–30 ft. boats) • Composite dock with water & electric hookups • Seawall space for additional watercraft UPGRADES & CONSTRUCTION QUALITY! • New flat tile roof—glued, screwed, with new sheathing & underlayment • 3,114 sq. ft. under air, designer ceramic wood-look plank flooring • 16-ft. ceilings in gathering room with 10-ft. pocket 90° sliders + custom electric shades CHEF’S DREAM KITCHEN! Three rows of modern white cabinetry, oversized quartz waterfall island, hidden walk-in pantry, double oven, and premium finishes—perfect for both casual meals and elegant entertaining. FLEXIBLE LUXURY LIVING! • 5 bedrooms / 4 full baths • 3 ensuite bedrooms (including an upstairs second master with private entry & laundry hook-up) OUTDOOR OASIS! Resort-style pool with spa & lap area, high-end outdoor kitchen with bar & sink, paver driveway & walkways, lush night-lit landscaping—all overlooking breathtaking coastal views where dolphins and manatees often visit. SIESTA ISLES HOMES RARELY OFFER THIS LEVEL OF LUXURY, BOATING ACCESS AND STORM PROTECTION!—Schedule your private showing today!



$1,325,000
Decrease*
$200K
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Siesta Isles

18404 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 2,258 ft² / 2,720 ft² - 2 Car Garage

5 Bed / 3 Baths / Pool / Spa

Built 1974
Siesta Isles Fort Myers Beach Homes for Sale: Luxury Waterfront Estate in Fort Myers Beach welcomes you to the pinnacle of coastal living! Your dream home awaits at this luxurious waterfront estate in the enchanting Fort Myers Beach! Set in the coveted enclave of Siesta Isles, this remarkable property offers an unparalleled opportunity to immerse yourself in a world where opulence meets the tranquil charm of canal-side living. With breathtaking views, sophisticated finishes, and an enviable location, this estate is the epitome of a perfect coastal retreat that will captivate the most discerning homeowners. The thoughtfully designed floor plan features floor-to-ceiling windows that invite an abundance of natural light while framing unobstructed views of the picturesque waterfront, a canvas of serene beauty that brings nature indoors. The heart of the home is the great room, an elegant space perfect for entertaining or unwinding in a peaceful environment. Every detail of this home has been meticulously crafted to offer modern luxury while maintaining the timeless charm that defines waterfront living. For the culinary enthusiast, the gourmet kitchen is a dream come true. Equipped with high-end stainless steel appliances, classic cabinetry, and a soothing organic palette, this kitchen is designed to inspire creativity. Step outside, and the luxurious lifestyle continues to flourish in your private outdoor oasis. The outdoor area is an entertainer's paradise, featuring a stunning heated swimming pool and spa, surrounded by towering palms. For the water enthusiasts, this estate truly shines with its very own private dock positioned on a spacious deep-water access canal. This exceptional feature accommodates large boats, offering seamless access to the aquatic adventures that Southwest Florida has to offer. Just minutes away from the pristine shores of Fort Myers Beach by car or boat, you'll have quick access to some of the most stunning white-sandy beaches and vibrant coastal communities, including the iconic Sanibel and Captiva Islands. The neighborhood is rich with local eateries, lively pubs, and diverse entertainment options, ensuring that fun and excitement are always just around the corner. Nestled on a cul-de-sac just steps from the bay, this estate positions you perfectly to take advantage of all the aquatic adventures the region has to offer. Whether you're an avid boater or simply appreciate the beauty of waterfront living, this property promises an enviable lifestyle for those who cherish the ocean. This luxurious waterfront estate is not just a house; it's a lifestyle choice that embodies the essence of coastal living. With stunning architecture, high-end finishes, and an unbeatable location, this property is a sanctuary where you can relax, rejuvenate, and bask in nature's beauty every day. Own your dream home in one of Florida's most sought-after locales and revel in the magic of everyday living.



$1,250,000
Decrease*
$225K
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Siesta Isles

18195 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 2,534 ft² / 3,124 ft² - 1 Car Garage

4 Bed / 3 Baths / Pool / Spa

Built 1970
Siesta Isles Fort Myers Beach Homes for Sale: HUGE PRICE REDUCTION,READY TO SELL!A Boater's Dream! This 4 bedroom, 3 bathroom waterfront pool home with over 2500 square feet under air is located in the sought-after Siesta Isles neighborhood. The interior of the home has been remodeled to perfection with high end finishings throughout, inclusive of porcelain wood plank tile, built in bar with wine refrigerator, custom tiled bathrooms, modern lighting and so much more. The chef's kitchen with soft close white shaker cabinetry, gorgeous quartz waterfall counters, and a huge Island overlooks the main living and dining areas, great for entertaining! Step outside and relax in your pool or hot tub while watching the dolphins and manatee. With 75 feet on this DEEP waterway, your boating and sailing options are endless from your private dock just minutes from the gulf. Nearly everything is new and has been fully permitted! Being sold turnkey furnished with no rental restrictions, this home is perfect for a snowbird, your new full-time residence, investment, or a combination thereof. Seller financing and/or lease options available.



$800,000
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Siesta Isles

18196 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 1,776 ft² / 1,776 ft² - 1 Car Garage

2 Bed / 2 Baths

Built 1969
Siesta Isles Fort Myers Beach Homes for Sale: Cutlass Dr in Siesta Isles is located in one of the best Boating Communities in SW Florida. Deep Water Direct Access. New Seawall and Cap. Lot is located Approximately 1 mile from the Gulf of Mexico. Quick out to North end of Ft. Myers Beach. Build your Dream Home on this lot. City Water/City Sewer. Killer Sunsets Every evening!



$1,450,000
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Siesta Isles

18548 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 2,172 ft² / 2,656 ft² - 2 Car Garage

5 Bed / 4 Baths / Pool / Spa

Built 1967
Siesta Isles Fort Myers Beach Homes Under Contract: Discover Your Dream Waterfront Estate, your ultimate slice of paradise in the heart of Fort Myers Beach! Nestled within the serene enclave of Siesta Isles, this stunning property offers a unique opportunity to experience the harmonious blend of opulence and tranquil canal-side living. With breathtaking views, high-end finishes, and an ideal locale, it is a dream come true for those seeking the perfect coastal retreat. As you step through the grand entrance, you'll immediately be captivated by the expansive, bright, and airy spaces that define this majestic estate. The cleverly designed floor plan features floor-to-ceiling windows that flood the interiors with natural light while providing unobstructed views of the picturesque waterfront inviting the beauty of nature indoors. The great room serves as the heart of the home, where you can entertain or simply unwind while soaking in the calming sights of the serene blue waters just beyond. Every inch of this home has been meticulously remodeled to offer modern luxury while maintaining its timeless charm. Equipped with brand new high-end stainless steel appliances and quartz counters, the gourmet kitchen is a culinary enthusiast's dream. Whether you're preparing a casual breakfast or hosting a lavish dinner party, this kitchen seamlessly integrates with the open concept living area, ensuring that you'll never miss a moment with your guests. Stepping outside, the luxurious lifestyle continues. The outdoor area is an entertainer's paradise, featuring a private heated swimming pool and spa surrounded by swaying majestic palms. For the water enthusiasts, the property comes complete with its very own private dock situated on a spacious deep-water access canal. This exceptional feature accommodates large boats, making it easy to embrace the aquatic adventures Southwest Florida has to offer. The location of this magnificent estate is unparalleled. Situated just minutes away from Fort Myers Beach by car or boat, you'll have easy access to some of the most stunning white sandy beaches and vibrant coastal communities, including Sanibel and Captiva Islands. The neighborhood is brimming with local eateries, lively pubs, and a variety of entertainment options, ensuring that you're always close to fun and excitement. There is no HOA, allowing you the freedom to enjoy your property to the fullest without any restrictions. Siesta Isles is recognized as one of the premier deep-water boating communities in Southwest Florida, offering quick access to the Gulf of Mexico. You're merely the third lot off the bay, positioning you perfectly to take advantage of all the aquatic adventures the region has to offer. Experience the magic of this tropical oasis where luxury meets tranquility and every day feels like a vacation.



$3,500,000
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Siesta Isles

18276 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 5,767 ft² / 9,059 ft² - 3 Car Garage

6 or More / 6 Baths / 1 Half / Pool / Spa

Built 2007
Siesta Isles Fort Myers Beach Homes Under Contract: Waterfront Living at Its Best! Welcome to your ultimate fun-filled getaway just minutes from Fort Myers Beach! This 6-bedroom, 7-bathroom canal-front home is designed for making unforgettable memories—whether you're cruising the waterways, hosting poolside parties, or soaking up sun-filled days with the people you love most. The ground level sets the vibe with a custom wrap-around bar—complete with a 12’ shark hanging overhead! Kick back in the theater room or perfect your swing on the indoor golf simulator. The relaxed lounge area flows seamlessly to your Private Saltwater Pool and Spa. A tiki hut adds a tropical touch, while the Massive Sun Deck with dining and lounge areas—features a boat lift and large slip for your water toys, so you’re always just moments from your next adventure. The 80' Wide Canal makes it easy to accommodate most vessels. Take the Private Elevator up to the second floor, where everyday living meets effortless entertaining. The open-concept layout includes a gourmet kitchen with built-in appliances, a center island cooktop, an oversized breakfast bar, and a spacious eat-in dining area. Exposed beams, a stone accent wall, and a cozy fireplace add warmth and style. Slide open the Collapsible Glass Doors and expand your living space onto a Huge Balcony overlooking the pool and canal. With a full Outdoor Kitchen and Built-in BBQ, it’s the perfect place to grill, gather, and enjoy the coastal breeze. Upstairs, the third floor features three additional bedrooms—including two spacious en-suite rooms and a Luxurious Primary Suite with a Spa-like Bathroom offering a soaking jet tub and an expansive walk-around shower. But the real showstopper? The Private, oversized third-floor balcony, where you’ll enjoy Epic Panoramic Views of the canal, nature preserve, and front-row seats to Southwest Florida’s jaw-dropping sunsets—a picture-perfect backdrop for peaceful mornings or starlit evenings. Conveniently tucked away from the tourist buzz yet just a short ride to Fort Myers Beach, Sanibel Island, and Cayo Costa State Park, this home delivers the perfect blend of adventure, comfort, and coastal lifestyle. From boat days and BBQ nights to movie marathons and poolside laughs—this is where lifelong memories are made! **Be sure to request the Cinematic Video Tour and 3D Walk-through!



$1,590,000
Sold Price:
$1,400,000
Sold Date:
03/24/2025
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Siesta Isles

18467 Deep Passage Ln, Fort Myers Beach, FL 33931

Homes - 2,300 ft² / 2,544 ft² - 3 Car Garage

4+Den / 3 Baths / Pool / Spa

Built 1977
Siesta Isles Fort Myers Beach Homes: Attention Boaters, this 4/3/3 Estate home sits in the prestigious deep water, sailboat access community of Siesta Isles with no bridges & direct access to the Gulf of Mexico just 1 mile from Fort Myers Beach. The home boasts an incredible back yard with a resort style pool area ideal for entertaining guests & picture-perfect views of the water basin. This beautifully updated home offers unparalleled direct access to the Gulf of Mexico, Mantanzas Pass, or the Beach & Islands—all within a mere 10 minutes from your brand new oversize Trex dock with two boat lifts (one covered 13,000 pound /the other set up for 10,000 pounds )with the seawall/ canal capacity to accommodate up to a 50’ vessel. Spanning nearly 2300 SQ FT of insurable, livable square footage, this residence presents a seamless blend of luxury and comfort. The kitchen, opens to the family room and dining area, creates an inviting atmosphere perfect for entertaining or relaxing with loved ones. Step onto the large fully glass, screened balcony and enjoy panoramic views of the pool, canal and basin… ideal spot for morning coffee or evening cocktails. Unwind in the spacious master bedroom featuring a walk-in closet, custom walk-in shower & separate soaker. The fully finished downstairs offers endless possibilities, whether for entertaining guests, in-law suite, or a kids haven. Plus, discover a versatile flex room perfect for a 3rd garage, fitness area or workshop, catering to your lifestyle needs. Step into outdoor living at its finest on the expansive natural travertine patio, complete with an outdoor kitchen featuring built-in gas grills, kitchen sink, in-counter coolers and set up for outdoor undercounter fridges among other amenities. This home underwent an extensive renovation. Every aspect of this property has been carefully remodeled, featuring numerous enhancements, such as elegant wood floors throughout, level 5 granite countertops, custom bathrooms, elegant chefs kitchen, a wet bar, all-new appliances, whole home water treatment & 2 laundry & recently installed A/C systems. Additionally, all windows and doors are full impact rated with electric sun shutters for added convenience and privacy & a long lasting, beautiful standing seam metal roof. Unlike most homes on the water, this home is PRE-FIRM meaning the downstairs is insurable, making it stand apart from the rest! This house has been immaculately well kept, with too many updates to list here but receipts are available to the seriously interested. Schedule your private showing today to experience the ultimate Florida lifestyle and let your waterfront dreams come true!



$860,000
Sold Price:
$820,000
Sold Date:
07/31/2025
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Siesta Isles

18307 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 2,452 ft² / 3,208 ft² - 2 Car Garage

3 Bed / 3 Baths / Pool

Built 1960
Siesta Isles Fort Myers Beach Homes: Design Your Dream Waterfront Escape in Fort Myers Beach! Imagine waking up every day in a stunning waterfront home that you designed just the way you wanted. Nestled in the highly sought-after Siesta Isles community, this luxury property is an incredible opportunity for you to finish building your dream home in one of the most prestigious boating communities in Southwest Florida. With direct sailboat access, you'll be just moments away from endless aquatic adventures, making every day feel like a vacation. As you step onto the property, you'll instantly be captivated by the open concept floor plan and floor to ceiling windowscapes. The outdoor entertainment area is designed to create unforgettable memories. A covered patio beckons you to relax in the shade while enjoying the gentle breeze, and the private swimming pool sparkles invitingly under the warm Florida sun. This is the perfect setting for hosting gatherings, or simply unwinding after a long day. Water enthusiasts will revel in the property's exceptional feature, a spacious private dock situated on a sprawling deep-water access canal. This prime docking space accommodates large boats with ease, providing you the freedom to explore the stunning waters of Southwest Florida at your leisure. Location is everything, and this magnificent estate offers unparalleled access to both the serenity of nature and the vibrancy of local culture. Just minutes away from Fort Myers Beach by car or boat, you'll find yourself immersed in some of the most stunning white sandy beaches in the world. Explore nearby Sanibel and Captiva Islands, where you can indulge in local cuisine, enjoy water sports, or simply bask in the sun. This property is the absence of an HOA, allowing you to have complete freedom over your home without any restrictions. Siesta Isles is celebrated as one of the premier deep-water boating communities in the region, facilitating quick access to the Gulf of Mexico. This waterfront estate in Fort Myers Beach is not just a house; it's a lifestyle choice that encapsulates the very essence of coastal living. With plumbing and framing nearly complete, the canvas is yours to finish according to your desires. Whether you envision a modern paradise or a charming coastal retreat, the options are endless. Don't miss out on this incredible opportunity to make your paradise dream home come true. With the option to build out your custom home with the seller's assistance, your waterfront oasis in one of Florida's most coveted locales is within reach. Seize the moment, start crafting the life you've always desired in the heart of Southwest Florida! Brand New Steel Roof & Brand New Pool Cage 2025!



$830,000
Sold Price:
$730,000
Sold Date:
08/29/2025
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Siesta Isles

18308 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 2,122 ft² / 2,690 ft² - 2 Car Garage

3 Bed / 3 Baths / Pool

Built 1961
Siesta Isles Fort Myers Beach Homes: Discover Your Dream Waterfront Home in Fort Myers Beach! Seize the opportunity to finish building your dream waterfront home in the exclusive Siesta Isles community of Fort Myers Beach, where luxury meets coastal living. This extraordinary property is perfectly situated to cater to boating enthusiasts and families alike, nestled in one of the best boating communities in the area, offering direct sailboat access to the open waters. Experience the thrill of customizing your home to reflect your personal taste and style. The possibilities are endless, allowing you to design a space that meets your every desire. Whether you envision an expansive open-concept living area, a gourmet kitchen, or serene bedrooms with sweeping water views, the canvas is yours to create. Step outside to discover an outdoor oasis designed for entertaining. The covered patio invites you to relax in the shade or host vibrant gatherings, while the private swimming pool offers a cool retreat on warm sunny days. Imagine making unforgettable memories as you bask in the sun or enjoy a tranquil evening by the water. For those who cherish life on the water, this property features a private slip spacious deep-water access canal, capable of accommodating large boats. Embrace the boating lifestyle and set sail into the sparkling waters of Southwest Florida, where adventure awaits at every turn. Indulge in fishing, water sports, or leisurely boat rides as you explore the stunning coastal landscapes of the Gulf of Mexico. This idyllic setting promises a peaceful retreat from the hustle and bustle of everyday life, allowing you to unwind and rejuvenate in the comfort of your own home. Just minutes away from Fort Myers Beach, you'll have convenient access to pristine white sandy beaches and vibrant coastal communities, including the renowned Sanibel and Captiva Islands. One of the standout features of this property is that there is no homeowners association (HOA), granting you the freedom to enjoy your property without restrictions. Whether you're an avid boater or simply appreciate the beauty and serenity of waterfront living, this estate offers the ultimate lifestyle for those who cherish the ocean. With the option to build out your custom home, this is not just a property; it is an invitation to a life of luxury and leisure. Option available to complete your paradise dream home with the Seller. Begin a new chapter in your life and embrace all the beauty and adventure that come with this exceptional waterfront estate in Fort Myers Beach!




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*Just Listed: new properties that came on the market within the last 30 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
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