Siesta Key, FL Homes

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  $635,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  5855 Midnight Pass Rd Unit 416, Sarasota, FL 34242

  Major Price Improvement! 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

  

  Suzy Kolaz

  KELLER WILLIAMS ON THE WATER S

  (941) 254-2344

  5855 Midnight Pass Rd Unit 416, Sarasota, FL 34242
• Explore Siesta Key

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  /22

  $4,800 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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  $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 $434,460

  Last Listing Agent Robin Jones EXIT KING REALTY

  6157 Midnight Pass Rd Unit E42, Sarasota, FL 34242
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  Not Listed For Sale

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

  915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242

  915 Seaside Dr Unit 607, Weeks 16-17, Sarasota, FL 34242
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  /77

  $1,795,000

  • 3 Beds
  • 3.5 Baths
  • 2,480 Sq Ft

  548 Beach Rd Unit 540A, Sarasota, FL 34242

  PRICE IMPROVEMENT! Rarely available on Siesta Key, this stunning Tiffany Sands townhome offers an open floor plan with three spacious bedrooms, each featuring walk-in closets, three and a half baths, and a versatile first-floor bonus room complete with a full bath and private entrance—ideal for guests, a home office, or flexible living space. Beautifully renovated, this exceptional residence

  

  Jennifer Thompson

  WILLIAM RAVEIS REAL ESTATE

  (941) 206-4108

  548 Beach Rd Unit 540A, 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) 213-8487

  5911 Midnight Pass Rd Unit 601, 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 $886,782 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 3,042 Sq Ft

  4439 Ocean Blvd, Sarasota, FL 34242

  4439 Ocean Blvd, Sarasota, FL 34242
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  /55

  $424,900

  • 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 IDILYING By and YOU HAVE BEACH ACCESS. BRING YOUR BOAT up to 30' because it only costs $1,000 ANNUALLY to berth your boat at your home! 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 &

  

  Scotty Ledford

  VUE REALTY, LLC

  (941) 207-7524

  1350 N Portofino Dr Unit 107, Sarasota, FL 34242
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  $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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  $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

  Current Estimated Value $1,480,325

  Last Listing Agent Jackie Eberley COLDWELL BANKER REALTY

  5033 Oxford Dr, Sarasota, FL 34242
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  /2

  Est $1,444,956 Not Listed For Sale

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

  6300 Midnight Pass Rd Unit 703, Sarasota, FL 34242

  6300 Midnight Pass Rd Unit 703, Sarasota, FL 34242
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  /92

  $575,000 Open Thu 9AM - 12PM

  • 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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  $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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  $2,200,000 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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  Est $951,211 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 926 Sq Ft

  451 Avenida de Mayo, Sarasota, FL 34242

  451 Avenida de Mayo, Sarasota, FL 34242
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  /94

  $949,000

  • 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! Set on an elevated lot that sustained NO storm damage, includes a NEW TAMKO hurricane proof ROOF with transferable workmanship warranty, new gutters, oversized side-entry 2-car garage, and circular driveway surrounded by lush tropical landscaping. Currently being used as an income producing home

  

  Tami Cashi

  COLDWELL BANKER REALTY

  (941) 273-8651

  635 Tropical Cir, Sarasota, FL 34242
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  /20

  $3,950 per month

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

  4822 Ocean Blvd Unit 3D, Siesta Key, FL 34242

  Property Id: 2175264This Siesta Key condominium in Siesta Towers offers two master suites. Welcome to this extraordinary living experience and location where every day you can enjoy the gulf views and the palm trees dotting the horizon. Swim and relax in the heated outdoor pool that sits right on the waterfront. Enjoy a drink on the cocktail pier while you watch the dolphins swim or bask

  4822 Ocean Blvd Unit 3D, Siesta Key, FL 34242
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  $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 $1,092,111

  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 $595,177 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,314 Sq Ft

  671 Avenida Del Norte, Sarasota, FL 34242

  671 Avenida Del Norte, Sarasota, FL 34242
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  $2,199,000

  • 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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  /16

  $9,500 per month

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft
  • Condo for Rent

  1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242

  Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
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  $1,000,000 Sold Jan 29, 2026

  4920 Higel Ave, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft
  • Built 1957

  Last Sold Summary

  • 17% Below List Price
  • $483/SF
  • 159 Days On Market

  Last Listing Agent Tony Andrews ANDREWS & ASSOCIATES REALTY

  4920 Higel Ave, Sarasota, FL 34242
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  /2

  Est $514,939 Not Listed For Sale

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

  5855 Midnight Pass Rd Unit 320, Sarasota, FL 34242

  5855 Midnight Pass Rd Unit 320, Sarasota, FL 34242
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  $825,000

  • 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) 698-6217

  5600 Beach Way Dr Unit 315, 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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  $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 $1,210,226

  Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

  1660 Summerhouse Ln Unit 102, Sarasota, FL 34242
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  /2

  Est $623,726 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft

  5855 Midnight Pass Rd Unit 225, Sarasota, FL 34242

  5855 Midnight Pass Rd Unit 225, Sarasota, FL 34242
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  $2,700,000 Pending

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

  222 Beach Rd Unit 7, Sarasota, FL 34242

  Under contract-accepting backup offers. 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

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  (941) 214-6182

  222 Beach Rd Unit 7, Sarasota, FL 34242
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  /25

  $12,296 per month

  • 2 Beds
  • 2 Baths
  • 1,319 Sq Ft
  • House for Rent

  6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

  Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience. Step into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
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  $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 $912,790

  Last Listing Agent Tracy Srodes FINE PROPERTIES

  361 Avenida Madera, Sarasota, FL 34242
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  Est $3,879,394 Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 3,234 Sq Ft

  5300 Avenida Del Mare, Sarasota, FL 34242

  5300 Avenida Del Mare, Sarasota, FL 34242
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  $2,149,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,657 Sq Ft

  4817 Ocean Blvd, Sarasota, FL 34242

  Welcome to 4817 Ocean Blvd – Your Private Lakefront Escape in the Heart ofSiesta KeySet on a tranquil spring-fed lake just moments from Siesta Beach and the Village, thisflood resilient and meticulously maintained coastal residence offers year-roundenjoyment or the perfect lock-and-leave retreat. Elevated and thoughtfully updated, itblends timeless coastal style with

  

  Gerard Healy

  WILLIAM RAVEIS REAL ESTATE

  (941) 541-8336

  4817 Ocean Blvd, Sarasota, FL 34242
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  /20

  $17,313 per month

  • 3 Beds
  • 2 Baths
  • 2,206 Sq Ft
  • Condo for Rent

  1038 Contento St Unit ID1366625P, Siesta Key, FL 34242

  Feel at home in this waterfront, 3-bedroom, 2-bath pool home in the heart of Siesta Key, offering a rare combination of canal-front serenity and walk-to-beach convenience.This waterfront retreat sleeps up to 8 guests and combines the relaxed luxury of island living with unbeatable access to boating, beaches, dining, and Siesta Key Village. The fully equipped kitchen includes a dishwasher,

  1038 Contento St Unit ID1366625P, Siesta Key, FL 34242
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  $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 $2,148,271

  Last Listing Agent Anthony Dalesandro BRIGHT REALTY

  1241 Big Oak Ln, Sarasota, FL 34242
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  Est $858,799 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft

  5968 Midnight Pass Rd Unit 164, Sarasota, FL 34242

  5968 Midnight Pass Rd Unit 164, Sarasota, FL 34242
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  $1,099,000

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

  5770 Midnight Pass Rd Unit 301, Sarasota, FL 34242

  Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium association. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi

  

  Anthony DeLuca

  DELUCA REALTY INC

  (941) 368-4048

  5770 Midnight Pass Rd Unit 301, Sarasota, FL 34242
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  /31

  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,345 Sq Ft
  • Condo for Rent

  1055 W Peppertree Dr Unit 405AA, Sarasota, FL 34242

  Nestled just a stone's throw from the pristine sands of Siesta Key beach, this midrise villa offers a luxurious retreat for those seeking a blend of comfort and convenience. With a 30-night minimum stay, guests can fully immerse themselves in the tranquil beach lifestyle. The villa boasts two bedrooms and two bathrooms, accommodating up to four guests, making it an ideal choice for families or

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 405AA, Sarasota, FL 34242
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  $1,450,000 Sold Nov 04, 2025

  4108 Roberts Point Rd, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,511 Sq Ft
  • Built 2001

  Last Sold Summary

  • 23% Below List Price
  • $577/SF
  • 142 Days On Market

  Last Listing Agent Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  4108 Roberts Point Rd, Sarasota, FL 34242
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  /42

  Est $835,147 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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