9,260

Siesta Key, FL Homes

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  • /59

    $1,250,000

    Open Sat 1PM - 4PM $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,908 Sq Ft

    5128 Oxford Dr, Sarasota, FL 34242

    Nestled beneath majestic oak trees, this beautifully updated home has a flexible floor plan. It boasts multiple sleeping areas that comfortably accommodates visiting family and guests. Tastefully furnished and decorated, this residence underwent extensive renovations in recent years and features a newly installed roof, new impact rated windows, restored terrazzo flooring complemented by updated

    Jessica Hoffman COLDWELL BANKER REALTY

    5128 Oxford Dr, Sarasota, FL 34242
  • /29

    $1,943

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,108 Sq Ft
    • Condo for Rent

    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242

    The advertised rate of $1,943/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

    6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
  • /2

    $3,450,000

    Sold Jun 02, 2026

    5263 Avenida de Cortez, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 3,122 Sq Ft
    • Built 2018

    Last Sold Summary

    • 10% Below List Price
    • $1,105/SF
    • 103 Days On Market

    Current Estimated Value $3,409,375

    Last Listing Agent Jessica Hoffman COLDWELL BANKER REALTY

    5263 Avenida de Cortez, Sarasota, FL 34242
    • /46

      Est $570,484

      Not Listed For Sale

      141 Avenida Messina Unit 1, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 900 Sq Ft
      • Built 1966
      141 Avenida Messina Unit 1, Sarasota, FL 34242

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Susan Christy BANZHAF & ASSOCIATES INC

  • /40

    $630,000

    $60K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 522 Sq Ft

    5400 Ocean Blvd Unit 8-05, Sarasota, FL 34242

    BEACH TERRACE - STUDIO GULF-FRONT RESIDENCE: YOUR PERFECT SIESTA KEY PIED-À-TERREDiscover your ideal coastal escape at Beach Terrace, perfectly positioned at the end of Siesta Key Village with direct Gulf of Mexico frontage. This charming studio residence offers the perfect pied-à-terre for those seeking an effortless weekend getaway to paradise.Whether you call Sarasota or

    Mickey Kiernan MICHAEL SAUNDERS & COMPANY

    5400 Ocean Blvd Unit 8-05, Sarasota, FL 34242
  • /45

    $9,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242

    Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
  • /2

    $2,680,000

    Sold May 15, 2026

    4881 Oxford Dr, Siesta Key, FL 34242

    • 4 Beds
    • 4 Baths
    • 2,819 Sq Ft
    • Built 2020

    Last Sold Summary

    • 7% Below List Price
    • $951/SF
    • 74 Days On Market

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    4881 Oxford Dr, Siesta Key, FL 34242
    • /2

      Est $3,967,445

      Not Listed For Sale

      5310 Avenida Del Mare, Siesta Key, FL 34242

      • 5 Beds
      • 8 Baths
      • 3,759 Sq Ft
      • Built 2023
      5310 Avenida Del Mare, Siesta Key, FL 34242

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  • /24

    $558,000

    • 1 Bed
    • 1 Bath
    • 728 Sq Ft

    5830 Midnight Pass Rd Unit 48, Sarasota, FL 34242

    Welcome to your own slice of paradise at Jamaica Royale, located directly on the world-famous shores of Siesta Key Beach. This beautifully remodeled one-bedroom, one-bath condominium, complete with a queen sleeper sofa, and a twin sleeper sofa, offers the perfect combination of coastal sophistication and exceptional rental income potential.Thoughtfully updated throughout, the stunning kitchen

    Eliza Miller PEPPERTREE BAY REALTY INC

    5830 Midnight Pass Rd Unit 48, Sarasota, FL 34242
  • /28

    $5,867

    Total Monthly Price

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

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242

    The advertised rate of $5,867/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

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
  • /2

    $425,000

    Sold Sep 11, 2025

    6029 E Peppertree Way Unit 116, Sarasota, FL 34242

    • 2 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1973

    Last Sold Summary

    • 27% Below List Price
    • $436/SF
    • 234 Days On Market

    Current Estimated Value $453,944

    Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

    6029 E Peppertree Way Unit 116, Sarasota, FL 34242
    • /36

      Est $710,981

      Not Listed For Sale

      5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,270 Sq Ft
      • Built 1974
      5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  • /71

    $625,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,462 Sq Ft

    206 Hourglass Way Unit V10, Sarasota, FL 34242

    Welcome to your coastal retreat in the form of this secluded, 2 bed/2 bath freestanding villa with one car garage in the premiere GULF FRONT property of Whispering Sands. OFFERED FURNISHED. This surprisingly large, 1,462 square foot property has been UPDATED in 2025 with fresh paint, NEW crown molding & baseboards, NEW kitchen and updated baths. The exceptionally large living room allows for

    Harriet Stopher COLDWELL BANKER REALTY

    206 Hourglass Way Unit V10, Sarasota, FL 34242
  • /30

    $5,370 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242

    Starting at $179/night! Welcome to your vibrant beachside retreat—a newly renovated 1-bedroom, 1-bathroom escape thoughtfully designed for modern comfort and coastal style. Featuring a luxurious king bed and a fully equipped kitchen with a cozy nearby dining space, this inviting getaway is your perfect base for both relaxation and adventure. Convenience begins with your own private carport just

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
  • /2

    $500,000

    Sold Aug 11, 2026

    4660 Ocean Blvd Unit Q1, Sarasota, FL 34242

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

    Last Sold Summary

    • 13% Below List Price
    • $417/SF
    • 303 Days On Market

    Current Estimated Value $594,444

    Last Listing Agent Halie Monde KW COASTAL LIVING III

    4660 Ocean Blvd Unit Q1, Sarasota, FL 34242
    • /47

      Est $699,637

      Not Listed For Sale

      1101 Lake House Cir Unit C-206, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 1981
      1101 Lake House Cir Unit C-206, Sarasota, FL 34242

      Last Sold Summary

      • 154 Days On Market

      Last Listing Agent Kenneth Ipox DOUGLAS ELLIMAN

  • /52

    $520,000

    $220K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 672 Sq Ft

    6020 Midnight Pass Rd Unit 63, Sarasota, FL 34242

    Welcome to Villa 63 at Aloha Kai, a beautifully renovated one-bedroom, one-bath villa located just steps from the world-famous quartz sands of Siesta Key Beach. This coastal retreat has been fully remodeled from top to bottom, offering the perfect combination of comfort, style, and income potential. From the moment you arrive, you’ll notice the fresh exterior with tropical landscaping, paver

    Natalie Gutwein MICHAEL SAUNDERS & COMPANY

    6020 Midnight Pass Rd Unit 63, 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

    $2,200,000

    Sold Jun 22, 2026

    467 Canal Rd Unit 467, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 3,228 Sq Ft
    • Built 2005

    Last Sold Summary

    • 30% Below List Price
    • $682/SF
    • 542 Days On Market

    Current Estimated Value $2,029,545

    Last Listing Agent Dan Miller PREFERRED SHORE LLC

    467 Canal Rd Unit 467, Sarasota, FL 34242
    • /2

      Est $1,060,080

      Not Listed For Sale

      5966 Midnight Pass Rd Unit G-92, Sarasota, FL 34242

      • 1 Bed
      • 1 Bath
      • 816 Sq Ft
      • Built 1970
      5966 Midnight Pass Rd Unit G-92, Sarasota, FL 34242

      Last Sold Summary

      • 214 Days On Market

      Last Listing Agent Robert Anderson Jr RE/MAX ALLIANCE GROUP

  • /17

    $4,650,000

    New Construction $250K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,723 Sq Ft

    5174 Sandy Cove Ave, Sarasota, FL 34242

    Under Construction. Welcome to 5174 Sandy Cove Ave, a pinnacle of contemporary elegance nestled in the heart of Sarasota, Florida. Designed by architect Mark Sultana. This 3900 sq foot new construction home epitomizes the fusion of exquisite design and impeccable craftsmanship, promising an unparalleled sanctuary for its new owner. Positioned just minutes from Sarasota's pristine white sand

    Troy Jenkins REALTY EXECUTIVES GALLERY

    5174 Sandy Cove Ave, Sarasota, FL 34242
  • /16

    $7,470 Per Month

    • 1 Bed
    • 1 Bath
    • 572 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242

    Villa 4 at Aloha Kai is the perfect beach getaway—light, bright, and designed to help you rest and relax. Spend your days lounging by the pool, soaking up the sun on the beach, or getting lost in a good book—the choice is yours. All you need is a willingness to unwind; everything else is provided for your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
  • /2

    $600,000

    Sold Aug 29, 2025

    4522 Banan Place, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 978 Sq Ft
    • Built 1962

    Last Sold Summary

    • 17% Below List Price
    • $613/SF
    • 191 Days On Market

    Current Estimated Value $674,494

    Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

    4522 Banan Place, Sarasota, FL 34242
    • /2

      Est $743,077

      Not Listed For Sale

      6266 Midnight Pass Rd Unit 204, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,263 Sq Ft
      • Built 1980
      6266 Midnight Pass Rd Unit 204, Sarasota, FL 34242

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Jack McSweeney COLDWELL BANKER REALTY

  • /93

    $550,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,271 Sq Ft

    225 Hourglass Way Unit 103, Sarasota, FL 34242

    Virtually Staged. GREAT PRICE IMPROVEMENT! Welcome to this RARE, 2 bed/2 bath, double lanai corner residence with peaceful lagoon views in the premiere Gulf front property of Whispering Sands! Nestled in the desirable Sunset House building, this freshly painted, updated unit offers a quiet, private setting, with serene views of lush landscaping and the shimmering lagoon with its abundant fish,

    Harriet Stopher COLDWELL BANKER REALTY

    225 Hourglass Way Unit 103, Sarasota, FL 34242
  • /35

    $7,473

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Condo for Rent

    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242

    The advertised rate of $7,473/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

    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
  • /2

    $5,600,000

    Sold Jan 22, 2026

    251 Cedar Park Cir, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 3,446 Sq Ft
    • Built 2013

    Last Sold Summary

    • 7% Below List Price
    • $1,625/SF
    • 20 Days On Market

    Current Estimated Value $5,741,662

    Last Listing Agent Steve Wexler PREMIER SOTHEBY'S INTERNATIONAL REALTY

    251 Cedar Park Cir, Sarasota, FL 34242
    • /2

      Est $1,415,340

      Not Listed For Sale

      5966 Midnight Pass Rd Unit G-73, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft
      • Built 1970
      5966 Midnight Pass Rd Unit G-73, Sarasota, FL 34242

      Last Sold Summary

      • 141 Days On Market

      Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  • /47

    $670,000

    $54K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    4900 Ocean Blvd Unit 201, Sarasota, FL 34242

    Enjoy coastal living in this updated 2-bedroom, 2-bath Siesta Key condo, just minutes from Siesta Key Village and the beach. The second-floor residence features a fresh coastal design and a kitchen remodeled in 2020 with granite countertops, stainless-steel appliances, and a washer/dryer. Natural light fills the space through large sliders that open to two spacious lanais with peaceful water and

    David Broecker PINPOINT REALTY GROUP LLC

    4900 Ocean Blvd Unit 201, Sarasota, FL 34242
  • /40

    $6,500 Per Month

    • 3 Beds
    • 4 Baths
    • 2,168 Sq Ft
    • House for Rent

    1256 Riegels Landing Dr, Sarasota, FL 34242

    This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full

    Christopher Davenport STARLINK REALTY INC

    1256 Riegels Landing Dr, Sarasota, FL 34242
  • /2

    $660,000

    Sold Aug 18, 2026

    797 Beach Rd Unit 509, Sarasota, FL 34242

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft
    • Built 1970

    Last Sold Summary

    • 17% Below List Price
    • $809/SF
    • 284 Days On Market

    Current Estimated Value $658,391

    Last Listing Agent Sandy Gamble Hulvat WATERSIDE REALTY LLC

    797 Beach Rd Unit 509, Sarasota, FL 34242
    • /2

      Est $553,783

      Not Listed For Sale

      5600 Beach Way Dr Unit 107, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,182 Sq Ft
      • Built 1970
      5600 Beach Way Dr Unit 107, Sarasota, FL 34242

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Glenn Zakaria NEW DOOR REAL ESTATE LLC

  • /52

    $699,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft

    6012 W Peppertree Way Unit 227B, Sarasota, FL 34242

    Gulf-Side Condo on Siesta Key! Don’t miss this great opportunity to own a beautiful condo with a pool view and just steps from the beach. This spacious first-floor unit features 2 bedrooms and 2 bathrooms, high ceilings, and generously sized rooms that provide plenty of space for family and guests. The condo also includes a private garage and the convenience of an in-unit washer and dryer.

    Cheryl Santelli PEPPERTREE BAY REALTY INC

    6012 W Peppertree Way Unit 227B, 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

    $1,950,000

    Sold Dec 18, 2025

    5430 Avenida Del Mare, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 2,010 Sq Ft
    • Built 1951

    Last Sold Summary

    • 22% Below List Price
    • $970/SF
    • 225 Days On Market

    Current Estimated Value $1,905,650

    Last Listing Agent Jonathan Minerick HOMECOIN.COM

    5430 Avenida Del Mare, Sarasota, FL 34242
    • /72

      Est $5,188,247

      Not Listed For Sale

      5119 Jungle Plum Rd, Sarasota, FL 34242

      • 4 Beds
      • 4 Baths
      • 4,131 Sq Ft
      • Built 2012
      5119 Jungle Plum Rd, Sarasota, FL 34242

      Last Sold Summary

      • 96 Days On Market

      Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  • /72

    $2,650,000

    $345K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,201 Sq Ft

    5303 Hidden Harbor Rd, Sarasota, FL 34242

    Now is your opportunity to own this waterfront tropical oasis on Siesta Key in the highly sought after exclusive community of Hidden Harbor. Comprised of just 36 homes, Hidden Harbor located on the North end of Siesta Key, is one of the most unique developments in Sarasota with its tropical landscaping reminiscent of old Florida. Most known for its waterfront lots and brick paver streets shaded

    Walter Shepherd COLDWELL BANKER REALTY

    5303 Hidden Harbor Rd, Sarasota, FL 34242
  • /60

    $15,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,259 Sq Ft
    • House for Rent

    5516 Avenida Del Mare, Sarasota, FL 34242

    This is a short term rental. Listing reflects peak season rate. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults

    Beth Dilley ASCENDIA REAL ESTATE

    5516 Avenida Del Mare, Sarasota, FL 34242
  • /2

    $4,095,000

    Sold Jan 26, 2026

    5078 Sandy Beach Ave, Sarasota, FL 34242

    • 4 Beds
    • 4 Baths
    • 3,164 Sq Ft
    • Built 2024

    Last Sold Summary

    • 5% Below List Price
    • $1,294/SF
    • 2 Days On Market

    Current Estimated Value $4,053,779

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    5078 Sandy Beach Ave, Sarasota, FL 34242
    • /2

      Est $2,321,204

      Not Listed For Sale

      452 Canal Rd, Sarasota, FL 34242

      • 5 Beds
      • 3.5 Baths
      • 3,384 Sq Ft
      • Built 2008
      452 Canal Rd, Sarasota, FL 34242

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Joseph Kesslak COLDWELL BANKER REALTY

Showing Results 201 - 240, Page 6 of 18

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