9,260

Siesta Key, FL Homes

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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

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 504, Weeks 6-7, Sarasota, FL 34242
  • /20

    $11,637

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 2,744 Sq Ft
    • Condo for Rent

    5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242

    The advertised rate of $11,637/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242
  • /2

    $1,525,000

    Sold May 07, 2026

    312 Canal Rd, Sarasota, FL 34242

    • 4 Beds
    • 4 Baths
    • 1,792 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Below List Price
    • $851/SF
    • 11 Days On Market

    Current Estimated Value $1,636,331

    Last Listing Agent Curtis Ware KW COASTAL LIVING III

    312 Canal Rd, Sarasota, FL 34242
    • /2

      Est $701,455

      Not Listed For Sale

      6310 Midnight Pass Rd Unit 405N, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 894 Sq Ft
      • Built 1968
      6310 Midnight Pass Rd Unit 405N, Sarasota, FL 34242

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Halie Monde KW COASTAL LIVING III

  • /72

    $1,199,000

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

    20 Whispering Sands Dr Unit 501, Sarasota, FL 34242

    Experience full gulf-front views and the lifestyle of island living on the world-renowned Siesta Key beach. This beautiful fifth-floor end-unit residence is in the south tower of Whispering Sands, a community in the heart of Siesta Key Village. This property offers the ideal blend of serenity and convenience. Residents enjoy private beach access and 800 feet of quartz sand beach, yet you are just

    Agent Photo

    Christopher Bush

    PREMIER SOTHEBY'S INTERNATIONAL REALTY

    20 Whispering Sands Dr Unit 501, Sarasota, FL 34242
  • /20

    $7,587

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 957 Sq Ft
    • Condo for Rent

    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242

    The advertised rate of $7,588/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
  • /2

    $650,000

    Sold Mar 31, 2026

    4660 Ocean Blvd Unit E2, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Below List Price
    • $542/SF
    • 25 Days On Market

    Current Estimated Value $643,987

    Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

    4660 Ocean Blvd Unit E2, Sarasota, FL 34242
    • /72

      Est $1,357,871

      Not Listed For Sale

      22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 1,876 Sq Ft
      • Built 1969
      22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

      Last Sold Summary

      • 360 Days On Market

      Last Listing Agent Jackie Eberley COLDWELL BANKER REALTY

  • /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

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242
  • /20

    $13,770

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 2,206 Sq Ft
    • Condo for Rent

    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242

    The advertised rate of $13,771/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 13, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it

    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
  • /2

    $1,285,000

    Sold Aug 26, 2026

    6300 Midnight Pass Rd Unit 708, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,271 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $1,011/SF
    • 126 Days On Market

    Current Estimated Value $1,318,411

    Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

    6300 Midnight Pass Rd Unit 708, Sarasota, FL 34242
    • /2

      Est $1,081,332

      Not Listed For Sale

      6312 Midnight Pass Rd Unit 702S, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 977 Sq Ft
      • Built 1968
      6312 Midnight Pass Rd Unit 702S, Sarasota, FL 34242

      Last Sold Summary

      • 122 Days On Market

      Last Listing Agent Jessica Uglik KW SUNCOAST

  • /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

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 511, Weeks 16-17, Sarasota, FL 34242
  • /15

    $2,579

    Total Monthly Price

    • Studio
    • 1 Bath
    • Condo for Rent

    60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242

    The advertised rate of $2,580/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 15, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242
  • /2

    $1,450,000

    Sold Nov 04, 2025

    4108 Roberts Point Rd, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 2,511 Sq Ft
    • Built 2001

    Last Sold Summary

    • 23% Below List Price
    • $577/SF
    • 142 Days On Market

    Current Estimated Value $1,457,652

    Last Listing Agent Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    4108 Roberts Point Rd, Sarasota, FL 34242
    • /2

      Est $2,224,798

      Not Listed For Sale

      5408 Plaza Des Las Palmas, Sarasota, FL 34242

      • 5 Beds
      • 5 Baths
      • 2,689 Sq Ft
      • Built 1953
      5408 Plaza Des Las Palmas, Sarasota, FL 34242

      Last Sold Summary

      • 273 Days On Market

      Last Listing Agent Doug Addeo COMMUNITY REALTY ASSOCIATES

  • /52

    $59,000

    $16K PRICE DROP
    • 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

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 606, Weeks 12-13, Sarasota, FL 34242
  • /20

    $3,996

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,001 Sq Ft
    • Condo for Rent

    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242

    The advertised rate of $3,996/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 2, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
  • /2

    $1,850,000

    Sold Mar 31, 2026

    3919 Roberts Point Rd, Sarasota, FL 34242

    • 4 Beds
    • 3 Baths
    • 2,497 Sq Ft
    • Built 2016

    Last Sold Summary

    • 22% Below List Price
    • $741/SF
    • 42 Days On Market

    Current Estimated Value $1,934,944

    Last Listing Agent Kathy White PREFERRED SHORE LLC

    3919 Roberts Point Rd, Sarasota, FL 34242
    • /2

      Est $446,165

      Not Listed For Sale

      6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

      • 2 Beds
      • 2.5 Baths
      • 1,332 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Julia Montei COLDWELL BANKER REALTY

  • /59

    $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 complex. If you are looking for a great investment or the perfect place to call home, look no further. 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

    Agent Photo

    Anthony DeLuca

    DELUCA REALTY INC

    5770 Midnight Pass Rd Unit 301, Sarasota, FL 34242
  • /14

    $5,292

    Total Monthly Price

    • Studio
    • 1 Bath
    • 312 Sq Ft
    • Condo for Rent

    60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242

    The advertised rate of $5,292/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 2, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242
  • /2

    $1,100,000

    Sold Jul 08, 2026

    5569 Shadow Lawn Dr, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1966

    Last Sold Summary

    • 12% Below List Price
    • $530/SF
    • 35 Days On Market

    Current Estimated Value $1,229,137

    Last Listing Agent Brittany McCord IRONGATE REALTY INC

    5569 Shadow Lawn Dr, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      915 Seaside Dr Unit 606, Weeks 6-7, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 1,780 Sq Ft
      • Built 2009
      915 Seaside Dr Unit 606, Weeks 6-7, Sarasota, FL 34242

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

  • /51

    $100,000

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

    915 Seaside Dr Unit 402, Weeks 10-13, Sarasota, FL 34242

    Fractional Ownership. Unique opportunity to own four consecutive weeks in March on Siesta Key Beach. Experience luxury beachfront living with this Winter Fractional Package, offering a 1/8th ownership share at The Residences on Siesta Key Beach. This rare offering provides the opportunity to own a piece of paradise on one of America’s most celebrated beaches while enjoying the comfort,

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 402, Weeks 10-13, Sarasota, FL 34242
  • /20

    $5,564

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • Condo for Rent

    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242

    The advertised rate of $5,564/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 18, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242
  • /2

    $1,113,000

    Sold May 06, 2026

    5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • Built 1976

    Last Sold Summary

    • 13% Below List Price
    • $866/SF
    • 126 Days On Market

    Current Estimated Value $1,112,934

    Last Listing Agent Beverly Schroeder PLUMLEE GULF BEACH REALTY

    5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242
    • /2

      Est $801,762

      Not Listed For Sale

      1273 Dockside Place Unit 116, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,343 Sq Ft
      • Built 1982
      1273 Dockside Place Unit 116, Sarasota, FL 34242

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC

  • /53

    $59,000

    $16K PRICE DROP
    • 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

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242
  • /20

    $5,175

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 2,443 Sq Ft
    • Condo for Rent

    4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242

    The advertised rate of $5,176/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242
  • /2

    $735,000

    Sold Nov 27, 2025

    1055 Beach Rd Unit B204, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $610/SF
    • 29 Days On Market

    Current Estimated Value $743,634

    Last Listing Agent Jason Wood CORCORAN DWELLINGS REALTY

    1055 Beach Rd Unit B204, Sarasota, FL 34242
    • /2

      Est $1,192,213

      Not Listed For Sale

      6312 Midnight Pass Rd Unit 301S, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,009 Sq Ft
      • Built 1968
      6312 Midnight Pass Rd Unit 301S, Sarasota, FL 34242

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Tom Ward WATERSIDE REALTY LLC

  • /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

    Agent Photo

    Daniel Hut

    HUT REALTY, LLC

    6006 Midnight Pass Rd Unit 51, Sarasota, FL 34242
  • /20

    $6,789

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 1,797 Sq Ft
    • Condo for Rent

    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242

    The advertised rate of $6,789/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 30, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242
  • /2

    $1,300,000

    Sold Jul 14, 2026

    5920 Midnight Pass Rd Unit 704, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,334 Sq Ft
    • Built 1971

    Last Sold Summary

    • 6% Below List Price
    • $975/SF
    • 144 Days On Market

    Current Estimated Value $1,257,514

    Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

    5920 Midnight Pass Rd Unit 704, Sarasota, FL 34242
    • /2

      Est $1,067,908

      Not Listed For Sale

      20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,464 Sq Ft
      • Built 1973
      20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

      Last Sold Summary

      • 117 Days On Market

      Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  • /52

    $584,500

    $15K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,287 Sq Ft

    6415 Midnight Pass Rd Unit 705, Sarasota, FL 34242

    Under contract-accepting backup offers. 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

    Agent Photo

    Anthony DeLuca

    DELUCA REALTY INC

    6415 Midnight Pass Rd Unit 705, Sarasota, FL 34242
  • /20

    $3,996

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,001 Sq Ft
    • Condo for Rent

    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242

    The advertised rate of $3,996/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 2, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
  • /2

    $580,000

    Sold Mar 13, 2026

    101 Whispering Sands Dr Unit 307, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,271 Sq Ft
    • Built 1969

    Last Sold Summary

    • 19% Below List Price
    • $456/SF
    • 261 Days On Market

    Current Estimated Value $583,717

    Last Listing Agent Todd Goodman KELLER WILLIAMS ON THE WATER S

    101 Whispering Sands Dr Unit 307, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      600 Beach Rd Unit 1 & 2, Sarasota, FL 34242

      • 6 Beds
      • 6 Baths
      • 2,838 Sq Ft
      • Built 1979
      600 Beach Rd Unit 1 & 2, Sarasota, FL 34242

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC

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