Siesta Key, FL Homes

• 

  

  /2

  $1,425,000 Sold May 08, 2025

  • 1,271 Sq Ft
  • $1,121/SF
  • 137 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  6300 Midnight Pass Rd Unit 606, Sarasota, FL 34242

  Undoubtedly the most recognizable building alongside Crescent Beach on Siesta Key, Crystal Sands boasts delicate curves intended to offer and maximize breathtaking views for its lucky owners. This serene retreat has undergone an innovative renovation with modern, chic furnishings that lend a casual yet distinguished ambience. As you step inside, you're greeted by a coastal inspired living space,

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  6300 Midnight Pass Rd Unit 606, Sarasota, FL 34242
• 

  

  

  /70

  Est $1,821,384 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 4,223 Sq Ft

  4099 Higel Ave, Sarasota, FL 34242

  4099 Higel Ave, Sarasota, FL 34242
• 

  

  

  /34

  $685,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5961 Midnight Pass Rd Unit 319, Sarasota, FL 34242

  Looking for the perfect balance of location, lifestyle and income potential? This one delivers all three. Welcome to your slice of paradise on world-renowned Siesta Key! This spacious 2-bedroom, 2-bath condo is located in the highly sought-after Palm Bay Club, offering the perfect blend of coastal living and resort-style amenities. Located on the second floor, step inside to an open-concept

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5961 Midnight Pass Rd Unit 319, Sarasota, FL 34242
• 

  

  /2

  $1,200,000 Sold May 07, 2025

  • 1,517 Sq Ft
  • $791/SF
  • 14 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1962

  822 Paradise Way, Sarasota, FL 34242

  Views, Views, Views! This property is located on the desirable Grand Canal and boasts one of the best wide canal views on Siesta Key. Enjoy gorgeous long water views on 122 ft. of Canal frontage. Situated on a quiet cul-de-sac on a beautiful tree lined street with easy access to beaches and Siesta Key Village. While this home did experience some water intrusion during Hurricane Helene, it has

  Sue Ann Levin COLDWELL BANKER REALTY

  822 Paradise Way, Sarasota, FL 34242
• 

  

  

  /54

  Est $1,622,796 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,758 Sq Ft

  3902 Somerset Dr Unit 10, Sarasota, FL 34242

  3902 Somerset Dr Unit 10, Sarasota, FL 34242
• 

  

  /91

  $15,950,000

  • 6 Beds
  • 9 Baths
  • 7,535 Sq Ft

  4315 Mangrove Place, Sarasota, FL 34242

  Private Island, Gated Home, Private access to deeded beach!Experience the epitome of exclusivity with unheard of waterfront views, unmatched privacy, and breathtaking, expensive vistas from your own private island retreat. Tucked away on a private island in Siesta Key’s South Cocoanut Bayou, this Tuscan-inspired estate feels like it’s been plucked from the pages of a storybook. The

  Inbal August DOUGLAS ELLIMAN

  4315 Mangrove Place, Sarasota, FL 34242
• 

  /2

  $850,000 Sold May 01, 2025

  • 1,550 Sq Ft
  • $548/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  6267 Midnight Pass Rd Unit 105, Sarasota, FL 34242

  Experience the ultimate beachfront lifestyle in this charming 2-bedroom, 2-bathroom condo, perfectly located in the heart of Siesta Key. Nestled in a sought-after community, this ground-floor unit offers easy access to the world-renowned quartz sand beaches and the crystal-clear waters of the Gulf of Mexico.Step inside to find a bright, open-concept living space with large windows that

  Jeff Bray LPT REALTY, LLC

  6267 Midnight Pass Rd Unit 105, Sarasota, FL 34242
• 

  

  /75

  Est $1,689,953 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,437 Sq Ft

  5400 Ocean Blvd Unit 9-3, Sarasota, FL 34242

  5400 Ocean Blvd Unit 9-3, Sarasota, FL 34242
• 

  

  /63

  $1,525,000

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft

  5740 Midnight Pass Rd Unit 405, Sarasota, FL 34242

  Welcome to Unit 405 in the highly sought-after Building F at Gulf & Bay Club, where breathtaking Gulf views and refined upgrades set the stage for an exceptional Siesta Key lifestyle. This spacious 2-bedroom, 2-bath residence showcases sweeping panoramas of the Gulf of Mexico, perfectly framed by hurricane-impact windows and sliding glass doors that fill the living spaces with natural light and

  Drew Jacobsen COMPASS FLORIDA LLC

  5740 Midnight Pass Rd Unit 405, Sarasota, FL 34242
• 

  /2

  $1,100,000 Sold May 01, 2025

  • 1,731 Sq Ft
  • $635/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2015

  3911 Roberts Point Rd, Sarasota, FL 34242

  Custom built by the current owner in 2015, the contemporary design exudes warmth and natural light inside. In a highly desirable location on the North End of Siesta Key, this 3 bedroom 2 bathroom home has thoughtful details throughout. From the Brazilian Cumaru flooring to the vaulted ceilings with oversized hurricane rated windows, you will realize the value. The open-concept kitchen features

  Barbara May MICHAEL SAUNDERS & COMPANY

  3911 Roberts Point Rd, Sarasota, FL 34242
• 

  

  /27

  Est $958,460 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,650 Sq Ft

  717 Edgemere Ln, Sarasota, FL 34242

  717 Edgemere Ln, Sarasota, FL 34242
• 

  

  /79

  $2,250,000

  • 3 Beds
  • 3.5 Baths
  • 2,611 Sq Ft

  546A Beach Rd Unit 544, Sarasota, FL 34242

  Gulf-front luxury townhome with private beach access on Siesta Key! Soak in the breathtaking, unobstructed views of the Gulf and iconic Siesta Beach from every level of this three-story, turnkey-furnished townhouse-style condominium. Just a short distance from the sand in the intimate, nine-residence enclave of Tiffany Sands, this rare Siesta Key offers blends relaxed beachside living with

  Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

  546A Beach Rd Unit 544, Sarasota, FL 34242
• 

  /2

  $630,000 Sold Apr 30, 2025

  • 1,512 Sq Ft
  • $417/SF
  • 69 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  5239 Winding Way, Sarasota, FL 34242

  ***PRICE IMPROVMENT*** ***PRICE IMPROVEMET*** Discover your own private oasis at 5239 Winding Way, just minutes from Siesta Beach. Come and see for yourself this lovely and charming home that is an absolute MUST SEE! Nestled in a canopy-protected neighborhood, this property features a spacious open floor plan that connects the kitchen and living areas, creating a perfect space for entertaining

  Brian Cirillo BALDWIN PARK REALTY LLC

  5239 Winding Way, Sarasota, FL 34242
• 

  

  /63

  Est $3,238,954 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,457 Sq Ft

  5349 Hidden Harbor Rd, Sarasota, FL 34242

  5349 Hidden Harbor Rd, Sarasota, FL 34242
• 

  

  /40

  $1,600,000

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

  6300 Midnight Pass Rd Unit 809, Sarasota, FL 34242

  Turnkey-furnished 8th-floor gem in Crystal Sands on Siesta Key! Renovated in 2022 with stunning Gulf views, custom wood beam ceilings, granite counters, laminate floors, and wind-rated glass. Designer kitchen with built-in banquet and seamless fridge/cabinet design. Both bedrooms feature walk-in closets; primary bath has dual sinks and luxe shower. Huge lanai for sunset views. This unit grossed

  Brad Tritschler, LLC PREMIER SOTHEBYS INTL REALTY

  6300 Midnight Pass Rd Unit 809, Sarasota, FL 34242
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  /2

  $1,175,000 Sold Apr 30, 2025

  • 2,147 Sq Ft
  • $547/SF
  • 76 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  1211 N View Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. This home had no water intrusion nor structural damage through hurricanes. Welcome to this beautifully updated home in the highly sought-after Siesta Cove neighborhood on Siesta Key, just a short distance from the world-renowned Siesta Beach and the vibrant Siesta Key Village, offering an array of shopping, dining, and entertainment options. This

  Thomas Cail RE/MAX ALLIANCE GROUP

  1211 N View Dr, Sarasota, FL 34242
• 

  

  /32

  Est $2,005,254 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,097 Sq Ft

  525 Treasure Boat Way, Sarasota, FL 34242

  525 Treasure Boat Way, Sarasota, FL 34242
• 

  

  /27

  $1,200,000

  • Land
  • 0.37 Acre
  • $3,243,243 per Acre

  4920 Higel Ave, Sarasota, FL 34242

  Opportunity Awaits on this .37 of an acre (approximate dimensions 100' x 158') on Siesta Key with Western Exposure. The existing structure is ready to be removed and a new home would be best suited for this great lot. Current structure features 3BR/2BA with a pool ~ but the home did suffer severe water damage and is now being "sold as is" for lot value only. This nice, oversized lot has a great

  Tony Andrews ANDREWS & ASSOCIATES REALTY

  4920 Higel Ave, Sarasota, FL 34242
• 

  /2

  $303,500 Sold Apr 28, 2025

  • 797 Sq Ft
  • $381/SF
  • 45 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1975

  5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242

  Lowest price condo on Siesta Key. Rarely available first-floor 1/1 condo located right across the street from Siesta Key public beach in beautiful White Sands Village. This affordable and well-maintained community with pavers throughout the roadways and carport areas is a hidden gem. Onsite management, heated pool, community boat docks that are available on a first-come basis for a small fee, and

  Mary Jo Violett MICHAEL SAUNDERS & COMPANY

  5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242
• 

  

  /40

  Est $3,469,260 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,416 Sq Ft

  250 Island Cir, Sarasota, FL 34242

  250 Island Cir, Sarasota, FL 34242
• 

  

  /35

  $5,500,000

  • 8 Beds
  • 8 Baths
  • 6,490 Sq Ft

  544 Canal Rd, Sarasota, FL 34242

  SIESTA KEY INVESTMENT PROPERTY. Great location! Welcome to the Wildflower. Just steps from the #1 Beach in USA. Nestled within a tropical oasis, this charming 8 plex 4 ground level units and 4 second level units, with 8 parking spaces offers a unique blend of comfort and natural beauty. Surrounded by vibrant tropical flora, enter the common area courtyard centered around a sparkling heated pool,

  Katie Cintron COLDWELL BANKER REALTY

  544 Canal Rd, Sarasota, FL 34242
• 

  /2

  $1,630,000 Sold Apr 28, 2025

  • 1,782 Sq Ft
  • $915/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1964

  320 Avenida Leona, Sarasota, FL 34242

  CANAL FRONT home only a 2 minute walk to Siesta Key Village loaded with upgrades and a BRIGHT, OPEN layout that's ideal for entertaining. Features include custom kitchen with quartz countertops, tile backsplash and stainless appliances, tile flooring throughout, impact sliders and windows, 6-panel doors, custom closets with motion-sensor lighting. Three bedrooms plus an office with a HUGE

  Ryan Vlasic COLDWELL BANKER REALTY

  320 Avenida Leona, Sarasota, FL 34242
• 

  

  /80

  Est $2,912,328 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,571 Sq Ft

  5322 Siesta Cove Dr, Sarasota, FL 34242

  5322 Siesta Cove Dr, Sarasota, FL 34242
• 

  

  /54

  $775,000

  • 2 Beds
  • 2 Baths
  • 939 Sq Ft

  6150 Midnight Pass Rd Unit 38, Sarasota, FL 34242

  Step into your slice of paradise with this amazing lifestyle opportunity in Siesta Key's esteemed Island House Beach Resort. This impeccable 2-bedroom, 2-bath luxurious coastal Villa, which was completely renovated in 2025, seamlessly blends comfort, style, and investment potential, making it the perfect choice for discerning buyers, seasonal residents, and savvy investors alike. From the moment

  Domanic Calamese KW COASTAL LIVING III

  6150 Midnight Pass Rd Unit 38, Sarasota, FL 34242
• 

  /2

  $650,000 Sold Apr 28, 2025

  • 1,453 Sq Ft
  • $447/SF
  • 209 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  631 Venice Ln, Sarasota, FL 34242

  Welcome to great potential and endless possibilities on Siesta Key. This three bedroom, 2 bath pool home on one third of an acre in the Waterside East neighborhood is conveniently located for easy access on and off the island via the north bridge, and just a short bike ride to the vibrant Siesta Key Village and the world-famous Siesta Key beach. Enjoyed as a permanent residence by the current

  Kelly Rosenberg COLDWELL BANKER REALTY

  631 Venice Ln, Sarasota, FL 34242
• 

  

  /75

  Est $3,587,028 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 5,098 Sq Ft

  5315 Hidden Harbor Rd, Sarasota, FL 34242

  5315 Hidden Harbor Rd, Sarasota, FL 34242
• 

  

  /41

  $1,895,000

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft

  4879 Commonwealth Dr, Sarasota, FL 34242

  Own a Rare Piece of Sarasota's Architectural History on Siesta Key!Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Originally crafted in 1957 by Frank Coleman and Tollen Twitchell, two influential figures in the Original Sarasota School of Architecture, this home seamlessly

  Daniel Petrilla PREFERRED SHORE LLC

  4879 Commonwealth Dr, Sarasota, FL 34242
• 

  /2

  $590,000 Sold Apr 25, 2025

  • 1,287 Sq Ft
  • $458/SF
  • 17 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  6415 Midnight Pass Rd Unit 508, Sarasota, FL 34242

  Real estate is always about location, and your new condominium has it. No need for a car when you live here! Leave your condo, down the elevator and walk out the front door of The Anchorage to the Daiquiri Deck, Captain Curt’s Crab & Oyster Bar, plus a variety of other restaurants and shops along with the Siesta Key Marina and private access to Siesta Key Beach! If you are looking for

  Anthony DeLuca DELUCA REALTY INC

  6415 Midnight Pass Rd Unit 508, Sarasota, FL 34242
• 

  

  /64

  Est $817,240 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft

  5740 Midnight Pass Rd Unit 207, Sarasota, FL 34242

  5740 Midnight Pass Rd Unit 207, Sarasota, FL 34242
• 

  

  /40

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  6308 Midnight Pass Rd Unit 6, Sarasota, FL 34242

  Coastal Luxury Villa with Thai-Inspired Elegance – Crescent Arms on Siesta KeyExperience beachside living at its finest in this stunningly renovated two-bedroom, two-bath villa located within the gated Gulfside community of Crescent Arms with exclusive private access to Siesta Key Beach.This meticulously updated villa blends custom coastal finishes with touches of Thai-inspired

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  6308 Midnight Pass Rd Unit 6, Sarasota, FL 34242
• 

  /2

  $1,200,000 Sold Apr 25, 2025

  • 2,111 Sq Ft
  • $568/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  5602 Cape Leyte Dr, Sarasota, FL 34242

  Nestled in the highly sought-after Siesta Isle neighborhood, this exceptional 14,000+ sq. ft. corner lot presents an unparalleled opportunity to create your dream home just steps from the main entrance of world-renowned Siesta Key Beach. Whether you choose to remodel the existing two-bedroom, two-bath single-family home to your specifications or build an exquisite custom estate, this prime

  Ben Angerami PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5602 Cape Leyte Dr, Sarasota, FL 34242
• 

  

  /64

  Est $1,339,122 Not Listed For Sale

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

  5400 Ocean Blvd Unit 5-4, Sarasota, FL 34242

  5400 Ocean Blvd Unit 5-4, Sarasota, FL 34242
• 

  

  /39

  $599,000

  • 2 Beds
  • 2 Baths
  • 940 Sq Ft

  915 Beach Rd Unit 321, Sarasota, FL 34242

  INVESTOR ALERT!! JUST REDUCED $26K!! This is the LOWEST PRICED 2/2 available in LA SIESTA where weekly rentals are permitted! Offered turnkey furnished, this spacious condo is located DIRECTLY ACROSS from the main entrance of world-renowned Siesta Key Public Beach, providing effortless access to the powdery white sand beach, shimmering Gulf waters, tennis and volleyball courts, food pavilion,

  Lori Madden MANGROVE REALTY ASSOCIATES

  915 Beach Rd Unit 321, Sarasota, FL 34242
• 

  /2

  $20,000 Sold Apr 25, 2025

  • 1,900 Sq Ft
  • $11/SF
  • 175 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2009

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

  Fractional Ownership. Introducing the Winter Fractional Package, offering 1/16th ownership in a stunning luxury residence on Siesta Key Beach. Now, your dream of owning a beachfront home on America's most celebrated shore can become a reality. Enjoy the benefits of owning a slice of paradise, complete with world-class amenities and services.This exclusive opportunity offers the ultimate in

  Kelly Mooney DOUGLAS ELLIMAN

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

  

  /47

  Est $1,771,549 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,616 Sq Ft

  615 Calle Del Otono, Sarasota, FL 34242

  615 Calle Del Otono, Sarasota, FL 34242
• 

  

  /9

  $799,000

  • Land
  • 0.29 Acre
  • $2,755,172 per Acre

  5587 Shadow Lawn Dr, Sarasota, FL 34242

  Nestled on picturesque Shadow Lawn Drive, this 12,800-square-foot lot offers an exceptional canvas for your custom home. Framed by mature live oaks on the front left and back right corners, the property blends natural beauty with an enviable location.Enjoy the best of Siesta Key living—just an 8-minute stroll to the powdery sands of world-famous Siesta Beach and just over a mile to the

  Nick Gard COLDWELL BANKER REALTY

  5587 Shadow Lawn Dr, Sarasota, FL 34242
• 

  /2

  $1,029,000 Sold Apr 22, 2025

  • 816 Sq Ft
  • $1,261/SF
  • 214 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1970

  5966 Midnight Pass Rd Unit G-92, Sarasota, FL 34242

  Siesta Key ~ Palm Bay Club ~ 9th Floor ~ Breathtaking "Direct" Siesta Key Beach & Gulf of Mexico Views ~ Direct Siesta Beach Access ~ Rental Income $90K +/- ~ this property is updated throughout (including windows) ~ 1 bedroom / 1 bath / open or closed balcony ~ sold turnkey furnished ~ managed on-site ~ offering an excellent investment with its rare three day minimum rental policy and on-site

  Robert Anderson Jr RE/MAX ALLIANCE GROUP

  5966 Midnight Pass Rd Unit G-92, Sarasota, FL 34242
• 

  

  /68

  Est $2,618,578 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,950 Sq Ft

  5132 Sandy Shore Ave, Sarasota, FL 34242

  5132 Sandy Shore Ave, Sarasota, FL 34242
• 

  

  /69

  $1,300,000

  • 3 Beds
  • 3.5 Baths
  • 2,798 Sq Ft

  3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242

  A unique opportunity to renovate and create your dream coastal retreat in one of Siesta Key’s sought-after gated enclaves Hamilton Club, an exclusive boating community on North Siesta Key. Rarely available, this spacious, elevated townhome is one of only 18 residences in a private, pet-friendly, deep-water boating community offering a deeded dock with sailboat-water access—no fixed bridges to

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242
• 

  /2

  $910,000 Sold Apr 22, 2025

  • 1,375 Sq Ft
  • $662/SF
  • 267 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  5300 Ocean Blvd Unit 803, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. ICONIC BEACH, ICONIC BUILDING, INCREDIBLE PRICE! NEW A/C, NEW PAINT! Are you ready for breathtaking views of the Gulf of Mexico from your luxury condominium? Discover a rare chance to own a condominium in the vibrant heart of Siesta Key Village with easy access to the beautiful quartz beach of Siesta Key. The island lifestyle is here for you.

  Diane Goodwin EXP REALTY LLC

  5300 Ocean Blvd Unit 803, Sarasota, FL 34242

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