Siesta Isles Homes with Waterfront

Siesta Isles Homes with Waterfront

Welcome to Siesta Isles, an enchanting waterfront subdivision nestled in the heart of sunny Florida. Known for its idyllic charm and stunning views, Siesta Isles offers residents a unique blend of tranquility and vibrant community life. This picturesque neighborhood is perfectly situated just minutes away from the world-renowned Siesta Key Beach, where powdery white sands and crystal-clear waters await.

Siesta Isles is distinguished by its stunning homes that boast direct waterfront access, making it a paradise for boating enthusiasts and nature lovers alike. Imagine waking up to the gentle lapping of waves and the soothing sounds of nature right outside your window. Each property in this exclusive community is designed to maximize the breathtaking views, with many featuring expansive decks, private docks, and lush landscaping that seamlessly blends with the natural beauty of the area.

The community is not just about breathtaking homes; it’s about lifestyle. Residents here enjoy a plethora of outdoor activities, from kayaking and paddleboarding to fishing and sunset cruises. The neighborhood fosters a strong sense of community, with friendly neighbors and organized events that bring everyone together.

Siesta Isles is more than just a place to live; it’s a lifestyle choice. Whether you’re looking for a vacation retreat or a permanent residence, this waterfront haven offers the perfect backdrop for creating lasting memories. Experience the charm and beauty of Siesta Isles, where your dream home awaits amidst the serene waters of Florida!

Newest Siesta Isles Homes with Waterfront

12122 Siesta Drive, Fort Myers Beach
$1,325,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
LIVE THE SW FLORIDA LIFESTYLE RIGHT HERE... IN THIS BEAUTIFUL, ELEVATED, GULF ACCESS HOME LOCATED IN THE MUCH SOUGHT AFTER NEIGHBORHOOD OF SIESTA ISLES, KNOWN BY THE LOCALS AS ONE OF FT MYERS BEACH'S FINEST, GULF ACCESS NEIGHBORHOODS...AND THERE'S NO HOA! AT FIRST GLANCE YOU'LL BE DRAWN TO THE SHARP CURB APPEAL AND ATTENTION TO DETAIL BEGINNING WITH THE PATTERNED, EXTRA WIDE PAVERED DRIVEWAY, THE LARGE CUSTOM EXTENDED BALCONIES, MATURE PALM TREES WITH PROFESSIONAL LIGHTING. THIS HOME INCLUDES AN ATTRACTIVE, STURDY BOATHOUSE WITH A 20K POUND LIFT, A WRAP AROUND DOCK WITH COMPOSITE DECKING, A CAPTAINS WALK, PREMIUM LIGHTING PACKAGE AND AN ADDITIONAL SLIP NEXT TO IT FOR YOUR FRIEND'S BOAT! SIESTA ISLES IS KNOWN FOR IT'S BEAUTIFUL HOMES, DEEP WATER CANALS AND QUICK ACCESS TO THE GULF. YOU CAN WALK, BIKE OR TAKE THE TROLLY ACROSS THE BRIDGE TO FT MYERS BEACH AND LISTEN TO LIVE MUSIC, TAKE A LEISURELY WALK ALONG THE BEACH WHILE WATCHING THE SUNSET OR ENJOY A WIDE SELECTION OF BARS, RESTAURANTS AND SHOPPING. FROM THE INSIDE, YOU'LL IMMEDIATELY BE DRAWN TO THE SPECTACULAR WATER VIEWS...VIEWS, VIEWS AND MORE VIEWS.. ON THE MAIN LEVEL YOU'LL FIND AN OPEN GREAT ROOM FLOORPLAN WITH VAULTED CEILINGS, UPGRADED LIGHTING FIXTURES, TRAVERTINE TILE FLOORING, LEVEL 5 CABINETRY & GRANITE, PLANTATION SHUTTERS ON ALL WINDOWS, THREE SPACIOUS BEDROOMS EACH WITH IT'S OWN PRIVATE, EXTENDED BALCONY, TWO LUXURIOUS BATHROOMS AND A WELL PLACED LAUNDRY ROOM. ON THE FIRST LEVEL, YOU'LL REALLY APPRECIATE THE OVERSIZED 3 CAR TANDEM GARAGE WITH BEAUTIFUL APOXY FLOORING PLUS THREE EXTRA, LARGE, AREAS TO STORE MOTORCYCLES, TRAILERS, FOR GENERAL STORAGE, A WORKSHOP, HOBBY AREA, ETC. YOU'LL HAVE PEACE OF MIND KNOWING YOU HAVE A NEWER (2021) STANDING SEAM METAL ROOF, IMPACT DOORS & WINDOWS (2021) AND DURABLE CELECT BRAND CELLULAR COMPOSITE SIDING (2021) ON THE EXTERIOR. THE FRONT BALCONY OFFERS A PEACEFUL AREA TO RELAX, SOAK UP THE SUN, READ A BOOK, ENJOY A GLASS OF WINE OR ENJOY LUNCH ALONG THE "COCKTAIL RAIL" WHILE WATCHING DOLPHINS AND MANATEES, MAMAS AND THEIR BABIES, PLAY IN THE CANAL RIGHT IN FRONT OF YOU! YOU'LL NEVER TIRE OF THAT!! THIS HOME HAS SO MUCH TO OFFER FROM IT'S FINE FINISHES AND QUALITY UPGRADES, TO IT'S WATERFRONT LIVING LIFESTYLE WHETHER BOATING OR KAYAKING IN THESE AMAZING CANALS, YOU WILL CONTINUOUSLY BE AMAZED BY THE NATURAL SCENERY, FROM DOLPHINS TO PINK SPOONBILLS, PELICANS, EGRETS AND HERONS. ONE THING YOU WILL NEVER EXPERIENCE HERE IS BOREDOM! THE SELLERS HAVE AN AFFORDABLY PRICED, TRANSFERABLE FLOOD POLICY. CALL TODAY TO SCHEDULE A SHOWING YOU WILL NOT BE DISAPPOINTED!

12122 Siesta Drive, Fort Myers Beach
5376 Shadow Lawn Drive, Siesta Key
$2,400,000
5 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv.
Some homes on Siesta Key are about the beach. Others are about boating. This one lets you have both. Set along a protected canal with direct boating access to Sarasota Bay through the Grand Canal, and from there to the Intracoastal Waterway and the Gulf, this Siesta Key waterfront home is made for the way life is meant to be lived. Take the boat out for the morning, launch a kayak or paddleboard from your own waterfront, spend some time at Siesta Key Beach, then come home to your private saltwater pool, outdoor kitchen and quiet canal view. The important updates are already here too: a 2021 reroof, impact windows and sliders installed in 2022, plus new first floor flooring, fresh interior paint, a luxury renovation of the first floor primary bath, an outdoor kitchen and waterfront pavers, all completed in 2026. Plantation shutters finish every window and slider. At the center of the home, a fully screened courtyard lanai with a tabletop fire pit extends the living space. Seven impact sliders connect several rooms directly to the courtyard, filling the home with natural light and creating an easy indoor outdoor flow toward the pool and waterfront. Additional sliders from the flex room open toward the pool. The home and pool sustained no storm damage during the 2024 storms. If you haven’t dropped anchor yet, wait until you see the two amazing primary suites. The first floor primary offers courtyard access, two walk in closets and a beautifully renovated 2026 ensuite bath with upscale finishes. Upstairs, the entire second level becomes a private retreat with canal views, a spacious bath, two more walk in closets and its own waterfront balcony. One closet is so large you may wonder if it could qualify as a New York City apartment. When it is time for a little quiet, open the sliders and take in sunset over the canal, or start your morning with fresh air and coffee on the balcony. A redesigned media and flex area now includes an additional bedroom while preserving an approximately 424 square foot flex room for a media room, gym, game room or lounge. Another bedroom includes a Murphy bed and built in desk, making it an easy guest room, home office or both. Outside is where this home really earns its Siesta Key address. The private saltwater pool is surrounded by tropical landscaping and spaces for relaxing, dining and entertaining. The seawall, bulkhead and davits were replaced in 2021, with the waterfront setup planned around a 45 foot Sea Ray. This is a home for boaters who want to use the water, not simply look at it. Set in the heart of Siesta Key, the home is just minutes from Siesta Key Beach, named the No. 1 in the U.S. for 2026 and recognized among the nation’s best many times over. Known for its powdery quartz sand and Gulf waters, it is one of the reasons living here is so special. Siesta Key Village is close by for restaurants, bars, live music and boutiques. Sarasota is just beyond the North Bridge, with downtown waterfront dining, shopping, galleries, theaters, performing arts and cultural attractions close at hand. Whether you are looking for a full time Siesta Key waterfront home or a second home for family and friends, 5376 Shadow Lawn Drive offers true boating access, a private saltwater pool, substantial updates, flexible living space and an exceptional island location. This is the kind of home where every day can include the beach, the boat and dinner by the pool. That is a pretty wonderful way to live.

5376 Shadow Lawn Drive, Siesta Key
5456 Azure Way, Siesta Key
$2,695,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
Siesta Isles Canal Front Pool Home with Boat Lift and Rental History Life in Siesta Isles comes with a short commute: a few minutes to the award winning quartz sand of Siesta Beach and a quick cruise from your own boat lift to the open waters of Sarasota Bay. Set on an oversized lot at the end of a quiet cul de sac, this single story residence offers roughly 190 feet of deep water canal frontage with sweeping views toward the Grand Canal. Built of block, stucco, and stone, the three bedroom, three bath split plan opens through a gated front porch and Brazilian mahogany door to soaring vaulted ceilings, a curved window wall, and a stone fireplace for those rare evenings when Florida remembers it has a winter. A wall of sliders leads to the covered lanai and heated pool, where a kitchen pass through window keeps the cook in the conversation. The owner's suite enjoys calm water views of its own The big ticket items have already been handled: a terracotta tile roof installed in late 2020, a new seawall with raised cap completed in 2021, a three zone HVAC system, hurricane shutters, an 8,000 lb boat lift, and an oversized two car garage with cabinet storage. Mature tropical gardens with plumeria, hibiscus, citrus, and palm trees round things out. Boating, beach days, and afternoons by the pool are all part of the routine here, and the west facing backyard saves the best for last with front row seats to Gulf Coast sunsets over the water. With established rental history, this home works beautifully as a full time residence, a seasonal escape, or both.

5456 Azure Way, Siesta Key
809 Idlewild Way, Siesta Key
$3,850,000
4 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv.
Completely remodeled from top to bottom and expanded with a new 1,200 square foot, two-level addition, 809 Idlewild Way is a one of one contemporary waterfront oasis offering the look, feel and comfort of a new home in a prime Siesta Key location. Set on a high elevation site that sustained zero water damage during the 2024 hurricanes, this boater’s paradise occupies a coveted cul-de-sac with 109 feet of water-frontage on the Grand Canal. The comprehensive renovation includes new electrical and plumbing, new HVAC systems, impact windows and doors, premium interior finishes and extensively redesigned outdoor living spaces. Extensive structural improvements opened the living room, kitchen and covered patio toward the water, removing obstructing columns and preserving uninterrupted views across the pool and waterfront. Expansive sliders surrounding the primary suite bring in natural light and further connect the room to the water. The renovation carries through the exterior, where lush landscaping, integrated architectural lighting, a distinctive pergola entry, standing seam metal roof and stone fascia reinforce the home’s modern architectural character. Inside, premium engineered hardwood flooring, custom tray ceilings with integrated designer lighting, meticulous level 5 drywall and masterfully executed finish carpentry create a sophisticated interior. The gourmet kitchen features custom cabinetry and natural quartzite surfaces, complemented by additional custom bar cabinetry and entertaining space in the dining area. Beautifully appointed bathrooms are extensively wrapped in tile with dramatic glass shower enclosures. The home is offered furnished and move-in ready. Resort style outdoor living, created with entertaining in mind, centers around a new saltwater pool with a sun shelf, integrated fire and water features, a sealed paver deck, outdoor kitchen and gathering spaces overlooking the waterfront. A custom U shaped dock with a 24,000lb boat lift, power, softened water and lighting completes the boating experience, with Sarasota Bay just a short boat ride away. The seller’s Formula boat is also available for purchase separately. A new elevated seawall cap and reinforcing wall, 500 gallon underground propane tank and whole home generator add comfort and resilience. All of this is complemented by the beaches, dining and relaxed island lifestyle that make Siesta Key such a distinctive place to call home.

809 Idlewild Way, Siesta Key
829 Idlewild Way, Siesta Key
$3,150,000
4 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv.
A boater’s paradise on Siesta Key! This sprawling single-story waterfront residence positioned on a half-acre home site adjacent to the Grand Canal comes with two lifts and dual personal watercraft platforms. Everything about this home invites its owners to relax and embrace the Siesta lifestyle. From the abundant outdoor space including a heated saltwater pool and spa, multiple entertaining areas overlooking the lush landscaping and water, to the easy-flowing floor plan with generous gathering areas, 829 Idlewild Way invites you to stay a while, every day. With 4 bedrooms and 3 and a half baths (two are en suites) positioned at the corners of the home, privacy is ensured for everyone. The extraordinary primary suite offers a luxurious respite at the end of the day with spa-like bath awash in natural light, with a dual-entry shower of travertine and glass and multiple showerheads, sliding privacy glass doors to the outdoor area, jetted spa tub, dual separate vanities and a water closet with a bidet, a large walk-in closet with custom built-ins and dressing area and a spacious bedroom featuring an architectural ceiling, fireplace and with abundant natural light, this elevated retreat awaits you. The center of the home is where everything and everyone comes together. Separate yet open areas flow seamlessly from dining to entertaining to lounging, ultimately leading through the four sets of impact-rated double doors to the resort-like environs beyond. At the center of all this is a kitchen that will inspire and satisfy accomplished and aspiring chefs. Miele appliances including dual ovens, microwave drawer, cooktop, two-drawer dishwasher, built-in separate refrigerator and freezer and central cooking island are surrounded by contemporary custom cabinetry, exotic granite surfaces and accent lighting throughout. Of course, if you prefer to present and serve alfresco, everything you need is just nearby. For those who value a bit of practicality beyond luxury, the oversized three-plus-car garage (a lift is included to accommodate four vehicles) will provide ample space for vehicles and toys. Additional practicality is possible given the orientation of two guest rooms, full bath and separate living room, potentially providing a generous guest/in-law suite within the home. If you are dreaming of a laid-back beach and boating lifestyle at the number one beach in the U.S., this is your place.

829 Idlewild Way, Siesta Key
12110/12112 Siesta Drive, Fort Myers Beach
$649,000
Siesta Isles SubDv.
Looking for that unique boating community, with deep water direct access out to the the Gulf of America and minutes to the beaches, well you just found it. The seller put in a new seawall, new dock, new electricity with two 50 amp and 30 amp services. Metered city water. There is currently one new pier, with boat slips on either side and you have the option of adding another pier to create two more boat slips for a total of 4 boat slips. (with Lee County Approval). An added bonus, directly across the street is a large vacant multi family lot ready to build on. There was a structure on this lot at one time which was scraped many years ago. You can build your multi family structure, rent out the other half or rent out the entire building and have your four boat slips right out your front door. The multi family lot and boats slips are sold as one property, one strap number. Can you imagine renting out the entire building and renting out all four boat slips, that could potentially be 6 income streams at one property. This is a unique property with the perfect set up for the avid boater, minutes out to the Gulf of America, beaches and barrier islands..

12110/12112 Siesta Drive, Fort Myers Beach
18291 Cutlass Drive, Fort Myers Beach
$700,000
Siesta Isles SubDv.
Rare opportunity to own a premier waterfront lot on a wide, deep-water canal with quick, unobstructed access to Fort Myers Beach and the sparkling Gulf of Mexico. This is boating at its finest—wide enough for effortless navigation, deep enough for serious vessels, and positioned for some of the best boating Southwest Florida has to offer. Whether you're chasing snook and tarpon, cruising to sunset dinners on the water, or paddling a kayak through quiet mangrove backwaters, this location delivers it all right from your own backyard. The lot is cleared, giving you a clean slate to design and construct the custom home you've always envisioned. The previous home has been removed, saving you time and expense, so you can move straight into planning your new build without delay. Set in a highly desirable neighborhood undergoing a wave of exciting redevelopment, this street is lined with spectacular new construction homes alongside classic properties being torn down and rebuilt to modern luxury standards. Buying here means joining a community on the rise, where property values are climbing alongside the caliber of homes being built around you. Location is everything, and this lot delivers a lifestyle few can match: minutes to Fort Myers Beach's sugar-sand shores, Direct Gulf access for world-class offshore and inshore fishing, nearby championship golf courses and a growing number of pickleball courts, Kayaking, paddleboarding, and every water sport right off your dock! Year-round sunshine and that unmistakable Florida waterfront way of life. This is more than a lot—it's a launching point for the waterfront home and lifestyle you've been searching for. Bring your builder, bring your vision, and start living the boating dream you deserve.

18291 Cutlass Drive, Fort Myers Beach
5572 Shadow Lawn Drive, Siesta Key
$4,795,000
4 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv.
Under Construction. New construction. An exceptional opportunity to own a brand-new waterfront residence in the highly sought-after Siesta Isles community. Expertly crafted by Nutter Custom Construction, this British West Indies-inspired custom home offers 3,523 square feet of air-conditioned living space and 5,146 total square feet designed for luxurious coastal living. Situated on a 14,300-square-foot lot with 104 feet of waterfront and a brand-new seawall, this thoughtfully designed residence features 4 bedrooms, 4.5 bathrooms, a 2-car garage, private pool and spa, and an expansive outdoor living area complete with a summer kitchen. Interior features include soaring 23.5-foot ceilings in the entry & foyer, 11.4-foot ceilings throughout the main living areas, custom wood beam details, wide-plank wood flooring, custom cabinetry, natural stone finishes, and a premium Thermador appliance package. The well-designed floor plan offers a first-floor primary suite, spacious great room, and seamless indoor-outdoor living. Upstairs, a flexible bonus room showcases dramatic glass corner sliders opening to a waterfront balcony with sunset views. The luxurious primary suite features a private lanai, spa-inspired bath with outdoor shower, and oversized walk-in closets. Located just minutes from Siesta Key Village and world-renowned Siesta Key Beach, this exceptional property combines the best of waterfront living with convenient access to dining, shopping, and entertainment. Buyers may have the opportunity to make select finishes and customization choices depending on the stage of construction. Estimated completion February 2027. Experience the unmatched craftsmanship and attention to detail that define every Nutter Custom Construction home.

5572 Shadow Lawn Drive, Siesta Key
813 Idlewild Way, Siesta Key
$3,795,000
4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
Tucked away near the end of a quiet cul-de-sac on an oversized, private waterfront lot in Siesta Isles with 109 feet of frontage on Siesta Key's Grand Canal, this exceptional 4,161-square-foot residence offers a rare combination of privacy, expansive living spaces, extensive upgrades, and breathtaking water views. Positioned at the canal's coveted "Big Bend," the home enjoys panoramic open-water vistas enhanced by neighboring county-owned green space, creating a lush natural backdrop and a remarkable sense of seclusion. Designed for both grand entertaining and everyday comfort, the light-filled floor plan features four bedrooms+bonus room, three full baths, multiple living areas, and rich wood flooring throughout.  At the heart of the home is a gourmet chef's kitchen appointed with premium appliances, seamlessly connecting to an expansive great room where floor-to-ceiling glass frames stunning waterfront views.  A separate entertaining bar features illuminated cabinetry, a wine refrigerator, sink, second Bosch dishwasher, and pass-through window to the lanai, making indoor-outdoor hosting effortless.  The great room easily accommodates a dining table for ten while offering multiple gathering spaces to relax and enjoy the ever-changing waterfront scenery. The spacious primary suite serves as a private retreat, featuring a newly replaced waterfront deck and captivating water views from nearly every angle. Extensively upgraded with an emphasis on durability and peace of mind, the home features impact-rated windows and doors, recently replaced metal and flat roofs, two elevated HVAC systems, an elevated whole-house generator, mini-split air conditioning in the garage, two water heaters, extensive electrical upgrades, and all cast-iron sewer lines replaced with PVC.  Outside, the resort-style living experience continues with expansive travertine patios, a heated saltwater pool and spa, multiple covered and open-air seating areas, and exceptional boating amenities including a new dock, 10,000-pound boat lift, and additional double jet ski/kayak lift. Professionally designed landscaping and architectural lighting enhance the home's tropical setting, creating a beautiful ambiance both day and night. With quick access to Roberts Bay and the Intracoastal Waterway, this property is perfectly suited for boating enthusiasts. Located just one mile from world-famous Siesta Key Beach and minutes from Sarasota's renowned dining, shopping, and cultural attractions, this extraordinary waterfront retreat offers the perfect blend of luxury, comfort, boating lifestyle, and privacy. This is truly A HOME FOR JOYFUL GATHERINGS!

813 Idlewild Way, Siesta Key
12070 Siesta Drive, Fort Myers Beach
$689,000
Siesta Isles SubDv.
Rare opportunity to own a duplex-zoned waterfront lot in the highly desirable Siesta Isles boating community, which allows non-restricted vacation rentals. There is no HOA, allowing you the freedom to enjoy your property to the fullest without restrictive rules or fees. Enjoy quick access to Fort Myers Beach by land or reach the Gulf of Mexico by boat in minutes. Siesta Isles offers deep-water, unrestricted boating with no bridges, making it ideal for serious boaters. The property features a newly constructed 80’ finger pier dock with nearly 200’ of total dockage. Dock amenities include two power pedestals with 50/30/20 amp service and water. Bonus the dock is currently income producing, there are three vessels that are currently leasing the dock. A pre-approved building permit for a duplex is in place, with building plans and pro forma included in the sale and available upon request. This is an exceptional opportunity for development, short-term rental income, or a waterfront investment in one of the area’s most sought-after neighborhoods.

12070 Siesta Drive, Fort Myers Beach
18164 Cutlass Drive, Fort Myers Beach
$799,000
Siesta Isles SubDv.
Located in the sought-after boating community of Siesta Isles, this cleared waterfront lot offers direct Gulf access with no bridges and quick, easy access to open water. Ideally positioned just before the bridge to Fort Myers Beach, the location allows you to enjoy boating and beach life while avoiding heavy island traffic. The property features new floating docks and a new bulkhead, providing a solid foundation for your future home. The seller has already invested in professional home renderings and is willing to include them with the sale—a valuable bonus for a buyer ready to build. Enjoy a short bike ride to Fort Myers Beach, along with nearby restaurants, bars, and live music. Seller financing is available, making this an excellent opportunity to build in one of the area’s most desirable waterfront neighborhoods.

18164 Cutlass Drive, Fort Myers Beach
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