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5362 Shadow Lawn Drive, Siesta Key
$4,490,000
3 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv.
Experience elevated coastal living in this award-winning “Marlin Model” by Nutter Custom Construction, perfectly positioned on Siesta Key’s coveted Grand Canal. Completed in 2023 and showcased as the builder’s signature home, this completely custom Yacht-Modern residence blends refined elegance, contemporary design, and exceptional waterfront functionality. With 4,294 sq. ft. under air and 6,405 total sq. ft., this home offers 3 ensuite bedrooms (please note gym can be converted into 4th bedroom), 3 full baths, 2 half baths—including a dedicated pool bath—plus multiple flexible indoor and outdoor living spaces ideal for relaxed luxury and entertaining. Floor-to-ceiling glass doors reveal sweeping water views and seamless indoor-outdoor flow. Elevated construction and smart-home technology offer modern security and peace of mind. No water intrusion or damage during recent hurricanes. The chef’s kitchen is a standout, featuring a 10-ft waterfall island, European white dolomite counters, hidden walk-in pantry, Wolf appliances, built-in coffee system, under-cabinet toe lighting, and formal dining with wine cooler and ice maker. The primary suite is a private retreat with dual walk-in closets, hidden entry doors, freestanding soaking tub, oversized designer shower and steam room, and private outdoor shower garden. Outside, enjoy resort-style living with a multi-level pool and raised spa with infinity spillover, expansive lounging deck, covered living and dining with motorized screens, full outdoor kitchen, turf backyard with putting green, and multiple terraces. For boating enthusiasts, the property offers 104 ft of waterfront, a new concrete seawall, 104 ft of composite dock, two Golden Gear boat lifts with remotes (20,000lb & 5,000lb), water and shore power. Hop on your boat and be in the Gulf in less than 15 minutes. This property has received prestigious recognition, earning Best Custom Home, Best Kitchen, and Best Staircase in the Parade of Homes awards — reflecting exceptional craftsmanship and design distinction. The oversized 2.5-car garage provides excellent storage and functionality, offering space for a golf cart or the option to create a golf simulator setup. Located in Siesta Isles with a voluntary HOA, less than one mile to Siesta Key Beach and moments to Siesta Village by golf cart or bike. Click on the Virtual Tour Link to get a behind the scenes look! ** Furniture negotiable

5362 Shadow Lawn Drive, Siesta Key

18276 Cutlass Drive, Fort Myers Beach
$2,850,000
6 Beds ⋅ 7 Baths ⋅ Siesta Isles SubDv.
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!

18276 Cutlass Drive, Fort Myers Beach

819 Paradise Way, Siesta Key
$2,225,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
Set on a beautiful street on Siesta Key near the world-renowned white quartz sands of Siesta Beach and the shops and dining of Siesta Key Village, this exceptional waterfront residence captures the essence of relaxed coastal living with deep boating water along the Grand Canal and direct access to Sarasota Bay and the Intracoastal Waterway. Beautifully landscaped on a nearly 14,000-square-foot homesite, the property welcomes with a circular paver drive, tile roof and timeless curb appeal. Thoughtfully above base flood elevation, the residence blends the beauty of waterfront living with the added comfort of elevated construction. Inside, volume ceilings and an open floor plan create a light-filled atmosphere designed for comfortable everyday living and effortless entertaining. Rich Le Château engineered wood flooring flows throughout the living spaces, complemented by refined finishes and thoughtfully selected details. The beautifully designed island kitchen is elegant and functional, featuring fine stone countertops, a gas cooktop, stainless steel appliances, custom cabinetry and a generous workspace for gathering and entertaining. The spacious floor plan offers three bedrooms, two-and-a-half baths, a private office, formal and casual living and dining areas, a split-bedroom layout and an interior laundry room. The primary suite is complemented by a spacious ensuite bath with dual vanities, a soaking tub and a separate walk-in shower, creating a private retreat within the home. Walls of glass open to an expansive 35-by-35-foot screened lanai with a freeform pool and spa overlooking the waterway, creating a seamless transition between indoor and outdoor living. A magnificent up-lit oak tree brings warmth and character to the backyard, enhancing the property’s tranquil setting. For boating enthusiasts, the Grand Canal provides easy access to Sarasota Bay and the Intracoastal Waterway with only one bridge to the bay and a mean tide clearance of approximately 13 to 14 feet. The seawall, dock and pilings for a future boat lift accommodating up to 14,000 pounds were all installed in 2020, creating an exceptional setting for enjoying life on the water. A rare opportunity to experience refined waterfront living in one of Siesta Key’s desirable locations.

819 Paradise Way, Siesta Key

951 Contento St., Siesta Key
$1,750,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
New low price and potential seller financing! Deep boating water on the Grand Canal and Siesta Key’s world-famous beaches just minutes away, experience the best of island living. This beautifully renovated three-bedroom, three-bath waterfront residence offers a peaceful island retreat with nearly 2,900 square feet of living space plus a private office, ideal for everyday living and entertaining. On a quiet cul-de-sac in the desirable Siesta Isles neighborhood, the property enjoys approximately 99 feet of canal frontage with deep boating water and convenient access to Sarasota Bay and the Gulf of Mexico via a single bridge. The dock, rebuilt in 2024, is ready for boating, paddleboarding, kayaking, fishing and enjoying Sarasota’s exceptional waterways. Recently completed renovations have transformed the home into a fresh, move-in-ready coastal residence. Bright and welcoming interiors feature new finishes and thoughtfully selected materials. The open living spaces are designed to capture the beauty of the waterfront setting, creating a natural flow for relaxed living and entertaining. The newly redesigned kitchen features classic shaker-style cabinetry, quartz countertops and new appliances, creating a functional and stylish centerpiece for the home. Impact-rated windows and doors, a newer roof (2024), and a freshly painted exterior provide beauty and peace of mind. The spacious primary suite enjoys tranquil canal views through French doors and includes a private sitting room, creating a comfortable retreat in the home. The large primary bath provides generous space and is designed for relaxation and convenience. Outdoor living is equally inviting. The expansive pool terrace with oversized pool and spa overlooks the canal, offering a private setting for relaxing or gathering with friends and family. Begin your day with coffee on the pool deck while enjoying brilliant sunrises and end the evening with Siesta Key’s vibrant sunsets just minutes away at nearby Siesta Beach. Ideally near Siesta Key’s renowned quartz-sand beaches, the boutiques and dining of Siesta Village, and cultural amenities of downtown Sarasota, including the Ringling Museum and Marie Selby Botanical Gardens, this location combines island tranquility with convenient access to the area’s best attractions. Offering the rare combination of a beautifully renovated waterfront home, deep boating water, and a peaceful Siesta Key setting, this exceptional property captures the essence of Sarasota’s island lifestyle. Possible seller financing for qualified buyers.

951 Contento St., Siesta Key

18468 Cutlass Drive, Fort Myers Beach
$1,700,000
5 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv.
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!

18468 Cutlass Drive, Fort Myers Beach

5348 Shadow Lawn Drive, Siesta Key
$1,650,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
Set along the Grand Canal in Siesta Isles, this inviting waterfront pool home offers an effortless blend of space, comfort and classic island living. Thoughtfully designed on a single level, the approximately 2,477-square-foot residence features a desirable three-way split floor plan with three private bedroom suites, three baths, a dedicated office or den, utility room and a two-car garage. Handsome double-entry doors open to a light-filled interior with high-volume ceilings and an easy, open flow, ideal for everyday living and entertaining. The great room connects seamlessly to the kitchen and breakfast area, all of which are positioned to capture long, tranquil canal views. A separate dining room with built-in cabinetry adds flexibility for hosting, while the kitchen is well-appointed with wood cabinetry, stone countertops, stainless steel appliances and a breakfast bar. French doors extend the living space outdoors to a large, screened paver lanai with covered seating, a pool and expansive water views, creating an indoor-outdoor lifestyle. A newer seawall, private dock with a kayak lift and a separate boat lift provide quick access to Sarasota Bay, the Intracoastal Waterway and the Gulf of Mexico, with open water within approximately 15 minutes. Ideally just minutes from Siesta Key’s world-famous quartz sand beaches, the shops and restaurants of Siesta Village, and cultural offerings of downtown Sarasota, this home delivers the best of waterfront living in one of the island’s sought-after neighborhoods. Whether as a full-time residence or a coastal retreat, this Siesta Isles property offers the lifestyle, location and boating access that define life on the water.

5348 Shadow Lawn Drive, Siesta Key

5448 Azure Way, Siesta Key
$1,600,000
Siesta Isles SubDv.
This property checks all the boxes for a fabulous Siesta Key residence: Close to the beach, boat lift in the back, newly raised seawall, and a quiet cul-de-sac. This exceptional waterfront homesite sits in the heart of Siesta Key, one of Florida’s most sought-after coastal destinations. It offers a rare opportunity to build your custom dream home in a serene, prestigious setting where world-class beach access, effortless boating, and exceptional privacy come together perfectly. Nestled on a quiet, no-through-traffic cul-de-sac in the exclusive Siesta Isles enclave, the property enjoys a coveted island-within-an-island feel that delivers tranquility while remaining conveniently located. Just a 5-minute walk or drive away lies world-famous Siesta Key Beach with its renowned powdery quartz sand. Boating enthusiasts will love the direct deep-water access, complete with a private dock and a recently updated (2022) 10,000-pound boat lift. From here, you can cruise easily into the Intracoastal Waterway and the Gulf of Mexico, passing only one bridge at Midnight Pass. The lot features a substantially raised seawall recently elevated an additional 24 inches to an approximate elevation of 5-feet, which is significantly higher than most nearby seawalls. This provides enhanced protection and peace of mind for the new owner. Additional waterfront amenities include concrete steps, a spacious deck, and a convenient water access ladder. A capped freshwater irrigation well is also in place for easy landscaping maintenance. This build-ready property comes with submitted architectural plans for a stunning nearly 4,000 square foot 4-bedroom, 4-bath custom home featuring an impressive master suite, private elevator, and pool. Buyers can choose to use these existing plans and continue working with the current architect, or create something entirely their own. The generous lot offers approximately over 15,000 square feet (per architectural calculations), providing ample space for your vision. You’ll also enjoy convenient proximity to world-class shopping, dining, and cultural attractions in nearby Sarasota.This is a rare blend of luxury, lifestyle, and long-term value. Build your dream coastal retreat where every day feels like a vacation — in one of the most desirable waterfront locations on Siesta Key.

5448 Azure Way, Siesta Key

18484 Deep Passage Lane, Fort Myers Beach
$1,595,000
4 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv.
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.

18484 Deep Passage Lane, Fort Myers Beach

822 Paradise Way, Siesta Key
$1,575,000
Siesta Isles SubDv.
Discover an exceptional waterfront homesite in the quiet, highly sought-after Siesta Isles community. Tucked away on a peaceful cul-de-sac with no through traffic, this cleared property offers a tranquil setting just five minutes from world-renowned Siesta Key Beach. Boating enthusiasts will appreciate direct water access, featuring a brand-new private dock and 16,000-pound boat lift, with easy navigation to the Intracoastal Waterway and the Gulf of Mexico via a single bridge at Midnight Pass. A newly constructed 122-foot seawall (2026) adds both value and peace of mind. Spanning 14,741 square feet, this build-ready homesite has been recently cleared and is ideally positioned at a canal intersection, providing expansive open water views from the rear of the property. This is a rare opportunity to design and build a custom coastal retreat in a serene and prestigious setting. Custom home plans are available for this build-to-suit property to expedite making your dream home a reality. Ideally located near Sarasota’s renowned shopping, dining, and cultural attractions, this offering embodies the perfect blend of luxury, lifestyle, and long-term value. Build your dream home where beach, boating, and privacy come together.

822 Paradise Way, Siesta Key

18443 Deep Passage Lane, Fort Myers Beach
$1,500,000
5 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
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.

18443 Deep Passage Lane, Fort Myers Beach

1038 Contento Street, Siesta Key
$1,500,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
Siesta Key Canal Front Home with 175’ of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world-famous Siesta Key Beach rated #1 in USA. This beautifully well-kept 3 bedroom, 2 bath Rutenberg built home is located on a quiet cul-de-sac that is a perennial favorite with lush tropical landscaping and great privacy. The home sits high up on almost a 1/3 of an acre. This home was not affected by hurricane damage. Enter thru the charming Spanish style courtyard with its new landscaping, double front doors and wide foyer. Boasting a flowing floor plan with tile floors and crown molding, the living room & dining room open to the custom gourmet kitchen, featuring handsome wood cabinets, granite counters, & tumbled stone backsplash, perfect for entertaining while overlooking the Grand Canal from any window. The master bedroom ensuite with private sitting area is nice to enjoy. A new lanai cage installed July 2025. The lanai area faces southeast . There is a paver sundeck & outdoor dining area along with a covered lanai with rectangular pool, boat lift, dock, and cement seawall. Relax while you enjoy the serene water views and fabulous Florida wildlife, manatee, native birds and many types of fish. You may also enjoy fishing or kayaking from your backyard! Tropical mature foliage in park-like yard. Minutes to the open bay by boat and near Siesta Key Village where you can enjoy shops and restaurants. This truly is Paradise! Isn't this the lifestyle you've been planning? Selling Turn Key! Great Rental Income!

1038 Contento Street, Siesta Key

5215 Cape Leyte Drive, Siesta Key
$1,400,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
JUST REDUCED!! SIESTA ISLES Waterfront Gem. Experience the best of Siesta Key living in this well maintained 3-bedroom + den, 3-bath pool home with 135+ feet of frontage on the Grand Canal. Situated on an oversized 15,269 sq ft /.35-acre lot, this residence offers the perfect blend of privacy, upgrades, and waterfront lifestyle. Situated well back from the street, the home opens with a welcoming foyer and expansive great room featuring vaulted ceilings, impact windows and impact sliding glass doors flooding the space with natural light while framing serene garden and waterway views. Two bedrooms feature en-suite baths and direct access to the back yard, while the primary suite’s bath connects conveniently to the pool area. Enjoy the privacy of this tropical retreat, swim in the sparkling pool, rinse off in the outdoor shower, or launch kayaks and paddleboards from the floating dock. With space to add a full dock or lift, boaters will love the water access via one fixed bridge to the Intracoastal Waterway. Practical updates bring peace of mind, including a durable metal roof and maintenance contracts for irrigation, AC, pest control, and alarm systems. The home has county water and sewer and there's a shared irrigation well that sustains the mature landscaping. The home experienced NO WATER INTRUSTION during last year’s storms and is truly move-in ready. A winding walkway through lush landscaping leads to the waterfront patio, while an extended brick paver driveway offers ample guest parking. Just minutes from Siesta Key’s world-famous beaches and The Village’s varied dining and shopping options, this home is ideal as a full-time residence or lucrative rental investment. Don’t miss your chance to own a slice of paradise on the Grand Canal—schedule your private showing today!

5215 Cape Leyte Drive, Siesta Key

5560 Shadow Lawn Drive, Siesta Key
$1,350,000
4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
One of the lowest priced homes on Siesta Key's deep boating water and only 3 blocks to the white quartz sand and aqua Gulf waters! An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this well-maintained residence is ideally positioned just minutes from the powdery white sands of world-famous Siesta Beach and the turquoise waters of the Gulf. Set on an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath home blends comfortable coastal living with everyday functionality in a highly desirable island setting. Designed for effortless entertaining and easy living, the open-concept floor plan centers on a spacious island kitchen with generous seating, a breakfast bar, and abundant workspace, flowing seamlessly into the dining and living areas for gatherings both large and small. A thoughtful split-bedroom layout offers privacy for owners and guests alike. The primary suite enjoys peaceful views of the pool and canal, while a secondary bath doubles conveniently as a pool bath—ideal for indoor-outdoor living. Step outside to the covered, screened lanai and unwind beside the sparkling pool, framed by tranquil water views and gentle coastal breezes. Tucked along a quiet harbor just off the Grand Canal, the setting is ideal for kayaking, paddleboarding, or boating, with frequent sightings of manatees and coastal birds adding to the natural charm. Evenings bring glowing “mango sunsets” nearby, while mornings begin with soft sunrises reflected on the water. Additional highlights include an oversized two-car garage and a concrete tile roof. Ideally located near the shops, dining, and energy of Siesta Village—and just 15 minutes from downtown Sarasota’s vibrant arts and cultural scene—this home presents a compelling opportunity to enjoy the best of island living, whether as a full-time residence or a serene coastal retreat.

5560 Shadow Lawn Drive, Siesta Key

18452 Cutlass Drive, Fort Myers Beach
$1,275,000
4 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
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.

18452 Cutlass Drive, Fort Myers Beach

18548 Cutlass Drive, Fort Myers Beach
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv.
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.

18548 Cutlass Drive, Fort Myers Beach

18404 Cutlass Drive, Fort Myers Beach
$1,114,000
5 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
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.

18404 Cutlass Drive, Fort Myers Beach

5569 Shadow Lawn Drive, Siesta Key
$1,100,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
NEW SOD AND LANDSCAPING JUST INSTALLED, and a brand-new irrigation system was installed as well to keep everything to paradise standards! Welcome to the heart of world-renowned Siesta Key, where coastal living meets modern luxury. This fully renovated, solidly constructed home offers exceptional quality and thoughtful upgrades throughout, including PGT hurricane-impact windows, multiple triple-panel sliding impact glass doors, and a 2019 tile roof. Step inside through beautifully etched, Florida-themed French doors into an open-concept floor plan filled with natural light streaming from the screened lanai. The spacious living and dining areas seamlessly connect to a chef-inspired kitchen, complete with an induction range, griddle, and premium finishes—perfect for entertaining. The home features wood-grain luxury vinyl flooring throughout and tastefully updated bathrooms. The private primary suite is situated on one side of the home and includes an attached office, offering a quiet retreat. Just beyond, you’ll find a generously sized laundry room with a brand-new stackable washer and dryer. The opposite side of the home hosts additional bedrooms and a guest bathroom, providing comfort and privacy for family or visitors. Outdoors, enjoy your own private oasis with a saltwater pool and a brand-new, state-of-the-art pump system. Located in the highly desirable Siesta Isles community, this property is ideally positioned for strong rental potential, offering opportunities for annual, monthly, or seasonal income. Enjoy the convenience of being just a 10-minute walk or 5-minute bike ride to Siesta Key Beach—without the need to access main roads. Move-in ready and perfectly situated, this exceptional home offers the ultimate in coastal living. Schedule your private showing today.

5569 Shadow Lawn Drive, Siesta Key

18195 Cutlass Drive, Fort Myers Beach
$1,095,000
4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
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.

18195 Cutlass Drive, Fort Myers Beach

1002 Glebe Lane, Siesta Key
$1,050,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
New price! Beautifully remodeled and ideally just minutes from world-renowned white sands of Siesta Beach, this chic island pool home offers an exceptional blend of style, comfort, and storm-ready peace of mind. Designed for effortless coastal living, the open main living area is highlighted by a vaulted ceiling, transom windows, and abundant natural light, with French doors opening seamlessly to the private outdoor entertaining space. Porcelain flooring flows throughout the home, complemented by solid wood cabinetry, quartz countertops, and a thoughtfully designed kitchen featuring KitchenAid appliances, an electric range with exhaust hood, and clean, timeless finishes. The interior is further enhanced by solid wood interior doors, custom lighting, and new Minka ceiling fans, creating a polished yet inviting atmosphere. Significant recent upgrades add substantial value and confidence for today’s buyers, including hurricane-impact windows, a new impact front door and rear French doors (2024), a new HVAC system (2024), a shingle roof (2021), and a hurricane-rated garage door. The primary suite features a custom closet system and a separate owner’s closet, ideal for part-time use or rental flexibility. Outdoors, enjoy a resort-style heated saltwater pool and spa, enhanced by a new pool heater (2025) and pool filter (2024), surrounded by mature tropical vegetation that provides exceptional privacy. Manicured front landscaping with lush plantings, an irrigation system, a paver driveway, and a Trex front walkway complete the home’s inviting curb appeal. Additional features include epoxy-finished garage floors and a Ring doorbell with exterior security cameras. Adjacent to Glebe Park and close to Siesta Key Village, this residence offers easy access to dining, shopping, entertainment, and the beach. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Equally suited as a full-time residence, seasonal retreat or potential income-producing investment, this home delivers refined island living in one of Siesta Key’s desirable neighborhoods.

1002 Glebe Lane, Siesta Key

5432 Cape Leyte Drive, Siesta Key
$1,010,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
Newly adjusted price - an exceptional opportunity to own a charming beach retreat on Siesta Key minutes from world-famous Siesta Beach—consistently ranked among the best beaches in the U.S. With powdery white sands, crystal-clear turquoise waters, and unforgettable Gulf sunsets close by, this home captures the essence of relaxed island living. Located in the desirable, deed-restricted community of Siesta Isles, this three-bedroom, two-bath residence is set on a lushly landscaped, nearly 15,000-square-foot lot adorned with more than 40 mature palm trees, bromeliads, and a rare, show-stopping staghorn fern. The expansive property offers exceptional outdoor privacy, ample room for entertaining or recreation, and space to add a pool. Inside, the open-concept floor plan features generously sized rooms filled with natural light. A wraparound wall of windows in the living and breakfast areas frames serene views of the tropical backyard, creating a seamless indoor-outdoor connection. The renovated kitchen is thoughtfully designed with white quartz countertops, glass tile backsplash, and newer appliances, while a separate dining room provides comfortable space for gatherings. The primary suite includes an en-suite bath and a tranquil retreat feel. Two additional bedrooms offer flexibility, including a third bedroom with contemporary barn doors—ideal for a home office, den, or guest space. With a base flood elevation of 8'8" the home remained high and dry with no water intrusion during the storms; the elevation certificate and inspection certification are available. Additional highlights include a private, low-maintenance, six-foot fenced backyard, an oversized circular paver driveway with generous parking, and a two-car garage for storage and convenience. The home may be purchased turnkey furnished (with a few exclusions), making it well-suited as a beach getaway, seasonal residence, or income-producing property. Recent improvements totaling over $100,000 add peace of mind and value, including a metal roof (2022), HVAC system (2023), paver driveway (2022), six-foot PVC fencing (2020), and re-piped sewer and water lines. Just one mile from Siesta Village’s boutiques, dining, and live music—and a short drive to downtown Sarasota’s cultural attractions, farmers markets, and waterfront destinations—this property also offers long-term potential as a future residential building site due to its prime island location. With a voluntary HOA of only $200 annually and a newly improved price, this is a compelling opportunity to secure your place on Siesta Key. Schedule your private showing today and experience the island lifestyle you’ve been waiting for.

5432 Cape Leyte Drive, Siesta Key

18292 Deep Passage Lane, Fort Myers Beach
$1,000,000
4 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv.
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!

18292 Deep Passage Lane, Fort Myers Beach

5353 Shadow Lawn Drive, Siesta Key
$933,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
With NO WATER DAMAGE OR WATER INTRUSION, you can have peace of mind that you are getting a MOVE IN READY piece of tranquility on the beautiful, world renown island of Siesta Key. Being offered Turnkey Finished negotiable, you are ready to move in and get to relaxing on this spacious lot of over a quarter acre of high and dry land. You will find yourself in a 3-bedroom, 2- bathroom ranch style home with an extra bonus room for friends and family. It has an attached one car garage with a nice extension for storage of bikes and beach items. A key part of this home is that it has an oversized portico in front of the home making it easy to unpack the car out of the rain and in the shade on beautiful Florida sunny days. This home comes with its own caged and heated pool overlooking the extremely private backyard that backs up to a park preserve so you will never have anyone built behind you. This tropical backyard is basically maintenance free with no grass to mow a very peaceful filtered Koi Pond. The property’s tropical landscaping is full of lighting and is watered by a well-fed irrigation system which also automatically fills the pond. It’s as easy as that! Inside the beautiful home you will find an open floor plan with premium tile floors and kitchen offering granite countertops and upgraded soft closing cabinets and drawers. This property has had the water and drainage pipes fully re-piped with PVC, has new A/C ducting, and an upgraded electrical box with a 200-watt service amp. The best part about this property is it is a short bike ride to the famous Siesta Village and .8 miles from the Public Parking Lot to Siesta Key Beach! You can get to both places without ever stepping a foot on the main roads. Schedule a showing today to the one-of-a-kind listing that you could call HOME!

5353 Shadow Lawn Drive, Siesta Key

18435 Deep Passage Lane, Fort Myers Beach
$900,000
2 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
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.

18435 Deep Passage Lane, Fort Myers Beach

18233 Cutlass Drive, Fort Myers Beach
$700,000
Siesta Isles SubDv.
Do not miss this opportunity to buy this deep water, direct access (no bridges) lot in Siesta Isles!!! Siesta Isles is in my opinion a diamond in the rough. Since Hurricane Ian, several homes have been scraped and new larger homes are being built on the vacant land. Since the waterfront land values have increased over the years, many of these homes built in the 70's and 80's are/may be obsolete and the waterfront land here commands larger more modern homes. At this time there are four new homes being built and two other homes recently completed and a large home is under going a major remodel now on this street. Siesta Isles is already one of the premier waterfront communities in South Fort Myers! Why you ask???? Deep Water access, (Accommodate larger boats) !!! Minutes out to the Gulf Of America (Mexico). Minutes to Fort Myers Beach by water, several restaurants, bars, marinas, shopping, beautiful white sand beaches, right there!!!! Head South to Dog Beach and Lovers Keys. Take the inland, Intracoastal Waterway(very well marked) or the Gulf side. You have choices. Or head North to our other Barrier Islands, Sanibel, Captiva, North Captiva, Cayo Costa Islands. In my opinion, as more and more larger modern high end homes get built in Siesta Isles, we are going to see property values shoot up in Siesta Isles. Get in now!!!! What's not to LOVE here!!!!!!!!!!

18233 Cutlass Drive, Fort Myers Beach

5587 Shadow Lawn Drive, Siesta Key
$700,000
Siesta Isles SubDv.
Nestled on picturesque Shadow Lawn Drive, this 12,800-square-foot lot offers an exceptional canvas for your custom home. Framed by mature live oaks on the front left and back right corners, the property blends natural beauty with an enviable location. Enjoy the best of Siesta Key living—just an 8-minute stroll to the powdery sands of world-famous Siesta Beach and just over a mile to the dining and shopping of Siesta Village. Despite its proximity to these sought-after amenities, the property feels peaceful and secluded, tucked away on a quiet street removed from the island’s main thoroughfares. With nearly 100 feet of street frontage and a depth of 120 feet, the lot offers a generous and flexible building footprint. Whether you envision a sleek, modern coastal retreat or a charming, classic island cottage, this is a rare opportunity to create your ideal Siesta Key home in one of its most desirable neighborhoods.

5587 Shadow Lawn Drive, Siesta Key

5223 Shadow Lawn Drive, Siesta Key
$700,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
One or more photo(s) has been virtually staged. Siesta Key Beach Retreat – Now $829,000 Welcome to 5223 Shadow Lawn Dr, a 3-bedroom, 2-bath home in coveted Siesta Isles, just 1 mile from the sugar sands of Siesta Key Beach. Located on a quiet cul-de-sac with preserve views and mature palms, this 1,459 sq. ft. property blends lifestyle, privacy, and investment potential. Inside, you'll find a bright open layout, modern laminate flooring, neutral finishes, and a renovated kitchen with granite countertops, stainless steel appliances, and crisp light cabinetry. The living area opens to a spacious screened lanai with a fully restored pool (completed October 2025)—now crystal clear and ready to enjoy. The primary suite features an updated en-suite bath, while two additional bedrooms and a second bath provide flexibility for guests, family, or a home office. With no HOA, 30-day rentals permitted, and a prime location near Siesta Village and Downtown Sarasota, this property delivers both lifestyle and upside. Highlights: - 3 Beds | 2 Baths | 1,459 Sq. Ft. - Fully restored pool (Oct 2025) - Renovated kitchen with granite & stainless - Spacious screened lanai + private preserve backdrop - Quiet cul-de-sac location - No HOA | 30-day rentals allowed - 1 mile to Siesta Key Beach One of the best-priced homes in Siesta Isles.

5223 Shadow Lawn Drive, Siesta Key