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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 Sale3$800K - $1.8M
Land For Sale3$689K - $799K
Sold ( Past 6 Months )10$725K - $3.5M
Last updated at 2:41pm 05/08/2026

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$1,799,000
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Siesta Isles

18260 Deep Passage Ln, Fort Myers Beach, FL 33931

Homes - 3,049 ft² / 5,700 ft² - 2 Car Garage

4 Bed / 4 Baths / Pool / Spa

Built 1983
Siesta Isles Fort Myers Beach Homes for Sale: Exceptional boating and exceptional 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. 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!



$1,488,000
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Siesta Isles NEW

18323 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 2,908 ft² / 3,436 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 1975
Siesta Isles Fort Myers Beach Homes for Sale: 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!!



$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!



$1,795,000
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Siesta Isles

18484 Deep Passage Ln, Fort Myers Beach, FL 33931

Homes - 3,228 ft² / 3,866 ft² - 2 Car Garage

4 Bed / 3 Baths / 1 Half / Pool / Spa

Built 1985
Siesta Isles Fort Myers Beach Homes Under Contract: Experience the ultimate Southwest Florida lifestyle in this stunning 2-story Gulf-access waterfront home in Siesta Isles—a highly sought-after boating community in Fort Myers Beach. Perfectly positioned with western exposure, this residence delivers breathtaking sunset views over wide bay waters and protected mangroves that will never be developed. Designed for entertaining on a grand scale, the ground level features an expansive chef’s kitchen equipped with an industrial 6-burner CPG gas range with hood, multiple ovens, wall microwave, Valpro refrigerator, stand-up refrigerator, cabinet freezer, dual sinks, shaker cabinetry, granite countertops, and two convenient pass-through windows to the lanai. This level also includes a guest suite with full bath and direct lanai access, a half bath, and a finished 2-car garage with tiled flooring. Step outside to your private tropical oasis—complete with a stone-paver lanai, heated pool (refinished September 2025), spillover spa, and a dramatic two-story screened enclosure. The composite dock is fully outfitted with water, electric, two fish-cleaning stations, and a charming tiki hut, 25,000 pound boat lift—perfect for enjoying peaceful waterfront living. The fenced yard is beautifully landscaped with clusia hedges, coconut palms, and accent lighting for added privacy and ambiance. Upstairs, a grand double-door entry opens to a light-filled great room with vaulted ceilings, travertine floors, and a custom built-in entertainment center with accent lighting. The main living level offers a second kitchen with dark wood cabinetry, granite counters, breakfast bar, and balcony access. Additional features include a den/bedroom with pocket doors and private balcony, a guest bedroom with its own balcony, full bath with laundry, and a luxurious primary suite. The primary retreat boasts private balcony access with spiral staircase to the pool, plus a spa-like bath with dual vanities, skylight, and rain shower. This meticulously updated home includes new A/C systems, ductwork, mini-splits, pool heater, and pool filter. Additional upgrades include impact windows and doors, two 100-lb propane tanks, ice machine, irrigation filtration system, and three water softeners. With abundant storage throughout and a relaxed Tommy Bahama-inspired design, this home is ideal for both everyday living and unforgettable entertaining. Enjoy effortless boating access to Sanibel Island, Captiva Island, and the Gulf, along with close proximity to waterfront dining and local favorites—making this the perfect coastal retreat.



$1,145,070
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Siesta Isles

18292 Deep Passage Ln, Fort Myers Beach, FL 33931

Homes - 4,699 ft² / 6,148 ft² - 2 Car Garage

4+Den / 4 Baths / 1 Half / Pool

Built 1976
Siesta Isles Fort Myers Beach Homes Under Contract: Boater’s Paradise & The Best Deal in Siesta Isles! Experience the ultimate waterfront lifestyle in this elevated 4BR/4.5BA coastal retreat. Nestled on a wide, deep-water canal, this property offers direct, bridge-free sailboat access to the Bay and Gulf in minutes. Yacht-Ready Waterfront: The wide, deep-water canal can accommodate large vessels such as a Hatteras, Viking, Bertram, or custom yacht, and includes a 12,000 lb boat lift for your immediate use. Enjoy world-class boating with outstanding inshore and exceptional offshore fishing right from your backyard. NEW POOL UPGRADES: The resort-style pool is a must-see, featuring brand-new tile, premium finish, and updated equipment since listing. The main level features gleaming hardwood floors, soaring ceilings, and a chef’s kitchen with custom cabinetry, granite countertops, and double wall ovens. Step out to the expansive open deck for sunset views over the canal. The private third-level Owner’s Retreat offers a luxurious master suite with expansive water views and an oversized walk-in closet. 1,700 SQ FT Bonus Space: Ground-level entry opens to a massive area ideal for a home gym, workshop, or storing all your offshore fishing and coastal gear. Located minutes from world-renowned beaches and fine dining, this is the premier value for serious boaters in Siesta Isles. Schedule your private showing today!



$1,095,000
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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 Under Contract: Price, Price, Priced to sell now!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.



$3,500,000
Sold Price:
$2,850,000
Sold Date:
11/21/2025
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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: 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!



$1,850,000
Sold Price:
$1,700,000
Sold Date:
02/27/2026
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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: CANNOT BEAT THE LOCATION, PRICE, BOAT LIFT AND DOCK AND HOME! 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!



$1,675,000
Sold Price:
$1,500,000
Sold Date:
03/31/2026
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Siesta Isles

18443 Deep Passage Ln, Fort Myers Beach, FL 33931

Homes - 3,170 ft² / 3,790 ft² - 2 Car Garage

5 Bed / 3 Baths / Pool / Spa

Built 1979
Siesta Isles Fort Myers Beach Homes: WELCOME TO SIESTA ISLES, ONE of the BEST WATERFRONT COMMUNITIES IN FT. MYERS BEACH AND SWFL! This immaculate home offers stunning views, looking down the deepest, quickest , sailboat, gulf access canal in the area. This beautiful 5 bedroom, 3 full bath home, with oversized 2 car garage offers 3170 sq. ft of AC living space. The upstairs interior has a great room floor plan designed for entertaining, and a kitchen fit for a chef. Quartz countertops , glass tile backsplash, and exqusite SS GE Monogram appliances, including counter depth French Door Fridge/Freezer, French Door Oven, warming drawer, and a Advantium convection/microwave. An expansive quartz center island is equipped with an induction cooktop and large prep sink. Additionally there is a beverage station/breakfast bar with wine cooler and dishwasher. The entire house has newer impact windows/doors and brand new exterior flood barriers on all first floor openings. The first floor level has all been redone, remediated and offers two spacious bedrooms, decorative full size bathroom, including washer and dryer, and family room for additional entertainment enjoyment. For the full Florida Lifestyle the exterior offers a heated salt water pool and spa, with decorative travertine tile decking. Top off the outside with your own 10,000 lb lift with framed cover, composite walkway and decking for the enthusiastic boater and fisherman.The seawall, metal roof and hardboard siding were all completed in 2020. All furnishings can be included for a TURN -KEY purchase.



$1,499,900
Sold Price:
$1,275,000
Sold Date:
03/31/2026
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Siesta Isles

18452 Cutlass Dr, Fort Myers Beach, FL 33931

Homes - 2,058 ft² / 2,933 ft² - 2 Car Garage

4 Bed / 2 Baths / Pool / Spa

Built 1969
Siesta Isles Fort Myers Beach Homes: The Pinnacle of Modern Waterfront Design: Designed for those who appreciate contemporary luxury and seamless indoor-outdoor living, this home offers an exceptional opportunity to command your own piece of paradise on Fort Myers Beach. Experience the art of Florida living in this stunning, fully remodeled residence in the highly desirable deep-water enclave of Siesta Isles. The entire main level is enveloped in light, thanks to dramatic, floor-to-ceiling panoramic windows that frame breathtaking, unobstructed views of the canal, private pool, and spa. This architectural feature creates a truly open and sophisticated space where the shimmering water views become a constant, calming backdrop for everyday life and grand entertaining. The sleek kitchen acts as the home's centerpiece, boasting high-end appliances and a generous island designed for gourmet prep and social gathering. The dedication to quality extends to the private quarters, where the newly remodeled bathrooms feature clean lines and luxurious walk-in showers, offering a tranquil, spa-like escape. The exterior rivals the interior in elegance and function. Enjoy year-round warmth on the spacious paver patio surrounding the private pool and spa. Crucially, for the avid boater, this property delivers a competitive edge: an extraordinarily large private dock, perfectly situated on a deep-water access canal. This exceptional amenity easily accommodates large vessels and provides rapid access to the Gulf of Mexico, positioning you for endless aquatic adventure. With no HOA and an unparalleled location just moments from the beaches, dining, and vibrant culture of Fort Myers Beach, this is where your coastal legacy begins.



$1,325,000
Sold Price:
$1,114,000
Sold Date:
03/02/2026
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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: 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.



$995,000
Sold Price:
$900,000
Sold Date:
03/03/2026
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Siesta Isles

18435 Deep Passage Ln, Fort Myers Beach, FL 33931

Homes - 1,155 ft² / 1,155 ft² - 2 Carport

2 Bed / 2 Baths / Pool / Spa

Built 1979
Siesta Isles Fort Myers Beach Homes: WELCOME TO SIESTA ISLES, ONE OF THE BEST WATERFRONT COMMUNITIES IN FT. MYERS AND SWFL! Don't let an opportunity like this pass you by! This remarkable cottage like home, located on a direct sailboat access canal, is as quaint of an oasis you'll find anywhere. This beautiful gem offers stunning views, looking down a wide, deep canal with quick , direct access to the Gulf. Home is immaculately maintained and is ideal for the boater enthusiast. The metal roof, colorful exterior, plush landscaping, combined with the lagoon style pool and spa makes living in paradise a reality. Home features many upgrades, a reinforced newer seawall (2019), newer roof (2022), 13000 lb. boat lift, fencing (2022), and AC units (2022). This community is conveniently located to fine waterfront restaurants, shopping and the beautiful sandy beaches of Sanibel and Ft. Myers Beach. Schedule an appoitment today , you will not be disappointed.




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