Siesta Key, FL Homes

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  /31

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,500 Sq Ft

  521 Cummings St, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Siesta Key Waterfront Retreat – Walk to the Beach & Village! Ready for immediate enjoyment this winter, this 3-bedroom, 2-bath Key West–inspired home embodies the essence of the Siesta Key lifestyle—boating from your backyard and strolling to the powdery white sands and vibrant Siesta Key Village with its renowned dining, boutiques, and nightlife.

  Ryan Ackerman COLDWELL BANKER REALTY

  521 Cummings St, Sarasota, FL 34242
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  /38

  $9,350 per month

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

  Unlisted Address

  Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Club Bayside. The Key West style cluster buildings afford you a quiet residential feel while you are just a short walk to the powdery white quartz sand of the world famous Siesta Key/Crescent Beach.New to the rental program, our condo has previously been owner occupied and

  Andy Moore GULF COAST REALTY & MANAGEMENT

  Unlisted Address
• 

  

  /2

  $725,000 Sold Jul 03, 2025

  • 2,390 Sq Ft
  • $303/SF
  • 82 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1955

  4710 Gleason Ave, Sarasota, FL 34242

  Take a Look!...This Unique Opportunity on Siesta Key JUST REDUCED...One of the Few Properties of Its Kind, Offering an Expansive 0.30-Acre Lot Overlooking a Serene Pond...Just a Short Stroll to the World-Famous White Sands of Siesta Key Beaches and the Vibrant Village, Full of Fine Dining, Boutique Shopping, and Entertainment...The Existing 4/3 Home Sustained Hurricane Damage, Making it an Ideal

  Bo Fuller FULLER GROUP REAL ESTATE, LLC

  4710 Gleason Ave, Sarasota, FL 34242
• 

  

  

  /57

  Est $1,731,660 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,490 Sq Ft

  1660 Summerhouse Ln Unit 104, Sarasota, FL 34242

  1660 Summerhouse Ln Unit 104, Sarasota, FL 34242
• 

  

  

  /41

  $1,950,000

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

  5880 Midnight Pass Rd Unit 907, Sarasota, FL 34242

  Casarina is poised elegantly on 7 acres of plush, tropical grounds and is located directly on world-renowned Crescent Beach. You will melt away on it’s powder white sand and float away in the shimmering waters of the Gulf of Mexico. This residence has been beautifully renovated to provide the ultimate beach home for you to call your own. Come and see for yourself the many features that truly

  Linda Stowe MICHAEL SAUNDERS & COMPANY

  5880 Midnight Pass Rd Unit 907, Sarasota, FL 34242
• 

  

  /27

  $6,900 per month

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

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

  Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key just offshore of Sarasota, Florida. Private access to Crescent Beach on the Gulf of Mexico - just steps to the beach. Free high-speed Internet connection. Please note the garage for this unit is the middle garage in the building to the right.*Taxes and Fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

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

  /2

  $925,000 Sold Jul 01, 2025

  • 1,840 Sq Ft
  • $503/SF
  • 110 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  1280 Dolphin Bay Way Unit 202, Sarasota, FL 34242

  Experience the natural Florida coastal environment from this extraordinary viewpoint and the one-of-a-kind walkout to a private beach nestled in mangroves on the Intracoastal Waterway—perfect for launching a kayak or paddleboard. A dynamic scene unfolds daily with visiting shore birds of every description, dolphins feeding in pods, jumping mullet, and manatee lazily cruising by—just outside your

  Bill McCue BRIGHT REALTY

  1280 Dolphin Bay Way Unit 202, Sarasota, FL 34242
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  /2

  Est $348,640 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 435 Sq Ft

  6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242

  6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242
• 

  

  /34

  $1,649,000

  • 2 Beds
  • 2 Baths
  • 1,187 Sq Ft

  5400 Ocean Blvd Unit 17-04, Sarasota, FL 34242

  The iconic Terrace building is a masterpiece designed by renowned architect Frank Folsom Smith. This modernist building, built of poured concrete exudes strength and durability. Situated directly on Siesta Key Beach, and built with walls of sliding glass doors in every room to take advantage of the diverse, magnificent views in all directions. This is the penthouse being offered turnkey

  Carol Thomas MICHAEL SAUNDERS & COMPANY

  5400 Ocean Blvd Unit 17-04, 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. Available peak season months: January 5th - February 6th 2026, April 2026. 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

  Beth Dilley ASCENDIA REAL ESTATE

  5516 Avenida Del Mare, Sarasota, FL 34242
• 

  /2

  $950,000 Sold Jul 01, 2025

  • 2,198 Sq Ft
  • $432/SF
  • 164 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1971

  322 Avenida de Paradisio, Sarasota, FL 34242

  This solid three-bedroom three bath pool/canal front home is located on a quiet cul-de-sac just behind Siesta Key village, and a mere 5-minute stroll to its eclectic shops, cafes, and fabulous restaurants, not to mention the world-renowned powder-white sands of Siesta Beach!Two of the bedrooms are en-suite. The living room, family room and one bedroom have access to the lanai and caged pool.

  Colleen Finnegan RE/MAX ALLIANCE GROUP

  322 Avenida de Paradisio, Sarasota, FL 34242
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  /64

  Est $605,456 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 975 Sq Ft

  1041 W Peppertree Dr Unit 1113, Sarasota, FL 34242

  1041 W Peppertree Dr Unit 1113, Sarasota, FL 34242
• 

  

  /91

  $650,000

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

  225 Hourglass Way Unit 103, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Welcome to this RARE, 2 bed/2 bath, double lanai corner residence with peaceful lagoon views in the premiere Gulf front property of Whispering Sands! Nestled in the desirable Sunset House building, this freshly painted, updated unit offers a quiet, private setting, with serene views of lush landscaping and the shimmering lagoon with its abundant

  Harriet Stopher COLDWELL BANKER REALTY

  225 Hourglass Way Unit 103, Sarasota, FL 34242
• 

  

  /65

  $8,700 per month

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Condo for Rent

  5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, April 2026. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot,

  Beth Dilley ASCENDIA REAL ESTATE

  5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
• 

  /2

  $1,300,000 Sold Jun 30, 2025

  • 1,886 Sq Ft
  • $689/SF
  • 98 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  5402 Shadow Lawn Dr, Sarasota, FL 34242

  Enjoy true Florida living on Siesta Key on this high & dry lot in beautiful Siesta Isles. This one level home offers nearly 1900 sf of living space set on a 104' wide deep-water canal lot with access to Roberts Bay, the Intracoastal, and the Gulf of Mexico. NO STORM DAMAGE during the recent hurricanes! Move right in and update it to make it your own. Offering a Split Plan of 3 bedrooms, two full

  Jimmy Raybon BERKSHIRE HATHAWAY HOMESERVICE

  5402 Shadow Lawn Dr, Sarasota, FL 34242
• 

  

  /14

  Est $967,928 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,319 Sq Ft

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

  6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
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  /52

  $600,000

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft

  6020 Midnight Pass Rd Unit 63, Sarasota, FL 34242

  Welcome to Villa 63 at Aloha Kai, a beautifully renovated one-bedroom, one-bath villa located just steps from the world-famous quartz sands of Siesta Key Beach. This coastal retreat has been fully remodeled from top to bottom, offering the perfect combination of comfort, style, and income potential. From the moment you arrive, you’ll notice the fresh exterior with tropical landscaping, paver

  Natalie Gutwein MICHAEL SAUNDERS & COMPANY

  6020 Midnight Pass Rd Unit 63, Sarasota, FL 34242
• 

  

  /98

  $18,000 per month

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft
  • House for Rent

  345 Avenida Leona, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a

  Beth Dilley ASCENDIA REAL ESTATE

  345 Avenida Leona, Sarasota, FL 34242
• 

  /2

  $1,860,000 Sold Jun 30, 2025

  • 3,721 Sq Ft
  • $500/SF
  • 118 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1964

  5376 Shadow Lawn Dr, Sarasota, FL 34242

  BRING ALL THE FAMILY - MOVE IN READY! Florida living on this high & dry lot on Siesta Key. Your own private tropical deep-water canal frontage. Large saltwater pool and spa, private screened courtyard adjacent to a large game room and theater room – perfect for entertaining. NO STORM DAMAGE during the recent hurricanes! This 4 BR spacious home offers 3700+ sq. ft. of living space including two

  Jimmy Raybon BERKSHIRE HATHAWAY HOMESERVICE

  5376 Shadow Lawn Dr, Sarasota, FL 34242
• 

  

  /43

  Est $683,640 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,365 Sq Ft

  1080 W Peppertree Ln Unit 303A, Sarasota, FL 34242

  1080 W Peppertree Ln Unit 303A, Sarasota, FL 34242
• 

  

  /21

  $8,500,000

  • Land
  • 0.86 Acre
  • $9,883,721 per Acre

  4050 Higel Ave, Siesta Key, FL 34242

  A rare Gulf-front offering, this 37,471 sq. ft. (.86-acre) parcel presents an extraordinary opportunity to create a signature coastal estate in one of Sarasota’s most coveted locations. Just steps from the sparkling waters of the Gulf of America and the Sarasota Bay, the nearly one-acre homesite provides a generous canvas for architectural vision—whether a sleek modern retreat, a timeless

  Faith Stutzman PHAM REALTY GROUP LLC

  4050 Higel Ave, Siesta Key, FL 34242
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  /46

  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Condo for Rent

  20 Whispering Sands Dr Unit 903, Sarasota, FL 34242

  Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bath condo in the Whispering Sands Community. This wonderful 55+ community offers you the convenience of village living but is very peaceful and private at the same time. Leave the hustle and bustle of

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
• 

  /2

  $1,075,000 Sold Jun 30, 2025

  • 1,337 Sq Ft
  • $804/SF
  • 186 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  5770 Midnight Pass Rd Unit 705, Sarasota, FL 34242

  Welcome to Gulf & Bay Club, the premiere Siesta Key condo complex nestled on 32 acres with 800 ft of private beach! Located in the middle of the C Building on the top floor, this condo offers fabulous views, both day and night, of the freshwater lake, fountains, island lagoon, swimming pools, sandy beach, and the Gulf of Mexico beyond. Take in the views on the Lanai, or sip your coffee in the

  Tina Johns COLDWELL BANKER REALTY

  5770 Midnight Pass Rd Unit 705, Sarasota, FL 34242
• 

  

  /41

  Est $1,323,877 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,976 Sq Ft

  6150 Midnight Pass Rd Unit 40, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 40, Sarasota, FL 34242
• 

  

  /72

  $1,180,000

  • 3 Beds
  • 3 Baths
  • 2,522 Sq Ft

  4830 Estrada de Costa, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Tucked away at the end of quiet Estrada De Costa, a single lane road with just three homes, this unique and spacious Siesta Key 3 bedroom/3 bath lakefront property offers rare privacy, flexibility, and charm. The home was expanded in 2001, the property includes a 2 bedroom/2 bath main house, and a fully equipped one bedroom/one bath separate suite

  Stacy Liljeberg MICHAEL SAUNDERS & COMPANY

  4830 Estrada de Costa, 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 decor. 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

  $1,970,000 Sold Jun 27, 2025

  • 2,088 Sq Ft
  • $943/SF
  • 7 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1970

  5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242

  BREATHTAKING amazing Gulf of Mexico views and ONCE IN A LIFETIME OPPORTUNITY for this ONE-OF-A-KIND condominium residence in the desirable Gulffront Tower building in the Palm Bay Club on the island of Siesta Key. This turnkey furnished residence is a combined 2-bedroom unit with the adjacent 1-bedroom unit, redesigned to create a fabulous 2-bedroom plus den/study, which could be converted back

  Carolyn Donnelly COLDWELL BANKER REALTY

  5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242
• 

  

  /33

  Est $808,251 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242
• 

  

  /32

  $764,000

  • 2 Beds
  • 2 Baths
  • 1,131 Sq Ft

  5141 Saint Albans Ave, Sarasota, FL 34242

  Tucked away on a quiet, tree-canopied street that sits high and did NOT flood, this Siesta Key property is more than a tropical retreat. It’s a rare opportunity to enjoy timeless island living today while unlocking tremendous future potential. Set on a nearly 10,000 sq ft lot with lush foliage and mature Live Oaks, this residence combines historic character, relaxed coastal charm, and valuable

  Anthony Dalesandro BRIGHT REALTY

  5141 Saint Albans Ave, Sarasota, FL 34242
• 

  

  /57

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Condo for Rent

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

  Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot

  Beth Dilley ASCENDIA REAL ESTATE

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
• 

  /2

  $1,100,000 Sold Jun 27, 2025

  • 2,519 Sq Ft
  • $437/SF
  • 83 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1957

  4857 Primrose Path, Sarasota, FL 34242

  Welcome to your dream home in the highly sought-after Harmony subdivision! This stunning single-family residence is situated on a serene canal, featuring an impressive 120' of newer concrete seawall, perfect for those looking to embrace the waterfront lifestyle. Bring your boats and jet skis, as you can easily add your own dock, allowing for quick access to Sarasota Bay and the breathtaking blue

  Nadiya Marisol-Pote MICHAEL SAUNDERS & COMPANY

  4857 Primrose Path, Sarasota, FL 34242
• 

  

  /59

  Est $691,244 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242
• 

  

  /44

  $640,000

  • 2 Beds
  • 2 Baths
  • 1,575 Sq Ft

  1345 Moonmist Dr Unit T6, Sarasota, FL 34242

  Welcome to your dream villa! This spacious coastal villa retreat on Siesta Key boasts 2-bedrooms and 2-bathrooms and offers 1,575 square feet of comfortable, open-concept living space, perfect for both relaxing and entertaining. Step inside to a freshly painted interior featuring a modern, neutral palette that complements any decor. This wonderful detached-villa is in a serene location just

  Dean Hall WATERSIDE REALTY LLC

  1345 Moonmist Dr Unit T6, Sarasota, FL 34242
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  /42

  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft
  • Condo for Rent

  6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

  Variable rent based on season

  Terry Dorrity INTEGRITY INVESTMENTS REALTY

  6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
• 

  /2

  $4,000,000 Sold Jun 26, 2025

  • 4,989 Sq Ft
  • $802/SF
  • 441 Days On Market

  • Built 2018

  645 Beach Rd, Siesta Key, FL 34242

  Featuring the highly coveted RMF zoning, this property offers legal short term rentals-a rarity across the region and a game-changer for income potential. Set on high ground, it has proven its durability by remaining high and dry during recent hurricanes, providing unmatched security and peace of mind.The property comes fully turnkey furnished, ensuring a seamless and effortless

  Cole Collins COLDWELL BANKER REALTY

  645 Beach Rd, Siesta Key, FL 34242
• 

  

  /39

  Est $721,532 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 939 Sq Ft

  6150 Midnight Pass Rd Unit 17, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 17, Sarasota, FL 34242
• 

  

  /71

  $1,300,000

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

  5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242

  Welcome to Your Siesta Key Sanctuary.Step into paradise with this turnkey furnished condo in the highly sought-after Casarina complex, offering 200 feet of private beach access on the world-renowned Crescent Beach. Nestled on a lush 7-acre property, Casarina features beautifully landscaped gardens, tennis and pickleball courts, a beachside pool and spa, an elevated beach deck, and a welcoming

  Suki Scollo COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242
• 

  

  /60

  $6,500 per month

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

  1250 N Portofino Dr Unit 102, Sarasota, FL 34242

  Available January to April 1, 2026! 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

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

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

  /2

  $990,000 Sold Jun 25, 2025

  • 1,464 Sq Ft
  • $676/SF
  • 117 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

  ***PRICE REDUCED*** This stunning beachfront condo offers a rare combination of luxury, convenience, and breathtaking natural beauty. Nestled on the powdery soft white sands of Siesta Key Beach, this end unit features an additional window which floods the space with an abundance of natural light and provides panoramic views of the sparkling Gulf of Mexico.This condo isn’t just a home;

  Christa Spalding COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 306, Sarasota, FL 34242
• 

  

  /57

  Est $721,669 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6150 Midnight Pass Rd Unit 7, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 7, Sarasota, FL 34242

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