Siesta Key, FL Homes

• 

  

  

  /55

  $373,900

  $56K PRICE DROP

  • 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

  1350 N Portofino Dr Unit 107, Sarasota, FL 34242
• Explore Siesta Key

• 

  

  

  /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

  1195 Coquille St Unit 309, Sarasota, FL 34242
• 

  

  /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

  Current Estimated Value $1,741,379

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC

  4929 Oxford Dr, Sarasota, FL 34242
• 

  

  /2

  Not Listed For Sale

  915 Seaside Dr Unit 606, Weeks 6-7, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 1,780 Sq Ft
  • Built 2009

  915 Seaside Dr Unit 606, Weeks 6-7, Sarasota, FL 34242

  Last Sold Summary

  • 47 Days On Market
• 

  

  

  /92

  $575,000

  $75K PRICE DROP

  • 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 - FLORIDA LLC

  5600 Beach Way Dr Unit 201, Sarasota, FL 34242
• 

  

  /20

  $5,488

  Total Monthly Price

  • 2 Beds
  • 1.5 Baths
  • 850 Sq Ft
  • Condo for Rent

  1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242

  The advertised rate of $5,488/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 3, 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

  1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
• 

  /2

  $360,000

  Sold Mar 31, 2026

  1250 N Portofino Dr Unit 305, Sarasota, FL 34242

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft
  • Built 1969

  Last Sold Summary

  • 28% Below List Price
  • $462/SF
  • 847 Days On Market

  Current Estimated Value $362,264

  Last Listing Agent Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 305, Sarasota, FL 34242
• 

  /2

  Est $1,050,673

  Not Listed For Sale

  20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • Built 1973

  20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

  Last Sold Summary

  • 117 Days On Market
• 

  

  /96

  $2,800,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,689 Sq Ft

  339 Treasure Boat Way, Sarasota, FL 34242

  Elegant Siesta Key Waterfront Living. Don’t just move. Arrive! Enter into your residence, and the world falls away. Picture-perfect postcard views from nearly every room await to welcome you home. Nestled on an unrivaled point at the intersection of the Grand Canal’s most impressive waterways, this newly renovated, rare find offers you the complete package. Luxury finishes, high-tech resilience,

  

  Tonna Gruber

  COLDWELL BANKER REALTY

  339 Treasure Boat Way, Sarasota, FL 34242
• 

  

  /56

  $17,000 Per Month

  • 5 Beds
  • 5 Baths
  • 3,126 Sq Ft
  • House for Rent

  5624 Cape Leyte Dr, Sarasota, FL 34242

  Prime Siesta Key Waterfront Retreat – Fully Furnished & Walk to the Beach Welcome to 5624 Cape Leyte Drive, a fully furnished luxury beach retreat just a short walk to world-famous Siesta Key Beach. This turnkey property showcases refined coastal elegance with designer furnishings, Italian tile and quartz finishes throughout, and spa-inspired bathrooms featuring rainfall showers. Every detail

  

  Wally Sabrii

  SARASOTA INTERNATIONAL REALTY

  5624 Cape Leyte Dr, Sarasota, FL 34242
• 

  /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

  Current Estimated Value $1,588,516

  Last Listing Agent Jackie Eberley COLDWELL BANKER REALTY

  5033 Oxford Dr, Sarasota, FL 34242
• 

  /2

  Est $1,871,904

  Not Listed For Sale

  4941 Commonwealth Dr, Sarasota, FL 34242

  • 4 Beds
  • 4.5 Baths
  • 3,744 Sq Ft
  • Built 2007

  4941 Commonwealth Dr, Sarasota, FL 34242

  Last Sold Summary

  • 3 Days On Market
• 

  

  /71

  $1,799,000

  $200K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  915 Seaside Dr Unit 412, Sarasota, FL 34242

  Welcome to a premier Siesta Key Beach condo that delivers the ultimate combination of luxury coastal living and high-performing rental income potential. This beautifully updated 3-bedroom, 2-bath condominium is professionally managed through an established onsite program, offering owners a seamless, turnkey experience with the ability to enjoy the home personally while also participating in a

  

  Kelly Mooney

  DOUGLAS ELLIMAN

  915 Seaside Dr Unit 412, Sarasota, FL 34242
• 

  

  /20

  $8,832

  Total Monthly Price

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

  6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242

  The advertised rate of $8,833/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 7, 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

  6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
• 

  /2

  $1,275,000

  Sold Mar 30, 2026

  5750 Midnight Pass Rd Unit 704, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Built 1984

  Last Sold Summary

  • 9% Below List Price
  • $955/SF
  • 30 Days On Market

  Current Estimated Value $1,287,546

  Last Listing Agent Adnan Dedic COMPASS FLORIDA LLC

  5750 Midnight Pass Rd Unit 704, Sarasota, FL 34242
• 

  /2

  Est $1,410,175

  Not Listed For Sale

  5140 Windward Ave, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Built 1963

  5140 Windward Ave, Sarasota, FL 34242

  Last Sold Summary

  • 163 Days On Market
• 

  

  /96

  $2,290,000

  $100K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  3941 Hamilton Club Cir Unit 9, Sarasota, FL 34242

  Welcome to coastal luxury living in the exclusive Hamilton Club community on Siesta Key. This beautifully updated 3-bedroom, 3.5-bath waterfront residence offers an exceptional blend of elegance, comfort, and boating convenience in one of the island’s most desirable locations. Designed for effortless everyday living and entertaining, the home features a private elevator, impact-rated windows and

  

  Jennifer Thompson

  WILLIAM RAVEIS - FLORIDA LLC

  3941 Hamilton Club Cir Unit 9, Sarasota, FL 34242
• 

  

  /27

  $9,975 Per Month

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft
  • House for Rent

  1232 Northport Dr, Sarasota, FL 34242

  Annual Rental: Waterfront 3BD/2BA home with private pool and sailboat water with boat slip. Looking for a laid-back Siesta Key flip-flop lifestyle with urban conveniences? Discover 1232 Northport Drive, a secluded, peaceful setting less than one mile from world-famous Siesta Key beach. This updated island one-story home awaits your annual escape from daily demands, but not too far, as high-speed

  

  Lynn Brock

  BROCK REALTY INC.

  1232 Northport Dr, Sarasota, FL 34242
• 

  /2

  $522,500

  Sold Jun 02, 2026

  5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft
  • Built 1962

  Last Sold Summary

  • 16% Below List Price
  • $718/SF
  • 255 Days On Market

  Current Estimated Value $516,454

  Last Listing Agent Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242
• 

  /2

  Est $649,724

  Not Listed For Sale

  5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242

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

  5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242

  Last Sold Summary

  • 48 Days On Market
• 

  

  /54

  $1,090,000

  $60K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,372 Sq Ft

  5300 Ocean Blvd Unit 202, Sarasota, FL 34242

  65 steps to the sand, 312 steps to the water from the Terrace East property are waiting for you! Walk inside and unwind in this updated, turnkey luxury condominium offering nightly sunset views of the #1 beach in the country. This is a rare opportunity to own a condominium in the vibrant heart of Siesta Key, walk to all the amenities and charm that Siesta Key village offers. The property is just

  

  Diane Goodwin

  EXP REALTY LLC

  5300 Ocean Blvd Unit 202, Sarasota, FL 34242
• 

  

  /20

  $8,597

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Condo for Rent

  349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242

  The advertised rate of $8,598/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 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

  349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
• 

  /2

  $1,075,000

  Sold Mar 24, 2026

  6140 Midnight Pass Rd Unit 601, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • Built 1967

  Last Sold Summary

  • 20% Below List Price
  • $693/SF
  • 175 Days On Market

  Current Estimated Value $1,150,395

  Last Listing Agent Suki Scollo COLDWELL BANKER REALTY

  6140 Midnight Pass Rd Unit 601, Sarasota, FL 34242
• 

  /2

  Est $1,336,335

  Not Listed For Sale

  5790 Midnight Pass Rd Unit 602, Sarasota, FL 34242

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

  5790 Midnight Pass Rd Unit 602, Sarasota, FL 34242

  Last Sold Summary

  • 131 Days On Market
• 

  

  /43

  $750,000

  $250K PRICE DROP

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

  5600 Beach Way Dr Unit 315, Sarasota, FL 34242

  Your Florida beach escape awaits — and with a motivated seller, this is an opportunity you won't want to miss.... take a look at this condo that is steps away from the quartz crystal white powdery sands and warm Gulf waters of the award-winning Siesta Key Beach? This wonderfully located turn-key, furnished end unit condo is oh so unique on the top floor with views of the beautiful white sandy

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  5600 Beach Way Dr Unit 315, Sarasota, FL 34242
• 

  

  /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

  5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
• 

  /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

  Current Estimated Value $2,182,885

  Last Listing Agent Jeremy Hartmark LPT REALTY, LLC

  6925 Bochi Cir, Sarasota, FL 34242
• 

  

  /50

  Est $4,754,330

  Not Listed For Sale

  3954 Roberts Point Rd, Sarasota, FL 34242

  • 5 Beds
  • 5 Baths
  • 4,214 Sq Ft
  • Built 2014

  3954 Roberts Point Rd, Sarasota, FL 34242

  Last Sold Summary

  • 9 Days On Market
• 

  

  /27

  $875,000

  $115K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft

  5026 Calle Minorga, Siesta Key, FL 34242

  This property in the heart of Siesta Key Village is zoned OPI — Office, Professional, and Institutional — making it one of a very small number of properties in the Village where a business can legally operate. Buyer to verify intended use with the county.The structure is a furnished 3-bedroom, 1-bath cottage with a full kitchen, Florida room, and laundry. The metal roof is approximately 8

  

  Kim Donahue

  MEDWAY REALTY

  5026 Calle Minorga, Siesta Key, FL 34242
• 

  

  /20

  $7,505

  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 $7,506/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 11, 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

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

  /2

  $1,290,000

  Sold Feb 19, 2026

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

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

  Last Sold Summary

  • 14% Below List Price
  • $1,006/SF
  • 86 Days On Market

  Current Estimated Value $1,282,446

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242
• 

  

  /60

  Est $7,492,247

  Not Listed For Sale

  5131 Jungle Plum Rd, Sarasota, FL 34242

  • 6 Beds
  • 6.5 Baths
  • 6,369 Sq Ft
  • Built 2001

  5131 Jungle Plum Rd, Sarasota, FL 34242

  Last Sold Summary

  • 252 Days On Market
• 

  

  /35

  $719,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,463 Sq Ft

  1200 E Peppertree Ln Unit 302, Sarasota, FL 34242

  PRICE IMPROVEMENT OF $20.000!! Turnkey coastal living in the desirable mid-rise tower at Peppertree Bay on Siesta Key. This sought-after split-plan residence offers bright open living spaces, exceptional privacy, and the convenience of effortless island living with resort-style Gulf-to-Bay amenities just moments from world-famous Siesta Beach. Offered fully turnkey furnished, this beautifully

  

  Renee Nadiv

  WILLIAM RAVEIS - FLORIDA LLC

  1200 E Peppertree Ln Unit 302, Sarasota, FL 34242
• 

  

  /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 THRU DECEMBER 2026. BOOKED FOR SEASON AND THEN AVAILABLE AGAIN APRIL 2027*** 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

  

  Anthony DeLuca

  AUDREY RAIN RENTALS, INC

  6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
• 

  /2

  $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

  Current Estimated Value $1,080,960

  Last Listing Agent Tony Andrews ANDREWS & ASSOCIATES REALTY

  4920 Higel Ave, Sarasota, FL 34242
• 

  /2

  Est $7,315,702

  Not Listed For Sale

  3960 Roberts Point Rd, Sarasota, FL 34242

  • 4 Beds
  • 7 Baths
  • 5,282 Sq Ft
  • Built 2024

  3960 Roberts Point Rd, Sarasota, FL 34242

  Last Sold Summary

  • 145 Days On Market
• 

  

  /50

  $625,000

  • 2 Beds
  • 1 Bath
  • 836 Sq Ft

  6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

  Welcome to Casa Blanca, one of Siesta Key's most sought-after beachfront communities. This beautifully renovated two-bedroom, one-bath villa is ideally located on the Gulf side of Midnight Pass Road, just steps from the world-famous white quartz sands and turquoise waters of Crescent Beach. Situated near Point of Rocks, residents and guests enjoy some of the island's best beach walking, shelling,

  

  Jennifer Thompson

  WILLIAM RAVEIS - FLORIDA LLC

  6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242
• 

  

  /20

  $3,970

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Condo for Rent

  5830 Jamaica Royale Unit SI ID1578366P, Siesta Key, FL 34242

  The advertised rate of $3,970/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 14, 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

  5830 Jamaica Royale Unit SI ID1578366P, Siesta Key, FL 34242
• 

  /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 $1,270,808

  Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

  1660 Summerhouse Ln Unit 102, Sarasota, FL 34242
• 

  /2

  Not Listed For Sale

  5961 Midnight Pass Rd Unit 306, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1974

  5961 Midnight Pass Rd Unit 306, Sarasota, FL 34242

  Last Sold Summary

  • 1 Day On Market

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