Siesta Key, FL Homes

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  $2,690,000 Open Sun 1PM - 3PM

  • 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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  $15,000 per month

  • 3 Beds
  • 3 Baths
  • 1,898 Sq Ft
  • Condo for Rent

  22 Sandy Cove Rd Unit 10-5, Sarasota, FL 34242

  RATES AND AVAILABILITY VARY. AVAILABLE SEASON 2026! Welcome to a completely renovated, light-filled penthouse in the exclusive Sandy Cove community — where coastal design meets breathtaking Gulf views in every direction. This professionally managed 3-bedroom, 3-bath residence is fully turnkey furnished and thoughtfully designed for relaxed, upscale living.Every inch of the home has been

  Cole Collins COLDWELL BANKER REALTY

  22 Sandy Cove Rd Unit 10-5, Sarasota, FL 34242
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  $650,000 Sold Jul 14, 2025

  4510 Banan Place, Sarasota, FL 34242

  • Land
  • 0.24 Acre
  • $2,708,333 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 163 Days On Market

  Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

  4510 Banan Place, Sarasota, FL 34242
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  Est $739,394 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,660 Sq Ft

  1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

  1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242
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  $575,000 Open Sun 12AM - 2PM

  • 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 screened-in 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

  Halie Monde KELLER WILLIAMS ON THE WATER S

  4660 Ocean Blvd Unit Q1, Sarasota, FL 34242
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  $14,000 per month

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • House for Rent

  211 Island Cir, Sarasota, FL 34242

  AVAILABLE for 2026... Jan., Feb and April Fantastic pool home located .4 mile from Siesta Beach access! Enjoy this completely renovated 3 bedroom / 2bath pool home in Palm Island on Siesta Key. With comfort in mind, vacation memories are waiting to be made here! All furnishings, appliances and flooring are new and decorated in coastal colors. Enjoy a morning walk to the powdery sand beach less

  Brenda Cozy COLDWELL BANKER REALTY

  211 Island Cir, Sarasota, FL 34242
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  $680,000 Sold Jun 12, 2025

  1155 Lake House Cir Unit C119, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1981

  Last Sold Summary

  • $503/SF
  • 8 Days On Market

  Current Estimated Value $652,177

  Last Listing Agent Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

  1155 Lake House Cir Unit C119, Sarasota, FL 34242
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  Est $537,273 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1600 Cove II Place Unit 421, Sarasota, FL 34242

  1600 Cove II Place Unit 421, Sarasota, FL 34242
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  $539,000

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 42, Sarasota, FL 34242

  Discover the charm of island living in this beautifully remodeled 1-bedroom, 1-bath condo on the Gulf side of Siesta Key. Designed with a laid-back coastal vibe, this home perfectly blends style, comfort, and functionality.The open-concept floor plan showcases luxury vinyl plank flooring throughout, creating a seamless flow from the spacious kitchen to the dining area and inviting living

  Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 42, Sarasota, FL 34242
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  $12,000 per month

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • House for Rent

  4879 Commonwealth Dr, Sarasota, FL 34242

  Lease a Rare Piece of Sarasota's Architectural History on Siesta Key! Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Originally crafted in 1957 by Frank Coleman and Tollen Twitchell, two influential figures in the Original Sarasota School of Architecture, this home seamlessly

  Daniel Petrilla PREFERRED SHORE LLC

  4879 Commonwealth Dr, Sarasota, FL 34242
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  /2

  $729,000 Sold Oct 17, 2025

  1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $570/SF
  • 96 Days On Market

  Last Listing Agent Gina LaRouche COLDWELL BANKER REALTY

  1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242
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  Est $789,505 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft

  5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

  5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242
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  $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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  $3,500 per month

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Condo for Rent

  1700 Cove II Place Unit 310, Sarasota, FL 34242

  Available 3500.00 Monthly - September 17th 2026 through December 31st 2026... Available January 2026 - 5,000.00 May be rented weekly. l – Stunning Water Views & Deeded Beach Access | Siesta Keyplus taxes and fees. Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the spacious patio, along with

  Robert Bevington SHOWTIME REALTY

  1700 Cove II Place Unit 310, Sarasota, FL 34242
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  $460,000 Sold Dec 04, 2025

  5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Below List Price
  • $455/SF
  • 92 Days On Market

  Last Listing Agent Janet Trefry RE/MAX ALLIANCE GROUP

  5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242
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  Est $687,681 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft

  5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

  5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242
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  $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 $25,000 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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  $5,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  4946 Commonwealth Dr, Sarasota, FL 34242

  Short Term Rental-Not available January-April of 2026Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the

  Beth Dilley ASCENDIA REAL ESTATE

  4946 Commonwealth Dr, Sarasota, FL 34242
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  $800,000 Sold Dec 19, 2025

  6300 Midnight Pass Rd Unit 2, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1969

  Last Sold Summary

  • 6% Below List Price
  • $617/SF
  • 127 Days On Market

  Last Listing Agent Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6300 Midnight Pass Rd Unit 2, Sarasota, FL 34242
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  Est $632,108 Not Listed For Sale

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

  5600 Beach Way Dr Unit 215, Sarasota, FL 34242

  5600 Beach Way Dr Unit 215, Sarasota, FL 34242
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  $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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  $14,000 per month

  • 4 Beds
  • 3 Baths
  • 2,341 Sq Ft
  • House for Rent

  412 Treasure Boat Way, Sarasota, FL 34242

  Discover your dream home with this exquisite single family residence available for annual rental. This remarkable property redefines elegance and comfort, featuring stunning one-of-a-kind architecture that combines exceptional design with spacious living. Crafted for discerning tenants who appreciate the finer things in life, the home boasts four generously sized bedrooms and three luxurious

  Beth Dilley ASCENDIA REAL ESTATE

  412 Treasure Boat Way, Sarasota, FL 34242
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  $4,000,000 Sold Jun 26, 2025

  645 Beach Rd, Siesta Key, FL 34242

  • 4,989 Sq Ft
  • Built 2018

  Last Sold Summary

  • 19% Below List Price
  • $802/SF
  • 441 Days On Market

  Current Estimated Value $4,641,279

  Last Listing Agent Cole Collins COLDWELL BANKER REALTY

  645 Beach Rd, Siesta Key, FL 34242
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  Est $611,120 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242

  5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242
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  $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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  /24

  $7,500 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • Condo for Rent

  6006 Midnight Pass Rd Unit 21, Sarasota, FL 34242

  Discover your beachside retreat on world-famous Siesta Key! This beautifully updated 1-bedroom, 1-bath ground-floor condo in the sought-after Casa Mar community offers the ultimate in coastal convenience—just a short stroll to private deeded beach access and the whi te sands of Siesta Beach. Step inside to a smoke-free, pet-free unit featuring wood plank flooring, modern leather furnishings, and

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 21, Sarasota, FL 34242
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  $1,200,000 Sold Apr 25, 2025

  5602 Cape Leyte Dr, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,111 Sq Ft
  • Built 1960

  Last Sold Summary

  • 9% Below List Price
  • $568/SF
  • 50 Days On Market

  Current Estimated Value $1,119,751

  Last Listing Agent Ben Angerami PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5602 Cape Leyte Dr, Sarasota, FL 34242
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  Est $644,022 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

  5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242
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  $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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  $7,500 per month

  • 4 Beds
  • 3 Baths
  • 2,392 Sq Ft
  • House for Rent

  306 Island Cir, Sarasota, FL 34242

  Available now. Lovely pool home with canal water frontage located in Siesta Key's peaceful and secluded neighborhood of PalmIsland. Completely renovated with new kitchen, bathrooms, and floor coverings throughout this island retreat. Walk four blocks to the crystalsands of world famous Siesta Beach, and just a short walk to the Village. Beautiful backyard with spacious patio, heated

  Timothy Bloch QUEST PROPERTIES INC

  306 Island Cir, Sarasota, FL 34242
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  $1,500,000 Sold Dec 01, 2025

  1038 Contento St, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,217 Sq Ft
  • Built 1972

  Last Sold Summary

  • 13% Below List Price
  • $677/SF
  • 169 Days On Market

  Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

  1038 Contento St, Sarasota, FL 34242
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  Est $1,009,219 Not Listed For Sale

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

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242
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  $699,000

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft

  1001 Beach Rd Unit A203, Sarasota, FL 34242

  Price Drop of 20K - best price for a Tower Unit in Our House at the Beach !Strong Rental Income – Across from Siesta Beach! Totally updated 2 bed / 2 bath condo in the West Tower of “Our House at the Beach”, directly across from Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor in 2024. This second-floor unit offers incredible natural light and nearly 270 degrees of wraparound views thanks

  Mike Winger TIDELINE REAL ESTATE BROKERS

  1001 Beach Rd Unit A203, Sarasota, FL 34242
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  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit B, Sarasota, FL 34242

  Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit B, Sarasota, FL 34242
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  $925,000 Sold Jan 28, 2025

  4439 Ocean Blvd, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 3,042 Sq Ft
  • Built 1951

  Last Sold Summary

  • 16% Below List Price
  • $304/SF
  • 67 Days On Market

  Current Estimated Value $853,620

  Last Listing Agent Jay Hogue DALTON WADE INC

  4439 Ocean Blvd, Sarasota, FL 34242
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  /27

  Est $668,899 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

  6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242
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  $3,500,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 3,471 Sq Ft

  5058 Windward Ave, Siesta Key, FL 34242

  This custom-built home received the “Best Overall” award in the 2021 Manatee and Sarasota County Parade of Homes. Experience the pinnacle of Siesta Key waterfront living in this 2019-built masterpiece by Nutter Custom Construction. Designed with precision and built to last, this solar-powered coastal retreat sits on high elevation and spans over 3,400 living square feet, offering 3 bedrooms, 3

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  5058 Windward Ave, Siesta Key, FL 34242
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  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit A, Sarasota, FL 34242

  Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated,

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit A, Sarasota, FL 34242
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  $3,300,000 Sold Apr 10, 2025

  317 Beach Rd, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 3,362 Sq Ft
  • Built 2009

  Last Sold Summary

  • 6% Below List Price
  • $982/SF
  • 14 Days On Market

  Current Estimated Value $3,277,405

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  317 Beach Rd, Sarasota, FL 34242
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  Est $543,882 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1500 Cove II Place Unit 532, Sarasota, FL 34242

  1500 Cove II Place Unit 532, Sarasota, FL 34242

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