Homes in ZIP Code 34242

• 

  

  

  /50

  $2,590,000

  $190K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,965 Sq Ft

  5073 Higel Ave, Sarasota, FL 34242

  Welcome to luxury coastal living on Siesta Key. Perfectly positioned in the exclusive Sara Sands community, this fully remodeled 4-bedroom, 3.5-bath waterfront residence offers the ultimate blend of modern elegance, boating lifestyle, and relaxed Florida luxury. Situated on a deep-water canal with quick access to Sarasota Bay and the Gulf, this exceptional property features a private dock and

  Abraham Ruth REALTY HUB

  5073 Higel Ave, Sarasota, FL 34242
• 

  

  

  /94

  $8,583

  Total Monthly Price

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft
  • Condo for Rent

  5780 Midnight Pass Rd Unit SI ID1591412P, Siesta Key, FL 34242

  The advertised rate of $8,583/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 19, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  5780 Midnight Pass Rd Unit SI ID1591412P, Siesta Key, FL 34242
• 

  

  /2

  $2,650,000

  Sold Oct 14, 2025

  512 Treasure Boat Way, Sarasota, FL 34242

  • 4 Beds
  • 4.5 Baths
  • 5,078 Sq Ft
  • Built 1979

  Last Sold Summary

  • 11% Below List Price
  • $522/SF
  • 88 Days On Market

  Current Estimated Value $2,766,527

  Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

  512 Treasure Boat Way, Sarasota, FL 34242
• 

  

  

  /39

  Est $1,827,962

  Not Listed For Sale

  340 Canal Rd Unit B, Sarasota, FL 34242

  • 4 Beds
  • 2.5 Baths
  • 2,234 Sq Ft
  • Built 2005

  340 Canal Rd Unit B, Sarasota, FL 34242

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Joseph Kesslak COLDWELL BANKER REALTY
• 

  

  

  /46

  $649,000

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 3, Sarasota, FL 34242

  Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan. Upgrades galore!! Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest

  Steve Cavanaugh TIDELINE REAL ESTATE BROKERS

  5830 Midnight Pass Rd Unit 3, Sarasota, FL 34242
• 

  

  /20

  $3,083

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,087 Sq Ft
  • Condo for Rent

  8977 Midnight Pass Rd Unit SI ID1591468P, Sarasota, FL 34242

  The advertised rate of $3,083/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 18, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  8977 Midnight Pass Rd Unit SI ID1591468P, Sarasota, FL 34242
• 

  /2

  $1,300,000

  Sold Jan 30, 2026

  5750 Midnight Pass Rd Unit 508, Sarasota, FL 34242

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

  Last Sold Summary

  • 7% Below List Price
  • $884/SF
  • 107 Days On Market

  Current Estimated Value $1,345,145

  Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY

  5750 Midnight Pass Rd Unit 508, Sarasota, FL 34242
• 

  

  /46

  Not Listed For Sale

  1166 W Peppertree Dr Unit 112, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1974

  1166 W Peppertree Dr Unit 112, Sarasota, FL 34242

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC
• 

  

  /26

  $689,000

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

  5600 Beach Way Dr Unit 111, Sarasota, FL 34242

  Virtually Staged. Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale.Welcome to Beach Way, where island living begins just steps from world-famous Siesta Key Beach! Perfectly positioned directly across from the powdery white quartz sands and turquoise Gulf waters, this

  Lisa Lococo KELLER WILLIAMS ON THE WATER S

  5600 Beach Way Dr Unit 111, Sarasota, FL 34242
• 

  

  /35

  $31,521

  Total Monthly Price

  • 6 Beds
  • 4 Baths
  • 6,113 Sq Ft
  • Condo for Rent

  1200 Tree Bay Ln Unit SI ID1578364P, Sarasota, FL 34242

  The advertised rate of $31,521/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 28, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  1200 Tree Bay Ln Unit SI ID1578364P, Sarasota, FL 34242
• 

  /2

  $625,000

  Sold Jun 22, 2026

  145 Avenida Messina Unit 3, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft
  • Built 1966

  Last Sold Summary

  • 10% Below List Price
  • $610/SF
  • 170 Days On Market

  Current Estimated Value $617,319

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

  145 Avenida Messina Unit 3, Sarasota, FL 34242
• 

  /2

  Est $2,018,355

  Not Listed For Sale

  3927 Somerset Dr, Sarasota, FL 34242

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

  3927 Somerset Dr, Sarasota, FL 34242

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent Patrick Dipinto, III OCEAN REAL ESTATE LLC
• 

  

  /60

  $1,999,999

  $249K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  5361 Siesta Ct, Sarasota, FL 34242

  PRICE IMPROVEMENT! Experience tranquility and peace of mind in Siesta Key! Located in the highly sought-after neighborhood of Siesta Cove, this 4-bedroom, 2.5-bath home has been meticulously maintained and generously updated. The current owners completed extensive renovations including a newly remodeled primary bathroom, a custom locally handcrafted iron front door, and stunning iron interior

  David James CHARLES RUTENBERG REALTY INC

  5361 Siesta Ct, Sarasota, FL 34242
• 

  

  /28

  $16,932

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Condo for Rent

  324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242

  The advertised rate of $16,933/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 3, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
• 

  /2

  $1,750,000

  Sold Jul 28, 2026

  951 Contento St, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,882 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $607/SF
  • 107 Days On Market

  Current Estimated Value $1,811,398

  Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  951 Contento St, Sarasota, FL 34242
• 

  /2

  Not Listed For Sale

  915 Seaside Dr Unit 613, Weeks 4-5, Sarasota, FL 34242

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft
  • Built 2009

  915 Seaside Dr Unit 613, Weeks 4-5, Sarasota, FL 34242

  Last Sold Summary

  • 228 Days On Market

  Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN
• 

  

  /77

  $15,900,000

  • 4 Beds
  • 4.5 Baths
  • 8,209 Sq Ft

  8132 Sanderling Rd, Sarasota, FL 34242

  Inspired by the timeless grandeur of Louisiana's legendary Oak Alley Plantation, this extraordinary Gulf-to-lagoon estate is one of the most architecturally distinctive residences on Siesta Key. Positioned on a rare 1.97-acre Gulf-to-bay homesite within the private gates of The Sanderling Club, this home evokes the sophistication of a Southern manor while embracing the relaxed sophistication of

  Joel Schemmel DOUGLAS ELLIMAN

  8132 Sanderling Rd, Sarasota, FL 34242
• 

  

  /16

  $3,627

  Total Monthly Price

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

  60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242

  The advertised rate of $3,627/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 22, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242
• 

  /2

  $3,000,000

  Sold Oct 15, 2025

  137 Big Pass Ln, Sarasota, FL 34242

  • 5 Beds
  • 4.5 Baths
  • 4,486 Sq Ft
  • Built 2006

  Last Sold Summary

  • 30% Below List Price
  • $669/SF
  • 148 Days On Market

  Last Listing Agent Dion Souza SARABAY REAL ESTATE INC

  137 Big Pass Ln, Sarasota, FL 34242
• 

  /2

  Est $594,858

  Not Listed For Sale

  8767 Midnight Pass Rd Unit 203F, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,303 Sq Ft
  • Built 1979

  8767 Midnight Pass Rd Unit 203F, Sarasota, FL 34242

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Marlene Marshall MICHAEL SAUNDERS & COMPANY
• 

  

  /57

  $2,349,000

  $341K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,341 Sq Ft

  4508 Woodside Rd, Sarasota, FL 34242

  WHY SPEND 30–45 MINUTES IDLING THROUGH CANALS WHEN YOU CAN REACH SARASOTA BAY IN LESS THAN 3 MINUTES? Offering exceptional open-water access on Siesta Key under $2.4 million, this waterfront residence delivers approximately 95 feet of waterfront, a 75-foot dock and protected deep-water dockage designed for the serious boating enthusiast.For buyers who prioritize time on the water, this

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  4508 Woodside Rd, Sarasota, FL 34242
• 

  

  /20

  $12,314

  Total Monthly Price

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

  5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242

  The advertised rate of $12,315/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 19, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
• 

  /2

  $1,050,000

  Sold May 27, 2026

  1002 Glebe Ln, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 1967

  Last Sold Summary

  • 9% Below List Price
  • $581/SF
  • 70 Days On Market

  Current Estimated Value $1,092,269

  Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1002 Glebe Ln, Sarasota, FL 34242
• 

  /2

  Not Listed For Sale

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

  • 3 Beds
  • 3 Baths
  • 2,255 Sq Ft
  • Built 2009

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

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN
• 

  /2

  $11,900,000

  New Construction Under Contract

  • 5 Beds
  • 5.5 Baths
  • 4,325 Sq Ft

  3550 Bayou Louise Ln, Sarasota, FL 34242

  Under contract-accepting backup offers. Pre-Construction. To be built. Pre-Construction. To be built. The lot is also available as vacant land (MLS #A4682294) ($6.7M). Introducing the Miller Floorplan designed by award winning Konstant Architecture (plans complete and available), a to be built waterfront estate set on one of the most extraordinary parcels on the north end of Siesta Key, one of

  Keith Curcio COLDWELL BANKER REALTY

  3550 Bayou Louise Ln, Sarasota, FL 34242
• 

  

  /20

  $11,340

  Total Monthly Price

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

  3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242

  The advertised rate of $11,340/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 6, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242
• 

  /2

  $1,640,000

  Sold Mar 24, 2026

  5880 Midnight Pass Rd Unit 710, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,713 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Below List Price
  • $957/SF
  • 27 Days On Market

  Current Estimated Value $1,626,610

  Last Listing Agent Kristina Rain MICHAEL SAUNDERS & COMPANY

  5880 Midnight Pass Rd Unit 710, Sarasota, FL 34242
• 

  /2

  Est $779,717

  Not Listed For Sale

  5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,211 Sq Ft
  • Built 1976

  5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Kelli Eggen COLDWELL BANKER REALTY
• 

  

  /30

  $6,700,000

  $295K PRICE DROP Under Contract

  • Land
  • 33,541 Sq Ft
  • $8,701,299 per Acre

  3550 Bayou Louise Ln, Sarasota, FL 34242

  Under contract-accepting backup offers. Gorgeous waterfront property offering sweeping views from Big Pass to Bayou Louise. Rarely available, one of only 10 properties with water access on the east and west, sitting on the coveted north end of Siesta Key, this exceptional parcel features 175 feet of water frontage and spans over three quarters of an acre. A property of this caliber is a

  Keith Curcio COLDWELL BANKER REALTY

  3550 Bayou Louise Ln, Sarasota, FL 34242
• 

  

  /34

  $9,128

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Condo for Rent

  8234 Midnight Pass Rd Unit SI ID1620595P, Sarasota, FL 34242

  The advertised rate of $9,128/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 18, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  8234 Midnight Pass Rd Unit SI ID1620595P, Sarasota, FL 34242
• 

  /2

  $452,000

  Sold Dec 18, 2025

  73 Avenida Messina Unit 15, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $1,108/SF

  Current Estimated Value $466,552

  Last Listing Agent Maxwell Mann MICHAEL SAUNDERS & COMPANY

  73 Avenida Messina Unit 15, Sarasota, FL 34242
• 

  /2

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • 175 Days On Market

  Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN
• 

  

  /77

  $3,347,500

  New Construction Open Sun 1PM - 4PM $310K PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 3,034 Sq Ft

  5103 Windward Ave, Sarasota, FL 34242

  Freshly completed and built safely 10 feet above the island’s flood plain, 5103 Windward is a spectacular new waterfront residence where elevated design meets effortless island living. Set on nearly one-third of an acre along the Grand Canal, with 90 feet of new seawall and saltwater boating access to the Intracoastal Waterway and Gulf beyond, this is the kind of home that turns everyday life

  Karen Greco GRECO REAL ESTATE

  5103 Windward Ave, Sarasota, FL 34242
• 

  

  /15

  $2,987

  Total Monthly Price

  • Studio
  • 1 Bath
  • Condo for Rent

  60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242

  The advertised rate of $2,987/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 19, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242
• 

  /2

  $630,000

  Sold Apr 01, 2026

  8735 Midnight Pass Rd Unit 404B, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,357 Sq Ft
  • Built 1980

  Last Sold Summary

  • $464/SF

  Current Estimated Value $627,782

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

  8735 Midnight Pass Rd Unit 404B, Sarasota, FL 34242
• 

  

  /68

  Est $595,772

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Daria Fairchild COLDWELL BANKER REALTY
• 

  

  /56

  $669,000

  Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,083 Sq Ft

  1141 W Peppertree Dr Unit 118B, Sarasota, FL 34242

  Discover effortless Siesta Key living in this beautifully updated and fully furnished 2-bedroom, 2-bath condo in the highly desirable Peppertree Bay community. Located on the Gulf side and just steps from the tennis and pickleball courts, heated pool, and private beach access, this second-floor residence offers a peaceful setting with scenic pond views.The interior has been thoughtfully

  Eliza Miller PEPPERTREE BAY REALTY INC

  1141 W Peppertree Dr Unit 118B, Sarasota, FL 34242
• 

  

  /53

  $4,000 Per Month

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft
  • Condo for Rent

  1250 N Portofino Dr Unit 301, Sarasota, FL 34242

  Gorgeous updated 2 BR, 2 Bath condo on a Canal Available Now Through December 31st or April 1, 2027 and beyond! Sailboat water, fishing pier, private beach access directly across the street. Beautifully furnished vacation home with water view from main bedroom, Livingroom and lanai. End unit so more light and larger kitchen space. Everything you will need for your beach vacation. Amenities

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 301, Sarasota, FL 34242
• 

  /2

  $4,750,000

  Sold Jan 22, 2026

  8440 Sanderling Rd, Sarasota, FL 34242

  • Land
  • 1.08 Acres
  • $4,398,148 per Acre

  Last Sold Summary

  • 29% Below List Price
  • 270 Days On Market

  Current Estimated Value $5,000,275

  Last Listing Agent Jeffrey Hinrichs MICHAEL SAUNDERS & COMPANY

  8440 Sanderling Rd, Sarasota, FL 34242
• 

  

  /84

  Est $633,767

  Not Listed For Sale

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1970

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Lisa Garcia COLDWELL BANKER REALTY

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