Siesta Key, FL Homes

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  $699,000 Pending

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

  6150 Midnight Pass Rd Unit 26, Sarasota, FL 34242

  Your dream Beachside villa is here. Smartly appointed with updated bathrooms and kitchen. Turn key furnished! Carport. Weekly rental can provide income for the owner. On-site manager. Island house is a superbly maintained complex featuring two beach cabanas, a beach, rinsing station, beach, chairs, a large heated, swimming pool, shuffleboard with a view, a game room, two gas grills available to

  Linda Stowe MICHAEL SAUNDERS & COMPANY

  6150 Midnight Pass Rd Unit 26, Sarasota, FL 34242
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  $14,000 per month

  • 4 Beds
  • 3 Baths
  • 2,341 Sq Ft
  • House for Rent

  412 Treasure Boat Way, Sarasota, FL 34242

  Discover your dream home with this exquisite single family residence available for annual rental. This remarkable property redefines elegance and comfort, featuring stunning one-of-a-kind architecture that combines exceptional design with spacious living. Crafted for discerning tenants who appreciate the finer things in life, the home boasts four generously sized bedrooms and three luxurious

  Beth Dilley ASCENDIA REAL ESTATE

  412 Treasure Boat Way, Sarasota, FL 34242
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  $2,260,000 Sold Mar 26, 2025

  815 Paradise Way, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 3,677 Sq Ft
  • Built 1961

  Last Sold Summary

  • 6% Below List Price
  • $615/SF
  • 9 Days On Market

  Current Estimated Value $2,120,954

  Last Listing Agent Doug Addeo COMMUNITY REALTY ASSOCIATES

  815 Paradise Way, Sarasota, FL 34242
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  Est $1,194,802 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,835 Sq Ft

  1345 Siesta Bayside Dr Unit 1345F, Sarasota, FL 34242

  1345 Siesta Bayside Dr Unit 1345F, Sarasota, FL 34242
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  $7,950,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 6,206 Sq Ft

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

  One or more photo(s) has been virtually staged. Experience luxury living at its finest in this breathtaking one-of-a-kind new construction condominium nestled directly on the pristine shores of world famous Siesta Beach. Spanning over 6200 square feet, this exclusive residence offers unparalleled opulence and panoramic views of the azure waters and fiery sunsets. Elegance meets convenience with a

  Thomas Cail RE/MAX ALLIANCE GROUP

  84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242
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  $7,500 per month

  • 4 Beds
  • 3 Baths
  • 2,392 Sq Ft
  • House for Rent

  306 Island Cir, Sarasota, FL 34242

  Available now. Lovely pool home with canal water frontage located in Siesta Key's peaceful and secluded neighborhood of PalmIsland. Completely renovated with new kitchen, bathrooms, and floor coverings throughout this island retreat. Walk four blocks to the crystalsands of world famous Siesta Beach, and just a short walk to the Village. Beautiful backyard with spacious patio, heated

  Timothy Bloch QUEST PROPERTIES INC

  306 Island Cir, Sarasota, FL 34242
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  $900,000 Sold Dec 30, 2025

  1100 Cove II Place Unit 910, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $526/SF
  • 7 Days On Market

  Last Listing Agent Peter Lev EXCEPTIONS REALTY

  1100 Cove II Place Unit 910, Sarasota, FL 34242
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  /59

  Est $696,868 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft

  5860 Midnight Pass Rd Unit 19, Sarasota, FL 34242

  5860 Midnight Pass Rd Unit 19, Sarasota, FL 34242
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  $450,000 Pending

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  6006 Midnight Pass Rd Unit 4, Sarasota, FL 34242

  Beachside Living at Its Best - Casa Mar on Siesta Key Welcome to Casa Mar, a sought-after beachfront community offering the perfect combination of island charm and modern convenience. This 1-bedroom, 1-bathroom furnished unit is a rare opportunity to create your very own coastal getaway or capitalize on a high-demand vacation rental investment. Located just a 1-minute walk from world-renowned

  Dawn Lacey LACEY REALTY INC

  6006 Midnight Pass Rd Unit 4, Sarasota, FL 34242
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  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit B, Sarasota, FL 34242

  Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit B, Sarasota, FL 34242
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  $578,000 Sold Oct 08, 2025

  6415 Midnight Pass Rd Unit 607, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $449/SF
  • 185 Days On Market

  Current Estimated Value $566,887

  Last Listing Agent James Hirschman SARASOTA LAND AND HOMES LLC

  6415 Midnight Pass Rd Unit 607, Sarasota, FL 34242
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  Est $1,125,892 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft

  5790 Midnight Pass Rd Unit 205, Sarasota, FL 34242

  5790 Midnight Pass Rd Unit 205, Sarasota, FL 34242
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  $960,000

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  711 Birdsong Ln, Sarasota, FL 34242

  Located in the heart of Siesta Key, this three-bedroom, two-bath home with a two-car garage offers a rare opportunity to experience island living just one mile from Siesta Key Beach—consistently ranked the #1 beach in the United States for its white quartz sand, turquoise waters, and year-round appeal.This property is perched on an elevated lot that has never experienced flooding. Recent

  Julianna Burns BERKSHIRE HATHAWAY HOMESERVICE

  711 Birdsong Ln, Sarasota, FL 34242
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  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit A, Sarasota, FL 34242

  Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated,

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit A, Sarasota, FL 34242
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  $655,000 Sold Jun 20, 2025

  5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $569/SF
  • 48 Days On Market

  Current Estimated Value $619,764

  Last Listing Agent Susan Retzke RE/MAX PALM

  5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242
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  Est $1,120,805 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,989 Sq Ft

  4929 Peaceable Way, Sarasota, FL 34242

  4929 Peaceable Way, Sarasota, FL 34242
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  $3,999,999

  • 3 Beds
  • 3 Baths
  • 2,374 Sq Ft

  5400 Ocean Blvd Unit 12-2, Sarasota, FL 34242

  SUNRISE TO SUNSET GULF AND BEACH VIEWS extend from public beach, Siesta Village, the north toward Lido and Longboat Keys! Welcome to a combination of 2 gulf front units into a spacious, open, airy luxury beach residence. As you enter, you are immersed in the breathtaking waters of the Gulf of Mexico in all directions! Stunning interior with an Italian flair! Venetian plaster walls, and imported

  Carol Thomas MICHAEL SAUNDERS & COMPANY

  5400 Ocean Blvd Unit 12-2, Sarasota, FL 34242
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  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,439 Sq Ft
  • House for Rent

  4852 Featherbed Ln, Sarasota, FL 34242

  SIESTA KEY, Sarasota, Single Family Pool Home....Well-positioned for convenience and natural attractions . . . and dinners are breezy on your patio! The advantages of this appealing home in the Siesta area of Siesta Key become apparent while you are still walking the perimeter. The clear blue pool and the patio are a perfect pairing of amenities, supporting a variety of social activities and

  Jane Hunter JENNETTE PROPERTIES INC

  4852 Featherbed Ln, Sarasota, FL 34242
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  $800,000 Sold Sep 10, 2025

  20 Whispering Sands Dr Unit 301, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1973

  Last Sold Summary

  • 15% Below List Price
  • $624/SF
  • 135 Days On Market

  Current Estimated Value $821,130

  Last Listing Agent Dion Souza SARABAY REAL ESTATE INC

  20 Whispering Sands Dr Unit 301, Sarasota, FL 34242
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  /2

  Est $740,503 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  5211 Avenida de Cortez, Sarasota, FL 34242

  5211 Avenida de Cortez, Sarasota, FL 34242
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  /22

  $1,175,000 Pending

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  6342 Midnight Pass Rd Unit 310, Sarasota, FL 34242

  Beachfront condo with full gulf views. Completely renovated unit in 2024 with direct access to the sugary white sand beaches. New tile floor throughout. All new kitchen with new custom kitchen cabinetry, granite counter tops and stainless-steel appliances. Turnkey furnished. Excellent rental history. Private end unit location on the southern end of the complex. Brand new gulf front community

  Brian Livesey WATERSIDE REALTY LLC

  6342 Midnight Pass Rd Unit 310, Sarasota, FL 34242
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  $8,900 per month

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft
  • Condo for Rent

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

  Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
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  $815,000 Sold Sep 15, 2025

  710 Birdsong Ln, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,522 Sq Ft
  • Built 1980

  Last Sold Summary

  • 32% Below List Price
  • $323/SF
  • 173 Days On Market

  Current Estimated Value $897,447

  Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.

  710 Birdsong Ln, Sarasota, FL 34242
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  Est $1,342,875 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,295 Sq Ft

  5310 Hidden Harbor Rd, Sarasota, FL 34242

  5310 Hidden Harbor Rd, Sarasota, FL 34242
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  $3,750,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,220 Sq Ft

  5355 Calle Florida, Sarasota, FL 34242

  Under Construction. New Construction | Modern Concrete Homes steps from Siesta Key Beach now under construction and scheduled for completion in approximately six months. These two identical, mirror-image modern residences are located on Sarasota Beach, just one short block from the world-renowned Siesta Key Beach.Built with solid concrete construction and full hurricane-rated specifications,

  Fernanda Girard COLDWELL BANKER REALTY

  5355 Calle Florida, Sarasota, FL 34242
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  $2,000 per month

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft
  • Condo for Rent

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242

  Available Nov through Dec 2025 for $2,000 per month. 55+ community. Available Jan-Mar 2026 for $4,000 per month. Welcome to your dream coastal escape in beautiful Siesta Harbor on Siesta Key! This turnkey furnished; spacious one-bedroom, two-bath condo is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere.

  Jonathan OSteen O'STEEN GROUP INC

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242
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  $600,000 Sold Oct 21, 2025

  4181 Roberts Point Cir Unit Lot 17, Sarasota, FL 34242

  • Land
  • 0.14 Acre
  • $4,285,714 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 183 Days On Market

  Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  4181 Roberts Point Cir Unit Lot 17, Sarasota, FL 34242
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  Est $1,489,070 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,143 Sq Ft

  395 Avenida Milano, Sarasota, FL 34242

  395 Avenida Milano, Sarasota, FL 34242
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  /7

  $1,705,900 Pending

  • 4 Beds
  • 3.5 Baths
  • 1,824 Sq Ft

  312 Avenida Leona, Siesta Key, FL 34242

  Under contract-accepting backup offers. Pre-Construction. To be built. Build Your Coastal Dream on Siesta Key – Hurricane-Ready Luxury by SeaSafe Homes. This offering includes both the canal-front lot on Avenida Leona in Siesta Key and the construction of the Battery Point Model by SeaSafe Homes. This is a rare opportunity to build a high-performance coastal home in one of Siesta Key’s most

  Ron Pepka KW SUNCOAST

  312 Avenida Leona, Siesta Key, FL 34242
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  /40

  $6,500 per month

  • 3 Beds
  • 4 Baths
  • 2,168 Sq Ft
  • House for Rent

  1256 Riegels Landing Dr, Sarasota, FL 34242

  This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full

  Christopher Davenport STARLINK REALTY INC

  1256 Riegels Landing Dr, Sarasota, FL 34242
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  $6,925,000 Sold Dec 29, 2025

  6100 Midnight Pass Rd Unit 401, Sarasota, FL 34242

  • 4 Beds
  • 4.5 Baths
  • 3,525 Sq Ft
  • Built 2019

  Last Sold Summary

  • 11% Below List Price
  • $1,965/SF
  • 0 Days On Market

  Last Listing Agent David Lehrman THE SARASOTA REAL ESTATE COMP.

  6100 Midnight Pass Rd Unit 401, Sarasota, FL 34242
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  Est $1,530,918 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft

  4926 Commonwealth Dr, Sarasota, FL 34242

  4926 Commonwealth Dr, Sarasota, FL 34242
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  /40

  $965,000

  • 2 Beds
  • 2 Baths
  • 1,760 Sq Ft

  1161 Coquille St Unit 206, Sarasota, FL 34242

  Welcome to coastal elegance and a rare opportunity to own one of only 27 townhomes in the highly sought-after Coquille community, nestled on the picturesque barrier island of Siesta Key, where you are steps to having your feet in the famous soft, white quartz sand that makes Siesta Beach famous. This spacious and light-filled, furnished 2-bedroom, 2-bathroom residence also includes a Florida room

  Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

  1161 Coquille St Unit 206, Sarasota, FL 34242
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  $7,500 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- This clean, updated, 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

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
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  $1,165,000 Sold Jun 13, 2025

  5916 Midnight Pass Rd Unit 404, Sarasota, FL 34242

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

  Last Sold Summary

  • $993/SF
  • 3 Days On Market

  Current Estimated Value $1,108,752

  Last Listing Agent Gloria Totti-Cervoni COLDWELL BANKER REALTY

  5916 Midnight Pass Rd Unit 404, Sarasota, FL 34242
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  Est $722,450 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft

  1200 E Peppertree Ln Unit 407, Sarasota, FL 34242

  1200 E Peppertree Ln Unit 407, Sarasota, FL 34242
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  $1,300,000

  • 2 Beds
  • 2 Baths
  • 1,187 Sq Ft

  5400 Ocean Blvd Unit 6-4, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. The Beach Terrace building is one of the most desirable addresses on Siesta Key with a direct Gulf of Mexico location and nestled at the end of the village. This 2 bedroom / 2 full bath corner residence offers panoramic views of the Siesta Key beach, village and aqua water of the Gulf of Mexico. The condominium offers 3 spacious balconies to enjoy

  Mickey Kiernan MICHAEL SAUNDERS & COMPANY

  5400 Ocean Blvd Unit 6-4, Sarasota, FL 34242
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  $9,000 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. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

  Chrissie Cummings JENNETTE PROPERTIES INC

  327 Avenida Milano, Sarasota, FL 34242
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  $2,100,000 Sold May 23, 2025

  5159 Oxford Dr, Sarasota, FL 34242

  • 3 Beds
  • 4 Baths
  • 2,692 Sq Ft
  • Built 1996

  Last Sold Summary

  • 19% Below List Price
  • $780/SF
  • 122 Days On Market

  Current Estimated Value $1,964,203

  Last Listing Agent Andrew Foltz PREFERRED SHORE LLC

  5159 Oxford Dr, Sarasota, FL 34242
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  Est $831,452 Not Listed For Sale

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

  1001 Beach Rd Unit A504, Sarasota, FL 34242

  1001 Beach Rd Unit A504, Sarasota, FL 34242

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