Siesta Key, FL Homes for Sale with Pool

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  /94

  $949,000

  • 3 Beds
  • 2 Baths
  • 2,255 Sq Ft

  635 Tropical Cir, Sarasota, FL 34242

  Discover luxurious coastal living on tropical Siesta Key, #1 beach in the US and #4 in the world! Set on an elevated lot that sustained NO storm damage, includes a NEW TAMKO hurricane proof ROOF with transferable workmanship warranty, new gutters, oversized side-entry 2-car garage, and circular driveway surrounded by lush tropical landscaping. Currently being used as an income producing home

  

  Tami Cashi

  COLDWELL BANKER REALTY

  (941) 273-8651

  635 Tropical Cir, Sarasota, FL 34242
• Explore Siesta Key

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  /61

  $2,199,000

  • 5 Beds
  • 5 Baths
  • 3,126 Sq Ft

  5624 Cape Leyte Dr, Sarasota, FL 34242

  Discover this newly upgraded coastal retreat ideally located just behind the iconic Siesta Key Beach, where crystal-clear waters and powder-soft sands are only a short walk away. View of the beach main entrances right from your backyard a true showcase of the timeless real estate principle: location, location, location! This stunning home blends elegance, comfort, and peace of mind, featuring a

  

  Wally Sabrii

  SARASOTA INTERNATIONAL REALTY

  (941) 401-1015

  5624 Cape Leyte Dr, Sarasota, FL 34242
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  /97

  $1,450,000

  • 2 Beds
  • 2 Baths
  • 1,642 Sq Ft

  5880 Midnight Pass Rd Unit 302, Sarasota, FL 34242

  GULF VIEWS! Welcome to Casarina, one of Siesta Key’s most beautifully updated beachfront communities—and a place that truly captures the best of coastal living. This beautifully renewed 2-bed, 2-bath residence in Unit 302 blends comfort, quality, and a relaxed island feel from the moment you walk in. The entry opens to a light-filled space accented with custom-built-in cabinetry, detailed

  

  Julia Montei

  COLDWELL BANKER REALTY

  (941) 294-5521

  5880 Midnight Pass Rd Unit 302, Sarasota, FL 34242
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  /43

  $825,000

  • 2 Beds
  • 2 Baths
  • 1,259 Sq Ft

  5600 Beach Way Dr Unit 315, Sarasota, FL 34242

  Are you ready to create your lifestyle in the sun, steps away from the quartz crystal white powdery sands and warm Gulf waters of the award-winning Siesta Key Beach? This wonderfully located tun-key, furnished condo end unit is oh so unique on the top floor with views of the beautiful beach and Gulf waters, a rare, remodeled find on the spectacular Gulf coasts of Florida! This recently,

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 698-6217

  5600 Beach Way Dr Unit 315, Sarasota, FL 34242
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  /100

  $635,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  5855 Midnight Pass Rd Unit 416, Sarasota, FL 34242

  Major Price Improvement! Step into the exclusive waterfront haven of Harbor Towers Yacht and Racquet Club, a true resort paradise that will capture your heart instantly. The building has recently undergone a comprehensive $13 million, four-year hurricane hardening and structural upgrade, completed in 2024. Designed to meet the latest safety standards for hurricane and wind protection, these

  

  Suzy Kolaz

  KELLER WILLIAMS ON THE WATER S

  (941) 254-2344

  5855 Midnight Pass Rd Unit 416, Sarasota, FL 34242
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  /55

  $424,900

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft

  1350 N Portofino Dr Unit 107, Sarasota, FL 34242

  SIESTA HARBOR...55+...BEAUTIFUL CANAL & Intercoastal Water Way VISTAS with boats slowly IDILYING By and YOU HAVE BEACH ACCESS. BRING YOUR BOAT up to 30' because it only costs $1,000 ANNUALLY to berth your boat at your home! BUT WAIT till you see this TOTALLY RENOVATED BEAUTIFUL 1 bedroom 2 full bathroom condo! NEW, NEW, NEW...everything is new...Ceramic tile flooring, baseboards, interior doors &

  

  Scotty Ledford

  VUE REALTY, LLC

  (941) 207-7524

  1350 N Portofino Dr Unit 107, Sarasota, FL 34242
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  /92

  $575,000

  • 2 Beds
  • 2 Baths
  • 1,259 Sq Ft

  5600 Beach Way Dr Unit 201, Sarasota, FL 34242

  SELLER SAYS BRING ALL OFFERS! MAJOR PRICE IMPROVEMENT!! Reduced over 75k! Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom

  

  Ashley Nevadomski

  WILLIAM RAVEIS REAL ESTATE

  (941) 304-5005

  5600 Beach Way Dr Unit 201, Sarasota, FL 34242
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  /53

  $75,000

  • 3 Beds
  • 3 Baths
  • 2,255 Sq Ft

  915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242

  Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 352-4595

  915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242
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  /59

  $125,000

  • 3 Beds
  • 3 Baths
  • 1,780 Sq Ft

  915 Seaside Dr Unit 606, Weeks 14-17, Sarasota, FL 34242

  Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Ownership Package, offering 2 one sixteenth ownership packages of an exceptional Siesta Key Beach residence. This is a rare opportunity to own four consecutive winter weeks (Weeks 14–17), plus 2 additional float weeks—providing extended beachfront living during the most desirable season on

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 256-2943

  915 Seaside Dr Unit 606, Weeks 14-17, Sarasota, FL 34242
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  /46

  $18,000

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft

  915 Seaside Dr Unit 613, Weeks 32-33, Sarasota, FL 34242

  Fractional Ownership. Summer Fractional Package, with 1/16th shares of ownership! Your dream of a new luxury home on Siesta Key Beach can now be a reality; an enviable lifestyle on America's top-rated beach! Here is your opportunity to own a piece of paradise without giving up all the amenities and services. An enviable lifestyle on America's top-rated beach! Your dream of a new luxury home on

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 269-1352

  915 Seaside Dr Unit 613, Weeks 32-33, Sarasota, FL 34242
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  /24

  $349,000

  • 1 Bed
  • 1 Bath
  • 797 Sq Ft

  5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242

  PRICE IMPROVEMENT. Exceptional Value on Siesta Key Rarely available and beautifully updated, this second-floor 1-bedroom, 1-bathroom residence in White Sands Village offers the perfect blend of coastal living and investment opportunity. Ideally located just across the street from Siesta Key Beach, the condo also enjoys a coveted view of the lush interior courtyard, providing a peaceful and serene

  

  Jim Gammello

  WILLIAM RAVEIS REAL ESTATE

  (941) 207-9258

  5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242
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  /81

  $2,149,000

  • 4 Beds
  • 3 Baths
  • 2,657 Sq Ft

  4817 Ocean Blvd, Sarasota, FL 34242

  Welcome to 4817 Ocean Blvd – Your Private Lakefront Escape in the Heart ofSiesta KeySet on a tranquil spring-fed lake just moments from Siesta Beach and the Village, thisflood resilient and meticulously maintained coastal residence offers year-roundenjoyment or the perfect lock-and-leave retreat. Elevated and thoughtfully updated, itblends timeless coastal style with

  

  Gerard Healy

  WILLIAM RAVEIS REAL ESTATE

  (941) 541-8336

  4817 Ocean Blvd, Sarasota, FL 34242
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  /47

  $1,099,000

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft

  5770 Midnight Pass Rd Unit 301, Sarasota, FL 34242

  Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium association. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi

  

  Anthony DeLuca

  DELUCA REALTY INC

  (941) 368-4048

  5770 Midnight Pass Rd Unit 301, Sarasota, FL 34242
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  /82

  $330,000

  • 1 Bed
  • 1 Bath
  • 797 Sq Ft

  5641 Midnight Pass Rd Unit 902, Sarasota, FL 34242

  PRICE IMPROVEMENT: Affordable, Pet-Friendly Siesta Key Beach Condo Now Offered at $330,000 Experience the allure of coastal living at White Sands Village, ideally located along Midnight Pass Road on stunning Siesta Key. This beautifully furnished one-bedroom, one-bathroom residence is just a short walk from the world-famous Siesta Key Public Beach, making it an exceptional opportunity for beach

  

  Jim Gammello

  WILLIAM RAVEIS REAL ESTATE

  (941) 206-4956

  5641 Midnight Pass Rd Unit 902, Sarasota, FL 34242
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  /44

  $115,000

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft

  915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242

  Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Ownership Package, offering 2 one sixteenth ownership packages of an exceptional Siesta Key Beach residence. This is a rare opportunity to own four consecutive winter weeks (Weeks 4-7), plus 2 additional float weeks—providing extended beachfront living during the most desirable season on America’s

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 842-0963

  915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242
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  /51

  $60,000

  • 4 Beds
  • 4 Baths
  • 2,625 Sq Ft

  915 Seaside Dr Unit 511, Weeks 16-17, Sarasota, FL 34242

  Fractional Ownership. Experience elevated beachfront living with this Deluxe, Guaranteed Gulf View, Spring (April) Fractional Ownership opportunity—offering one-sixteenth ownership on Siesta Key Beach, consistently ranked as America’s #1 beach. This rare fractional real estate offering delivers luxury coastal living, prime spring usage, and true Gulf-front views without the full-ownership price

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 369-8950

  915 Seaside Dr Unit 511, Weeks 16-17, Sarasota, FL 34242
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  /88

  $2,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,764 Sq Ft

  4712 Higel Ave, Sarasota, FL 34242

  Gated Siesta Key Estate with Guest House & Boating Access. Experience the best of Siesta Key living, where award-winning white quartz sand beaches meet a relaxed island lifestyle, just minutes from Sarasota’s vibrant arts, dining, and cultural attractions. Tucked inside its own gated enclave, this exceptional waterfront estate with a detached guest house is surrounded by lush tropical

  

  Carla Rayman Kidd

  COLDWELL BANKER REALTY

  (941) 401-0936

  4712 Higel Ave, Sarasota, FL 34242
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  /52

  $75,000

  • 3 Beds
  • 3 Baths
  • 1,780 Sq Ft

  915 Seaside Dr Unit 606, Weeks 12-13, Sarasota, FL 34242

  Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 271-5462

  915 Seaside Dr Unit 606, Weeks 12-13, Sarasota, FL 34242
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  /85

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 2,185 Sq Ft

  746 Plymouth St, Sarasota, FL 34242

  Nestled in the heart of Siesta Key, this home offers the perfect blend of relaxation and opportunity. Whether you're seeking a serene beach getaway, a lucrative vacation rental, or a full-time residence, this property checks all the boxes. The home’s unique floor plan is flooded with natural light, creating a bright, inviting atmosphere throughout. A rare find, both the home and the garage are

  

  Carla Rayman Kidd

  COLDWELL BANKER REALTY

  (941) 239-2641

  746 Plymouth St, Sarasota, FL 34242
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  /54

  $80,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  915 Seaside Dr Unit 312, Weeks 8-9, Sarasota, FL 34242

  Fractional Ownership. Introducing the Winter Fractional Package, offering 1/16th ownership in a stunning luxury residence on Siesta Key Beach. Now, your dream of owning a beachfront home on America's most celebrated shore can become a reality. Enjoy the benefits of owning a slice of paradise, complete with world-class amenities and services. This exclusive opportunity offers the ultimate in

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 389-0934

  915 Seaside Dr Unit 312, Weeks 8-9, Sarasota, FL 34242
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  /9

  $4,800,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,765 Sq Ft

  533 Venice Ln, Sarasota, FL 34242

  Under Construction. Expected completion in January 2026, this stunning new waterfront home is perfectly positioned on Siesta Key’s Grand Canal, offering excellent boating water with quick access to Sarasota Bay. The residence features 4 bedrooms, 5 full baths (including a pool bath), and 1 half bath, along with two laundry rooms conveniently located on the first and third floors. A spacious

  

  Cassandra Meyer

  BRIGHT REALTY

  (941) 206-4697

  533 Venice Ln, Sarasota, FL 34242
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  /11

  $4,950,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 4,158 Sq Ft

  527 Venice Ln, Sarasota, FL 34242

  Under Construction. Be the first owner of this exceptional new construction home, expected to be completed in January 2026. Enjoy gorgeous, wide Grand Canal views with quick access to Sarasota Bay—a true boater’s dream. This home showcases high-end construction at its core, featuring a standing seam metal roof, hurricane-impact windows and sliders, elegant stone detailing, and meticulous

  

  Cassandra Meyer

  BRIGHT REALTY

  (941) 390-2066

  527 Venice Ln, Sarasota, FL 34242
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  /69

  $2,695,000

  • 5 Beds
  • 3.5 Baths
  • 3,205 Sq Ft

  430 Island Cir, Sarasota, FL 34242

  Welcome to 430 Island Circle, where island living feels both luxurious and refreshingly relaxed. Set on Palm Island, the “heart of Siesta Key”, just moments from the sugar-white sands of Siesta Key Beach, this home offers the perfect balance of modern comfort and coastal charm. Completely reimagined from top to bottom, this five bedroom, three and a half bathroom residence opens with sun-filled

  Jesse Bauer KELLER WILLIAMS ON THE WATER S

  430 Island Cir, Sarasota, FL 34242
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  /90

  $2,590,000 Open Tue 12PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,238 Sq Ft

  4508 Woodside Rd, Sarasota, FL 34242

  Luxury Exclusive Living – Boaters’ Paradise Welcome to 4508 Woodside Rd., a true waterfront retreat on Siesta Key offering privacy, boating convenience, and refined coastal living. Positioned on one of the deepest canals on the island, this home delivers three-minute access to the Intracoastal and Sarasota Bay. With 97 feet of water frontage and a 75-foot new dock, this is a legitimate boater’s

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  4508 Woodside Rd, Sarasota, FL 34242
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  /66

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  4660 Ocean Blvd Unit Q1, Sarasota, FL 34242

  Experience million-dollar, direct Gulf views from this ground floor condominium in the sought after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring throughout, and

  Halie Monde KELLER WILLIAMS ON THE WATER S

  4660 Ocean Blvd Unit Q1, Sarasota, FL 34242
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  /100

  $2,550,000

  • 4 Beds
  • 3 Baths
  • 3,541 Sq Ft

  5012 Higel Ave, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Discover this FULLY RENOVATED four-bedroom, three-bathroom sanctuary spanning 3,541 square feet, where luxury living meets WATERFRONT tranquility. Situated on almost a half acre lot, with rear views facing west for colorful sunsets, this meticulously crafted residence boasts a heated pool, a floating dock and long seawall inviting water enthusiasts

  Rachelle Tirey PREFERRED SHORE LLC

  5012 Higel Ave, Sarasota, FL 34242
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  /32

  $595,000

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242

  An investor’s dream! Discover unbeatable income potential with this fully renovated 1 bed, 1 bath condo at Jamaica Royale—a proven high-performing rental generating up to $58,000 annually and already secured with over $30,000 in bookings for 2026. Whether you're seeking a profitable income property, a personal beach retreat, or both, this turnkey unit is positioned to deliver.The spacious

  Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242
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  /27

  $639,000

  • 1 Bed
  • 1.5 Baths
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242

  Experience the best of Gulf-side living in this beautifully renovated 1-bed, 1.5-bath condo on Siesta Key — just steps from the world-famous quartz-sand beaches of Siesta Key. Completely updated from top to bottom, this turnkey coastal retreat features brand-new designer furniture and appliances, making it move-in or rental-ready from the moment you arrive. The spacious layout includes a highly

  Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242
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  /73

  $6,400,000

  • 5 Beds
  • 7 Baths
  • 6,928 Sq Ft

  5132 Jungle Plum Rd, Sarasota, FL 34242

  Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm

  Joel Schemmel DOUGLAS ELLIMAN

  5132 Jungle Plum Rd, Sarasota, FL 34242
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  /66

  $790,000

  • 2 Beds
  • 1.5 Baths
  • 840 Sq Ft

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

  Welcome to your Siesta Key Beach escape at 6006 Midnight Pass Rd, Unit 44! This charming, fully furnished 2-bedroom condo places you steps from the world-famous powdery white sands and turquoise waters of Siesta Key Beach. Enjoy direct private beach access, breathtaking Gulf views, and endless sunsets right from this coveted coastal community. Inside, an open and inviting layout features vaulted

  Michael Mitchell MITCHELL REAL ESTATE

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
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  /51

  $2,295,000

  • 3 Beds
  • 3 Baths
  • 2,676 Sq Ft

  518 Venice Ln, Sarasota, FL 34242

  ELEGANT SIESTA KEY WATERFRONT RETREAT - Welcome to a truly distinguished canal-front residence, where timeless design meets the effortless beauty of waterfront living. Set beneath majestic oaks and tropical landscaping, the canopied circular paver driveway greets you. This exquisite pool home offers privacy, sophistication and an extraordinary outdoor lifestyle. An avid boater's dream with 110

  Pamela Pileggi PREFERRED SHORE LLC

  518 Venice Ln, Sarasota, FL 34242
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  /56

  $2,190,000

  • 3 Beds
  • 2.5 Baths
  • 2,233 Sq Ft

  5155 Hidden Harbor Rd, Sarasota, FL 34242

  Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded.Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating

  Matt Buttner LIST NOW REALTY, LLC

  5155 Hidden Harbor Rd, Sarasota, FL 34242
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  /59

  $730,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242

  Wow, WHAT A VIEW! Gulf and sunset views from both bedrooms and the living room of this 5th-floor condo. Beautifully turnkey furnished, this large 2 bedroom, 2 bath condo boasts a double master layout, an extended living room/sunroom, and a gorgeously updated kitchen with stainless steel appliances and granite counter tops. Both bathrooms have also been exquisitely updated to maximize space and

  Shana Hamel NEXTHOME EXCELLENCE

  5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242
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  /60

  $2,900,000

  • 4 Beds
  • 4.5 Baths
  • 4,254 Sq Ft

  5236 Siesta Cove Dr, Sarasota, FL 34242

  No Hurricane or Flood Damage. A coastal modern oasis in Siesta Cove, Siesta Key’s premier neighborhood, highlights 80 feet of waterfront with convenient boat access to Gulf and Bay, with newer seawall, boat dockage, and an extraordinary pool that invites you to enjoy Siesta Key’s relaxed lifestyle. Breathtaking Sarasota Bay vistas along the many peaceful panoramic patio terraces provide endless

  Bradley Kayser COLDWELL BANKER REALTY

  5236 Siesta Cove Dr, Sarasota, FL 34242
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  /60

  $2,249,000

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  5361 Siesta Ct, Sarasota, FL 34242

  Experience tranquility and peace of mind in Siesta Key! Located in the highly sought-after neighborhood of Siesta Cove, this 4-bedroom, 2.5-bath home has been meticulously maintained and generously updated. The current owners completed extensive renovations including a newly remodeled primary bathroom, a custom locally handcrafted iron front door, and stunning iron interior doors with switchable

  David James CHARLES RUTENBERG REALTY INC

  5361 Siesta Ct, Sarasota, FL 34242
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  /36

  $599,000

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft

  5950 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  Gulf-side living at its best! This cute-as-a-button 2-bedroom, 2-bath ground-floor unit has been completely remodeled from top to bottom, featuring new electrical and plumbing, impact windows and doors, stylish new flooring, beautifully updated baths, and a stunning new kitchen with quartz countertops, tile backsplash, countertop breakfast bar, and stainless-steel appliances. The primary bedroom

  Christine Green COLDWELL BANKER REALTY

  5950 Midnight Pass Rd Unit 201, Sarasota, FL 34242
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  /61

  $3,657,625 New Construction

  • 3 Beds
  • 4.5 Baths
  • 3,034 Sq Ft

  5103 Windward Ave, Sarasota, FL 34242

  Under Construction. Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white sand

  Karen Greco GRECO REAL ESTATE

  5103 Windward Ave, Sarasota, FL 34242
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  /77

  $385,000

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft

  1250 N Portofino Dr Unit 305, Sarasota, FL 34242

  $55,000 PRICE IMPROVEMENT. Relax in Paradise for under $500,000! MOTIVATED SELLER!!! Stunning, Oversized One Bedroom Waterfront condo with 2 full Bathrooms in the highly sought after Siesta Harbor community on Siesta Key! Whether you enjoy the sunrise over your morning coffee or work from your glass-enclosed lanai, enjoy beautiful views of the canal and Intracoastal Waterway, where you watch for

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 305, Sarasota, FL 34242
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  /56

  $1,395,000

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft

  5750 Midnight Pass Rd Unit 704, Sarasota, FL 34242

  Poised above the world-famous quartz sands of Siesta Key, this penthouse-level residence delivers a front-row seat to the Gulf of Mexico—where breathtaking beach views, refined modern design, and resort-style living come together in one extraordinary coastal retreat. Welcome to 5750 Midnight Pass Road, Unit #704, a top-floor, move-in-ready condominium located within the prestigious Gulf & Bay

  Adnan Dedic COMPASS FLORIDA LLC

  5750 Midnight Pass Rd Unit 704, Sarasota, FL 34242
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  /29

  $549,000

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242

  Turnkey furnished 1 bedroom, 1 bathroom condo at Jamaica Royale on Siesta Key, offering a true hands-off investment opportunity with onsite rental office and future bookings already in place for 2026. This fully renovated condo features high-end finishes and thoughtful upgrades throughout, making it ideal as a vacation rental, second home, or full-time residence. The updated kitchen showcases

  Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242

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