Siesta Key, FL Homes

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  $1,520,000 Sold Sep 02, 2025

  4408 Midnight Pass Rd, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 2,611 Sq Ft
  • Built 1951

  Last Sold Summary

  • 10% Below List Price
  • $582/SF
  • 124 Days On Market

  Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

  4408 Midnight Pass Rd, Sarasota, FL 34242
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  /68

  Est $2,565,447 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,950 Sq Ft

  5132 Sandy Shore Ave, Sarasota, FL 34242

  5132 Sandy Shore Ave, Sarasota, FL 34242
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  /37

  $685,000

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft

  1350 N Portofino Dr Unit 402, Sarasota, FL 34242

  UNUSALLLY AVAILABLE! DIRECT INTRACOASTAL VIEW! Stunning ICW Water View on Siesta Key with direct, full view of the Intracoastal Waterway and private beach access across the street. Sought-after Tarpon Building in Siesta Harbor 55+ Community with only 8 units facing directly to the main Intracoastal waterway-- Views are Outstanding! Open Floor Plan, large open dining and living room leading to

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1350 N Portofino Dr Unit 402, Sarasota, FL 34242
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  $680,000 Sold Jan 24, 2025

  5855 Midnight Pass Rd Unit 225, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • Built 1976

  Last Sold Summary

  • 1% Below List Price
  • $576/SF
  • 5 Days On Market

  Current Estimated Value $623,291

  Last Listing Agent Roger Grenier PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5855 Midnight Pass Rd Unit 225, Sarasota, FL 34242
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  /47

  Est $800,862 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,224 Sq Ft

  4532 Ocean Blvd Unit 209, Sarasota, FL 34242

  4532 Ocean Blvd Unit 209, Sarasota, FL 34242
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  /43

  $899,000

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft

  625 Beach Rd Unit 407, Sarasota, FL 34242

  Welcome to your newly reimagined Siesta Key retreat! Perfectly positioned just steps from the world-famous Siesta Key Beach and vibrant Siesta Key Village, this 2 bedroom, 2 bathroom turnkey property offers a rare combination of modern luxury, coastal charm, and unbeatable convenience. Every inch of this residence has been thoughtfully renovated, which means brand new everything! From the

  Toni Zarghami KW COASTAL LIVING III

  625 Beach Rd Unit 407, Sarasota, FL 34242
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  $1,577,000 Sold Dec 04, 2025

  5164 Windward Ave, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft
  • Built 1974

  Last Sold Summary

  • 12% Below List Price
  • $800/SF
  • 92 Days On Market

  Last Listing Agent Taylor Thompson WILLIAM RAVEIS REAL ESTATE

  5164 Windward Ave, Sarasota, FL 34242
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  /52

  Est $982,394 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  1334 Siesta Bayside Dr Unit 1334B, Sarasota, FL 34242

  1334 Siesta Bayside Dr Unit 1334B, Sarasota, FL 34242
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  $927,000

  • 3 Beds
  • 2.5 Baths
  • 2,358 Sq Ft

  6415 Midnight Pass Rd Unit 211, Sarasota, FL 34242

  Deeded beach access, Intracoastal waterway frontage with boat dockage AND room for the whole family! Discover the epitome of coastal living in this fabulous three-bedroom, two-and-a-half-bath residence, boasting 2,358 square feet of interior space and a 95-foot balcony spanning the entire length of the home. Recently upgraded with $80,000 worth of high-impact hurricane sliders, the spacious floor

  Mina Johnson MICHAEL SAUNDERS & COMPANY

  6415 Midnight Pass Rd Unit 211, Sarasota, FL 34242
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  $735,000 Sold Nov 05, 2025

  717 Treasure Boat Way, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,978 Sq Ft
  • Built 1973

  Last Sold Summary

  • 18% Below List Price
  • $372/SF
  • 175 Days On Market

  Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  717 Treasure Boat Way, Sarasota, FL 34242
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  /50

  Est $477,724 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  5667 Midnight Pass Rd Unit 304, Sarasota, FL 34242

  5667 Midnight Pass Rd Unit 304, Sarasota, FL 34242
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  /79

  $2,099,000

  • 2 Beds
  • 2 Baths
  • 1,772 Sq Ft

  5569 Contento Dr, Sarasota, FL 34242

  New Price ~ Siesta Key ~ Siesta Isles Neighborhood ~ 123' Water-Frontage ~ Close To Siesta Key Beach ~ Home Updated Throughout (Inside - Outside) ~ Oversized Lot: 12,000+ Square Feet ~ Pool ~ Two Boat Docks With Lifts ~ New Seawall ~ Pool / Yard / Docks All South Facing ~ Prime Location With Privacy (Dead End Street)! "SOLD" Turn Key Furnished (seller will consider leaving two boats on two lifts

  Robert Anderson Jr RE/MAX ALLIANCE GROUP

  5569 Contento Dr, Sarasota, FL 34242
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  $800,000 Sold Jul 11, 2025

  5522 Calle Del Verano, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • Built 1956

  Last Sold Summary

  • 16% Below List Price
  • $589/SF
  • 16 Days On Market

  Current Estimated Value $799,575

  Last Listing Agent Mary Kassen PREFERRED SHORE LLC

  5522 Calle Del Verano, Sarasota, FL 34242
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  Est $738,615 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 925 Sq Ft

  5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242
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  /75

  $850,000

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft

  4822 Ocean Blvd Unit 2A, Sarasota, FL 34242

  Luxurious Gulf-Front Condominium – Your Coastal Paradise Awaits! Step into a world of elegance and tranquility in this stunning condominium, perfectly situated along the breathtaking coastline of Siesta Key. Featuring two lavish ensuite bedrooms, this residence offers you the ultimate in coastal living. The primary bedroom boasts full panoramic views of the crystal blue waters of the Gulf,

  Beth Dilley ASCENDIA REAL ESTATE

  4822 Ocean Blvd Unit 2A, Sarasota, FL 34242
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  $1,970,000 Sold Jun 27, 2025

  5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,088 Sq Ft
  • Built 1970

  Last Sold Summary

  • 6% Below List Price
  • $943/SF
  • 7 Days On Market

  Current Estimated Value $1,964,070

  Last Listing Agent Carolyn Donnelly COLDWELL BANKER REALTY

  5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242
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  Est $627,528 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 921 Sq Ft

  5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242

  5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242
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  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft

  5790 Midnight Pass Rd Unit 209, Sarasota, FL 34242

  QUICK BEACH ACCESS! Welcome to highly sought-after "Building A" at the Gulf & Bay Club located on Siesta Key Beach! As you enter the gated community, you will feel like you've landed in paradise as you make your way down the brick paved streets to the building closest to the beach. Offered TURN-KEY FURNISHED, this nicely updated 2-bedroom, 2-bathroom condo located on the second floor offers quick

  Jamie Mullis COLDWELL BANKER REALTY

  5790 Midnight Pass Rd Unit 209, Sarasota, FL 34242
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  $1,050,000 Sold Dec 16, 2025

  460 Beach Rd Unit B2, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,363 Sq Ft
  • Built 1980

  Last Sold Summary

  • 12% Below List Price
  • $770/SF
  • 105 Days On Market

  Last Listing Agent Tamatha Spangler NORTHGROUP REAL ESTATE, INC

  460 Beach Rd Unit B2, Sarasota, FL 34242
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  Est $1,143,353 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,915 Sq Ft

  1240 Dolphin Bay Way Unit 303, Sarasota, FL 34242

  1240 Dolphin Bay Way Unit 303, Sarasota, FL 34242
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  $1,950,000

  • 3 Beds
  • 2 Baths
  • 1,713 Sq Ft

  5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242

  INCREDIBLE FULL Sunset & Gulf Views!....INCREDIBLE "Everything" UPDATES & FINISHES!....INCREDIBLE Boutique Beachside Community!....Rarely Available, You will be WOWED! by this Stunning (3) Bedroom TOP FLOOR residence with GARAGE PARKING in Sought After Casarina---a Resort Style Pet Friendly "low density" plush 7 acre residential complex with over 200' feet of Powdery Quartz sand frontage along

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242
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  $2,260,000 Sold Mar 26, 2025

  815 Paradise Way, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 3,677 Sq Ft
  • Built 1961

  Last Sold Summary

  • 6% Below List Price
  • $615/SF
  • 9 Days On Market

  Current Estimated Value $2,120,467

  Last Listing Agent Doug Addeo COMMUNITY REALTY ASSOCIATES

  815 Paradise Way, Sarasota, FL 34242
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  /77

  Est $1,291,189 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,740 Sq Ft

  5319 Siesta Cove Dr, Sarasota, FL 34242

  5319 Siesta Cove Dr, Sarasota, FL 34242
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  /13

  $9,400,000 Pending

  • 3 Beds
  • 4 Baths
  • 4,510 Sq Ft

  70 Avenida Veneccia Unit 402, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Introducing Sunset Beach, the premier boutique condominium on Siesta Key, offering refined beachfront living with breathtaking Gulf views. This exclusive collection features 11 residences with open-concept, flow-through floor plans and expansive glass walls. The spacious terraces and thoughtfully designed great room

  David Lehrman THE SARASOTA REAL ESTATE COMP.

  70 Avenida Veneccia Unit 402, Sarasota, FL 34242
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  $680,000 Sold Aug 21, 2025

  1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Above List Price
  • $585/SF
  • 4 Days On Market

  Current Estimated Value $659,013

  Last Listing Agent Jim Gammello WILLIAM RAVEIS REAL ESTATE

  1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242
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  Est $442,562 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  6006 Midnight Pass Rd Unit 56, Sarasota, FL 34242

  6006 Midnight Pass Rd Unit 56, Sarasota, FL 34242
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  $375,000

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit D31, Sarasota, FL 34242

  Discover the perfect blend of coastal luxury and investment opportunity. This beautifully furnished modern condo, SLEEPS UP TO SIX! Located just minutes from the world-famous Siesta Key Beach. Whether you're looking for a dream getaway or a highly desirable rental property, with weekly rentals allowed. This gem checks all the boxes!Built to last, this sturdy unit has stood strong through past

  Dena Dominiczak EXIT KING REALTY

  6157 Midnight Pass Rd Unit D31, Sarasota, FL 34242
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  $578,000 Sold Oct 08, 2025

  6415 Midnight Pass Rd Unit 607, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $449/SF
  • 185 Days On Market

  Last Listing Agent James Hirschman SARASOTA LAND AND HOMES LLC

  6415 Midnight Pass Rd Unit 607, Sarasota, FL 34242
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  Est $493,520 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242
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  $595,000

  • Land
  • 0.16 Acre
  • $3,718,750 per Acre

  5219 Calle de Rio, Siesta Key, FL 34242

  Prime Buildable Lot Near Siesta Key Village! ?? Seize this rare opportunity to own a ready-to-build lot just steps from Siesta Key Village in one of the island’s most sought-after locations! Why You'll Love This Property:~Cleared & Ready to Build – No demolition needed—just bring your vision to life!~Flexible Use – Ideal for a luxury residence, vacation retreat, or high-income

  Robert Bevington SHOWTIME REALTY

  5219 Calle de Rio, Siesta Key, FL 34242
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  $655,000 Sold Jun 20, 2025

  5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $569/SF
  • 48 Days On Market

  Current Estimated Value $618,321

  Last Listing Agent Susan Retzke RE/MAX PALM

  5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242
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  /78

  Est $670,665 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  105 Whispering Sands Dr Unit V48, Sarasota, FL 34242

  105 Whispering Sands Dr Unit V48, Sarasota, FL 34242
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  /30

  $1,295,000

  • 3 Beds
  • 4 Baths
  • 2,337 Sq Ft

  5502 Shadow Lawn Dr, Sarasota, FL 34242

  Build your Dream Home or renovate the existing home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Siesta Key. This 14,200 square foot lot boasts approximately 80 feet on a deep canal with a boat dock. New homes and extensive renovations are occurring in this highly sought after neighborhood with its excellent boating water and close proximity to the

  Dan Miller PREFERRED SHORE LLC

  5502 Shadow Lawn Dr, Sarasota, FL 34242
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  $660,000 Sold Mar 28, 2025

  1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $584/SF
  • 108 Days On Market

  Current Estimated Value $631,897

  Last Listing Agent Kaitlin Kuhn MICHAEL SAUNDERS & COMPANY

  1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
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  Est $1,048,909 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,320 Sq Ft

  115 Sand Dollar Ln, Sarasota, FL 34242

  115 Sand Dollar Ln, Sarasota, FL 34242
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  $2,730,950 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  105 Island Cir, Sarasota, FL 34242

  Pre-Construction. To be built. Pre-Construction. To be built. IMAGINE a Custom Coastal Contemporary Home on Palm Island, Siesta Key. Picture a thoughtfully designed residence offering 2,750 sf of indoor living space and 3,467 sf of total indoor/outdoor space. E/M Custom Homes is renowned for their impeccable craftsmanship and modern coastal design creating a one-of-a-kind residence to be

  Linda Scheller COLDWELL BANKER REALTY

  105 Island Cir, Sarasota, FL 34242
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  $800,000 Sold Sep 10, 2025

  20 Whispering Sands Dr Unit 301, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1973

  Last Sold Summary

  • 15% Below List Price
  • $624/SF
  • 135 Days On Market

  Current Estimated Value $830,803

  Last Listing Agent Dion Souza SARABAY REAL ESTATE INC

  20 Whispering Sands Dr Unit 301, Sarasota, FL 34242
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  Est $1,015,882 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,103 Sq Ft

  1033 Shadow Lawn Way, Sarasota, FL 34242

  1033 Shadow Lawn Way, Sarasota, FL 34242
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  /88

  $2,995,000

  • 5 Beds
  • 6 Baths
  • 3,206 Sq Ft

  5246 Avenida Del Mare, Sarasota, FL 34242

  Welcome to your dream coastal retreat—where luxury meets relaxation—just 3 blocks from the award-winning Siesta Key Beach. This custom-built all block elevated home is crafted for those who crave the ultimate Florida lifestyle. Perfect for a full-time resident or a part-time snowbird. A stunning 5-bedroom, 4 full baths, with 2 powder rooms affords unmatched elegance. Step into your backyard oasis

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  5246 Avenida Del Mare, Sarasota, FL 34242
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  $815,000 Sold Sep 15, 2025

  710 Birdsong Ln, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,522 Sq Ft
  • Built 1980

  Last Sold Summary

  • 32% Below List Price
  • $323/SF
  • 173 Days On Market

  Current Estimated Value $870,679

  Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.

  710 Birdsong Ln, Sarasota, FL 34242

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