9,352

Siesta Key, FL Homes

Section Image Section Image
  • /82

    $2,999,900

    $500K PRICE DROP Pending
    • 6 Beds
    • 4.5 Baths
    • 4,700 Sq Ft

    1240 Solitude Ln, Sarasota, FL 34242

    Under contract-accepting backup offers. Two Canal Front Unrivaled Coastal Homes Just Steps from Siesta Key Beach! This rare gem features a meticulously remodeled Main house with stunning partial views of the bay. And a charming guest cottage serves as an ideal retreat or rental for additional cash flow. The main residence boasts a contemporary design with open and spacious layouts, highlighted by

    Agent Photo

    Karl Helbig

    SUNREAL ESTATE INC

    1240 Solitude Ln, Sarasota, FL 34242
  • /80

    $8,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • House for Rent

    5216 Calle de Costa Rica, Sarasota, FL 34242

    Listing reflects peak season rate. Available months: July 2026, August 2026, October 2026, November 2026 December 2026, January 2027, March 2027 and April 2027. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key

    Beth Dilley ASCENDIA REAL ESTATE

    5216 Calle de Costa Rica, Sarasota, FL 34242
  • /2

    $815,000

    Sold Apr 28, 2026

    6140 Midnight Pass Rd Unit A10, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Built 1967

    Last Sold Summary

    • 7% Below List Price
    • $763/SF
    • 157 Days On Market

    Current Estimated Value $826,697

    Last Listing Agent Jaci Krawtschenko PREMIER SOTHEBY'S INTERNATIONAL REALTY

    6140 Midnight Pass Rd Unit A10, Sarasota, FL 34242
    • /2

      Est $835,675

      Not Listed For Sale

      1273 Dockside Place Unit 116, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,343 Sq Ft
      • Built 1982
      1273 Dockside Place Unit 116, Sarasota, FL 34242

      Last Sold Summary

      • 41 Days On Market

  • /72

    $1,199,000

    • 2 Beds
    • 2 Baths
    • 1,282 Sq Ft

    20 Whispering Sands Dr Unit 501, Sarasota, FL 34242

    Experience full gulf-front views and the lifestyle of island living on the world-renowned Siesta Key beach. This beautiful fifth-floor end-unit residence is in the south tower of Whispering Sands, a community in the heart of Siesta Key Village. This property offers the ideal blend of serenity and convenience. Residents enjoy private beach access and 800 feet of quartz sand beach, yet you are just

    Agent Photo

    Christopher Bush

    PREMIER SOTHEBY'S INTERNATIONAL REALTY

    20 Whispering Sands Dr Unit 501, Sarasota, FL 34242
  • /42

    Call for Price

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

    797 Beach Rd Unit 305, Sarasota, FL 34242

    Welcome to Your Slice of Paradise – Crescent Royale 3053D Tour URL: AVAILABILITY, PRICING and BOOKING HERE: Note: 7 day minimum required booking.Fully remodeled and infused with a modern coastal flair, this deluxe one-bedroom, one-bath condo is the ultimate Siesta Key escape. With over 820 square feet of bright, open living space, you’ll find all the bells and

    797 Beach Rd Unit 305, Sarasota, FL 34242
  • /2

    $650,000

    Sold Sep 12, 2025

    6415 Midnight Pass Rd Unit 502, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,287 Sq Ft
    • Built 1975

    Last Sold Summary

    • 6% Below List Price
    • $505/SF
    • 11 Days On Market

    Current Estimated Value $639,371

    Last Listing Agent Mina Johnson MICHAEL SAUNDERS & COMPANY

    6415 Midnight Pass Rd Unit 502, Sarasota, FL 34242
    • /2

      Est $1,194,551

      Not Listed For Sale

      6312 Midnight Pass Rd Unit 301S, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,009 Sq Ft
      • Built 1968
      6312 Midnight Pass Rd Unit 301S, Sarasota, FL 34242

      Last Sold Summary

      • 11 Days On Market

  • /44

    $115,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    915 Seaside Dr Unit 410, Weeks 4-7, 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 4-7), plus 2 additional float weeks—providing extended beachfront living during the most desirable season on America’s

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 410, Weeks 4-7, Sarasota, FL 34242
  • /49

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,438 Sq Ft
    • House for Rent

    5253 Avenida Del Mare, Sarasota, FL 34242

    This is a short-term rental. Listing price reflects off season rate, in season rates will be higher. Escape to paradise at this beautiful vacation retreat located on the coveted north end of Siesta Key. Nestled in a quiet residential neighborhood, this spacious and elegantly appointed home offers the perfect blend of privacy, comfort, and convenience—just minutes from world-famous Siesta Key

    Beth Dilley ASCENDIA REAL ESTATE

    5253 Avenida Del Mare, Sarasota, FL 34242
  • /2

    $500,500

    Sold May 01, 2026

    1125 W Peppertree Dr Unit 302, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft
    • Built 1974

    Last Sold Summary

    • 5% Below List Price
    • $430/SF
    • 25 Days On Market

    Current Estimated Value $525,194

    Last Listing Agent Christine Green COLDWELL BANKER REALTY

    1125 W Peppertree Dr Unit 302, Sarasota, FL 34242
    • /2

      Est $523,880

      Not Listed For Sale

      6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,101 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242

      Last Sold Summary

      • 40 Days On Market

  • /51

    $60,000

    • 4 Beds
    • 4 Baths
    • 2,625 Sq Ft

    915 Seaside Dr Unit 511, Weeks 16-17, Sarasota, FL 34242

    Fractional Ownership. Experience elevated beachfront living with this Deluxe, Guaranteed Gulf View, Spring (April) Fractional Ownership opportunity—offering one-sixteenth ownership on Siesta Key Beach, consistently ranked as America’s #1 beach. This rare fractional real estate offering delivers luxury coastal living, prime spring usage, and true Gulf-front views without the full-ownership price

    Agent Photo

    Kelly Mooney

    DOUGLAS ELLIMAN

    915 Seaside Dr Unit 511, Weeks 16-17, Sarasota, FL 34242
  • /44

    $6,495 Per Month

    • 3 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • House for Rent

    5456 Azure Way, Siesta Key, FL 34242

    This is an unfurnished 3 bedroom, 3 bathroom home with a screened pool and Grand Canal waterfront in the Siesta Isles community on Siesta Key! This residence features a terracotta tile roof, a paver driveway, an oversized two-car garage, and a stone-accented exterior framed by mature tropical landscaping. Inside, the home offers an open, split-bedroom floor plan with vaulted and cathedral

    5456 Azure Way, Siesta Key, FL 34242
  • /2

    $1,075,000

    Sold Apr 13, 2026

    567 Venice Ln, Sarasota, FL 34242

    • 4 Beds
    • 2 Baths
    • 1,915 Sq Ft
    • Built 1971

    Last Sold Summary

    • 10% Below List Price
    • $561/SF
    • 100 Days On Market

    Current Estimated Value $1,082,559

    Last Listing Agent Conner Ashley PREFERRED SHORE LLC

    567 Venice Ln, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      600 Beach Rd Unit 1 & 2, Sarasota, FL 34242

      • 6 Beds
      • 6 Baths
      • 2,838 Sq Ft
      • Built 1979
      600 Beach Rd Unit 1 & 2, Sarasota, FL 34242

      Last Sold Summary

      • 112 Days On Market

  • /52

    $1,385,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,376 Sq Ft

    6144 Midnight Pass Rd Unit 3N, Sarasota, FL 34242

    Island House Dream Condo on Siesta Key! Experience the best of beachfront living at Island House on world-famous Siesta Key, where breathtaking Gulf views, unbeatable location, and effortless island living come together. Perfectly positioned in one of the most desirable beachfront buildings in the community, this second-floor condo offers truly unobstructed beach and water views with no other

    Agent Photo

    Christine Walker

    COLDWELL BANKER REALTY

    6144 Midnight Pass Rd Unit 3N, Sarasota, FL 34242
  • /54

    $9,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,835 Sq Ft
    • Condo for Rent

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

    Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
  • /2

    $800,000

    Sold Apr 21, 2026

    6140 Midnight Pass Rd Unit B6, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Built 1967

    Last Sold Summary

    • 5% Below List Price
    • $749/SF
    • 38 Days On Market

    Current Estimated Value $799,260

    Last Listing Agent Kristina Waskom MICHAEL SAUNDERS & COMPANY

    6140 Midnight Pass Rd Unit B6, Sarasota, FL 34242
    • /39

      Est $2,044,975

      Not Listed For Sale

      340 Canal Rd Unit B, Sarasota, FL 34242

      • 4 Beds
      • 2.5 Baths
      • 2,234 Sq Ft
      • Built 2005
      340 Canal Rd Unit B, Sarasota, FL 34242

      Last Sold Summary

      • 17 Days On Market

  • /90

    $6,400,000

    • 12 Beds
    • 11 Baths
    • 5,313 Sq Ft

    662 Calle Del Otono, Siesta Key, FL 34242

    Charming mini-resort with lagoon-style pool and waterfall, sun decks, tropical landscaped gardens. Just steps from Siesta Key Public Beach. Free Trolley transports guests to Siesta Key Village for shopping, dining and a supermarket. Income Producing Property priced to sell at a Seven Cap. Two lots, 19 & 20 with 2 Duplexes.

    Agent Photo

    Tonna Gruber

    COLDWELL BANKER REALTY

    662 Calle Del Otono, Siesta Key, FL 34242
  • /51

    $3,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • Annual UNfurnished Siesta Key Gulf front 2/2 condo with water views!

    4822 Ocean Blvd, Sarasota, FL 34242

    Annual – Unfurnished | Gulffront Living on Siesta Key Live on the water and enjoy breathtaking Gulf views from this beautiful condo in Siesta Towers. This luxury 11-story, 65-unit beachfront building sits directly on the Gulf of Mexico, offering spectacular panoramic views and an unbeatable island lifestyle. The condo features an open floor plan filled with natural light from large sliding glass

    4822 Ocean Blvd, Sarasota, FL 34242
  • /2

    $2,650,000

    Sold Oct 14, 2025

    512 Treasure Boat Way, Sarasota, FL 34242

    • 4 Beds
    • 4.5 Baths
    • 5,078 Sq Ft
    • Built 1979

    Last Sold Summary

    • 11% Below List Price
    • $522/SF
    • 88 Days On Market

    Current Estimated Value $2,690,393

    Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

    512 Treasure Boat Way, Sarasota, FL 34242
    • /2

      Est $1,896,876

      Not Listed For Sale

      3927 Somerset Dr, Sarasota, FL 34242

      • 3 Beds
      • 3.5 Baths
      • 2,758 Sq Ft
      • Built 1990
      3927 Somerset Dr, Sarasota, FL 34242

      Last Sold Summary

      • 64 Days On Market

  • /52

    $59,000

    $16K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,780 Sq Ft

    915 Seaside Dr Unit 606, Weeks 12-13, 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 606, Weeks 12-13, Sarasota, FL 34242
  • /28

    $7,050 Per Month

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

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242

    This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
  • /2

    $1,300,000

    Sold Jan 30, 2026

    5750 Midnight Pass Rd Unit 508, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,471 Sq Ft
    • Built 1984

    Last Sold Summary

    • 7% Below List Price
    • $884/SF
    • 107 Days On Market

    Current Estimated Value $1,307,051

    Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY

    5750 Midnight Pass Rd Unit 508, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,255 Sq Ft
      • Built 2009
      915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242

      Last Sold Summary

      • 40 Days On Market

  • /56

    $759,000

    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft

    104 Whispering Sands Dr Unit V27, Sarasota, FL 34242

    NEWLY REMODELED 3-bedroom, 2-bath freestanding villa with attached 2-car garage in Whispering Sands, one of Siesta Key's premier Gulf-front communities. Offering 1,562 SF of beautifully updated living space, this move-in-ready residence is just a short two-minute walk to your PRIVATE beach access on Siesta Key's world-famous quartz sand beach, consistently ranked among the nation's best.*****

    Agent Photo

    Tracy Srodes

    FINE PROPERTIES

    104 Whispering Sands Dr Unit V27, Sarasota, FL 34242
  • /64

    $6,000 Per Month

    • 1 Bed
    • 2 Baths
    • Condo for Rent

    5400 Ocean Blvd, Sarasota, FL 34242

    SEASONAL OR ANNUAL RENTAL AVAILABLE AT BEACH TERRACE ON SIESTA KEY! Experience Siesta Key beachfront living at it's best in this beautifully renovated, fifth-floor corner condo directly on world-renowned Siesta Beach, ranked #1 in the U.S. This turnkey furnished 1-bedroom, 1.5-bath retreat features floor-to-ceiling impact sliding glass doors opening to three private balconies, creating over 1,280

    5400 Ocean Blvd, Sarasota, FL 34242
  • /2

    $625,000

    Sold Jun 22, 2026

    145 Avenida Messina Unit 3, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft
    • Built 1966

    Last Sold Summary

    • 10% Below List Price
    • $610/SF
    • 170 Days On Market

    Current Estimated Value $616,066

    Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

    145 Avenida Messina Unit 3, Sarasota, FL 34242
    • /2

      Est $793,400

      Not Listed For Sale

      5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,211 Sq Ft
      • Built 1976
      5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

      Last Sold Summary

      • 80 Days On Market

  • /59

    $600,000

    $400K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 1,373 Sq Ft

    5019 Commonwealth Dr, Sarasota, FL 34242

    Under contract-accepting backup offers. PRICED to Sell! A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal

    Agent Photo

    Dawn Bear

    WILLIAM RAVEIS - FLORIDA LLC

    5019 Commonwealth Dr, Sarasota, FL 34242
  • /45

    $9,500 Per Month

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

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242

    Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
  • /2

    $650,000

    Sold Jul 30, 2025

    813 Plymouth St, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 2,919 Sq Ft
    • Built 1953

    Last Sold Summary

    • 43% Below List Price
    • $223/SF
    • 130 Days On Market

    Current Estimated Value $1,043,281

    Last Listing Agent Georgia Salaverri COMPASS FLORIDA LLC

    813 Plymouth St, Sarasota, FL 34242
    • /2

      Not Listed For Sale

      915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 1,900 Sq Ft
      • Built 2009
      915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242

      Last Sold Summary

      • 175 Days On Market

  • /37

    $825,000

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

    4822 Ocean Blvd Unit 3D, Sarasota, FL 34242

    This condominium at Siesta Towers offers two master suites. Welcome to this extraordinary living experience and location where every day you can enjoy the gulf views and the palm trees dotting the horizon. Swim and relax in the heated outdoor pool that sits right on the waterfront. Enjoy a drink on the cocktail pier while you watch the dolphins swim or bask in the glowing light of the stunning

    Agent Photo

    Daniel Robinson

    HOUWZER INC

    4822 Ocean Blvd Unit 3D, Sarasota, FL 34242
  • /30

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242

    Starting at $179/night! Welcome to your vibrant beachside retreat—a newly renovated 1-bedroom, 1-bathroom escape thoughtfully designed for modern comfort and coastal style. Featuring a luxurious king bed and a fully equipped kitchen with a cozy nearby dining space, this inviting getaway is your perfect base for both relaxation and adventure. Convenience begins with your own private carport just

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
  • /2

    $3,000,000

    Sold Oct 15, 2025

    137 Big Pass Ln, Sarasota, FL 34242

    • 5 Beds
    • 4.5 Baths
    • 4,486 Sq Ft
    • Built 2006

    Last Sold Summary

    • 30% Below List Price
    • $669/SF
    • 148 Days On Market

    Last Listing Agent Dion Souza SARABAY REAL ESTATE INC

    137 Big Pass Ln, Sarasota, FL 34242
    • /68

      Est $627,394

      Not Listed For Sale

      101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,271 Sq Ft
      • Built 1969
      101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

      Last Sold Summary

      • 51 Days On Market

Showing Results 81 - 120, Page 3 of 18

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