Siesta Isles Real Estate

Siesta Isles Real Estate

Welcome to Siesta Isles, a hidden gem nestled in the heart of sunny Florida! This picturesque subdivision is located in the vibrant community of Siesta Key, known for its stunning beaches and laid-back lifestyle. Siesta Isles offers a unique blend of waterfront living and tropical charm, making it an ideal destination for both families and retirees seeking a serene escape.

As you stroll through the tree-lined streets of Siesta Isles, you’ll find an array of beautifully designed homes, many boasting private docks and direct access to the sparkling waters of the Gulf of Mexico. Whether you’re a boating enthusiast or simply love the idea of sunset views from your backyard, this community caters to all lifestyles. The homes in Siesta Isles range from quaint beach cottages to luxurious waterfront estates, ensuring there’s something for everyone.

Living in Siesta Isles means embracing the Florida lifestyle to the fullest. Residents enjoy proximity to the world-renowned Siesta Beach, consistently ranked among the best beaches in the United States. With powdery white sands and crystal-clear waters, it’s the perfect spot for sunbathing, swimming, or enjoying a leisurely beach stroll.

Moreover, the vibrant local scene is just a stone's throw away. From charming boutiques to gourmet restaurants, Siesta Key offers an array of options to satisfy every palate and preference. Whether you’re in the mood for fresh seafood or a cozy café, you’ll find it all nearby.

Siesta Isles is more than just a place to live; it’s a lifestyle choice. Come and discover the enchanting allure of this coastal paradise, where every day feels like a vacation!

Newest Listings in Siesta Isles

$859,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
Virtually Staged. Live the ultimate island life in the highly sought-after waterfront community of Siesta Isles. Perfectly positioned just 0.8 miles from the public parking lot of world-famous Siesta Beach, you can easily stroll to the powdery white sands that make this area America's number one beach. Enjoy a short, breezy bike ride to the charming shops and incredible dining of Siesta Village, all without ever having to step foot on the main roads. This three-bedroom, two-and-a-half-bathroom single-family home presents an incredible opportunity to design your ideal coastal retreat. Serving as a true artist's blank canvas, the residence invites you to bring your creative vision and reimagine every room into a custom masterpiece. You will have piece of mind knowing the roof and AC are only 2 years old! The newer kitchen and updated appliances shine. The exterior boasts lush, mature landscaping with a gorgeous canopy of trees and gardens, providing a beautifully serene and shaded oasis for outdoor living. For boating enthusiasts, you are merely fifteen minutes by water to the spectacular Sarasota Bay, featuring direct Gulf access with just a single bridge. When you are ready for a change of pace, a quick fifteen-minute drive transports you to the vibrant heart of downtown Sarasota, rich with cultural and urban amenities. This is a one-of-a-kind opportunity to craft a dream home in an absolutely unbeatable location.

5451 Shadow Lawn Drive, Siesta Key
$4,795,000
4 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv.
Under 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 3,568 square feet of air-conditioned living space and 5,725 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
$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
$1,488,000
2 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
Stepping into this home, you’re immediately welcomed by a bright, open living space designed for both comfort and entertainment. The expansive great room flows seamlessly into the chef’s kitchen, with exotic Brazilian Quartzite countertops, a large center island with generous seating, Bosch double ovens, cooktop, and dishwasher, LG refrigerator makes dual ice, Sharp Pull-out drawer Microwave, A pot-filler and Kraus sink create a true culinary experience. A full bar with matching Brazilian Quartzite, beverage cooler and icemaker opens to the living area complete with a fireplace, making the entire space ideal for gatherings. 2024 updates include all new kitchen cabinetry, new porcelain 3x3 tile floors throughout the entire first floor. Impact windows and doors throughout, with the exception of one upstairs slider equipped with manual hurricane shutters. A flex room is off the living area. The first floor also offers a large bedroom, a bathroom with double vanity with leather granite and walk in shower. A large laundry room with cabinets, granite countertops and utility sink. Large sliders open to offer indoor/outdoor living. Stepping out, you’re greeted by the ultimate waterfront lifestyle. Relax by the pool while watching dolphins and manatees glide through the wide, deep-water canal. With 80-foot frontage on a true DEEP waterway canal, this property is yacht ready and can accommodate substantial vessels. Your boating options are endless with quick access to the Gulf from your private dock. The outdoor living areas include a covered seating space, screened lanai around the pool, and a large open pavered sun deck overlooking the canal. A vinyl louvered privacy fence provides privacy and the circular driveway adds ample parking. A metal roof and Certainteed Cedar Shingles for maintenance free living Back inside, the spiral staircase leads to a loft with a Murphy bed adding flexible sleeping or workspace options with windows overlooking the water. The oversized primary suite provides a private retreat with a sitting area. The primary bath offers a large walk in shower, a jetted tub, double vanities and double sinks. The impact French doors from primary suite lead to an upper deck and cat walk with Brazilian wood railing. Enjoy the sunrise from the back deck and sunsets from the front deck. Being sold furnished, this home offers perfect waterfront living. Minutes to Fort Myers Beach by boat or car. One of the best opportunities in Siesta Isles and SW Florida!!

18323 Cutlass Drive, Fort Myers Beach
$1,699,000
4 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv.
Exceptional boating and incredible value in one of the best waterfront locations in the entire region! Situated on a quiet cul-de-sac in desirable Siesta Isles, this 3,049 sq ft fully furnished home offers direct sailboat access and sits on one of the deepest and widest canals in the area, approximately 160 feet wide, making it an outstanding setup for larger vessels and serious boaters. The run to open Gulf waters is among the shortest in the region, while allowing you to enjoy minutes to the beach without island traffic, bridges, or premium island pricing. And it's not just the boating that's exceptional—this remarkable location also provides a front-row seat to numerous dolphins, manatees, snook, and a wide variety of marine life that frequently visit these waters. What truly sets this home apart is the way it blends indoor and outdoor living across three levels. The property opens to a series of generous outdoor spaces including a massive pool deck and multiple balconies, creating a natural extension of the living areas and a seamless coastal flow throughout the home. Designed for both entertaining and everyday coastal living, the home features 3 stories of interior living space, an oversized garage, abundant parking, and strong connection to the water from nearly every level. Enjoy a heated pool, included spa, a large second floor balcony, and an additional private balcony off the upper living level with beautiful sunset views over the canal. The wide waterway also provides an added sense of privacy rarely found in waterfront settings. Inside, you’ll find soaring vaulted ceilings in the main living area, skylights, real hardwood flooring throughout much of the home, and flexible living spaces designed for both comfort and entertaining. The upper level includes the primary suite with an adjoining loft, while the first floor offers an additional bonus room complete with a large TV area and impressive bar right off the pool. Major updates have already been completed, including a new standing seam metal roof (June 2025) and nearly $100,000 of new windows and doors installed in 2023. The seller has even listed the home at a $100,000 discount to generously account for the older kitchen, creating immediate value and clear upside for the next owner. With only a voluntary HOA of just $250 per year and no restrictive HOA limitations, plus nearby new construction currently asking millions more, this is a rare opportunity to secure a well-positioned waterfront property in a location that continues to grow in desirability. Be sure to view the virtual tour for larger photos, detailed floorplans, and a full 3D walkthrough of this impressive waterfront home. Easy to see!

18260 Deep Passage Lane, Fort Myers Beach
$1,945,000
4 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island’s most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, the property provides privacy, scenic water views, and easy boating access to the Bay with only one higher bridge to navigate. A standout feature is the expansive Florida room, a light-filled living space designed for year-round comfort with floor-to-ceiling windows and seamless views of the water and surrounding greenery—ideal for relaxing or entertaining. The home has been thoughtfully maintained and is in excellent condition, allowing for immediate occupancy or rental income potential. Additional highlights include a heated pool, open and functional layout, and spacious living areas. Located just minutes from Siesta Key Beach and Siesta Key Village, this property combines prime location, generous living space, and waterfront charm, making it ideal as a primary residence, vacation home, or investment property. The house did not get flooded from the recent 2024 storms, a new roof was replaced in 2024, A/C was replaced in 2023, a pool heat pump was installed in 2023, re-piped and remodeled in 2022.

814 Paradise Way, Siesta Key
$699,000
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
$1,599,999
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv.
A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying the island lifestyle! This home features great water view on the widest part of the canal! Brand new landscaping and freshly painted exterior. Sold furnished with a few exceptions. The heated pool and panoramic pool cage create a serene setting. Mostly Hurricane rated windows, new dishwasher and refrigerator, wine refrigerator, custom wood cabinets, granite counters and breakfast bar. Tile floors and engineered wood, built-out closets, open floor plan, 2 car garage, circular driveway, outdoor shower. 3 bedrooms and 3 full bathrooms plus laundry room. A few blocks from world famous SIESTA BEACH, short drive to downtown Sarasota, St Armand's, Lido and much more. ***THIS HOME HAS NOT HAD ANY STORM DAMAGE AND NO FLOODING.****BASE ELEVATION 10 Ft***SELLER MOTIVATED***

5507 Contento Drive, Siesta Key
$995,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity awaits. A prime 12,229-square-foot property in sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create your dream home in one of Sarasota’s desirable beach neighborhoods. Offering a clean slate for visionary design to renovate or build new. The generous size of the property and ideal location make it ideally suited for a luxury custom home with room for a pool, tropical landscaping and seamless indoor-outdoor living. Enjoy beach access just .2 miles away, or go less than a mile to Siesta Village, where eclectic shops, lively dining and local entertainment await. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. 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 the Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Unlock the potential to create a one-of-a-kind island residence just moments from world-renowned Siesta Beach.

734 Canal Road, Siesta Key
$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
$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
$749,000
2 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv.
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!

18196 Cutlass Drive, Fort Myers Beach
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