9,352

Siesta Key, FL Homes

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  • /53

    $400,000

    $75K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 845 Sq Ft

    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

    Welcome to the world-famous Siesta Key! Now available a second-floor one-bedroom, one-bath condominium in the desirable Gulf and Bay Club Bayside. This particular condo had zero flood or storm damage. This home is just waiting for your personal touch! Enjoy direct deeded beach access just across the street to Siesta Key Beach and live a true resort-style life with wonderful amenities at your

    Agent Photo

    Jessica Ross, PA

    COLDWELL BANKER REALTY

    1200 Siesta Bayside Dr Unit 1200G, 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

  • /64

    $595,800

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

    6415 Midnight Pass Rd Unit 306, Sarasota, FL 34242

    Welcome to one of the best locations on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Location is fantastic! Wait until you see the grounds! You have the best of both worlds. Your new condominium is a 2 bedroom 2 bathroom split plan with brand-new hurricane sliding doors. Inside you have abundant

    Agent Photo

    Anthony DeLuca

    DELUCA REALTY INC

    6415 Midnight Pass Rd Unit 306, 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

  • /52

    $75,000

    • 3 Beds
    • 3 Baths
    • 1,780 Sq Ft

    915 Seaside Dr Unit 504, Weeks 6-7, Sarasota, FL 34242

    Fractional Ownership. Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Package—featuring one-sixteenth ownership of an extraordinary Siesta Key Beach residence. Your dream of owning a new, high-end home on America’s #1 beach can now be a reality, offering an effortless way to enjoy the best of beachfront living without compromise. Step into an

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 504, Weeks 6-7, 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

    $4,950,000

    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
  • /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

  • /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
  • /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

  • /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
  • /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

  • /49

    $1,050,000

    $22K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,168 Sq Ft

    611 Venice Ln, Sarasota, FL 34242

    Island living meets easy everyday comfort in this turnkey furnished Siesta Key pool home. With 3 bedrooms, 2 bathrooms, approximately 2,168 square feet of living space and a 2-car garage, there is room for full-time living, a vacation getaway, or a high-demand rental.Built of concrete block, this Ruth Richmond home offers peace of mind with major updates already done: brand new metal roof

    Christine Pope MICHAEL SAUNDERS & COMPANY

    611 Venice Ln, 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

  • /45

    $549,000

    • 1 Bed
    • 1 Bath
    • 728 Sq Ft

    5830 Midnight Pass Rd Unit 51, Sarasota, FL 34242

    Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. Fantastic opportunity to own your own slice of paradise. This 1 bed, 1 bath villa located at Jamaica Royale is ready for immediate occupancy. This beachfront complex is the perfect place to relax and unwind. Featuring 3 pools, beachfront lounge chairs, grills, shuffleboard, and other

    Steve Cavanaugh TIDELINE REAL ESTATE BROKERS

    5830 Midnight Pass Rd Unit 51, 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

  • /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
  • /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

  • /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
  • /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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