9,257

Siesta Key, FL Homes

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  • /44

    $340,000

    $79K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 820 Sq Ft

    4822 Ocean Blvd Unit 11E, Sarasota, FL 34242

    Milestone completed with no repairs required. THE LOWEST price in this building over the last 5 years to be had at an amazing bargain.Pound for pound dollar for dollar one of the best bargains on the beach.11th-floor Gulf views, Siesta Key Beach right down the road, and a price point that gives you real upside.This the kind of condo/value combination people hope for. The unit has

    Nathan Shirk EXP REALTY LLC

    4822 Ocean Blvd Unit 11E, Sarasota, FL 34242
  • /19

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,264 Sq Ft
    • House for Rent

    143 Whispering Sands Dr, Sarasota, FL 34242

    Available for season 2027! This 2 bedroom 2 bath villa with easy ground floor entry features tile flooring in the main living areas and plush new carpeting in the bedrooms. The stylish galley kitchen has been fully updated with custom white cabinetry, granite countertops and backsplash, recessed lighting, and brand-new GE appliances, perfect for preparing meals after a day at the beach.Enjoy

    Maureen Plichta STRINGER MANAGEMENT INC

    143 Whispering Sands Dr, Sarasota, FL 34242
  • /2

    $1,835,000

    Sold Jan 29, 2026

    5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft
    • Built 1982

    Last Sold Summary

    • 6% Below List Price
    • $1,071/SF
    • 23 Days On Market

    Current Estimated Value $1,781,213

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

    5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242
    • /63

      Est $673,438

      Not Listed For Sale

      6015 W Peppertree Way Unit 237, Sarasota, FL 34242

      • 2 Beds
      • 2.5 Baths
      • 1,310 Sq Ft
      • Built 1974
      6015 W Peppertree Way Unit 237, Sarasota, FL 34242

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Rachel Tritschler RE/MAX ALLIANCE GROUP

  • /76

    $1,950,000

    • 2 Beds
    • 2 Baths
    • 1,449 Sq Ft

    5740 Midnight Pass Rd Unit 403, Sarasota, FL 34242

    A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf

    Drew Jacobsen COMPASS FLORIDA LLC

    5740 Midnight Pass Rd Unit 403, Sarasota, FL 34242
  • /25

    $8,500 Per Month

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

    1125 W Peppertree Dr Unit 707, Sarasota, FL 34242

    2 BR - 2 BA - 4 Person Max - Gulf side - Mid-Rise - Approx.150 yards from beach This property is a 30 night minimum.This 2-bedroom, 2 bath located on the gulf side is approx. 150 yards from the beach. This unit is on the 7th floor, accessible via elevator or stairs. Plenty of room for dining at the 6-service dining table. Couches, a ceiling fan, and TV in the living room for

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 707, Sarasota, FL 34242
  • /2

    $630,000

    Sold Jan 07, 2026

    753 Tropical Cir, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,695 Sq Ft
    • Built 1979

    Last Sold Summary

    • 21% Below List Price
    • $372/SF
    • 82 Days On Market

    Current Estimated Value $750,717

    Last Listing Agent Patrick Ritchey RE/MAX ALLIANCE GROUP

    753 Tropical Cir, Sarasota, FL 34242
    • /2

      Est $1,699,214

      Not Listed For Sale

      1031 Contento St, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,853 Sq Ft
      • Built 1971
      1031 Contento St, Sarasota, FL 34242

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /19

    $419,000

    Pending
    • 1 Bed
    • 1 Bath
    • 751 Sq Ft

    5855 Midnight Pass Rd Unit 514, Sarasota, FL 34242

    Virtually Staged. COASTAL RESORT LIVING JUST MINUTES FROM SIESTA KEY BEACH! Enjoy the best of Siesta Key living in this beautifully updated and move-in-ready condominium at Harbor Towers, one of the island's most sought-after waterfront communities. Located just a short distance from the world-renowned Siesta Key Beach, this large one-bedroom, one-bath residence offers beautiful bay and

    Jamie Zeigler ENGEL & VOLKERS NEW SMYRNA

    5855 Midnight Pass Rd Unit 514, Sarasota, FL 34242
  • /9

    $10,770 Per Month

    • 2 Beds
    • 2 Baths
    • 1,043 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242

    We welcome you to stay in our updated oceanfront condo on Siesta Key Crescent Beach - the best beach in Florida! Our spacious 2 bed/2 bath oceanfront home is 1080 square feet with an ocean view that cannot be beat! Unit #206 is part of the Casa Blanca Vacation Beach Resort, and the crystal white sand is steps away! Remodeled in 2023, fully equipped kitchen with quiet dishwasher, spacious living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242
  • /2

    $660,000

    Sold Sep 17, 2025

    6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Built 1975

    Last Sold Summary

    • 12% Below List Price
    • $512/SF
    • 187 Days On Market

    Current Estimated Value $677,195

    Last Listing Agent Crystal Saly RE/MAX PALM

    6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242
    • /85

      Est $1,421,225

      Not Listed For Sale

      459 Avenida de Mayo, Sarasota, FL 34242

      • 4 Beds
      • 3 Baths
      • 1,805 Sq Ft
      • Built 1996
      459 Avenida de Mayo, Sarasota, FL 34242

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Jackie Eberley COLDWELL BANKER REALTY

  • /39

    $2,299,000

    $191K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,277 Sq Ft

    4708 Ocean Blvd Unit E7, Sarasota, FL 34242

    Under contract-accepting backup offers. Experience refined coastal living in North Siesta Key at 4708 Ocean Boulevard, a fully renovated 2025 corner residence ideally positioned on the Gulf of Mexico at Big Pass. This exceptional 3-bedroom, 3-bath condominium offers unobstructed panoramic views of the Gulf, Sarasota Bay, and distant vistas of Lido Key and downtown Sarasota. Encompassing 2,277

    Stacey King MICHAEL SAUNDERS & COMPANY

    4708 Ocean Blvd Unit E7, Sarasota, FL 34242
  • /41

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • House for Rent

    5577 Contento Dr, Sarasota, FL 34242

    This is a short term (weekly) rental. Listing reflects off season rate. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates

    Beth Dilley ASCENDIA REAL ESTATE

    5577 Contento Dr, Sarasota, FL 34242
  • /2

    $801,000

    Sold Jun 18, 2026

    1700 Cove II Place Unit 324, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft
    • Built 1979

    Last Sold Summary

    • 6% Below List Price
    • $466/SF
    • 63 Days On Market

    Current Estimated Value $816,371

    Last Listing Agent Kim Sheridan WATERSIDE REALTY LLC

    1700 Cove II Place Unit 324, Sarasota, FL 34242
    • /78

      Est $1,587,295

      Not Listed For Sale

      5168 Sandy Shore Ave, Sarasota, FL 34242

      • 4 Beds
      • 2 Baths
      • 2,256 Sq Ft
      • Built 1963
      5168 Sandy Shore Ave, Sarasota, FL 34242

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jackie Eberley COLDWELL BANKER REALTY

  • /39

    $499,900

    • 1 Bed
    • 1 Bath
    • 751 Sq Ft

    5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242

    THE VIEW, THE VIEW, Location, Location. This is IT! RESORT LIVING UNDER $500,000! EVERY AMENITY AT YOUR FINGERTIPS! BEAUTIFULLY APPOINTED, IMPRESSIVE ENTRANCE WITH WATERFALL, WALK INTO THE LUXURY APPOINTED HUGE FOYER--TURN KEY INCOME GENERATING VACATION HOME! STUNNINGLY SELECTED AND DESIGNED UNIT OVERLOOKING THE POOL AND VIEW OF INTRACOASTAL WATERWAY---DESIRABLE 2 WEEK RENTAL WHEN YOURE NOT HERE,

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
  • /30

    $7,000 Per Month

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

    1360 Siesta Bayside Dr, Sarasota, FL 34242

    This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key's world- renowned white sandy beach on the

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1360 Siesta Bayside Dr, Sarasota, FL 34242
  • /2

    $9,400,000

    Sold Jul 31, 2026

    70 Avenida Veneccia Unit 402, Sarasota, FL 34242

    • 3 Beds
    • 4 Baths
    • 4,510 Sq Ft
    • Built 2025

    Last Sold Summary

    • $2,084/SF
    • 0 Days On Market

    Last Listing Agent David Lehrman THE SARASOTA REAL ESTATE COMP.

    70 Avenida Veneccia Unit 402, Sarasota, FL 34242
    • /2

      Est $1,482,472

      Not Listed For Sale

      1302 Roberts Bay Ln, Sarasota, FL 34242

      • 4 Beds
      • 3 Baths
      • 2,095 Sq Ft
      • Built 1985
      1302 Roberts Bay Ln, Sarasota, FL 34242

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Tori Harless COLDWELL BANKER REALTY

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