9,352

Siesta Key, FL Homes

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  • /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
  • /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

    $1,050,000

    Sold May 27, 2026

    1002 Glebe Ln, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Built 1967

    Last Sold Summary

    • 9% Below List Price
    • $581/SF
    • 70 Days On Market

    Current Estimated Value $1,142,852

    Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1002 Glebe Ln, Sarasota, FL 34242
    • /84

      Est $610,310

      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

  • /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
  • /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

    $1,640,000

    Sold Mar 24, 2026

    5880 Midnight Pass Rd Unit 710, Sarasota, FL 34242

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

    Last Sold Summary

    • 3% Below List Price
    • $957/SF
    • 27 Days On Market

    Current Estimated Value $1,607,368

    Last Listing Agent Kristina Rain MICHAEL SAUNDERS & COMPANY

    5880 Midnight Pass Rd Unit 710, 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

  • /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
  • /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

    $452,000

    Sold Dec 18, 2025

    73 Avenida Messina Unit 15, Sarasota, FL 34242

    • 1 Bed
    • 1 Bath
    • 408 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Below List Price
    • $1,108/SF

    Current Estimated Value $458,166

    Last Listing Agent Maxwell Mann MICHAEL SAUNDERS & COMPANY

    73 Avenida Messina Unit 15, Sarasota, FL 34242
    • /2

      Est $1,369,994

      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

  • /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
  • /16

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 672 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242

    Beach or pool today? Or perhaps you'd rather stay in and enjoy a good book on the charming porch of Villa 53 at Aloha Kai. This beautifully remodeled retreat features an updated kitchen and bath, paired perfectly with coastal-inspired furnishings that create a relaxing home away from home. The spacious bedroom offers generous closet space, ensuring comfort and convenience during your stay.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
  • /2

    $400,000

    Sold Aug 20, 2025

    6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft
    • Built 1974

    Last Sold Summary

    • 26% Below List Price
    • $300/SF
    • 86 Days On Market

    Current Estimated Value $441,615

    Last Listing Agent Julia Montei COLDWELL BANKER REALTY

    6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242
    • /27

      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

  • /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
  • /25

    $12,296 Per Month

    • 2 Beds
    • 2 Baths
    • 1,319 Sq Ft
    • House for Rent

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

    Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience. Step into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
  • /2

    $1,230,000

    Sold Feb 20, 2026

    5354 Calle Florida, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 2,659 Sq Ft
    • Built 1954

    Last Sold Summary

    • 7% Below List Price
    • $463/SF
    • 96 Days On Market

    Current Estimated Value $1,244,265

    Last Listing Agent Angelica Ridley KW COASTAL LIVING III

    5354 Calle Florida, Sarasota, FL 34242
    • /53

      Est $491,008

      Not Listed For Sale

      44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

      • 1 Bed
      • 1 Bath
      • 561 Sq Ft
      • Built 1968
      44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

      Last Sold Summary

      • 3 Days On Market

  • /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
  • /41

    $7,600 Per Month

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

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

    Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
  • /2

    $575,000

    Sold Apr 27, 2026

    5830 Midnight Pass Rd Unit 94, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 921 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Below List Price
    • $624/SF
    • 56 Days On Market

    Current Estimated Value $585,946

    Last Listing Agent Kaitlin Kuhn MICHAEL SAUNDERS & COMPANY

    5830 Midnight Pass Rd Unit 94, Sarasota, FL 34242
    • /2

      Est $532,700

      Not Listed For Sale

      1257 S Portofino Dr Unit 406, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 929 Sq Ft
      • Built 1968
      1257 S Portofino Dr Unit 406, Sarasota, FL 34242

      Last Sold Summary

      • 22 Days On Market

  • /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
  • /72

    $5,000 Per Month

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft
    • Condo for Rent

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242

    Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

    Margaret Young JENNETTE PROPERTIES, INC.

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
  • /2

    $650,000

    Sold Jul 14, 2025

    4510 Banan Place, Sarasota, FL 34242

    • Land
    • 10,454 Sq Ft
    • $2,708,333 per Acre

    Last Sold Summary

    • 13% Below List Price
    • 163 Days On Market

    Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

    4510 Banan Place, Sarasota, FL 34242
    • /2

      Est $559,257

      Not Listed For Sale

      1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 975 Sq Ft
      • Built 1974
      1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242

      Last Sold Summary

      • 36 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
  • /31

    $7,000 Per Month

    • 2 Beds
    • 11 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242

    This property is a 30 night minimum.1200-303 is a Bay side Mid-rise unit, located approximately 150 yards away from the Bay.Newly remodeled kitchen with stainless steel appliances. Grab bars located in both bathrooms. Guest bedroom T.V is mounted on the wall. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding:

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
  • /2

    $729,000

    Sold Oct 17, 2025

    1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $570/SF
    • 96 Days On Market

    Current Estimated Value $718,207

    Last Listing Agent Gina LaRouche COLDWELL BANKER REALTY

    1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242
    • /77

      Est $641,093

      Not Listed For Sale

      6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,068 Sq Ft
      • Built 1968
      6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

      Last Sold Summary

      • 20 Days On Market

  • /100

    $2,249,000

    $451K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,541 Sq Ft

    5012 Higel Ave, Sarasota, FL 34242

    Virtually Staged. Discover this FULLY RENOVATED four-bedroom, three-bathroom sanctuary spanning 3,541 square feet, where luxury living meets WATERFRONT tranquility. Situated on almost a half acre lot, with rear views facing west for colorful sunsets, this meticulously crafted residence boasts a heated pool, a floating dock and long seawall inviting water enthusiasts to enjoy exploring the canals

    Rachelle Tirey PREFERRED SHORE LLC

    5012 Higel Ave, Sarasota, FL 34242
  • /30

    $3,500 Per Month

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

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242

    BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane glass lanai,

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
  • /2

    $460,000

    Sold Dec 04, 2025

    5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $455/SF
    • 92 Days On Market

    Current Estimated Value $467,807

    Last Listing Agent Janet Trefry RE/MAX ALLIANCE GROUP

    5649 Midnight Pass Rd Unit 804, Sarasota, FL 34242
    • /66

      Est $537,838

      Not Listed For Sale

      23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

      • 1 Bed
      • 1 Bath
      • 561 Sq Ft
      • Built 1967
      23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

      Last Sold Summary

      • 24 Days On Market

  • /73

    $5,985,000

    $915K PRICE DROP
    • 5 Beds
    • 7 Baths
    • 6,928 Sq Ft

    5132 Jungle Plum Rd, Sarasota, FL 34242

    Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm

    Joel Schemmel DOUGLAS ELLIMAN

    5132 Jungle Plum Rd, Sarasota, FL 34242
  • /16

    $8,370 Per Month

    • 2 Beds
    • 1 Bath
    • 780 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242

    Villa 45 at Aloha Kai is a light-filled coastal retreat featuring an updated kitchen that perfectly complements its bright, beachy furnishings. Whether you prefer a refreshing swim in the Gulf of Mexico or a relaxing afternoon by the pool, the choice is yours. With a king bed and two twin beds, this villa comfortably accommodates guests, making it ideal for a family visit. The front porch and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 45, Sarasota, FL 34242
  • /2

    $865,000

    Sold Mar 05, 2026

    315 Avenida de Paradisio, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft
    • Built 1971

    Last Sold Summary

    • 9% Below List Price
    • $591/SF
    • 105 Days On Market

    Current Estimated Value $893,337

    Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC

    315 Avenida de Paradisio, Sarasota, FL 34242
    • /41

      Est $645,825

      Not Listed For Sale

      141 Avenida Messina Unit 3, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,016 Sq Ft
      • Built 1966
      141 Avenida Messina Unit 3, Sarasota, FL 34242

      Last Sold Summary

      • 1 Day On Market

Showing Results 121 - 160, Page 4 of 18

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