9,352

Siesta Key, FL Homes

Section Image Section Image
  • /52

    $584,500

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,287 Sq Ft

    6415 Midnight Pass Rd Unit 705, Sarasota, FL 34242

    Welcome to the best location 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. Walk to bars, restaurants, the beach. You can walk across the street and rent a boat. Speaking of boats you can dock your boat on our giant seawall for $10.00... yes...ten dollars a month. Your new condominium is an open floor

    Agent Photo

    Anthony DeLuca

    DELUCA REALTY INC

    6415 Midnight Pass Rd Unit 705, Sarasota, FL 34242
  • /20

    $5,488

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 850 Sq Ft
    • Condo for Rent

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242

    The advertised rate of $5,488/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 3, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
  • /2

    $1,525,000

    Sold May 07, 2026

    312 Canal Rd, Sarasota, FL 34242

    • 4 Beds
    • 4 Baths
    • 1,792 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Below List Price
    • $851/SF
    • 11 Days On Market

    Current Estimated Value $1,817,034

    Last Listing Agent Curtis Ware KW COASTAL LIVING III

    312 Canal Rd, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      5963 Midnight Pass Rd Unit 344, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 1974
      5963 Midnight Pass Rd Unit 344, Sarasota, FL 34242

      Last Sold Summary

      • 1 Day On Market

  • /71

    $1,725,000

    • 3 Beds
    • 3.5 Baths
    • 2,080 Sq Ft

    548A Beach Rd, Sarasota, FL 34242

    Beautifully renovated Tiffany Sands townhome offering the perfect combination of coastal elegance, spacious living, and an exceptional Siesta Key location with tranquil beach views. This 3-bedroom, 3.5-bath residence features an open, light-filled floor plan designed for effortless island living. Each generously sized bedroom includes a walk-in closet, providing ample comfort and storage. A

    Agent Photo

    Jennifer Thompson

    WILLIAM RAVEIS - FLORIDA LLC

    548A Beach Rd, Sarasota, FL 34242
  • /20

    $8,832

    Total Monthly Price

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

    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242

    The advertised rate of $8,833/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
  • /2

    $650,000

    Sold Mar 31, 2026

    4660 Ocean Blvd Unit E2, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Below List Price
    • $542/SF
    • 25 Days On Market

    Current Estimated Value $647,892

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

    4660 Ocean Blvd Unit E2, Sarasota, FL 34242
    • /72

      Est $624,541

      Not Listed For Sale

      101 Whispering Sands Dr Unit 206, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,271 Sq Ft
      • Built 1969
      101 Whispering Sands Dr Unit 206, Sarasota, FL 34242

      Last Sold Summary

      • 1 Day On Market

  • /59

    $125,000

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

    915 Seaside Dr Unit 606, Weeks 14-17, Sarasota, FL 34242

    Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Ownership Package, offering 2 one sixteenth ownership packages of an exceptional Siesta Key Beach residence. This is a rare opportunity to own four consecutive winter weeks (Weeks 14–17), plus 2 additional float weeks—providing extended beachfront living during the most desirable season on

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 606, Weeks 14-17, Sarasota, FL 34242
  • /16

    $9,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Condo for Rent

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242

    Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
  • /2

    $1,450,000

    Sold Nov 04, 2025

    4108 Roberts Point Rd, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 2,511 Sq Ft
    • Built 2001

    Last Sold Summary

    • 23% Below List Price
    • $577/SF
    • 142 Days On Market

    Current Estimated Value $1,465,487

    Last Listing Agent Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    4108 Roberts Point Rd, Sarasota, FL 34242
    • /36

      Est $869,729

      Not Listed For Sale

      1600 Cove II Place Unit 420, Sarasota, FL 34242

      • 3 Beds
      • 2.5 Baths
      • 1,720 Sq Ft
      • Built 1979
      1600 Cove II Place Unit 420, Sarasota, FL 34242

      Last Sold Summary

      • 57 Days On Market

  • /96

    $449,900

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft

    1257 S Portofino Dr Unit 104, Sarasota, FL 34242

    Bring your boat and dock steps from your back door.. Turnkey living in Siesta Harbor, a 55+ waterfront community, with beautiful canal water views and private beach access. This fully renovated 1-bedroom, 2-bath condo offers an open floor plan, updated kitchen and bathrooms, newer impact sliding doors, and a newer HVAC system (2021). Enjoy peaceful water views from the enclosed lanai as boats

    Agent Photo

    Suzy Kolaz

    KELLER WILLIAMS ON THE WATER S

    1257 S Portofino Dr Unit 104, Sarasota, FL 34242
  • /73

    $5,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,595 Sq Ft
    • ALL THE CHARM! - Siesta Key 1+ acre on the Bay - 3 bed/ 2 bath pool home

    4237 Higel Ave, Siesta Key, FL 34242

    Charming 3 bed/2 bath waterfront estate located on the coveted north end of Siesta Key. This parcel is one of the last of its kind, featuring 1.3 acres of prime waterfront property overlooking Cocoanut Bayou. Completely private by its original growth of lush tropical landscaping, this property is captivating for all your senses.  This 1,500 sqft home was built in 1946 and will wow you from the

    4237 Higel Ave, Siesta Key, FL 34242
  • /2

    $1,113,000

    Sold May 06, 2026

    5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • Built 1976

    Last Sold Summary

    • 13% Below List Price
    • $866/SF
    • 126 Days On Market

    Current Estimated Value $1,178,508

    Last Listing Agent Beverly Schroeder PLUMLEE GULF BEACH REALTY

    5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242
    • /35

      Est $2,159,274

      Not Listed For Sale

      6900 Bochi Cir, Sarasota, FL 34242

      • 4 Beds
      • 4.5 Baths
      • 3,774 Sq Ft
      • Built 2012
      6900 Bochi Cir, Sarasota, FL 34242

      Last Sold Summary

      • 242 Days On Market

  • /50

    $48,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    915 Seaside Dr Unit 312, Weeks 16-17, Sarasota, FL 34242

    Fractional Ownership. Experience luxury beachfront living with this Winter Fractional Package offering a 1/16th share of ownership at The Residences on Siesta Key Beach. This is a rare opportunity to own a piece of paradise on one of America’s top-rated beaches while enjoying the comfort, convenience, and services of a luxury resort. This expansive residence features a primary suite, junior

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 312, Weeks 16-17, Sarasota, FL 34242
  • /35

    $7,400 Per Month

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

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242

    Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
  • /2

    $735,000

    Sold Nov 27, 2025

    1055 Beach Rd Unit B204, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $610/SF
    • 29 Days On Market

    Current Estimated Value $728,029

    Last Listing Agent Jason Wood CORCORAN DWELLINGS REALTY

    1055 Beach Rd Unit B204, Sarasota, FL 34242
    • /47

      Est $834,833

      Not Listed For Sale

      1321 Dockside Place, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,307 Sq Ft
      • Built 1982
      1321 Dockside Place, Sarasota, FL 34242

      Last Sold Summary

      • 3 Days On Market

  • /24

    $349,000

    $26K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242

    PRICE IMPROVEMENT. Exceptional Value on Siesta Key Rarely available and beautifully updated, this second-floor 1-bedroom, 1-bathroom residence in White Sands Village offers the perfect blend of coastal living and investment opportunity. Ideally located just across the street from Siesta Key Beach, the condo also enjoys a coveted view of the lush interior courtyard, providing a peaceful and serene

    Agent Photo

    Jim Gammello

    WILLIAM RAVEIS - FLORIDA LLC

    5641 Midnight Pass Rd Unit 904, Sarasota, FL 34242
  • /20

    $6,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,288 Sq Ft
    • Key West style home on Siesta Key minutes to village and beaches

    5157 Sandy Beach Ave, Siesta Key, FL 34242

    ANNUAL RENTAL. Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee. 4 bedrooms and 2.5 baths brings you back inside with a large open

    5157 Sandy Beach Ave, Siesta Key, FL 34242
  • /2

    $580,000

    Sold Mar 13, 2026

    101 Whispering Sands Dr Unit 307, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,271 Sq Ft
    • Built 1969

    Last Sold Summary

    • 19% Below List Price
    • $456/SF
    • 261 Days On Market

    Current Estimated Value $589,559

    Last Listing Agent Todd Goodman KELLER WILLIAMS ON THE WATER S

    101 Whispering Sands Dr Unit 307, Sarasota, FL 34242
    • /2

      Est $7,028,350

      Not Listed For Sale

      1250 Hidden Harbor Way, Sarasota, FL 34242

      • 5 Beds
      • 5.5 Baths
      • 7,506 Sq Ft
      • Built 2002
      1250 Hidden Harbor Way, Sarasota, FL 34242

      Last Sold Summary

      • 502 Days On Market

  • /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
  • /36

    $7,500 Per Month

    • 1 Bed
    • 1 Bath
    • 728 Sq Ft
    • Condo for Rent

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

    Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

    Robert Bevington SHOWTIME REALTY

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
  • /2

    $692,000

    Sold Oct 06, 2025

    6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,387 Sq Ft
    • Built 1981

    Last Sold Summary

    • 13% Below List Price
    • $499/SF
    • 165 Days On Market

    Current Estimated Value $698,594

    Last Listing Agent Marci McFarland MICHAEL SAUNDERS & COMPANY

    6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242
    • /72

      Est $1,362,816

      Not Listed For Sale

      22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 1,876 Sq Ft
      • Built 1969
      22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

      Last Sold Summary

      • 360 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
  • /21

    $2,200 Per Month

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

    212 Pass Key Rd, Sarasota, FL 34242

    Oceanview unit in Siesta Key

    212 Pass Key Rd, Sarasota, FL 34242
  • /2

    $2,850,000

    Sold Apr 17, 2026

    4651 Higel Ave, Sarasota, FL 34242

    • 4 Beds
    • 3 Baths
    • 3,500 Sq Ft
    • Built 2007

    Last Sold Summary

    • 5% Below List Price
    • $814/SF
    • 0 Days On Market

    Current Estimated Value $2,842,848

    Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

    4651 Higel Ave, Sarasota, FL 34242
    • /67

      Est $2,488,402

      Not Listed For Sale

      304 Calle Miramar Unit 2, Sarasota, FL 34242

      • 4 Beds
      • 3.5 Baths
      • 3,236 Sq Ft
      • Built 2009
      304 Calle Miramar Unit 2, Sarasota, FL 34242

      Last Sold Summary

      • 44 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
  • /18

    $5,970 Per Month

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

    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242

    This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
  • /2

    $1,400,000

    Sold Dec 18, 2025

    4865 Featherbed Ln, Sarasota, FL 34242

    • 4 Beds
    • 4 Baths
    • 4,482 Sq Ft
    • Built 1955

    Last Sold Summary

    • 26% Below List Price
    • $312/SF
    • 348 Days On Market

    Current Estimated Value $1,588,667

    Last Listing Agent Janet Boyden PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4865 Featherbed Ln, Sarasota, FL 34242
    • /2

      Est $2,306,348

      Not Listed For Sale

      5408 Plaza Des Las Palmas, Sarasota, FL 34242

      • 5 Beds
      • 5 Baths
      • 2,689 Sq Ft
      • Built 1953
      5408 Plaza Des Las Palmas, Sarasota, FL 34242

      Last Sold Summary

      • 273 Days On Market

  • /13

    $6,400,000

    • 8 Beds
    • 8.5 Baths
    • 5,313 Sq Ft

    5610 Avenida Del Mare, Sarasota, FL 34242

    Prime Siesta Key investment opportunity or dream family compound just steps from the world-famous Siesta Key Public Beach! This exceptional multi-family property features two beautifully updated duplexes (totaling 8 bedrooms and 8.5 baths across 5,331 sq ft) on combined large lots, offering flexible zoning for short-term rentals (1-7 days), long-term income, or a luxurious private residence.

    Agent Photo

    Tonna Gruber

    COLDWELL BANKER REALTY

    5610 Avenida Del Mare, Sarasota, FL 34242
  • /36

    $2,595 Per Month

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Condo for Rent

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
  • /2

    $859,000

    Sold Apr 15, 2026

    4822 Ocean Blvd Unit 8D, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1973

    Last Sold Summary

    • 4% Below List Price
    • $597/SF
    • 7 Days On Market

    Current Estimated Value $877,152

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    4822 Ocean Blvd Unit 8D, Sarasota, FL 34242
    • /2

      Est $445,523

      Not Listed For Sale

      6157 Midnight Pass Rd Unit E42, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,101 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit E42, Sarasota, FL 34242

      Last Sold Summary

      • 74 Days On Market

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home