Siesta Key, FL Homes

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  /74

  $4,495,000 New Construction

  • 4 Beds
  • 6 Baths
  • 5,238 Sq Ft

  656 Tropical Cir, Sarasota, FL 34242

  Welcome to Tropical Circle nestled away in a quiet neighborhood centrally located on Siesta Key. Designed and built by Jeff Tucker, Design 2 Build, this home combines elegance with functionality not to mention it also sits upon 15+ ft of elevation. With easy access from either bridge, minutes from world renowned Siesta Key Beach, close to Out of Door Academy and a quick ride to Siesta Key Village

  Carey Hibbs HARRY ROBBINS ASSOC INC

  656 Tropical Cir, Sarasota, FL 34242
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  /71

  $6,900 per month

  • 2 Beds
  • 2 Baths
  • 1,217 Sq Ft
  • Condo for Rent

  1269 Dockside Place Unit 115, Sarasota, FL 34242

  A BOATER'S PARADISE! THE BEST OF THE BEACH AND THE BAY!! Great canal front first floor condo with large deck! Best of both worlds - across the street from Siesta Beach and a gated bayside community open to the intracoastal. Large kitchen with granite countertops, open to living/dining room. Bonus Florida room with plantation shuttered sliders that recess for an open air concept. Two bedroom, each

  Susan Brooks COLDWELL BANKER SUNSTAR REALTY

  1269 Dockside Place Unit 115, Sarasota, FL 34242
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  /2

  $1,735,000 Sold May 23, 2025

  • 1,380 Sq Ft
  • $1257/SF
  • 32 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1947

  303 Beach Rd, Sarasota, FL 34242

  Location is Everything with this Fantastic Property. Only a few short steps to having your feet in the Crystal Sands of Siesta Beach and a short leisurely walk to Siesta Village. Zoned Multi-Family with NO HOA. You can rebuild one of the 1940's bungalows and repair the other two or start all over with a fresh new look. This has been a huge income producing property over the years for the

  Michelle Shiver KELLER WILLIAMS ON THE WATER S

  303 Beach Rd, Sarasota, FL 34242
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  /68

  Est $680,480 Not Listed For Sale

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

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

  101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242
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  /91

  $1,175,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,840 Sq Ft

  1280 Dolphin Bay Way Unit 202, Sarasota, FL 34242

  Under contract-accepting backup offers. 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

  Bill McCue BRIGHT REALTY

  1280 Dolphin Bay Way Unit 202, Sarasota, FL 34242
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  /36

  $7,000 per month

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

  6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242

  No roads to cross to get to the beach! Just listed- clean and cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your suit and

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
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  /2

  $2,100,000 Sold May 23, 2025

  • 2,692 Sq Ft
  • $780/SF
  • 122 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1996

  5159 Oxford Dr, Sarasota, FL 34242

  The best value for amenities offered anywhere on Siesta Key - elevated, hurricane-safe, and with a pool and boat lift! Welcome to your dream waterfront oasis, nestled in the heart of Siesta Key, FL. This exquisite home, featuring 3 bedrooms and 4 baths across 2,692 square feet of elegantly remodeled living space, is a true testament to luxury and comfort. Ideal floor plan for AIRBNB with 3

  Andrew Foltz PREFERRED SHORE LLC

  5159 Oxford Dr, Sarasota, FL 34242
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  /66

  Est $2,013,062 Not Listed For Sale

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

  3927 Somerset Dr Unit 8, Sarasota, FL 34242

  3927 Somerset Dr Unit 8, Sarasota, FL 34242
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  /72

  $3,500,000

  • 6 Beds
  • 4.5 Baths
  • 4,699 Sq Ft

  1240 Solitude Ln, Sarasota, FL 34242

  Discover Unrivaled Coastal Elegance Steps from Siesta Key Beach!This rare gem features two meticulously remodeled canal-front homes with stunning partial views of the bay, perfectly situated in a prestigious neighborhood. The main residence boasts a contemporary design with open and spacious layouts, highlighted by soaring 24 ft ceilings adorned with stylish gray wooden accent beams.Culinary

  Karl Helbig SUNREAL ESTATE INC

  1240 Solitude Ln, Sarasota, FL 34242
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  /30

  $4,995 per month

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

  5770 Midnight Pass Rd Unit 405, Sarasota, FL 34242

  Immaculate well maintained 2 beds 2 bath condo situated in the desirable Gulf & Bay Club on Siesta Key. This 4th floor unit is meticulously maintained and tastefully decorated. Amenities include three pools, saunas, fitness center, tennis, basketball, racquetball, & 24hr security. A must see! Wake up to views of the Gulf and enjoy living your Siesta Key dream. Available for annual rent at $4,500

  Pamala Casey CASEY REALTY CORPORATION

  5770 Midnight Pass Rd Unit 405, Sarasota, FL 34242
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  /2

  $475,000 Sold May 22, 2025

  • 1,264 Sq Ft
  • $376/SF
  • 52 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1968

  147 Whispering Sands Dr Unit V-29, Sarasota, FL 34242

  GREAT GULF FRONT OPPORTUNITY! This incredibly well priced 2 bed/2 bath villa represents an exceptional opportunity to start fresh with almost new construction in the idyllic GULF FRONT property of Whispering Sands on Siesta Key. This lovely unit experienced flooding last fall and is now being sold post remediation and pre rebuild – providing the next owner with the wonderful opportunity to

  Harriet Stopher COLDWELL BANKER REALTY

  147 Whispering Sands Dr Unit V-29, Sarasota, FL 34242
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  /84

  Est $607,398 Not Listed For Sale

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

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242
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  /45

  $749,900

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

  6265 Midnight Pass Rd Unit 205, Sarasota, FL 34242

  Don’t miss this rare opportunity to own a beautifully updated 2-bedroom, 2-bath condo in the highly sought-after Excelsior community on world-famous Siesta Key Beach. This spacious unit offers an open-concept layout with coastal-inspired finishes, updated kitchen and baths, in-unit laundry, and a private screened lanai.Enjoy resort-style amenities including two heated pools, tennis and pickleball

  Jake Wittmer THE SUNSHINE STATE COMPANY

  6265 Midnight Pass Rd Unit 205, Sarasota, FL 34242
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  /23

  $2,500 per month

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

  111 Pass Key Rd Unit 111, Sarasota, FL 34242

  Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private beach access, and a fishing pier for those who love to cast a line. Enjoy the convenience of in-unit laundry and make use of the outdoor BBQ for al fresco dining. The clubhouse is perfect for social

  Ray Shope ROSEBAY INTERNATIONAL REALTY, INC

  111 Pass Key Rd Unit 111, Sarasota, FL 34242
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  /2

  $1,225,000 Sold May 22, 2025

  • 2,732 Sq Ft
  • $448/SF
  • 78 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  716 Tropical Cir, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Luxurious Serenity with Breathtaking Bayou and Nature Preserve Views. This exceptional two-story home, nestled on a sprawling oversized lot, offers a rare blend of natural beauty and sophisticated design, providing an unparalleled living experience. Set back from the road and framed by majestic oaks, this home offers panoramic views of a tranquil

  Stacey King MICHAEL SAUNDERS & COMPANY

  716 Tropical Cir, Sarasota, FL 34242
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  /27

  Est $747,129 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft

  5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

  5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242
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  /32

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft

  6312 Midnight Pass Rd Unit 102S, Sarasota, FL 34242

  Siesta Key Beachfront Gem - Just Like New! Welcome to your slice of paradise on world-famous Siesta Key Beach! This stunning 2 bedroom, 2 bath elevated first floor end unit offers the ultimate in coastal living with direct beach access and breathtaking Gulf views. Step into a fully remodeled interior, professionally remediated and redesigned from top to bottom--including stylish furnishings--so

  Kristina Rain MICHAEL SAUNDERS & COMPANY

  6312 Midnight Pass Rd Unit 102S, Sarasota, FL 34242
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  /43

  $17,000 per month

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Condo for Rent

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242

  Beachfront Bliss at Casa Mar – Siesta KeyDiscover this beautifully updated two-bedroom, two-bathroom beachfront condo in Casa Mar, offering direct access to Crescent Beach, a serene and less crowded alternative to Siesta Key’s main beach.Why You’ll Love This Condo:Prime Beachfront Location – Step right onto the powdery white sands of Crescent BeachClassic Coastal Charm – Thoughtfully designed

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
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  /2

  $2,750,000 Sold May 20, 2025

  • 3,070 Sq Ft
  • $896/SF
  • 218 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1998

  3920 Roberts Point Rd, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. CERTAIN CRYPTOCURRENCIES ACCEPTED. An exquisite waterfront retreat in SIESTA KEY, SARASOTA, FL – a sanctuary of COASTAL LUXURY. Enter the fully REMODELED CONTEMPORARY residence with CUSTOM WOOD CABINETRY, DELUXE APPLIANCES, and STONE COUNTERTOPS. The great room with 11-FOOT CEILINGS and SLIDING DOORS flows to a 50-FOOT PORCH overlooking the water.

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  3920 Roberts Point Rd, Sarasota, FL 34242
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  /53

  Est $521,306 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft

  44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

  44 Sandy Cove Rd Unit A4, Sarasota, FL 34242
• 

  

  /65

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft

  5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242

  Gulf & Bay is one of the finest properties on the island with 32 acres of manicured grounds and 800 feet of private white quartz powder beach. Lush tropical courtyard featuring 3 swimming pools, commercial grade fitness center, racquetball courts, tennis courts, freshwater lake with a unique island barbeque area, two clubhouses, dry saunas and hot tub, and electric charging stations. This is

  Brian Livesey WATERSIDE REALTY LLC

  5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242
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  /9

  $3,950 per month

  • 2 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Condo for Rent

  4708 Ocean Blvd Unit E2, Sarasota, FL 34242

  ENJOY INCREDIBLE SUNSETS AND BREATHTAKING VIEWS OF BIG PASS AND DOWNTOWN FROM TWO LARGE BALCONIES, ONE ENCLOSED AND ONE OPEN-AIR! UNIT INCLUDES DESIGNER KITCHEN WITH GRANITE COUNTERS, UPDATED BATHROOM, MARBLE FLOORING, NEW GE PROFILE APPLIANCES, REFRIGERATOR, RANGE, MICROWAVE, AND DISHWASHER. LARGE 2 CAR GARAGE WITH STORAGE CABINETS. CLOSE PROXIMITY TO RESTAURANTS AND SHOPS OF SIESTA VILLAGE.

  Curt Cogan COGAN REALTY LLC

  4708 Ocean Blvd Unit E2, Sarasota, FL 34242
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  /2

  $1,675,000 Sold May 20, 2025

  • 1,202 Sq Ft
  • $1394/SF
  • 182 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  6142 Midnight Pass Rd Unit 14N, Sarasota, FL 34242

  Welcome to 14N, located at Island House Beach Resort! This is an exquisite coastal retreat nestled along the widest expanse of one of Florida's most celebrated beaches. This impeccably maintained complex is a sanctuary where the pristine white sands meet the tranquil turquoise waters of the Gulf of Mexico. From the moment you step inside this 3rd-floor, 2-bedroom, 2-bathroom residence, spanning

  Domanic Calamese KW COASTAL LIVING III

  6142 Midnight Pass Rd Unit 14N, Sarasota, FL 34242
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  /20

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 5,986 Sq Ft

  84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242

  84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242
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  /80

  $2,600,000

  • 4 Beds
  • 3.5 Baths
  • 2,757 Sq Ft

  3959 Somerset Dr Unit 5, Sarasota, FL 34242

  Boaters, this one’s rare. On deep, protected water in Cocoanut Bayou with no fixed bridges, this fully remodeled home on Siesta Key’s north end includes a deeded dock with water, electric, and a 20,000-pound lift—currently holding a 36-foot boat—with fast access to Sarasota Bay and the Gulf in under 10 minutes. Inside and out, this free-standing four-bedroom, 3.5-bath home has been thoughtfully

  Peter Mason PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3959 Somerset Dr Unit 5, Sarasota, FL 34242
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  /84

  $16,000 per month

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • House for Rent

  327 Avenida Milano, Sarasota, FL 34242

  Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street, this home has so much to offer. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with

  Chrissie Cummings JENNETTE PROPERTIES INC

  327 Avenida Milano, Sarasota, FL 34242
• 

  /2

  $840,000 Sold May 16, 2025

  • 1,343 Sq Ft
  • $625/SF
  • 41 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  1273 Dockside Place Unit 116, Sarasota, FL 34242

  Price Reduction!! Your island paradise awaits!! The perfect retreat for the boater and beach-goer! Just across the street from world renowned Siesta Key public beach, this 2 bedroom, 2 bath unit has been beautifully renovated to include an open kitchen with marble-topped wood cabinets, a stunning tiled backsplash and stainless steel appliances. Other renovations include wood-look tile flooring,

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  1273 Dockside Place Unit 116, Sarasota, FL 34242
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  /77

  Est $678,307 Not Listed For Sale

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

  6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

  6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242
• 

  

  /16

  $995,000

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

  5880 Midnight Pass Rd Unit 202, Sarasota, FL 34242

  Seize this opportunity to own a second-floor condominium in the heart of Siesta Key, at one of the beach's widest, most breathtaking stretches. Spacious 1,500-square-foot getaway is mid-kitchen remodel, offered as-is at an unbeatable price for a swift sale, ideal for those eager to personalize their coastal escape! Choose your colors, finishes, and design touches to transform this gem into your

  Maureen Morris PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5880 Midnight Pass Rd Unit 202, Sarasota, FL 34242
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  /81

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • Condo for Rent

  4822 Ocean Blvd Unit 2F, Sarasota, FL 34242

  Gulf Views!!Siesta Key!This 2/2 condo is close to restaurants and outdoor recreation! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The

  Jane Hunter JENNETTE PROPERTIES INC

  4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
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  /2

  $930,000 Sold May 16, 2025

  • 1,473 Sq Ft
  • $631/SF
  • 114 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  5780 Midnight Pass Rd Unit 205, Sarasota, FL 34242

  Overlooking the pristine 32-acre gated property of the Gulf & Bay Club on Siesta Key, find yourself surrounded by coastal charm and modern accents in this two bedroom, two bathroom home offering a distinguished renovation. The kitchen, with handsome driftwood inspired flooring, will please the most discerning chef with tasteful, modern white cabinetry. Prepare and create your treasured cuisine

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5780 Midnight Pass Rd Unit 205, Sarasota, FL 34242
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  /66

  Est $583,922 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft

  23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

  23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242
• 

  

  /55

  $719,000

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

  101 Whispering Sands Dr Unit 307, Sarasota, FL 34242

  Experience the pinnacle of coastal luxury in this completely updated, fully furnished end-unit condo located in the relaxing community of Whispering Sands on Siesta Key. Overlooking a tranquil lagoon and offering private beachfront access, this 2-bedroom, 2-bath residence seamlessly blends modern comfort with serene island living. This rare end-unit offers extra privacy and natural light, along

  Todd Goodman KELLER WILLIAMS ON THE WATER S

  101 Whispering Sands Dr Unit 307, Sarasota, FL 34242
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  /56

  $5,250 per month

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • House for Rent

  726 Birdsong Ln, Sarasota, FL 34242

  AVAILABLE October, November 2025! Currently booked through September 2025. Also booked December - March 2026. WOW! Enjoy a little slice of heaven on the World Famous Siesta Key! This beautifully renovated turnkey 3 bedroom 2 bath, heated pool home, is just a short distance to the #1 rated beaches and the quaint shops and restaurants in the downtown village. Whether it’s our million-dollar

  Scott Nold TNG PROPERTY MANAGEMENT

  726 Birdsong Ln, Sarasota, FL 34242
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  /54

  $861,360 Sold May 15, 2025

  • 1,282 Sq Ft
  • $672/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  19 Whispering Sands Dr Unit 303, Sarasota, FL 34242

  BREATHTAKING GULF VIEWS AWAIT! Discover the perfect blend of comfort and coastal beauty in this wonderful 2 bed/2 bath, 3rd floor North Tower residence in the premiere 55+ GULF FRONT property of Whispering Sands! With expansive 180 degree views of the shimmering Gulf, this unit provides the perfect retreat against an unparalleled backdrop of sand, sea, sky, and lush greenery. You’ll enjoy

  Harriet Stopher COLDWELL BANKER REALTY

  19 Whispering Sands Dr Unit 303, Sarasota, FL 34242
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  /41

  Est $704,571 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,016 Sq Ft

  141 Avenida Messina Unit 3, Sarasota, FL 34242

  141 Avenida Messina Unit 3, Sarasota, FL 34242
• 

  

  /74

  $1,295,000

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

  20 Whispering Sands Dr Unit 1201, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. A truly RARE offering, this TOP floor, GULF FRONT PENTHOUSE residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL

  Harriet Stopher COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 1201, 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

  $1,375,000 Sold May 09, 2025

  • 2,299 Sq Ft
  • $598/SF
  • 193 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2007

  702 Treasure Boat Way, Sarasota, FL 34242

  Mediterranean Estate Masterpiece nestled on the peaceful tranquil island of Siesta Key.. world renowned for its world-class beach and romantic sunset. ENTERTAINING AT ITS BEST - JUST MINUTES FROM THE BEACH *** Welcome to your dream residence on Siesta Key where your family can fully enjoy this stunning 3 story 4 bedroom home filled with unique features., This home is well constructed to endure

  Mark Borg MARKANGEL REALTY

  702 Treasure Boat Way, Sarasota, FL 34242
• 

  

  /68

  Est $574,170 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1600 Cove II Place Unit 421, Sarasota, FL 34242

  1600 Cove II Place Unit 421, Sarasota, FL 34242

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