9,261

Siesta Key, FL Homes

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  • /37

    $7,950,000

    New Construction $2M PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 6,206 Sq Ft

    84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242

    Virtually Staged. Experience luxury living at its finest in this breathtaking one-of-a-kind new construction condominium nestled directly on the pristine shores of world famous Siesta Beach. Spanning over 6200 square feet, this exclusive residence offers unparalleled opulence and panoramic views of the azure waters and fiery sunsets. Elegance meets convenience with a private elevator whisking you

    Thomas Cail RE/MAX ALLIANCE GROUP

    84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242
  • /96

    $4,500 Per Month

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

    1257 S Portofino Dr Unit 38, Sarasota, FL 34242

    Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice décor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the

    Kay Esposito SIGNATURE REALTY ASSOCIATES

    1257 S Portofino Dr Unit 38, Sarasota, FL 34242
  • /2

    $900,000

    Sold Aug 29, 2025

    5108 Saint Albans Ave, Sarasota, FL 34242

    • 3 Beds
    • 3.5 Baths
    • 1,767 Sq Ft
    • Built 1968

    Last Sold Summary

    • 20% Below List Price
    • $509/SF
    • 57 Days On Market

    Current Estimated Value $949,266

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5108 Saint Albans Ave, Sarasota, FL 34242
    • /2

      Est $429,025

      Not Listed For Sale

      1350 N Portofino Dr Unit 310, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,123 Sq Ft
      • Built 1969
      1350 N Portofino Dr Unit 310, Sarasota, FL 34242

      Last Sold Summary

      • 335 Days On Market

      Last Listing Agent Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  • /54

    $1,150,000

    • 4 Beds
    • 3 Baths
    • 2,165 Sq Ft

    4114 Roberts Point Cir, Sarasota, FL 34242

    Set along a quiet bayou in Roberts Point, one of North Siesta Key’s most coveted and established neighborhoods, this well-cared-for waterfront residence offers an appealing combination of immediate livability, flexible space and exceptional future potential. Enjoy the home as it is, thoughtfully update it over time or create an entirely new island retreat among the neighborhood’s impressive

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4114 Roberts Point Cir, Sarasota, FL 34242
  • /50

    $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 in

    Robert Bevington SHOWTIME REALTY

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

    $550,000

    Sold Aug 10, 2026

    5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242

    • 1 Bed
    • 1.5 Baths
    • 728 Sq Ft
    • Built 1963

    Last Sold Summary

    • 14% Below List Price
    • $755/SF
    • 181 Days On Market

    Current Estimated Value $577,038

    Last Listing Agent Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

    5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242
    • /80

      Est $2,961,306

      Not Listed For Sale

      5322 Siesta Cove Dr, Sarasota, FL 34242

      • 4 Beds
      • 3 Baths
      • 3,571 Sq Ft
      • Built 1979
      5322 Siesta Cove Dr, Sarasota, FL 34242

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /94

    $1,349,000

    • 3 Beds
    • 3.5 Baths
    • 2,691 Sq Ft

    3942 Hamilton Club Cir Unit 13, Sarasota, FL 34242

    Siesta Key, exclusive gated community of only 18 homes with Marina, pool and tennis all within a private, lush, tropical paradise . Walking paths around the lagoon as well as the beautiful Marina make Hamilton Club a truly unique lifestyle. Inspired by the architcture of Bermuda with its close ties to 17th Century Great Britian is recognised by its striking pastel colored walls and "welcoming

    Barbara Dumbaugh MICHAEL SAUNDERS & COMPANY

    3942 Hamilton Club Cir Unit 13, Sarasota, FL 34242
  • /9

    $7,500 Per Month

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

    6154 Midnight Pass Rd Unit 15, Sarasota, FL 34242

    njoy your stay at our remodeled private (no shared walls) detached large 2 bedroom 2 bath villa on Siesta Key (Villa "C15" at Casa Blanca Vacation Rentals (CBVR) - no common walls, 1100 sq ft, sleeps 6). We remodeled C15 with a new air conditioner system, kitchen appliances, bedroom/living room/dining room/lanai furniture, new mattresses & Laura Ashley bedding, new plates/dishes/glasses, new

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 15, Sarasota, FL 34242
  • /2

    $800,000

    Sold May 28, 2026

    0 Midnight Pass Rd Unit MFRA4692398, Sarasota, FL 34242

    • Land
    • 8,276 Sq Ft
    • $4,210,526 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

    0 Midnight Pass Rd Unit MFRA4692398, Sarasota, FL 34242
    • /2

      Est $2,653,529

      Not Listed For Sale

      497 Island Cir, Sarasota, FL 34242

      • 4 Beds
      • 3.5 Baths
      • 2,964 Sq Ft
      • Built 2007
      497 Island Cir, Sarasota, FL 34242

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /47

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,916 Sq Ft

    622 Tropical Cir, Sarasota, FL 34242

    Beautifully reimagined and thoughtfully updated, this modern coastal residence on Siesta Key offers the relaxed island lifestyle so many buyers are seeking, with a wonderful blend of style, comfort and low-maintenance living. Set on an oversized lot in a peaceful neighborhood near the world-famous white quartz sands of Siesta Beach and the charm of Siesta Village, this move-in-ready home feels

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    622 Tropical Cir, Sarasota, FL 34242
  • /73

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Condo for Rent

    1355 S Portofino Dr Unit 103, Sarasota, FL 34242

    Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in stunning the stunning views from your own private vantage points. This

    Teresa Ribaudo JENNETTE PROPERTIES INC

    1355 S Portofino Dr Unit 103, Sarasota, FL 34242
  • /2

    $925,000

    Sold Dec 08, 2025

    396 Avenida Madera, Sarasota, FL 34242

    • 3 Beds
    • 3 Baths
    • 1,964 Sq Ft
    • Built 1958

    Last Sold Summary

    • 20% Below List Price
    • $471/SF
    • 148 Days On Market

    Current Estimated Value $982,856

    Last Listing Agent Michael Nogueira LUXURY & BEACH REALTY INC

    396 Avenida Madera, Sarasota, FL 34242
    • /2

      Est $1,031,255

      Not Listed For Sale

      615 Avenida Del Norte, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1962
      615 Avenida Del Norte, Sarasota, FL 34242

      Last Sold Summary

      • 90 Days On Market

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

  • /68

    $479,000

    • 1 Bed
    • 1 Bath
    • 708 Sq Ft

    6006 Midnight Pass Rd Unit 60, Sarasota, FL 34242

    Beautifully Updated One-Bedroom Condo on Siesta KeyEnjoy the best of island living in this beautifully updated one-bedroom, one-bath condominium on Siesta Key. This inviting unit has been completely updated and features all-new appliances and a new water heater, offering a fresh, move-in-ready interior.The community offers an impressive selection of on-site amenities, including:• Two

    Dawn Lacey LACEY REALTY INC

    6006 Midnight Pass Rd Unit 60, Sarasota, FL 34242
  • /81

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • Condo for Rent

    4822 Ocean Blvd Unit 2F, Sarasota, FL 34242

    Gulf Views!!Siesta Key! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key and is close to restaurants and outdoor recreation. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The large

    Jane Hunter JENNETTE PROPERTIES INC

    4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
  • /2

    $357,000

    Sold Sep 19, 2025

    1300 N Portofino Dr Unit 208, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 991 Sq Ft
    • Built 1969

    Last Sold Summary

    • 29% Below List Price
    • $360/SF
    • 403 Days On Market

    Current Estimated Value $406,835

    Last Listing Agent Jill Thomas BERKSHIRE HATHAWAY HOMESERVICE

    1300 N Portofino Dr Unit 208, Sarasota, FL 34242
    • /47

      Est $1,828,620

      Not Listed For Sale

      615 Calle Del Otono, Sarasota, FL 34242

      • 3 Beds
      • 3.5 Baths
      • 2,616 Sq Ft
      • Built 2022
      615 Calle Del Otono, Sarasota, FL 34242

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Dale OHara, LLC PREFERRED SHORE LLC

  • /100

    $6,300,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 4,841 Sq Ft

    1355 Roberts Bay Ln, Sarasota, FL 34242

    NEW 2026 MODERN TROPICAL ESTATE | 5 BEDROOMS | 2 PRIMARY SUITES | 3-CAR GARAGE | POOL CABANA | INTRACOASTAL VIEWSCompleted in 2026 by CribbsCo Development, this modern tropical residence makes an architectural statement with an approximately 9.5' x 9' Sapele wood pivot entry door handcrafted in the U.S. Two primary suites feature custom finished walk-in closets. The upstairs main primary

    Carolyn LoBue PREFERRED SHORE LLC

    1355 Roberts Bay Ln, Sarasota, FL 34242
  • /33

    $8,500 Per Month

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

    1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242

    Embrace coastal living in this inviting 2-bedroom, 2-bathroom first-level condo nestled within the prestigious Gulf & Bay Club Bayside in Siesta Key, Florida. Step inside to discover a thoughtfully designed space adorned with coastal-inspired décor and an abundance of natural light. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating an ideal space for

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
  • /2

    $700,000

    Sold Aug 27, 2025

    1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242

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

    Last Sold Summary

    • 18% Below List Price
    • $547/SF
    • 155 Days On Market

    Current Estimated Value $715,680

    Last Listing Agent Fred Sieger Jr COMPASS FLORIDA LLC

    1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242
    • /2

      Est $1,189,662

      Not Listed For Sale

      1260 Dolphin Bay Way Unit 402, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,915 Sq Ft
      • Built 1997
      1260 Dolphin Bay Way Unit 402, Sarasota, FL 34242

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Pam Charron COMPASS FLORIDA LLC

  • /53

    $1,649,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft

    6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242

    It's all about THE VIEW and the DIRECT SIESTA KEY BEACH ACCESS!!! This first floor condominium has a FULL GULF VIEW from the living room and glassed-in lanai. The water views are amazing, and the sunsets are gorgeous! You'll walk out your front door right down to the sand to enjoy the warm Gulf water in minutes. There was no water intrusion or water damage to this unit in past storms, as several

    Susan Keal MICHAEL SAUNDERS & COMPANY

    6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242
  • /72

    $4,500 Per Month

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

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242

    Available April 1, 2027! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor Fishing Pier.

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
  • /2

    $1,350,000

    Sold Dec 08, 2025

    5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,498 Sq Ft
    • Built 1982

    Last Sold Summary

    • 7% Below List Price
    • $901/SF
    • 38 Days On Market

    Current Estimated Value $1,347,740

    Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

    5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242
    • /2

      Est $762,531

      Not Listed For Sale

      5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 925 Sq Ft
      • Built 1971
      5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  • /33

    $874,900

    Open Sat 2PM - 4PM
    • 2 Beds
    • 2 Baths
    • 1,282 Sq Ft

    19 Whispering Sands Dr Unit 201, Sarasota, FL 34242

    ENDLESS POSSIBILITIES ON SIESTA KEY. Welcome to 19 Whispering Sands Drive, Unit 201, an exceptional opportunity to create your own Gulf Coast retreat in one of Siesta Key’s most established beachfront communities. Whether you choose to enjoy the residence as it is, renovate it over time, or completely reimagine the interior to reflect your own style, the possibilities are nearly endless. For

    Frank Golio LEGACY BAY PARTNERS

    19 Whispering Sands Dr Unit 201, Sarasota, FL 34242
  • /18

    $2,500 Per Month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Property for Rent

    6020 Midnight Pass Rd, Sarasota, FL 34242

    DIRECT BEACH ACCESS! Beautifully located 1 bed/1 bath second-floor unit in the sought-after Aloha Kai community on Midnight Pass Rd, This fully furnished unit offers relaxing pool views and is move-in ready in this well-maintained beachside community. Available for 2 adults, no pets. Water and electricity included in rent. On-site parking available. Steps from the sand — perfect for tenants

    Koen Roelens ROELENS REALTY & PROPERTY MANA

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

    $1,340,000

    Sold Jun 29, 2026

    20 Whispering Sands Dr Unit 1102, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,464 Sq Ft
    • Built 1973

    Last Sold Summary

    • 4% Below List Price
    • $915/SF
    • 83 Days On Market

    Current Estimated Value $1,359,049

    Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

    20 Whispering Sands Dr Unit 1102, Sarasota, FL 34242
    • /2

      Est $592,428

      Not Listed For Sale

      5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1976
      5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Christine Green COLDWELL BANKER REALTY

  • /31

    $679,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 921 Sq Ft

    5830 Midnight Pass Rd Unit 93, Sarasota, FL 34242

    Under contract-accepting backup offers. Welcome to Jamaica Royale #93, a beautifully remodeled two-bedroom, two-bath garden-view condominium nestled within the lush tropical grounds of Jamaica Royale on world-renowned Siesta Key. Offering 921 square feet of thoughtfully updated living space, this inviting coastal retreat showcases a complete 2025 renovation with quality finishes throughout,

    Robert Bevington SHOWTIME REALTY

    5830 Midnight Pass Rd Unit 93, Sarasota, FL 34242
  • /55

    $5,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft
    • House for Rent

    4946 Commonwealth Dr, Sarasota, FL 34242

    This is a short term vacation rental. Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the private dock, watching

    Beth Dilley ASCENDIA REAL ESTATE

    4946 Commonwealth Dr, Sarasota, FL 34242
  • /2

    $420,000

    Sold Jan 05, 2026

    6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242

    • 2 Beds
    • 1.5 Baths
    • 860 Sq Ft
    • Built 1979

    Last Sold Summary

    • 14% Below List Price
    • $488/SF
    • 30 Days On Market

    Current Estimated Value $440,640

    Last Listing Agent Nancie Kalin MICHAEL SAUNDERS & COMPANY

    6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242
    • /2

      Est $972,001

      Not Listed For Sale

      4439 Ocean Blvd, Sarasota, FL 34242

      • 1 Bed
      • 1 Bath
      • 3,042 Sq Ft
      • Built 1951
      4439 Ocean Blvd, Sarasota, FL 34242

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Jay Hogue DALTON WADE INC

  • /39

    $449,000

    $16K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft

    5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242

    Welcome to Unit 201 at White Sands Condominium — a bright, airy coastal retreat perfectly positioned on iconic Midnight Pass Road, Siesta Key. This spacious 1,012 sq ft, two-bedroom, two-bathroom condo is your gateway to the laid-back island lifestyle you've been dreaming of. Whether you choose to walk, cycle, or simply stroll, the world-famous Siesta Key Beach — voted the #1 beach in the USA —

    Meredith French COLDWELL BANKER REALTY

    5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242
  • /36

    $9,500 Per Month

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

    1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242

    Welcome to your elevated sanctuary in paradise – a second-floor two-bedroom condo at Gulf & Bay Bayside on the enchanting Siesta Key, Florida. Upon entering, you're immediately greeted by an open-concept living space that seamlessly integrates the interior with the scenic beauty beyond. The living area, adorned with coastal-inspired décor, invites you to relax in comfort while large

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
  • /2

    $852,500

    Sold Jan 07, 2026

    5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $626/SF
    • 20 Days On Market

    Current Estimated Value $864,224

    Last Listing Agent Curtis Ware KW COASTAL LIVING III

    5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242
    • /77

      Est $1,511,393

      Not Listed For Sale

      5319 Siesta Cove Dr, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,740 Sq Ft
      • Built 1989
      5319 Siesta Cove Dr, Sarasota, FL 34242

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Tammy Garner COLDWELL BANKER REALTY

Showing Results 481 - 520, Page 13 of 18

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