Recently Sold Siesta Key, FL Homes

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  $550,000 Sold Nov 12, 2025

  5222 Winding Way, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,137 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $484/SF
  • 35 Days On Market

  Current Estimated Value $572,072

  Last Listing Agent Robert Moffatt MICHAEL SAUNDERS & COMPANY

  5222 Winding Way, Sarasota, FL 34242
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  $1,150,000 Sold Oct 22, 2025

  4915 Primrose Path, Sarasota, FL 34242

  • 6 Beds
  • 5 Baths
  • 3,549 Sq Ft
  • Built 1960

  Last Sold Summary

  • 38% Below List Price
  • $324/SF
  • 320 Days On Market

  Current Estimated Value $1,192,942

  Last Listing Agent Tony Andrews ANDREWS & ASSOCIATES REALTY

  4915 Primrose Path, Sarasota, FL 34242
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  $850,000 Sold Jun 05, 2025

  5750 Midnight Pass Rd Unit 105, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,471 Sq Ft
  • Built 1984

  Last Sold Summary

  • 17% Below List Price
  • $578/SF
  • 165 Days On Market

  Current Estimated Value $897,919

  Last Listing Agent Peg Davant PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5750 Midnight Pass Rd Unit 105, Sarasota, FL 34242
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  $470,000 Sold Mar 02, 2026

  116 Pass Key Rd Unit 116, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 656 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $716/SF
  • 5 Days On Market

  Current Estimated Value $397,686

  Last Listing Agent Veronica Murphy KELLER WILLIAMS ON THE WATER S

  116 Pass Key Rd Unit 116, Sarasota, FL 34242
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  $1,200,000 Sold May 07, 2025

  822 Paradise Way, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 1,517 Sq Ft
  • Built 1962

  Last Sold Summary

  • 8% Below List Price
  • $791/SF
  • 14 Days On Market

  Current Estimated Value $1,158,692

  Last Listing Agent Sue Ann Levin COLDWELL BANKER REALTY

  822 Paradise Way, Sarasota, FL 34242
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  $762,000 Sold Jan 14, 2026

  4894 Oxford Dr, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 1,831 Sq Ft
  • Built 1967

  Last Sold Summary

  • 13% Below List Price
  • $416/SF
  • 63 Days On Market

  Current Estimated Value $780,553

  Last Listing Agent Marc Overfelt FLORIDA BAY REALTY INC

  4894 Oxford Dr, Sarasota, FL 34242
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  $910,000 Sold Apr 22, 2025

  5300 Ocean Blvd Unit 803, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • Built 1973

  Last Sold Summary

  • 37% Below List Price
  • $662/SF
  • 267 Days On Market

  Current Estimated Value $914,378

  Last Listing Agent Diane Goodwin EXP REALTY LLC

  5300 Ocean Blvd Unit 803, Sarasota, FL 34242
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  $625,000 Sold Oct 24, 2025

  199 Whispering Sands Dr Unit 105, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $401/SF
  • 62 Days On Market

  Current Estimated Value $606,080

  Last Listing Agent Tracy Srodes FINE PROPERTIES

  199 Whispering Sands Dr Unit 105, Sarasota, FL 34242
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  $482,500 Sold Jun 06, 2025

  5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1975

  Last Sold Summary

  • 3% Below List Price
  • $477/SF
  • 7 Days On Market

  Current Estimated Value $466,611

  Last Listing Agent Linda Williams GULF SHORES REALTY ERA POWERED

  5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242
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  $860,000 Sold Oct 03, 2025

  1055 Beach Rd Unit B302, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 1981

  Last Sold Summary

  • 7% Below List Price
  • $714/SF
  • 262 Days On Market

  Current Estimated Value $837,007

  Last Listing Agent Michele Tanner PREFERRED SHORE LLC

  1055 Beach Rd Unit B302, Sarasota, FL 34242
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  $1,600,000 Sold Mar 12, 2026

  5121 Sandy Shore Ave, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,726 Sq Ft
  • Built 2000

  Last Sold Summary

  • $587/SF

  Current Estimated Value $1,745,695

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  5121 Sandy Shore Ave, Sarasota, FL 34242
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  $2,535,000 Sold Feb 13, 2026

  4757 Higel Ave, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 3,232 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $784/SF
  • 44 Days On Market

  Current Estimated Value $2,659,654

  Last Listing Agent Victoria Turner MICHAEL SAUNDERS & COMPANY

  4757 Higel Ave, Sarasota, FL 34242
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  $2,900,000 Sold Jul 31, 2025

  875 Siesta Key Cir, Sarasota, FL 34242

  • 3 Beds
  • 3.5 Baths
  • 5,423 Sq Ft
  • Built 1990

  Last Sold Summary

  • 23% Below List Price
  • $535/SF
  • 117 Days On Market

  Current Estimated Value $2,976,488

  Last Listing Agent Thomas Cail RE/MAX ALLIANCE GROUP

  875 Siesta Key Cir, Sarasota, FL 34242
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  $930,000 Sold May 16, 2025

  5780 Midnight Pass Rd Unit 205, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $631/SF
  • 114 Days On Market

  Current Estimated Value $926,867

  Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5780 Midnight Pass Rd Unit 205, Sarasota, FL 34242
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  $650,000 Sold Aug 22, 2025

  670 Venice Ln, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft
  • Built 1971

  Last Sold Summary

  • 34% Below List Price
  • $307/SF
  • 118 Days On Market

  Current Estimated Value $759,972

  Last Listing Agent Debbie Lane RE/MAX ALLIANCE GROUP

  670 Venice Ln, Sarasota, FL 34242
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  $1,650,000 Sold Apr 01, 2025

  5598 Siesta Estates Ct, Sarasota, FL 34242

  • 6 Beds
  • 5.5 Baths
  • 3,924 Sq Ft
  • Built 2000

  Last Sold Summary

  • 15% Below List Price
  • $420/SF
  • 353 Days On Market

  Current Estimated Value $1,634,908

  Last Listing Agent Darren Duffy RE/MAX PALM REALTY

  5598 Siesta Estates Ct, Sarasota, FL 34242
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  $2,500,000 Sold Dec 04, 2025

  91 Avenida Veneccia, Sarasota, FL 34242

  • 5 Beds
  • 4 Baths
  • 2,498 Sq Ft
  • Built 1946

  Last Sold Summary

  • 28% Below List Price
  • $1,001/SF
  • 202 Days On Market

  Current Estimated Value $2,426,510

  Last Listing Agent Jay Travis RE/MAX ALLIANCE GROUP

  91 Avenida Veneccia, Sarasota, FL 34242
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  $625,000 Sold Sep 30, 2025

  1311 Siesta Bayside Dr Unit 1311A, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Built 1988

  Last Sold Summary

  • 16% Below List Price
  • $553/SF
  • 115 Days On Market

  Current Estimated Value $620,084

  Last Listing Agent Marni Hayden CHROME REALTY LLC

  1311 Siesta Bayside Dr Unit 1311A, Sarasota, FL 34242
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  $635,000 Sold Jan 30, 2026

  1255 E Peppertree Dr Unit 506, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,462 Sq Ft
  • Built 1972

  Last Sold Summary

  • 15% Below List Price
  • $434/SF
  • 256 Days On Market

  Current Estimated Value $658,255

  Last Listing Agent Patti O Grady WATERSIDE REALTY LLC

  1255 E Peppertree Dr Unit 506, Sarasota, FL 34242
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  $632,500 Sold Nov 12, 2025

  1200 E Peppertree Ln Unit 607, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1973

  Last Sold Summary

  • 27% Below List Price
  • $527/SF
  • 306 Days On Market

  Current Estimated Value $630,977

  Last Listing Agent Eliza Miller PEPPERTREE BAY REALTY INC

  1200 E Peppertree Ln Unit 607, Sarasota, FL 34242
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  $1,150,000 Sold Aug 28, 2025

  5790 Midnight Pass Rd Unit 702, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Built 1979

  Last Sold Summary

  • 11% Below List Price
  • $861/SF
  • 12 Days On Market

  Current Estimated Value $1,132,143

  Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

  5790 Midnight Pass Rd Unit 702, Sarasota, FL 34242
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  $2,100,000 Sold Apr 14, 2025

  3927 Somerset Dr, Sarasota, FL 34242

  • 3 Beds
  • 3.5 Baths
  • 2,758 Sq Ft
  • Built 1990

  Last Sold Summary

  • 10% Below List Price
  • $761/SF
  • 64 Days On Market

  Current Estimated Value $1,816,573

  Last Listing Agent Patrick Dipinto, III OCEAN REAL ESTATE LLC

  3927 Somerset Dr, Sarasota, FL 34242
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  $20,000 Sold Apr 25, 2025

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

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 2009

  Last Sold Summary

  • 74% Below List Price
  • $11/SF
  • 175 Days On Market

  Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

  915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242
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  $890,000 Sold Apr 01, 2025

  5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1981

  Last Sold Summary

  • 9% Below List Price
  • $654/SF
  • 124 Days On Market

  Current Estimated Value $902,212

  Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242
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  $875,000 Sold Jan 15, 2026

  757 Beach Rd Unit 300, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,181 Sq Ft
  • Built 1970

  Last Sold Summary

  • $741/SF

  Current Estimated Value $869,092

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  757 Beach Rd Unit 300, Sarasota, FL 34242
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  $1,125,000 Sold Feb 19, 2026

  5916 Midnight Pass Rd Unit 102, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Built 1971

  Last Sold Summary

  • 4% Below List Price
  • $959/SF
  • 6 Days On Market

  Current Estimated Value $1,084,157

  Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5916 Midnight Pass Rd Unit 102, Sarasota, FL 34242
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  $450,000 Sold Dec 19, 2025

  1350 N Portofino Dr Unit 208, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft
  • Built 1969

  Last Sold Summary

  • 18% Below List Price
  • $484/SF
  • 188 Days On Market

  Current Estimated Value $447,868

  Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

  1350 N Portofino Dr Unit 208, Sarasota, FL 34242
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  $2,200,000 Sold Apr 02, 2025

  447 Canal Rd Unit 447, Sarasota, FL 34242

  • 3 Beds
  • 4 Baths
  • 2,635 Sq Ft
  • Built 2003

  Last Sold Summary

  • 12% Below List Price
  • $835/SF
  • 81 Days On Market

  Current Estimated Value $2,082,866

  Last Listing Agent Joseph Kesslak COLDWELL BANKER REALTY

  447 Canal Rd Unit 447, Sarasota, FL 34242
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  $810,000 Sold Nov 21, 2025

  1080 W Peppertree Ln Unit 506A, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Built 1974

  Last Sold Summary

  • 25% Below List Price
  • $696/SF
  • 264 Days On Market

  Current Estimated Value $813,793

  Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1080 W Peppertree Ln Unit 506A, Sarasota, FL 34242
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  $900,000 Sold Aug 29, 2025

  5108 Saint Albans Ave, Sarasota, FL 34242

  • 3 Beds
  • 3.5 Baths
  • 1,767 Sq Ft
  • Built 1968

  Last Sold Summary

  • 20% Below List Price
  • $509/SF
  • 57 Days On Market

  Current Estimated Value $901,674

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  5108 Saint Albans Ave, Sarasota, FL 34242
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  $925,000 Sold Dec 08, 2025

  396 Avenida Madera, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 1,964 Sq Ft
  • Built 1958

  Last Sold Summary

  • 20% Below List Price
  • $471/SF
  • 148 Days On Market

  Current Estimated Value $924,233

  Last Listing Agent Michael Nogueira LUXURY & BEACH REALTY INC

  396 Avenida Madera, Sarasota, FL 34242
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  $3,990,000 Sold Aug 12, 2025

  4815 Featherbed Ln, Sarasota, FL 34242

  • 5 Beds
  • 4 Baths
  • 3,329 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $1,199/SF
  • 178 Days On Market

  Current Estimated Value $3,723,596

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  4815 Featherbed Ln, Sarasota, FL 34242
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  $357,000 Sold Sep 19, 2025

  1300 N Portofino Dr Unit 208, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft
  • Built 1969

  Last Sold Summary

  • 29% Below List Price
  • $360/SF
  • 403 Days On Market

  Current Estimated Value $391,893

  Last Listing Agent Jill Thomas BERKSHIRE HATHAWAY HOMESERVICE

  1300 N Portofino Dr Unit 208, Sarasota, FL 34242
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  $700,000 Sold Aug 27, 2025

  1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1988

  Last Sold Summary

  • 18% Below List Price
  • $547/SF
  • 155 Days On Market

  Current Estimated Value $688,236

  Last Listing Agent Fred Sieger Jr COMPASS FLORIDA LLC

  1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242
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  $1,350,000 Sold Dec 08, 2025

  5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $901/SF
  • 38 Days On Market

  Current Estimated Value $1,324,977

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242
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  $420,000 Sold Jan 05, 2026

  6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242

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

  Last Sold Summary

  • 14% Below List Price
  • $488/SF
  • 30 Days On Market

  Current Estimated Value $425,839

  Last Listing Agent Nancie Kalin MICHAEL SAUNDERS & COMPANY

  6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242
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  $852,500 Sold Jan 07, 2026

  5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $626/SF
  • 20 Days On Market

  Current Estimated Value $856,375

  Last Listing Agent Curtis Ware KW COASTAL LIVING III

  5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242
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  $650,000 Sold Nov 25, 2025

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1974

  Last Sold Summary

  • 21% Below List Price
  • $650/SF
  • 199 Days On Market

  Current Estimated Value $651,560

  Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242
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  $1,266,700 Sold Dec 19, 2025

  307 Avenida de Paradisio, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,511 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $838/SF
  • 28 Days On Market

  Current Estimated Value $1,227,143

  Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC

  307 Avenida de Paradisio, Sarasota, FL 34242
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  $325,000 Sold Dec 31, 2025

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $256/SF
  • 25 Days On Market

  Current Estimated Value $381,633

  Last Listing Agent Julie Froeschle BERKSHIRE HATHAWAY HOMESERVICE

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242

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