Siesta Key, FL Homes

• 

  

  

  /58

  $1,580,000

  • 4 Beds
  • 4 Baths
  • 2,397 Sq Ft

  1014 Contento St, Sarasota, FL 34242

  Here's the opportunity you have been waiting for. Incredible floor plan with this concrete block home. Large bedrooms with three on one side and the owner's suite on the other. Large in-home laundry, oversized garage and a corner lot. Wonderful private waterfront living with a pool, dock and easy access to Siesta Beach. The existing floor plan makes it easy to update and if you love terrazzo

  Brian Snyder PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1014 Contento St, Sarasota, FL 34242
• 

  

  

  /25

  $12,000 per month

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft
  • House for Rent

  5519 Azure Way, Sarasota, FL 34242

  Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car! A brand new beautiful granite topped Kitchen space opens to a family room all

  Catherine Foley JENNETTE PROPERTIES, INC.

  5519 Azure Way, Sarasota, FL 34242
• 

  

  /2

  $4,600,000 Sold Feb 21, 2025

  • 3,844 Sq Ft
  • $1197/SF
  • 182 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1945

  4049 Shell Rd, Sarasota, FL 34242

  A rare opportunity to own a charming private home on almost an acre with 84 ft. of seawall located directly on Big Pass with incredible views of the Gulf of Mexico, South Lido Key Beach and Sarasota Bay. The island residence boasts mature trees and lush landscaping providing an old Florida feel nestled above the home and back patio. The walkway leads you to your own private beach and stairs that

  Andrew Martell KELLER WILLIAMS ON THE WATER S

  4049 Shell Rd, Sarasota, FL 34242
• 

  

  

  /39

  Est $821,645 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
• 

  

  

  /67

  $1,750,000

  • 3 Beds
  • 3.5 Baths
  • 2,756 Sq Ft

  436 Canal Rd Unit A, Sarasota, FL 34242

  Welcome to 436 Canal Road, a beautifully appointed 3-bedroom, 3.5-bathroom retreat with 2,756 square feet of luxury living, just a short walk to world-famous Siesta Key Beach and the lively Siesta Key Village. This turnkey furnished home is a rare find with strong investment potential—projected to generate over $180,000 annually in rental income(approved for STR). From the moment you enter,

  Vincent LaMaida COLDWELL BANKER REALTY

  436 Canal Rd Unit A, Sarasota, FL 34242
• 

  /2

  $1,100,000 Sold Feb 20, 2025

  • 1,444 Sq Ft
  • $762/SF
  • 34 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  421 Island Cir, Sarasota, FL 34242

  Your island escape awaits! Nestled on the serene Palm Island in the heart of Siesta Key and just two blocks from the iconic Siesta Key Beach, this charming pool home invites you to embrace the ultimate coastal lifestyle. Built with sturdy block construction and elevated over 10 feet, this home has withstood recent hurricanes unscathed, offering peace of mind for years to come. Sitting on nearly a

  Kaisen Mitchell COLDWELL BANKER REALTY

  421 Island Cir, Sarasota, FL 34242
• 

  

  /48

  Est $752,202 Not Listed For Sale

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

  6140 Midnight Pass Rd Unit D8, Sarasota, FL 34242

  6140 Midnight Pass Rd Unit D8, Sarasota, FL 34242
• 

  

  /37

  $599,000

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1200 Cove II Place Unit 832, Sarasota, FL 34242

  Turnkey 2BR/1.5BA Condo with Stunning Water Views – Steps from Crescent & Siesta Beaches!Welcome to your slice of paradise! This beautifully maintained 2-bedroom, 1.5-bath condo sits on the 3rd floor, directly across from the sugar sands of Crescent Beach and just a short stroll to world-famous Siesta Beach.Enjoy breathtaking views overlooking the marina and Intracoastal Waterway from your

  Peter Lev EXCEPTIONS REALTY

  1200 Cove II Place Unit 832, Sarasota, FL 34242
• 

  /2

  $1,125,000 Sold Feb 19, 2025

  • 2,200 Sq Ft
  • $511/SF
  • 49 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1998

  1240 Dolphin Bay Way Unit 204, Sarasota, FL 34242

  INCREDIBLE OPPORTUNITY for (3) Bedroom (3) Bath Well Appointed Residence in Premier "Boutique" Community---Dolphin Bay on Siesta Key.....Multiple Outdoor Spaces; 2200 Square Feet Interior Living Spaces; Hurricane Impact Sliding Doors; Plantation Shutters; Updated Kitchen; Tile Throughout & Your Own PRIVATE GARAGE!...Enjoy Morning Coffees, Evening Cocktails, Watching Boats on the Intracoastal, or

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  1240 Dolphin Bay Way Unit 204, Sarasota, FL 34242
• 

  

  /57

  Est $822,016 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,212 Sq Ft

  6140 Midnight Pass Rd Unit B1, Sarasota, FL 34242

  6140 Midnight Pass Rd Unit B1, Sarasota, FL 34242
• 

  

  /50

  $355,000

  • 1 Bed
  • 1 Bath
  • 857 Sq Ft

  5631 Midnight Pass Rd Unit 1007, Sarasota, FL 34242

  Experience the ultimate paradise at Sands Village in Siesta Key! Whether you're seeking an investment opportunity or a personal oasis, this property has it all. Turn-key furnished, open concept living, full tile flooring, abundance of natural light and plenty of living space are just the beginning of what this property offers. Enjoy access to a beautiful pool, community clubhouse, dedicated

  Emily Williams KW COASTAL LIVING III

  5631 Midnight Pass Rd Unit 1007, Sarasota, FL 34242
• 

  /2

  $1,650,000 Sold Feb 14, 2025

  • 2,672 Sq Ft
  • $618/SF
  • 23 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1972

  4820 Higel Ave, Sarasota, FL 34242

  This Move-in Ready waterfront property is the epitome of tropical luxury living in the heart of Siesta Key, Florida. Just a 5-minute drive from the world-renowned Siesta Key Beach, this home offers the best of both worlds: a serene retreat tucked behind private gates and a vibrant coastal lifestyle.The grand property welcomes you with a circular driveway and lush natural surroundings.

  Ryan Skrzypkowski COLDWELL BANKER REALTY

  4820 Higel Ave, Sarasota, FL 34242
• 

  

  /14

  Est $769,499 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,212 Sq Ft

  6140 Midnight Pass Rd Unit A7, Sarasota, FL 34242

  6140 Midnight Pass Rd Unit A7, Sarasota, FL 34242
• 

  

  /57

  $3,200,000

  • 4 Beds
  • 4 Baths
  • 2,854 Sq Ft

  238 Island Cir, Sarasota, FL 34242

  Welcome to your dream island retreat, perfectly nestled in the heart of Siesta Key’s Palm Island, just minutes away from the world-famous Siesta Beach and vibrant Siesta Village. This beautifully renovated 4-bedroom, 4-bathroom home is the epitome of coastal luxury, offering the ultimate island lifestyle where you can enjoy sun, sand, and all the amenities of this exclusive locale. Meticulously

  Thomas Cail RE/MAX ALLIANCE GROUP

  238 Island Cir, Sarasota, FL 34242
• 

  /2

  $865,000 Sold Feb 14, 2025

  • 1,361 Sq Ft
  • $636/SF
  • 581 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  5780 Midnight Pass Rd Unit 402, Sarasota, FL 34242

  Unquestionally Gulf & Bay is the finest beachfront complex on Siesta Key. With its 800 feet of frontage on luxurious Siesta Key Beach you will be captivated by the beautiful aqua waters and so soft crystal sands that have been the subject of “Finest” beaches over many years. This is in addition to the view of private pools, lagoon and fountains all bringing you the tropical lifestyle so

  Stephanie Kitsemble COLDWELL BANKER REALTY

  5780 Midnight Pass Rd Unit 402, Sarasota, FL 34242
• 

  

  /21

  Est $638,581 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 766 Sq Ft

  5128 Calle Minorga Unit 5128, Sarasota, FL 34242

  5128 Calle Minorga Unit 5128, Sarasota, FL 34242
• 

  

  /50

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,659 Sq Ft

  5432 Cape Leyte Dr, Sarasota, FL 34242

  Grab your sunglasses and flip-flops, because this charming Siesta Key retreat is just minutes from world-famous Siesta Beach, the #1 beach in the USA! With powdery white sands and crystal-clear, turquoise waters right around the corner, your beach getaway is within easy reach. Whether you're basking in the sun by day or catching the mesmerizing Gulf sunsets every evening, this is island living at

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5432 Cape Leyte Dr, Sarasota, FL 34242
• 

  /2

  $13,000 Sold Feb 12, 2025

  • 1,750 Sq Ft
  • $7/SF
  • 159 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 2009

  915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242

  Fractional Ownership. Summer Fractional Package, with 1/16th shares of ownership! Your dream of a new luxury home on Siesta Key Beach can now be a reality; an enviable lifestyle on America's top-rated beach! Here is your opportunity to own a piece of paradise without giving up all the amenities and services. An enviable lifestyle on America's top-rated beach! Your dream of a new luxury home on

  Kelly Mooney THE SARASOTA REAL ESTATE COMP.

  915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242
• 

  

  /64

  Est $655,416 Not Listed For Sale

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

  225 Hourglass Way Unit 307, Sarasota, FL 34242

  225 Hourglass Way Unit 307, Sarasota, FL 34242
• 

  

  /30

  $1,389,000

  • 3 Beds
  • 4 Baths
  • 2,337 Sq Ft

  5502 Shadow Lawn Dr, Sarasota, FL 34242

  Build your Dream Home or renovate the existing home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Siesta Key. This 14,200 square foot lot boasts approximately 80 feet on a deep canal with a boat dock. New homes and extensive renovations are occurring in this highly sought after neighborhood with its excellent boating water and close proximity to the

  Dan Miller PREFERRED SHORE LLC

  5502 Shadow Lawn Dr, Sarasota, FL 34242
• 

  /2

  $800,000 Sold Feb 11, 2025

  • 3,119 Sq Ft
  • $256/SF
  • 66 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1964

  4534 Banan Place, Sarasota, FL 34242

  Welcome to 4534 Banan Place. Located in the heart of the world-renowned Siesta Key, this spacious 5-bedroom, 3 bath, 3,100+ sq. ft. home offers an unbeatable combination of location, potential, and value. Nestled on a tranquil street, this property captures the essence of island living, just minutes from the #1-rated Siesta Beach with its powdery white sands and vibrant village life filled with

  Johnny Hopper PREFERRED SHORE LLC

  4534 Banan Place, Sarasota, FL 34242
• 

  

  /72

  Est $619,721 Not Listed For Sale

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

  225 Hourglass Way Unit 205, Sarasota, FL 34242

  225 Hourglass Way Unit 205, Sarasota, FL 34242
• 

  

  /18

  $799,900

  • Land
  • 0.18 Acre
  • $4,443,889 per Acre

  0 Avenida Leona, Siesta Key, FL 34242

  20% Down Seller Financing Offered. Design Your Legacy on Siesta Key – Premier Waterfront Lot in Siesta ManorWelcome to Lot 17 on Avenida Leona—an extraordinary opportunity to create your own masterpiece in one of Florida’s most coveted coastal enclaves. Nestled along a private, tree-lined lane in Siesta Manor, this canal-front parcel offers the rare combination of deep water access, walkability

  Ron Pepka KELLER WILLIAMS ON THE WATER

  0 Avenida Leona, Siesta Key, FL 34242
• 

  /2

  $995,000 Sold Feb 10, 2025

  • Land
  • 0.19 Acre
  • $5,236,842 per Acre

  • 50 Days On Market

  361 Avenida Madera, Sarasota, FL 34242

  Home Damaged by recent storms. Being sold for land value. Home can be repaired and has solid bones. Roof 2011 [No leaks from recent events], Impact Windows- 2017 SELLER FINANCING WOULD BE CONSIDERED. 30% DOWN.Water access to the Intracoastal Waterway via Grand Canal. Great location in Siesta Key Village. Just a short walk to all the village shops, restaurants and world

  Tracy Srodes FINE PROPERTIES

  361 Avenida Madera, Sarasota, FL 34242
• 

  

  /34

  Est $619,065 Not Listed For Sale

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

  4660 Ocean Blvd Unit F1, Sarasota, FL 34242

  4660 Ocean Blvd Unit F1, Sarasota, FL 34242
• 

  

  /22

  $1,389,000

  • Land
  • 0.33 Acre
  • $4,209,091 per Acre

  5502 Shadow Lawn Dr, Sarasota, FL 34242

  Build your Dream Home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Siesta Key. This 14,200 square foot lot is located boasts approximately 80 feet on a deep canal with a boat dock. New homes and extensive renovations are occurring in this fabulous neighborhood with its excellent boating water and close proximity to the beach. The current home

  Dan Miller PREFERRED SHORE LLC

  5502 Shadow Lawn Dr, Sarasota, FL 34242
• 

  /2

  $5,000,000 Sold Feb 07, 2025

  • 4,230 Sq Ft
  • $1182/SF
  • 5 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2020

  5418 Siesta Cove Dr, Sarasota, FL 34242

  Experience the pinnacle of luxurious waterfront living, where your dreams of boating, entertaining, and relaxation converge in unparalleled splendor. This exquisite elevated custom-built estate on Siesta Key redefines elegance, had NO flood damage, offering sweeping, private vistas of the vibrant intracoastal waterway and showcasing masterful design at every turn.Spanning two levels of

  Adnan Dedic COMPASS FLORIDA LLC

  5418 Siesta Cove Dr, Sarasota, FL 34242
• 

  

  /47

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,469 Sq Ft

  6267 Midnight Pass Rd Unit 107, Sarasota, FL 34242

  6267 Midnight Pass Rd Unit 107, Sarasota, FL 34242
• 

  

  /56

  $685,000

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

  225 Hourglass Way Unit 101, Sarasota, FL 34242

  Completely renovated from top to bottom, this stunning 2-bedroom, 2-bath condo is located in the highly desirable Whispering Sands community on Siesta Key. Designed with a modern coastal aesthetic, the open-concept layout features luxury vinyl plank flooring, 5-inch baseboards, and all-new 2-panel and louvered doors throughout. The air conditioning ducts in the living areas have been rerouted

  Cooper Daves WILLIAM RAVEIS REAL ESTATE

  225 Hourglass Way Unit 101, Sarasota, FL 34242
• 

  /2

  $1,890,000 Sold Feb 07, 2025

  • 2,704 Sq Ft
  • $699/SF
  • 16 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1992

  5125 Oxford Dr, Sarasota, FL 34242

  Experience the quintessential Siesta Key lifestyle in this enchanting waterfront home full of Florida charm. 5125 Oxford Road offers four bedrooms, four baths and a two-car garage. Along the Grand Canal beneath a lush canopy of trees, this multi-level retreat ideally balances charm, comfort and functionality. Step onto the covered front porch from the paver driveway and walk-up, and enter

  Joel Schemmel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5125 Oxford Dr, Sarasota, FL 34242
• 

  

  /55

  Est $1,206,833 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,214 Sq Ft

  6342 Midnight Pass Rd Unit 425, Sarasota, FL 34242

  6342 Midnight Pass Rd Unit 425, Sarasota, FL 34242
• 

  

  /56

  $499,000

  • 1 Bed
  • 1 Bath
  • 751 Sq Ft

  5855 Midnight Pass Rd Unit 512, Sarasota, FL 34242

  Experience the epitome of coastal living in this beautifully renovated, turn-key furnished 1 bedroom, 1 bath condo, perfectly situated on the 5th floor with breathtaking views of the Intracoastal Waterway. This condo boasts an updated kitchen and bathroom, featuring modern finishes and appliances. Enjoy peace of mind with new hurricane windows and sliding glass doors complete with plantation

  Julie Kell COLDWELL BANKER REALTY

  5855 Midnight Pass Rd Unit 512, Sarasota, FL 34242
• 

  /2

  $2,200,000 Sold Feb 06, 2025

  • 3,384 Sq Ft
  • $650/SF
  • 29 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2008

  452 Canal Rd, Sarasota, FL 34242

  Prime Investment Opportunity! This exceptional property is an investor’s dream! Ideally situated just one block from Siesta Beach and two blocks from local dining, shopping, and entertainment in Siesta Village. Perfectly positioned for short and long-term rentals, this spacious home offers an incredible opportunity to host large gatherings, family reunions, or celebratory

  Joseph Kesslak COLDWELL BANKER REALTY

  452 Canal Rd, Sarasota, FL 34242
• 

  

  /86

  Est $661,991 Not Listed For Sale

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

  6415 Midnight Pass Rd Unit 506, Sarasota, FL 34242

  6415 Midnight Pass Rd Unit 506, Sarasota, FL 34242
• 

  

  /31

  $450,000

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit B51, Sarasota, FL 34242

  Investor Alert Rental History, Vacation home. SIESTA KEY BEACH! This is the #1 beach in the US and # 4 in the world! relax in your chaise lounge, on the beach, Listening to Jimmy Buffet and sipping a cold margarita? sounds perfect. Well, It’s here, and just a short walk to the crystal powdery white sandy beach and turquoise waters at your footsteps. The dream of owning Siesta Key is still

  Robin Jones EXIT KING REALTY

  6157 Midnight Pass Rd Unit B51, Sarasota, FL 34242
• 

  /2

  $1,175,000 Sold Feb 05, 2025

  • 1,915 Sq Ft
  • $614/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  1260 Dolphin Bay Way Unit 402, Sarasota, FL 34242

  Welcome to Dolphin Bay, a gated, mid-rise waterfront community with just 50 fortunate owners. This completely updated and immaculate 4th-floor residence offers breathtaking views of the Intracoastal Waterway, where boats pass by and dolphins play. This condo is fully furnished and beautifully decorated with 1,915 sq. ft. of living space, plus an enclosed Lanai and a charming front courtyard

  Pam Charron COMPASS FLORIDA LLC

  1260 Dolphin Bay Way Unit 402, Sarasota, FL 34242
• 

  

  /40

  Est $508,454 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  5681 Midnight Pass Rd Unit 103, Sarasota, FL 34242

  5681 Midnight Pass Rd Unit 103, Sarasota, FL 34242
• 

  

  /33

  $449,900

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft

  1250 N Portofino Dr Unit 304, Sarasota, FL 34242

  Wake up to sunrises over the marina, spend your afternoons boating or relaxing on the powdery sands of Siesta Key Beach, and unwind in the evening on your enclosed balcony, enjoying the tranquil views of the boats below and colorful evening skies. Located in Siesta Harbor, this furnished 1-bedroom, 2-bath condo offers a comfortable, coastal lifestyle just steps from the water. Beautifully updated

  Marci McFarland MICHAEL SAUNDERS & COMPANY

  1250 N Portofino Dr Unit 304, Sarasota, FL 34242
• 

  /2

  $915,000 Sold Jan 31, 2025

  • 1,265 Sq Ft
  • $723/SF
  • 6 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  5968 Midnight Pass Rd Unit 164, Sarasota, FL 34242

  With southern exposure, enjoy gulf views over Casa Mar from this third floor corner club unit in the Palm Bay Club. Light and bright with turnkey furnishings, beginning or expanding your vacation property portfolio has never been easier. A true beach to bay community, your access to the impressive Palm Bay Club amenities is unlimited and includes: private Crescent Beach access, two heated

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5968 Midnight Pass Rd Unit 164, Sarasota, FL 34242
• 

  

  /54

  Est $1,053,204 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft

  4660 Ocean Blvd Unit K1, Sarasota, FL 34242

  4660 Ocean Blvd Unit K1, Sarasota, FL 34242

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