9,257

Siesta Key, FL Homes

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  • /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

    $26,832

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,711 Sq Ft
    • Condo for Rent

    339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242

    The advertised rate of $26,832/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 3, 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

    339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242
  • /2

    $692,000

    Sold Oct 06, 2025

    6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,387 Sq Ft
    • Built 1981

    Last Sold Summary

    • 13% Below List Price
    • $499/SF
    • 165 Days On Market

    Current Estimated Value $711,902

    Last Listing Agent Marci McFarland MICHAEL SAUNDERS & COMPANY

    6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242
    • /46

      Not Listed For Sale

      1166 W Peppertree Dr Unit 112, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1974
      1166 W Peppertree Dr Unit 112, Sarasota, FL 34242

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

  • /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
  • /17

    $5,368

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • Condo for Rent

    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242

    The advertised rate of $5,369/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 1, 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

    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
  • /2

    $2,850,000

    Sold Apr 17, 2026

    4651 Higel Ave, Sarasota, FL 34242

    • 4 Beds
    • 3 Baths
    • 3,500 Sq Ft
    • Built 2007

    Last Sold Summary

    • 5% Below List Price
    • $814/SF
    • 0 Days On Market

    Current Estimated Value $2,814,105

    Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

    4651 Higel Ave, Sarasota, FL 34242
    • /2

      Est $1,847,175

      Not Listed For Sale

      3927 Somerset Dr, Sarasota, FL 34242

      • 3 Beds
      • 3.5 Baths
      • 2,758 Sq Ft
      • Built 1990
      3927 Somerset Dr, Sarasota, FL 34242

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Patrick Dipinto, III OCEAN REAL ESTATE LLC

  • /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
  • /17

    $2,364

    Total Monthly Price

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

    60 Avenida Veneccia Unit SI FL2-ID1591442P, Siesta Key, FL 34242

    The advertised rate of $2,365/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 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 FL2-ID1591442P, Siesta Key, FL 34242
  • /2

    $770,000

    Sold Jul 02, 2026

    6236 Midnight Pass Rd Unit 305, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1979

    Last Sold Summary

    • 14% Below List Price
    • $616/SF
    • 181 Days On Market

    Current Estimated Value $802,542

    Last Listing Agent Alex Chau COLDWELL BANKER REALTY

    6236 Midnight Pass Rd Unit 305, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,255 Sq Ft
      • Built 2009
      915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

  • /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

    $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

    $1,400,000

    Sold Dec 18, 2025

    4865 Featherbed Ln, Sarasota, FL 34242

    • 4 Beds
    • 4 Baths
    • 4,482 Sq Ft
    • Built 1955

    Last Sold Summary

    • 26% Below List Price
    • $312/SF
    • 348 Days On Market

    Current Estimated Value $1,578,436

    Last Listing Agent Janet Boyden PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4865 Featherbed Ln, Sarasota, FL 34242
    • /2

      Est $779,029

      Not Listed For Sale

      5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,211 Sq Ft
      • Built 1976
      5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Kelli Eggen 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
  • /20

    $9,466

    Total Monthly Price

    • 3 Beds
    • 3 Baths
    • 1,732 Sq Ft
    • Condo for Rent

    5780 Midnight Pass Rd Unit SI ID1591412P, Siesta Key, FL 34242

    The advertised rate of $9,467/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 19, 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

    5780 Midnight Pass Rd Unit SI ID1591412P, Siesta Key, FL 34242
  • /2

    $859,000

    Sold Apr 15, 2026

    4822 Ocean Blvd Unit 8D, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1973

    Last Sold Summary

    • 4% Below List Price
    • $597/SF
    • 7 Days On Market

    Current Estimated Value $868,268

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    4822 Ocean Blvd Unit 8D, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 1,900 Sq Ft
      • Built 2009
      915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242

      Last Sold Summary

      • 175 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

    $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

    $815,000

    Sold Apr 28, 2026

    6140 Midnight Pass Rd Unit A10, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Built 1967

    Last Sold Summary

    • 7% Below List Price
    • $763/SF
    • 157 Days On Market

    Current Estimated Value $810,719

    Last Listing Agent Jaci Krawtschenko PREMIER SOTHEBY'S INTERNATIONAL REALTY

    6140 Midnight Pass Rd Unit A10, Sarasota, FL 34242
    • /68

      Est $602,949

      Not Listed For Sale

      101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,271 Sq Ft
      • Built 1969
      101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Daria Fairchild COLDWELL BANKER REALTY

  • /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

    $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

    $650,000

    Sold Sep 12, 2025

    6415 Midnight Pass Rd Unit 502, Sarasota, FL 34242

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

    Last Sold Summary

    • 6% Below List Price
    • $505/SF
    • 11 Days On Market

    Current Estimated Value $646,900

    Last Listing Agent Mina Johnson MICHAEL SAUNDERS & COMPANY

    6415 Midnight Pass Rd Unit 502, Sarasota, FL 34242
    • /84

      Est $626,390

      Not Listed For Sale

      5600 Beach Way Dr Unit 113, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,282 Sq Ft
      • Built 1970
      5600 Beach Way Dr Unit 113, Sarasota, FL 34242

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Lisa Garcia COLDWELL BANKER REALTY

  • /100

    $4,800,000

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

    533 Venice Ln, Sarasota, FL 34242

    Virtually Staged. 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

    Agent Photo

    Cassandra Meyer

    BRIGHT REALTY

    533 Venice Ln, 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

    $480,000

    Sold Jul 16, 2026

    1255 E Peppertree Dr Unit 201, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 1972

    Last Sold Summary

    • 14% Below List Price
    • $329/SF
    • 299 Days On Market

    Current Estimated Value $508,846

    Last Listing Agent Mina Johnson MICHAEL SAUNDERS & COMPANY

    1255 E Peppertree Dr Unit 201, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242

      • 2 Beds
      • 3 Baths
      • 1,750 Sq Ft
      • Built 2009
      915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242

      Last Sold Summary

      • 159 Days On Market

      Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

  • /100

    $4,950,000

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

    527 Venice Ln, Sarasota, FL 34242

    Virtually Staged. 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

    Agent Photo

    Cassandra Meyer

    BRIGHT REALTY

    527 Venice Ln, Sarasota, FL 34242
  • /11

    $2,500

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 710 Sq Ft
    • Condo for Rent

    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242

    Fully furnished, intercoastal waterfront detached garage apartment on one of the most desirable streets on far north end of Siesta Key. Could be set up as 1 or 2 bedroom. Month to month lease available, discount for longer commitments. All standard services and utilities included in rent price. Price includes one bay of a two car garage for covered parking. Unlimited pool and dock use 7a-9p

    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242
  • /2

    $500,500

    Sold May 01, 2026

    1125 W Peppertree Dr Unit 302, Sarasota, FL 34242

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

    Last Sold Summary

    • 5% Below List Price
    • $430/SF
    • 25 Days On Market

    Current Estimated Value $520,396

    Last Listing Agent Christine Green COLDWELL BANKER REALTY

    1125 W Peppertree Dr Unit 302, Sarasota, FL 34242
    • /2

      Est $1,370,652

      Not Listed For Sale

      312 Calle Miramar Unit S1, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 2008
      312 Calle Miramar Unit S1, Sarasota, FL 34242

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  • /99

    $5,392,000

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

    4819 Higel Ave, Sarasota, FL 34242

    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 and two half baths. Step

    Agent Photo

    Cassandra Meyer

    BRIGHT REALTY

    4819 Higel Ave, Sarasota, FL 34242
  • /11

    $2,500

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 710 Sq Ft
    • Condo for Rent

    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242

    Fully furnished, intercoastal waterfront detached garage apartment on one of the most desirable streets on far north end of Siesta Key. Could be set up as 1 or 2 bedroom. Month to month lease available, discount for longer commitments. All standard services and utilities included in rent price. Price includes one bay of a two car garage for covered parking. Unlimited pool and dock use 7a-9p

    3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242
  • /2

    $1,075,000

    Sold Apr 13, 2026

    567 Venice Ln, Sarasota, FL 34242

    • 4 Beds
    • 2 Baths
    • 1,915 Sq Ft
    • Built 1971

    Last Sold Summary

    • 10% Below List Price
    • $561/SF
    • 100 Days On Market

    Current Estimated Value $1,075,436

    Last Listing Agent Conner Ashley PREFERRED SHORE LLC

    567 Venice Ln, Sarasota, FL 34242
    • /27

      Est $715,296

      Not Listed For Sale

      5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,043 Sq Ft
      • Built 1975
      5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Linda Stowe MICHAEL SAUNDERS & COMPANY

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