9,352

Siesta Key, FL Homes

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  • /56

    $1,995,000

    $195K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,233 Sq Ft

    5155 Hidden Harbor Rd, Sarasota, FL 34242

    Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded.Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating

    Matt Buttner LIST NOW REALTY, LLC

    5155 Hidden Harbor Rd, Sarasota, FL 34242
  • /10

    $8,340 Per Month

    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242

    C6 is a lovely unit, has been remodeled and is awaiting your arrival. It can accommodate up to 6. The spacious living room/dining room has all new furniture, including a large couch, two recliners, coffee, and end tables. In the dining area you will find a new dining table and chairs and a ceiling fan. There is also a wall-mounted 55” UHD Smart TV. The very large Master Bedroom has a king-size

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit C06, Sarasota, FL 34242
  • /2

    $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

    Current Estimated Value $790,559

    Last Listing Agent Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

      Est $918,381

      Not Listed For Sale

      1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,660 Sq Ft
      • Built 1988
      1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

      Last Sold Summary

      • 124 Days On Market

  • /50

    $2,400,000

    • 4 Beds
    • 3.5 Baths
    • 2,965 Sq Ft

    5073 Higel Ave, Sarasota, FL 34242

    Welcome to luxury coastal living on Siesta Key. Perfectly positioned in the exclusive Sara Sands community, this fully remodeled 4-bedroom, 3.5-bath waterfront residence offers the ultimate blend of modern elegance, boating lifestyle, and relaxed Florida luxury. Situated on a deep-water canal with quick access to Sarasota Bay and the Gulf, this exceptional property features a private dock and

    Abraham Ruth REALTY HUB

    5073 Higel Ave, Sarasota, FL 34242
  • /49

    $10,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft
    • Condo for Rent

    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242

    Welcome to your perfect Siesta Key getaway! This beautifully updated 2-bedroom, 2-bath end-unit condo in the Palm Bay Club offers stunning bay views, a bright, open interior, and resort-style amenities—just steps from the Bayfront pool.At 1,270 sq. ft., this is one of the largest condos in Palm Bay. You'll love the driftwood-style cabinetry, quartz countertops, and stainless steel appliances

    Robert Bevington SHOWTIME REALTY

    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
  • /2

    $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 $3,975,456

    Last Listing Agent Cole Collins COLDWELL BANKER REALTY

    645 Beach Rd, Siesta Key, FL 34242
    • /2

      Est $2,741,309

      Not Listed For Sale

      1358 Roberts Bay Ln, Siesta Key, FL 34242

      • 4 Beds
      • 6 Baths
      • 5,034 Sq Ft
      • Built 1978
      1358 Roberts Bay Ln, Siesta Key, FL 34242

      Last Sold Summary

      • 0 Days On Market

  • /46

    $649,000

    • 1 Bed
    • 1 Bath
    • 728 Sq Ft

    5830 Midnight Pass Rd Unit 3, Sarasota, FL 34242

    Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan. Upgrades galore!! Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest

    Steve Cavanaugh TIDELINE REAL ESTATE BROKERS

    5830 Midnight Pass Rd Unit 3, Sarasota, FL 34242
  • /10

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242

    This comfortable large 2 bedrooms 2 bathrooms villa is just steps away from Casa Blanca. Steps to the the white pristine beach voted #1 and the over sized pool for a cool dip. This villa comfortably sleeps up to 4 with a king size and 2 twin beds. Shopping and restaurants within steps or ride the trolley into Siesta Key Village or south to Turtle Beach. Come relax and enjoy the gulf breezes in

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
  • /2

    $2,500,000

    Sold Apr 15, 2026

    5770 Midnight Pass Rd Unit 608, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 2,085 Sq Ft
    • Built 1980

    Last Sold Summary

    • $1,199/SF
    • 3 Days On Market

    Current Estimated Value $2,151,220

    Last Listing Agent Sylvia Wilk PREFERRED SHORE LLC

    5770 Midnight Pass Rd Unit 608, Sarasota, FL 34242
    • /68

      Est $560,409

      Not Listed For Sale

      1600 Cove II Place Unit 421, Sarasota, FL 34242

      • 2 Beds
      • 1.5 Baths
      • 860 Sq Ft
      • Built 1979
      1600 Cove II Place Unit 421, Sarasota, FL 34242

      Last Sold Summary

      • 4 Days On Market

  • /60

    $1,999,999

    $249K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    5361 Siesta Ct, Sarasota, FL 34242

    PRICE IMPROVEMENT! Experience tranquility and peace of mind in Siesta Key! Located in the highly sought-after neighborhood of Siesta Cove, this 4-bedroom, 2.5-bath home has been meticulously maintained and generously updated. The current owners completed extensive renovations including a newly remodeled primary bathroom, a custom locally handcrafted iron front door, and stunning iron interior

    David James CHARLES RUTENBERG REALTY INC

    5361 Siesta Ct, Sarasota, FL 34242
  • /21

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242

    Villa 22 at Aloha Kai is where memories are made while spending time at the beach with family and friends, offering the perfect spacious setting. Its open floor plan fosters conversation and connection, encouraging moments away from screens. After a day of sunshine and sandy toes, gather in the updated kitchen, featuring a casual dining bar designed to invite everyone to join in meal preparation.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242
  • /2

    $1,400,000

    Sold May 15, 2026

    915 Seaside Dr Unit 604, Sarasota, FL 34242

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • Built 2009

    Last Sold Summary

    • 18% Below List Price
    • $729/SF
    • 481 Days On Market

    Current Estimated Value $1,687,451

    Last Listing Agent Matthew Hickey EXP REALTY LLC

    915 Seaside Dr Unit 604, Sarasota, FL 34242
    • /42

      Not Listed For Sale

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

      • 1 Bed
      • 1 Bath
      • 816 Sq Ft
      • Built 1970
      5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

      Last Sold Summary

  • /57

    $2,450,000

    Open House 7/05 $240K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,341 Sq Ft

    4508 Woodside Rd, Sarasota, FL 34242

    The Fastest Open-Water Access Available on Siesta Key Under $2.5 MillionLess than 3 minutes to Sarasota Bay, 95 feet of waterfront, and a 75-foot dock designed for serious boating enthusiasts. If you’ve been searching for a waterfront home that prioritizes boating convenience over lengthy canal runs, this is one of the most compelling opportunities currently available on Siesta Key.Why

    Derek Edwards KELLER WILLIAMS ON THE WATER S

    4508 Woodside Rd, Sarasota, FL 34242
  • /57

    $7,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Property for Rent

    4660 Ocean Blvd Unit N1, Sarasota, FL 34242

    Escape to Paradise on Siesta Key! Your dream seasonal getaway awaits at 4660 Ocean Blvd Unit N1, Sarasota, FL 34242. Immerse yourself in the tranquil beauty of the Gulf Coast, where pristine sands meet crystal-clear waters.This exquisite 2-bedroom, 2-bathroom condo is your ticket to an unforgettable retreat. Step into your sun-drenched sanctuary, tastefully furnished to embody comfort and

    Robert Bevington SHOWTIME REALTY

    4660 Ocean Blvd Unit N1, Sarasota, FL 34242
  • /2

    $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

    Current Estimated Value $1,521,074

    Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

    1038 Contento St, Sarasota, FL 34242
    • /43

      Not Listed For Sale

      5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,270 Sq Ft
      • Built 1974
      5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

      Last Sold Summary

      • 29 Days On Market

  • /66

    $525,000

    $50K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    4660 Ocean Blvd Unit Q1, Sarasota, FL 34242

    Under contract-accepting backup offers. PRICED TO SELL! NEW impact-rated sliding glass doors were installed in June 2026, providing enhanced storm protection and complementing the home’s existing hurricane-impact windows. 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

    Halie Monde KW COASTAL LIVING III

    4660 Ocean Blvd Unit Q1, Sarasota, FL 34242
  • /14

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242

    Find your Happy Place here in this LARGE 2 bedroom/2 bathroom, private entrance villa. There is new granite in the kitchen which is fully equipped. The master bedroom is furnished with a king size bed. The master vanity for the ladies comes with a hairdryer. The master bath features a walk-in shower with new tile and granite, all new from top to bottom. The second bedroom provides two double

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit B02, Sarasota, FL 34242
  • /2

    $1,954,700

    Sold May 28, 2026

    5024 Commonwealth Dr, Sarasota, FL 34242

    • 3 Beds
    • 3.5 Baths
    • 2,468 Sq Ft
    • Built 2003

    Last Sold Summary

    • 30% Below List Price
    • $792/SF
    • 320 Days On Market

    Current Estimated Value $2,309,794

    Last Listing Agent Gabi Charity CHARITY & WEISS INTERNATIONAL LLC

    5024 Commonwealth Dr, Sarasota, FL 34242
    • /73

      Est $633,517

      Not Listed For Sale

      5600 Beach Way Dr Unit 215, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,259 Sq Ft
      • Built 1970
      5600 Beach Way Dr Unit 215, Sarasota, FL 34242

      Last Sold Summary

      • 142 Days On Market

  • /77

    $3,539,000

    New Construction Open Sun 1PM - 4PM $119K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,034 Sq Ft

    5103 Windward Ave, Sarasota, FL 34242

    Completed new construction! Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white

    Karen Greco GRECO REAL ESTATE

    5103 Windward Ave, Sarasota, FL 34242
  • /50

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • Condo for Rent

    1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242

    Welcome to this stunning 2-bedroom, 2-bathroom lakefront condo located on the second floor in Gulf and Bay Bayside, Siesta Key. This two-story retreat features two primary bedrooms, each with a luxurious king-size bed, spacious walk-in closets, and beautifully appointed bathrooms with walk-in showers. In the second floor primary bedroom there is additional sleeping accommodations with a full-size

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
  • /2

    $1,250,000

    Sold Apr 30, 2026

    5770 Midnight Pass Rd Unit 404, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft
    • Built 1980

    Last Sold Summary

    • 7% Below List Price
    • $935/SF
    • 37 Days On Market

    Current Estimated Value $1,288,844

    Last Listing Agent Tina Johns COLDWELL BANKER REALTY

    5770 Midnight Pass Rd Unit 404, Sarasota, FL 34242
    • /45

      Not Listed For Sale

      5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1974
      5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242

      Last Sold Summary

      • 172 Days On Market

  • /50

    $2,200,000

    • 4 Beds
    • 2 Baths
    • 2,073 Sq Ft

    589 Commonwealth Ln, Sarasota, FL 34242

    Welcome to your canal front pool home on beautiful Siesta Key. It is a 4 bedroom,2 full bathroom home on approximately .24 acres (10,623 sq ft).It was built in 1972 and now rebuilt in 2026. The house is 2,154 sq ft under air with a 2 car garage which is 462 sq ft. There are brand new Champion windows and sliders,throughout all hurricane impact resistant. The new HVAC system was put in in 2024,

    June Mceleavy PREMIER PLUS REALTY

    589 Commonwealth Ln, Sarasota, FL 34242
  • /26

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 63, Sarasota, FL 34242

    Starting at $179/night! Welcome to your vibrant beachside retreat! This inviting 1-bedroom, 1-bathroom condo is the perfect gateway to both relaxation and adventure. Prepare delicious meals in the fully equipped kitchen and enjoy them in the cozy nearby dining area. Convenience is a priority with your own private carport just steps from the door. At Casa Mar, indulge in resort-style amenities

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 63, Sarasota, 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 $3,712,674

    Last Listing Agent Jessica Hoffman COLDWELL BANKER REALTY

    5263 Avenida de Cortez, Sarasota, FL 34242
    • /45

      Not Listed For Sale

      5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 1974
      5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

      Last Sold Summary

      • 18 Days On Market

  • /9

    $1,950,000

    • Land
    • 15,246 Sq Ft
    • $5,571,429 per Acre

    5174 Sandy Cove Ave, Sarasota, FL 34242

    This oversized cul-de-sac lot has just been cleared and is currently permitted and the slab has been poured. In addition a new 275 foot seawall has also been completed along with a dock and 10,000 lb boat lift. This lot is ready for your new home plans or use the existing plans that have been permitted and approved. Plans with existing builder can be taken over if desired or design your own home

    Troy Jenkins REALTY EXECUTIVES GALLERY

    5174 Sandy Cove Ave, Sarasota, FL 34242
  • /36

    $9,300 Per Month

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

    1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242

    Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute walk. Tile floors throughout and completely re-decorated and furnished with many amenities for your family’s enjoyment. King bed in the master and two doubles in the guest room.*Taxes and fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1272 Siesta Bayside Dr Unit 1272C, 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
    • /47

      Est $1,282,446

      Not Listed For Sale

      20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,282 Sq Ft
      • Built 1973
      20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

      Last Sold Summary

      • 15 Days On Market

  • /67

    $775,000

    • 2 Beds
    • 2 Baths
    • 894 Sq Ft

    6312 Midnight Pass Rd Unit 305S, Sarasota, FL 34242

    Positioned directly on the sands of world-famous Siesta Key, this 2-bedroom, 2-bath en-suite condominium offers the perfect blend of personal getaway and income-producing investment. Fully furnished and thoughtfully configured for vacation living, this residence is already an active vacation rental with proven historical returns, making it an ideal opportunity for buyers seeking a property that

    Ryndie Brusco MICHAEL SAUNDERS & COMPANY

    6312 Midnight Pass Rd Unit 305S, Sarasota, FL 34242
  • /37

    $6,500 Per Month

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

    1215 S Portofino Dr Unit 202, Sarasota, FL 34242

    BEAUTIFUL WATERFRONT CONDO ON SIESTA KEY AVAILABLE NOW AND the month of January! CANAL VIEW • BEACH ACCESS • BOAT SLIPS UPON AVAILABILITY - REASONABLY PRICED. Now available In Season and as an annual Rental! Private, beautifully furnished condo with a gorgeous view of the Harbor and Sailboat Water Canal in Siesta Harbor. Enjoy water views of the canal from your enclosed balcony and just a quick,

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 202, 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 $445,641

    Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

    6029 E Peppertree Way Unit 116, Sarasota, FL 34242
    • /27

      Est $645,533

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,068 Sq Ft
      • Built 1967
      6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

      Last Sold Summary

      • 0 Days On Market

Showing Results 161 - 200, Page 5 of 18

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