Siesta Key, FL Homes

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  /46

  $1,895,000 Open Sat 12PM - 3PM

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

  4108 Roberts Point Rd, Sarasota, FL 34242

  Welcome to one of the most desirable streets on Siesta Key, Roberts Point Road. Just steps from Shell Beach and minutes from the north bridge, this home blends island charm with thoughtful updates, including a brand-new roof in 2024. Enter through a tranquil, private courtyard, ideal for quiet mornings or intimate entertaining before stepping into a stunning interior with soaring 22' ceilings and

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  4108 Roberts Point Rd, Sarasota, FL 34242
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  /51

  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft
  • Condo for Rent

  5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  Available April 2025 this Luxury Siesta Key Beach Front Unit in The Exclusive Gulf and Bay Club... - Enjoy Full Gulf of Mexico Views for the entire month in Paradise of Siesta Key Enjoy panoramic views of the #1 beach in the USA, Siesta Key! This beautiful 2 Bedroom, 2 Bathroom unit is fully updated with hardwood floors, granite countertops, and an amazing amount of cabinet space. Bathrooms are

  Robert Bevington SHOWTIME REALTY

  5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
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  /2

  $850,000 Sold May 08, 2025

  • 2,341 Sq Ft
  • $363/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  700 Tropical Cir, Sarasota, FL 34242

  INCREDIBLE Views!....INCREDIBLE Privacy!....INCREDIBLE Siesta Key Neighborhood!....Only (2) Owners have Enjoyed this Peaceful Island Oasis along the Edward C. Wright Nature Preserve & Bird Sanctuary---just a short Bike Ride to the Powdery Quartz Sands of TOP-RATED Siesta Key Beach!....Conveniently Located, with easy access to the North Bridge, in the "park-like" Bayside Club community along a

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  700 Tropical Cir, Sarasota, FL 34242
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  /42

  Est $825,592 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft

  5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

  5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242
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  /52

  $875,000

  • 2 Beds
  • 2 Baths
  • 1,253 Sq Ft

  6300 Midnight Pass Rd Unit 5, Sarasota, FL 34242

  Rarely available beach villa on Siesta Key in Crystal Sands. Experience the ultimate in island living with this beautifully renovated, free-standing villa in Crystal Sands — a sought-after beachfront community ideally positioned on the powdery white sands of world-renowned Siesta Beach. Offering the privacy and comfort of a single-family home with ease of condominium ownership, this rare

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6300 Midnight Pass Rd Unit 5, Sarasota, FL 34242
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  /48

  $2,600 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  4660 Ocean Blvd Unit G1, Sarasota, FL 34242

  Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added

  Beth Dilley ASCENDIA REAL ESTATE

  4660 Ocean Blvd Unit G1, Sarasota, FL 34242
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  /2

  $1,425,000 Sold May 08, 2025

  • 1,271 Sq Ft
  • $1121/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
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  /43

  Est $719,114 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft

  5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

  5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242
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  /53

  $800,000 Open Sun 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft

  1255 E Peppertree Dr Unit 507, Sarasota, FL 34242

  Magnificent water views!  It is like watching a boat parade every day! Welcome to Peppertree Bay, a sought-after beach to bay community on Siesta Key. This pristine 2-bedroom 2-bath condo has been beautifully updated to appeal to the modern discerning buyer, with clean contemporary finishes showcasing its coastal charm. Step inside to find a spacious open floor plan incorporating gorgeous

  Ethel Lovelace MICHAEL SAUNDERS & COMPANY

  1255 E Peppertree Dr Unit 507, Sarasota, FL 34242
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  /50

  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Condo for Rent

  1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242

  Welcome to this stunning 2-bedroom, 2-bathroom lakefront condo located on the second floor in Gulf and Bay Bayside, Siesta Key. This two-story retreat features two primary bedrooms, each with a luxurious king-size bed, spacious walk-in closets, and beautifully appointed bathrooms with walk-in showers. In the second floor primary bedroom there is additional sleeping accommodations with a full-size

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
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  /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
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  /45

  Est $672,451 Not Listed For Sale

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

  5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

  5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242
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  /41

  $750,000 Open Sun 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242

  Paradise awaits at Gulf & Bay Club Bayside on Siesta Key. FIRST-FLOOR, TURNKEY FURNISHED, 2-bedroom, 2-bathroom residence includes a deep one-car GARAGE. Flexibility of weekly rentals, perfect for personal enjoyment or as a lucrative income-producing property. Located in a popular gated community just steps from DEEDED BEACH ACCESS to world-famous Siesta Key and Crescent Beach. This home invites

  Dana Cook Westmark MICHAEL SAUNDERS & COMPANY

  1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
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  $3,400 per month

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

  5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242

  Available 06/03/2025 Annually or 2026 Season $6000/mo.This gorgeous 1 bedroom 1 bathroom fully furnished unit in the exclusive Terrace building on Siesta Key beach steps away from Siesta Key Village. Enjoy a swim from the elevated pool and catch a sunset with a drink steps away from the unit. This unit includes a private parking spot, direct beach access, WIFI, cable and all utilities included.

  Brenda Cozy COLDWELL BANKER REALTY

  5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242
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  /2

  $1,225,000 Sold May 05, 2025

  • 1,473 Sq Ft
  • $832/SF
  • 58 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242

  Nestled along the pristine shores of the world-renowned Siesta Key Beach, this stunning Gulf & Bay Club condo offers an unparalleled beachfront lifestyle with breathtaking, direct Gulf views. Just steps from putting your toes in the soft, powdery quartz sand, this renovated two-bedroom plus office, two-bath unit has been thoughtfully designed to maximize space and light, featuring raised ceilings

  Joanna Benante MICHAEL SAUNDERS & COMPANY

  5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
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  /47

  Est $992,564 Not Listed For Sale

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

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242
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  /26

  $875,000

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  5855 Midnight Pass Rd Unit 621, Sarasota, FL 34242

  Breathtaking Gulf Views and Spectacular Sunsets Await!Perched on the 6th floor, this beautifully updated condo offers sweeping views of the Gulf and stunning nightly sunsets. The building has recently completed a $12 million structural renovation, featuring all-new hurricane-impact windows and sliding glass doors, along with fresh exterior stucco and paint—making it one of the most modern and

  Heidi Scholten MEDWAY REALTY

  5855 Midnight Pass Rd Unit 621, Sarasota, FL 34242
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  $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 piece of paradise at Jamaica Royale, your unit is 5 steps from the refreshing waters of heated pool #1, while a mere twominute stroll takes you to the pristine Siesta Key beach. Jamaica Royale's prime location on these dazzling sands provides easy access to all. Enjoy assigned covered parking space just steps from your front door. This updated, tastefully decorated

  Robert Bevington SHOWTIME REALTY

  5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
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  /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 invite in

  Jeff Bray LPT REALTY, LLC

  6267 Midnight Pass Rd Unit 105, Sarasota, FL 34242
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  /27

  Est $728,156 Not Listed For Sale

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

  6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

  6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242
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  /55

  $2,050,000

  • 3 Beds
  • 3 Baths
  • 2,210 Sq Ft

  868 Siesta Key Cir, Sarasota, FL 34242

  This island-style, ranch waterfront home offers an incredible opportunity to renovate and make it your own. While it did take on water during Hurricanes Helene and Milton, it boasts several key updates including a newer roof, fresh exterior paint, impact windows and doors, vaulted ceilings, and charming plantation shutters—just a few of the features that make this Siesta Key property so

  Jennifer Thompson WILLIAM RAVEIS REAL ESTATE

  868 Siesta Key Cir, Sarasota, FL 34242
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  /26

  $7,800 per month

  • 4 Beds
  • 3 Baths
  • 2,248 Sq Ft
  • House for Rent

  5153 Sandy Cove Ave, Sarasota, FL 34242

  You will Never Want to Leave this 4-bedroom house on Siesta Key! Mid-Century Modern, 4 bedroom home with saltwater, heated Pool with canal views. Located within a 6 minute bike ride to Siesta Key's Beach Access #5 and walking distance to everything that Siesta Key Village has to offer. This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, "Sarasota School of Architecture style"

  Kelly Anderson RE/MAX ALLIANCE GROUP

  5153 Sandy Cove Ave, Sarasota, FL 34242
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  /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
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  /73

  Est $614,364 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1500 Cove II Place Unit 532, Sarasota, FL 34242

  1500 Cove II Place Unit 532, Sarasota, FL 34242
• 

  

  /40

  $1,999,900

  • 3 Beds
  • 3 Baths
  • 3,324 Sq Ft

  681 Avenida de Mayo, Sarasota, FL 34242

  Price REDUCED so you can BUY your boat and bring it with you to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations.Step inside to find over-sized rooms that can be utilized for

  Colette Jay HORIZON REALTY INTERNATIONAL

  681 Avenida de Mayo, Sarasota, FL 34242
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  /17

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • House for Rent

  339 Avenida de Paradisio, Sarasota, FL 34242

  scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort.??? Just a 3-Min Drive to Siesta Beach??? 10 Minutes to Crescent Beach????? 13-Min Walk to a Local BeachDiscover the best of Sarasota with us!

  Valerie McInerney LPT REALTY, LLC

  339 Avenida de Paradisio, Sarasota, FL 34242
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  /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
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  /79

  Est $720,465 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft

  1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

  1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242
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  /38

  $810,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  6204 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  Just two walkways from the powdery sands of Siesta Key Beach, this turnkey 2-bedroom, 2-bath condo offers the perfect blend of coastal living and investment potential. Withstanding recent hurricanes without issue, this unit is a solid choice for peace of mind and performance. In 2023 alone, it generated over $62,000 in rental income, supported by a strong short-term rental history and top-notch

  Nili Blaha VUE REALTY, LLC

  6204 Midnight Pass Rd Unit 201, Sarasota, FL 34242
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  /57

  $7,900 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Property for Rent

  4660 Ocean Blvd Unit N1, Sarasota, FL 34242

  Escape to Paradise on Siesta Key! Your dream seasonal getaway awaits at 4660 Ocean Blvd Unit N1, Sarasota, FL 34242. Immerse yourself in the tranquil beauty of the Gulf coast, where pristine sands meet crystal-clear waters. This exquisite 2-bedroom, 2-bathroom condo is your ticket to an unforgettable retreat. Step into your sun-drenched sanctuary, tastefully furnished to embody

  Robert Bevington SHOWTIME REALTY

  4660 Ocean Blvd Unit N1, 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
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  /79

  Est $864,176 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  1600 Cove II Place Unit 424, Sarasota, FL 34242

  1600 Cove II Place Unit 424, Sarasota, FL 34242
• 

  

  /70

  $925,000

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft

  625 Beach Rd Unit 207, Sarasota, FL 34242

  Rare opportunity to experience the ultimate Siesta Key lifestyle in this beautifully appointed, turnkey furnished 2-bedroom, 2-bathroom coveted end unit condo on the desirable second floor, perfectly positioned with direct access to Siesta Key Beach through the exclusive private Tivoli beach entrance. Be captivated by the stunning gulf views and spectacular sunsets from your updated unit

  Pamela Wall MICHAEL SAUNDERS & COMPANY

  625 Beach Rd Unit 207, Sarasota, FL 34242
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  /35

  $5,000 per month

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

  6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

  Welcome to Siesta Dreams at Casa Mar! This 1br/1ba fully equipped condo is perfect for your next beach vacation! Enjoy the resort's private beach in the provided lounge chairs while you dig your toes into the quartz sand. Need a break from the salt water? Take a swim in one of two pools on the property instead. Shuffleboard, tennis, or pickleball interest you? We've got it! The serene

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
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  /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
• 

  

  /17

  Est $584,038 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242
• 

  

  /29

  $925,000

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft

  5780 Midnight Pass Rd Unit 410, Sarasota, FL 34242

  Welcome to Siesta Keys most prestigious resort community. This end unit is full of natural sunlight with views of lakes, fountains, 2 swimming pool, beach and the beautiful Gulf of Mexico. Gulf & Bay Club is 32 acres of gated resort grounds with 800 sq. ft. of pristine, private beach. Amenities include 3 heated swimming pools, tennis, pickleball, saunas, electric car charging stations, new

  Carol Thomas MICHAEL SAUNDERS & COMPANY

  5780 Midnight Pass Rd Unit 410, Sarasota, FL 34242
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  /44

  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Condo for Rent

  5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242

  SHORT TERM RENTAL This 2 bedroom condo offers bay views, is an end unit, has a light and bright interior and is just steps from the Bayfront pool! There is a sleeper sofa in the living room to accommodate 2 as well. This condo has been beautifully updated and is one of the larger Palm Bay condos boasting 1270 square feet! Spacious open kitchen with driftwood cabinets, stunning quartz

  Robert Bevington SHOWTIME REALTY

  5963 Midnight Pass Rd Unit 332, 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
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  /69

  Est $561,456 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  5600 Beach Way Dr Unit 209, Sarasota, FL 34242

  5600 Beach Way Dr Unit 209, Sarasota, FL 34242

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