Siesta Key, FL Homes

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  /94

  $1,129,000

  • 3 Beds
  • 2 Baths
  • 2,255 Sq Ft

  635 Tropical Cir, Sarasota, FL 34242

  Discover luxurious coastal living on tropical Siesta Key, #1 beach in the US and #4 in the world! You will love this beautifully updated 3-bedroom, 2-bath single-level residence offering nearly 2,300 sq. ft. of refined comfort. Perfectly situated just minutes from the world-famous powder-white sands and vibrant and eclectic Siesta Village, this home captures the essence of island elegance.The

  

  Tami Cashi

  COLDWELL BANKER REALTY

  (941) 273-8651

  635 Tropical Cir, Sarasota, FL 34242
• Explore Siesta Key

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  /49

  $9,500 per month

  • 2 Beds
  • 2 Baths
  • 1,489 Sq Ft
  • Condo for Rent

  6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242

  ***AVAILABLE MAY 2026*** one MONTH MIN***Welcome to the Beach! Prime Siesta Key location. This large, spacious 2 Bedroom/2 Bath split floor plan condo comes with a full-length balcony with views of the gulf and intracoastal waterway, as well as the beautiful sunsets. Available as a monthly rental, the interior boasts a decorative fireplace, reclining sofa, two walk-in closets, washer and dryer in

  

  Anthony DeLuca

  AUDREY RAIN RENTALS, INC

  (941) 271-7125

  6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
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  /2

  $540,000 Sold Oct 23, 2025

  1900 Cove II Place Unit 114, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $628/SF
  • 4 Days On Market

  Last Listing Agent Rachel Tritschler RE/MAX ALLIANCE GROUP

  1900 Cove II Place Unit 114, Sarasota, FL 34242
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  /2

  Est $683,977 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  5961 Midnight Pass Rd Unit 306, Sarasota, FL 34242

  5961 Midnight Pass Rd Unit 306, Sarasota, FL 34242
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  /61

  $2,275,000

  • 5 Beds
  • 5 Baths
  • 3,126 Sq Ft

  5624 Cape Leyte Dr, Sarasota, FL 34242

  Discover this newly upgraded coastal retreat ideally located just behind the iconic Siesta Key Beach, where crystal-clear waters and powder-soft sands are only a short walk away. View of the beach main entrances right from your backyard a true showcase of the timeless real estate principle: location, location, location! This stunning home blends elegance, comfort, and peace of mind, featuring a

  

  Wally Sabrii

  SARASOTA INTERNATIONAL REALTY

  (941) 401-1015

  5624 Cape Leyte Dr, Sarasota, FL 34242
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  /27

  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,455 Sq Ft
  • Condo for Rent

  1195 Coquille St Unit 309, Sarasota, FL 34242

  Beautiful 2 Bedroom 2 Bathroom Townhome available! Come see this gorgeous home ready for you to call home! Large living spaces including full kitchen, living room and dining room, 3 seasons room and loft area. Loft area ideal for office space or second floor den. Two large bedrooms including plenty of closet and storage space. Nice patio with grill to enjoy evenings and entertaining. Large full

  

  Anna Fattore

  COMPASS FLORIDA LLC

  (941) 390-0370

  1195 Coquille St Unit 309, Sarasota, FL 34242
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  /2

  $440,000 Sold Jun 17, 2025

  6157 Midnight Pass Rd Unit E42, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft
  • Built 1974

  Last Sold Summary

  • 9% Below List Price
  • $400/SF
  • 74 Days On Market

  Current Estimated Value $435,752

  Last Listing Agent Robin Jones EXIT KING REALTY

  6157 Midnight Pass Rd Unit E42, Sarasota, FL 34242
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  /2

  Est $519,722 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft

  1257 S Portofino Dr Unit 406, Sarasota, FL 34242

  1257 S Portofino Dr Unit 406, Sarasota, FL 34242
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  /98

  $1,450,000

  • 2 Beds
  • 2 Baths
  • 1,642 Sq Ft

  5880 Midnight Pass Rd Unit 302, Sarasota, FL 34242

  Welcome to Casarina, one of Siesta Key’s most beautifully updated beachfront communities—and a place that truly captures the best of coastal living. This beautifully renewed 2-bed, 2-bath residence in Unit 302 blends comfort, quality, and a relaxed island feel from the moment you walk in. The entry opens to a light-filled space accented with custom-built-in cabinetry, detailed mouldings, and

  

  Julia Montei

  COLDWELL BANKER REALTY

  (941) 294-5521

  5880 Midnight Pass Rd Unit 302, Sarasota, FL 34242
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  /22

  $6,000 per month

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

  4660 Ocean Blvd Unit Q2, Sarasota, FL 34242

  Available January through April, this stylishly furnished 2-bedroom, 2-bath Siesta Key condo offers an effortless blend of modern comfort and laid-back coastal living. Located just moments from Siesta Key Village and world-famous Siesta Beach, renowned for its powdery quartz sand and consistently ranked the #1 beach in the U.S., this updated second-floor retreat places you in the heart of island

  

  Kevin Bryceland

  RANCH REALTY

  (941) 688-9685

  4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
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  /2

  $1,761,000 Sold Nov 10, 2025

  4929 Oxford Dr, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,878 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $612/SF
  • 2 Days On Market

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  4929 Oxford Dr, Sarasota, FL 34242
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  /2

  Est $8,446,339 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 6,838 Sq Ft

  241 Cedar Park Cir, Sarasota, FL 34242

  241 Cedar Park Cir, Sarasota, FL 34242
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  /43

  $850,000

  • 2 Beds
  • 2 Baths
  • 1,259 Sq Ft

  5600 Beach Way Dr Unit 315, Sarasota, FL 34242

  Are you ready to create your lifestyle in the sun, steps away from the quartz crystal white powdery sands and warm Gulf waters of the award-winning Siesta Key Beach? This wonderfully located tun-key, furnished condo end unit is oh so unique on the top floor with views of the beautiful beach and Gulf waters, a rare, remodeled find on the spectacular Gulf coasts of Florida! This recently,

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 401-0728

  5600 Beach Way Dr Unit 315, Sarasota, FL 34242
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  /50

  $6,300 per month

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Condo for Rent

  5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242

  RARE OPPORTUNITY to RENT THE PENTHOUSE. 3 BEDS/2.5 BATHS full size washer/dryer and a roof top deck with panoramic views available September 2025 stay for a year, 2 or 3+ owner wants this beautiful turnkey home with a BOAT DOCK (no lift yet)RENTED LONG TERM. Owner open to lift discussion. You will enjoy Penthouse end unit in Boca Siesta is located in the heart of Siesta Key the #1 Beach in the

  

  Marianne LeBar

  ROSEBAY INTERNATIONAL REALTY, INC

  (941) 294-2866

  5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
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  /2

  $1,527,000 Sold Sep 26, 2025

  5033 Oxford Dr, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,496 Sq Ft
  • Built 1960

  Last Sold Summary

  • 24% Below List Price
  • $612/SF
  • 124 Days On Market

  Last Listing Agent Jackie Eberley COLDWELL BANKER REALTY

  5033 Oxford Dr, Sarasota, FL 34242
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  /2

  Est $1,129,717 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,562 Sq Ft

  5880 Midnight Pass Rd Unit 508, Sarasota, FL 34242

  5880 Midnight Pass Rd Unit 508, Sarasota, FL 34242
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  /100

  $695,000

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

  5855 Midnight Pass Rd Unit 416, Sarasota, FL 34242

  Step into the exclusive waterfront haven of Harbor Towers Yacht and Racquet Club, a true resort paradise that will capture your heart instantly. The building has recently undergone a comprehensive $13 million, four-year hurricane hardening and structural upgrade, completed in 2024. Designed to meet the latest safety standards for hurricane and wind protection, these enhancements include

  

  Suzy Kolaz

  KELLER WILLIAMS ON THE WATER S

  (941) 254-2344

  5855 Midnight Pass Rd Unit 416, Sarasota, FL 34242
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  /20

  $5,850 per month

  • 3 Beds
  • 3 Baths
  • 1,590 Sq Ft
  • House for Rent

  314 Avenida de Paradisio, Siesta Key, FL 34242

  Property Id: 2218418Walk through your private courtyard to this 3 bedroom, 3 bath home. This Split plan home has 2 bedrooms and 2 baths on one side and master bedroom and spa bath adjacent. Feature's a modern kitchen design with all stainless appliances and granite countertops and placement for easy entertaining and accessibility to living room and pool. Floors in the home have been

  314 Avenida de Paradisio, Siesta Key, FL 34242
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  /2

  $2,200,000 Sold Dec 12, 2025

  6925 Bochi Cir, Sarasota, FL 34242

  • 4 Beds
  • 4.5 Baths
  • 3,796 Sq Ft
  • Built 2011

  Last Sold Summary

  • 4% Below List Price
  • $580/SF
  • 32 Days On Market

  Last Listing Agent Jeremy Hartmark LPT REALTY, LLC

  6925 Bochi Cir, Sarasota, FL 34242
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  /2

  Est $979,778 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,134 Sq Ft

  4949 Commonwealth Dr, Sarasota, FL 34242

  4949 Commonwealth Dr, Sarasota, FL 34242
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  /31

  $549,900

  • 1 Bed
  • 1 Bath
  • 531 Sq Ft

  5858 Midnight Pass Rd Unit 27, Sarasota, FL 34242

  Beautifully remodeled 1 bedroom condo located in Beachaven on #1 voted beach, Siesta Key. You can sleep 4 in this unit. This community has a private beach directly on the Gulf of America. Remodeled by Licensed contractor with all necessary permits and building codes. Everything in the unit is new. Cabinetry, flooring, appliances, and furniture. Only steps away from putting your feet in the sand.

  

  Paula Mapp

  MAPP REALTY & INVESTMENT CO

  (941) 231-3520

  5858 Midnight Pass Rd Unit 27, Sarasota, FL 34242
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  /34

  $7,900 per month

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

  19 Whispering Sands Dr Unit 106, Sarasota, FL 34242

  Still available for season January - April 2026l! Two bedroom 2 bath ground floor with view of the Gulf. Step outside and your on the sand! Escape the winter and be on the beach. Located in the heart of Siesta Key’s most desirable area, this property offers exceptional appeal with being just steps from the world-famous powdery white sand beach. Siesta Key Village is within easy walking distance,

  Maureen Plichta STRINGER MANAGEMENT INC

  19 Whispering Sands Dr Unit 106, Sarasota, FL 34242
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  /2

  $1,125,000 Sold Feb 19, 2025

  1240 Dolphin Bay Way Unit 204, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 1998

  Last Sold Summary

  • 10% Below List Price
  • $511/SF
  • 49 Days On Market

  Current Estimated Value $1,104,840

  Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

  1240 Dolphin Bay Way Unit 204, Sarasota, FL 34242
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  /2

  Est $2,403,839 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,973 Sq Ft

  4866 Commonwealth Dr, Siesta Key, FL 34242

  4866 Commonwealth Dr, Siesta Key, FL 34242
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  /55

  $424,900 Open Sun 1PM - 4PM

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft

  1350 N Portofino Dr Unit 107, Sarasota, FL 34242

  SIESTA HARBOR...55+...BEAUTIFUL CANAL & Intercoastal Water Way VISTAS with boats slowly idling by and YOU HAVE BEACH ACCESS. BRING YOUR BOAT up to 30' because it only costs $1,000 ANNUALLY to berth your boat! BUT WAIT till you see this TOTALLY RENOVATED BEAUTIFUL 1 bedroom 2 full bathroom condo! NEW, NEW, NEW...everything is new...Ceramic tile flooring, baseboards, interior doors & hardware,

  

  Scotty Ledford

  VUE REALTY, LLC

  (941) 207-7524

  1350 N Portofino Dr Unit 107, Sarasota, FL 34242
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  /18

  $5,850 per month

  • 2 Beds
  • 2 Baths
  • 1,285 Sq Ft
  • Condo for Rent

  5830 Midnight Pass Rd Unit 802, Sarasota, FL 34242

  Property Id: 2194753The stunning vistas of The Jamaica Royale Penthouse welcome you to your dream condo located on the 8th floor, overlooking the magnificent Siesta Key Beach. This fully remodeled and elegantly furnished 2-bedroom, 2-bathroom condo is the perfect getaway for anyone looking to enjoy the beauty of the Gulf Coast.As soon as you step into the condo, you'll be struck

  5830 Midnight Pass Rd Unit 802, Sarasota, FL 34242
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  /2

  $1,200,000 Sold Jul 22, 2025

  1660 Summerhouse Ln Unit 102, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,110 Sq Ft
  • Built 2007

  Last Sold Summary

  • 28% Below List Price
  • $569/SF
  • 481 Days On Market

  Current Estimated Value $1,204,716

  Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

  1660 Summerhouse Ln Unit 102, Sarasota, FL 34242
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  /42

  Est $849,850 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  5966 Midnight Pass Rd Unit G-42, Sarasota, FL 34242

  5966 Midnight Pass Rd Unit G-42, Sarasota, FL 34242
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  /92

  $575,000

  • 2 Beds
  • 2 Baths
  • 1,259 Sq Ft

  5600 Beach Way Dr Unit 201, Sarasota, FL 34242

  SELLER SAYS BRING ALL OFFERS! MAJOR PRICE IMPROVEMENT!! Reduced over 75k! Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom

  

  Ashley Nevadomski

  WILLIAM RAVEIS REAL ESTATE

  (941) 304-5005

  5600 Beach Way Dr Unit 201, Sarasota, FL 34242
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  /51

  $6,500 per month

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

  5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  This luxury Siesta Key beachfront unit in the exclusive Gulf and Bay Club offers full panoramic views of the Gulf of Mexico and the #1 beach in the USA, Siesta Key! This beautifully updated 2-bedroom, 2-bathroom unit features hardwood floors, granite countertops, and an abundance of cabinet space. The bathrooms are elegantly updated with tile and granite counters, making this a truly turnkey

  Robert Bevington SHOWTIME REALTY

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

  $995,000 Sold Feb 10, 2025

  361 Avenida Madera, Sarasota, FL 34242

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

  Last Sold Summary

  • 13% Below List Price
  • 50 Days On Market

  Current Estimated Value $913,474

  Last Listing Agent Tracy Srodes FINE PROPERTIES

  361 Avenida Madera, Sarasota, FL 34242
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  /60

  Est $709,251 Not Listed For Sale

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

  5970 Midnight Pass Rd Unit 166, Sarasota, FL 34242

  5970 Midnight Pass Rd Unit 166, Sarasota, FL 34242
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  /61

  $2,700,000

  • 4 Beds
  • 3.5 Baths
  • 2,952 Sq Ft

  222 Beach Rd Unit 7, Sarasota, FL 34242

  Waterfront Condominium-Glide down Beach Road and feel the Gulf breeze usher you toward 222 Beach Road, Residence #7—an iconic Tim Seibert masterpiece offering over 2,900 square feet of elevated coastal living. Accessible by elevator, this four-bedroom, three-and-a-half-bath residence captures Seibert’s signature devotion to light, openness, and architectural clarity. Inside, each bedroom turns

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 214-6182

  222 Beach Rd Unit 7, Sarasota, FL 34242
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  /21

  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Apartment for Rent

  5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242

  Newly remodeled and furnished “Bougie beach bungalow” on Siesta Key Island. This Condo will “wow” you from the first moment you enter. Just say Alexa turn lights on and your command will be answered. This condo is on the first floor and it’s just a few minutes walk from the siesta key public beach access. The community is very welcoming to all guest and has a heated pool year-round and also many

  Stephanie Fox EXP REALTY LLC

  5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242
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  /2

  $2,250,000 Sold Jun 03, 2025

  1241 Big Oak Ln, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1979

  Last Sold Summary

  • 13% Below List Price
  • $1,218/SF
  • 49 Days On Market

  Current Estimated Value $2,120,039

  Last Listing Agent Anthony Dalesandro BRIGHT REALTY

  1241 Big Oak Ln, Sarasota, FL 34242
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  /50

  Est $4,655,515 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,214 Sq Ft

  3954 Roberts Point Rd, Sarasota, FL 34242

  3954 Roberts Point Rd, Sarasota, FL 34242
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  /53

  $75,000

  • 3 Beds
  • 3 Baths
  • 2,255 Sq Ft

  915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242

  Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 352-4595

  915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242
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  /70

  $6,900 per month

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Condo for Rent

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242

  **FULLY REMODELED, GROUND FLOOR CONDO, ACROSS FROM SIESTA KEY BEACH ** Seasonal Rental only, $6,900/mo plus fees, Minimum Stay required Sandy Feet Retreat is a fully remodeled ground-floor condo located directly across the street from Siesta Key’s main beach access. Recently updated throughout, the residence features a brand-new kitchen with modern appliances, beautifully renovated bathrooms, and

  Dave Holt PMI SOUTHWEST FLORIDA

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242
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  /2

  $3,025,000 Sold Jan 21, 2025

  850 Siesta Key Cir, Sarasota, FL 34242

  • 5 Beds
  • 5 Baths
  • 3,647 Sq Ft
  • Built 2005

  Last Sold Summary

  • 5% Below List Price
  • $829/SF
  • 0 Days On Market

  Current Estimated Value $2,843,434

  Last Listing Agent Mark McCann, PA MICHAEL SAUNDERS & COMPANY

  850 Siesta Key Cir, Sarasota, FL 34242
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  /60

  Est $7,207,973 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 6,369 Sq Ft

  5131 Jungle Plum Rd, Sarasota, FL 34242

  5131 Jungle Plum Rd, Sarasota, FL 34242

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