Siesta Key, FL Homes for Sale with AC

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  /55

  $374,900

  • 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
• Explore Siesta Key

• 

  

  

  /43

  $780,000

  • 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 turn-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! The rental income is

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 698-6217

  5600 Beach Way Dr Unit 315, 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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  /96

  $3,000,000

  • 4 Beds
  • 3 Baths
  • 2,689 Sq Ft

  339 Treasure Boat Way, Sarasota, FL 34242

  Elegant Siesta Key Waterfront Living. Don’t just move. Arrive! Enter into your residence, and the world falls away. Picture-perfect postcard views from nearly every room await to welcome you home. Nestled on an unrivaled point at the intersection of the Grand Canal’s most impressive waterways, this newly renovated, rare find offers you the complete package. Luxury finishes, high-tech resilience,

  

  Tonna Gruber

  COLDWELL BANKER REALTY

  (941) 239-7863

  339 Treasure Boat Way, Sarasota, FL 34242
• 

  

  

  /96

  $2,290,000

  • 3 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  3941 Hamilton Club Cir Unit 9, Sarasota, FL 34242

  PRICE IMPROVEMENT... Located in the highly sought-after Hamilton Club community on Siesta Key, this beautifully updated 3-bedroom, 3.5-bath residence offers the ideal blend of coastal comfort, boating convenience, and island living. A large screened-in porch overlooking the water provides a peaceful setting to enjoy morning coffee and gentle coastal breezes. Designed for both everyday living and

  

  Jennifer Thompson

  WILLIAM RAVEIS REAL ESTATE

  (941) 352-2339

  3941 Hamilton Club Cir Unit 9, Sarasota, FL 34242
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  /35

  $729,000

  • 2 Beds
  • 2 Baths
  • 1,463 Sq Ft

  1200 E Peppertree Ln Unit 302, Sarasota, FL 34242

  PRICE IMPROVEMENT OF $20.000!! Turnkey coastal living in the desirable mid-rise tower at Peppertree Bay on Siesta Key. This sought-after split-plan residence offers bright open living spaces, exceptional privacy, and the convenience of effortless island living with resort-style Gulf-to-Bay amenities just moments from world-famous Siesta Beach. Offered fully turnkey furnished, this beautifully

  

  Renee Nadiv

  WILLIAM RAVEIS REAL ESTATE

  (941) 421-5862

  1200 E Peppertree Ln Unit 302, Sarasota, FL 34242
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  /35

  $669,000

  • 2 Beds
  • 2 Baths
  • 1,083 Sq Ft

  1050 W Peppertree Ln Unit 116B, Sarasota, FL 34242

  Turnkey coastal living on Siesta Key. Beautifully renovated first-floor Gulf-side garden condominium in the highly sought-after Peppertree Bay Gulf-to-Bay community. This exceptional two-bedroom, two-bath residence has been thoughtfully updated throughout and is offered fully turnkey furnished, creating an effortless opportunity to arrive and immediately enjoy the island lifestyle. The bright

  

  Renee Nadiv

  WILLIAM RAVEIS REAL ESTATE

  (941) 207-0490

  1050 W Peppertree Ln Unit 116B, Sarasota, FL 34242
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  /46

  $1,250,000

  • 3 Beds
  • 4 Baths
  • 3,050 Sq Ft

  5324 Siesta Ct, Sarasota, FL 34242

  In a market where location defines value, this contemporary residence in Siesta Cove delivers on every level. Positioned on more than a quarter-acre just minutes from Siesta Key Beach and Siesta Key Village, the property pairs architectural character with rare privacy and scale. Equally important, it offers something increasingly essential in coastal real estate: confidence. The property has

  

  Renee Nadiv

  WILLIAM RAVEIS REAL ESTATE

  (941) 401-1686

  5324 Siesta Ct, Sarasota, FL 34242
• 

  

  /71

  $1,999,000

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

  915 Seaside Dr Unit 412, Sarasota, FL 34242

  Welcome to a premier Siesta Key Beach condo that delivers the ultimate combination of luxury coastal living and high-performing rental income potential. This beautifully updated 3-bedroom, 2-bath condominium is professionally managed through an established onsite program, offering owners a seamless, turnkey experience with the ability to enjoy the home personally while also participating in a

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 392-7730

  915 Seaside Dr Unit 412, Sarasota, FL 34242
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  /54

  $1,130,000

  • 2 Beds
  • 2 Baths
  • 1,372 Sq Ft

  5300 Ocean Blvd Unit 202, Sarasota, FL 34242

  Step inside and unwind in this updated, turnkey luxury condominium offering nightly sunset views of the #1 beach in the country. This is a rare opportunity to own a condominium in the vibrant heart of Siesta Key, walk to all the amenities and charm that Siesta Key village offers. The property is just steps from the world-famous quartz sands of Siesta Key Beach.Tastefully decorated and truly

  

  Diane Goodwin

  EXP REALTY LLC

  (941) 207-7951

  5300 Ocean Blvd Unit 202, 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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  /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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  /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 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 elevated,

  

  Carla Rayman Kidd

  COLDWELL BANKER REALTY

  (941) 239-2641

  746 Plymouth St, Sarasota, FL 34242
• 

  

  /59

  $675,000

  • 2 Beds
  • 1 Bath
  • 1,373 Sq Ft

  5019 Commonwealth Dr, Sarasota, FL 34242

  PRICED to Sell! A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision whether you’re

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 842-0059

  5019 Commonwealth Dr, 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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  /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
• 

  

  /24

  $575,000

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  6006 Midnight Pass Rd Unit 51, Sarasota, FL 34242

  PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an

  

  Daniel Hut

  HUT REALTY, LLC

  (941) 292-7027

  6006 Midnight Pass Rd Unit 51, Sarasota, FL 34242
• 

  

  /53

  $475,000

  • 1 Bed
  • 1 Bath
  • 845 Sq Ft

  1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

  Welcome to the world-famous Siesta Key! Now available a second-floor one-bedroom, one-bath condominium in the desirable Gulf and Bay Club Bayside. This particular condo had zero flood or storm damage. This home is just waiting for your personal touch! Enjoy direct deeded beach access just across the street to Siesta Key Beach and live a true resort-style life with wonderful amenities at your

  

  Jessica Ross, PA

  COLDWELL BANKER REALTY

  (941) 292-2778

  1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
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  /52

  $75,000

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

  915 Seaside Dr Unit 504, Weeks 6-7, Sarasota, FL 34242

  Fractional Ownership. Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Package—featuring one-sixteenth ownership of an extraordinary Siesta Key Beach residence. Your dream of owning a new, high-end home on America’s #1 beach can now be a reality, offering an effortless way to enjoy the best of beachfront living without compromise. Step into an

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 279-2172

  915 Seaside Dr Unit 504, Weeks 6-7, Sarasota, FL 34242
• 

  

  /90

  $6,400,000

  • 12 Beds
  • 11 Baths
  • 5,313 Sq Ft

  662 Calle Del Otono, Siesta Key, FL 34242

  Charming mini-resort with lagoon-style pool and waterfall, sun decks, tropical landscaped gardens. Just steps from Siesta Key Public Beach. Free Trolley transports guests to Siesta Key Village for shopping, dining and a supermarket. Income Producing Property priced to sell at a Seven Cap. Two lots, 19 & 20 with 2 Duplexes.

  

  Tonna Gruber

  COLDWELL BANKER REALTY

  (941) 732-8615

  662 Calle Del Otono, Siesta Key, FL 34242
• 

  

  /13

  $6,400,000

  • 8 Beds
  • 8.5 Baths
  • 5,313 Sq Ft

  5610 Avenida Del Mare, Sarasota, FL 34242

  Prime Siesta Key investment opportunity or dream family compound just steps from the world-famous Siesta Key Public Beach! This exceptional multi-family property features two beautifully updated duplexes (totaling 8 bedrooms and 8.5 baths across 5,331 sq ft) on combined large lots, offering flexible zoning for short-term rentals (1-7 days), long-term income, or a luxurious private residence.

  

  Tonna Gruber

  COLDWELL BANKER REALTY

  (941) 841-7869

  5610 Avenida Del Mare, Sarasota, FL 34242
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  /52

  $584,500

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  6415 Midnight Pass Rd Unit 705, Sarasota, FL 34242

  Welcome to the best location on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Walk to bars, restaurants, the beach. You can walk across the street and rent a boat. Speaking of boats you can dock your boat on our giant seawall for $10.00... yes...ten dollars a month. Your new condominium is an open floor

  

  Anthony DeLuca

  DELUCA REALTY INC

  (941) 419-2073

  6415 Midnight Pass Rd Unit 705, 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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  /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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  /47

  $1,074,000

  • 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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  /60

  $2,150,000

  • 4 Beds
  • 3.5 Baths
  • 2,971 Sq Ft

  116 Garden Ln, Sarasota, FL 34242

  Effortless Island Living on Siesta Key’s Coveted North End.Discover the perfect blend of modern luxury and low-maintenance living in thiscontemporary coastal retreat, ideally located on the quiet North End of Siesta Key.Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortlessproximity to Siesta Village, the North Bridge, and downtown Sarasota.Built in

  

  Gerard Healy

  WILLIAM RAVEIS REAL ESTATE

  (941) 337-4899

  116 Garden Ln, Sarasota, FL 34242
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  /53

  $59,000

  • 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
• 

  

  /52

  $59,000

  • 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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  /99

  $5,392,000 New Construction

  • 4 Beds
  • 6 Baths
  • 4,220 Sq Ft

  4819 Higel Ave, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. New Construction. Come see this coastal Siesta Key home located on the Grand Canal. The home is located on prime waterfront property with the best views of the Grand Canal, which provides easy access to the bay. A boater's dream! This three-level waterfront property offers the best in luxurious living, with four spacious bedrooms and four full baths

  

  Cassandra Meyer

  BRIGHT REALTY

  (941) 394-0863

  4819 Higel Ave, 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. New Construction. 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 third-floor loft

  

  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. 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 craftsmanship throughout—no detail has been

  

  Cassandra Meyer

  BRIGHT REALTY

  (941) 390-2066

  527 Venice Ln, Sarasota, FL 34242
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  /100

  $2,249,000

  • 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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  /73

  $5,985,000

  • 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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  /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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  /56

  $1,995,000

  • 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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  /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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  /75

  $2,450,000 Open Sun 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,276 Sq Ft

  4508 Woodside Rd, Sarasota, FL 34242

  Luxury Waterfront Living Now Priced to Move Welcome to 4508 Woodside Rd, a true boater’s paradise on Siesta Key offering privacy, deep-water access, and refined coastal living. Positioned on one of the island’s deepest canals, this property provides quick access to the Intracoastal and Sarasota Bay, with 95 feet of waterfront and a 75-foot dock designed for serious boating. Inside, the home

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  4508 Woodside Rd, Sarasota, FL 34242
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  /27

  $598,000

  • 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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  /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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