9,352

Siesta Key, FL Homes

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  • /71

    $640,000

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

    206 Hourglass Way Unit V10, Sarasota, FL 34242

    Welcome to your coastal retreat in the form of this secluded, 2 bed/2 bath freestanding villa with one car garage in the premiere GULF FRONT property of Whispering Sands. OFFERED FURNISHED. This surprisingly large, 1,462 square foot property has been UPDATED in 2025 with fresh paint, NEW crown molding & baseboards, NEW kitchen and updated baths. The exceptionally large living room allows for

    Harriet Stopher COLDWELL BANKER REALTY

    206 Hourglass Way Unit V10, Sarasota, FL 34242
  • /58

    $8,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,002 Sq Ft
    • House for Rent

    5640 Cape Leyte Dr, Sarasota, FL 34242

    It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

    Beth Dilley ASCENDIA REAL ESTATE

    5640 Cape Leyte Dr, Sarasota, FL 34242
  • /2

    $640,000

    Sold Dec 08, 2025

    141 Avenida Messina Unit 4, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,035 Sq Ft
    • Built 1966

    Last Sold Summary

    • 8% Below List Price
    • $618/SF
    • 60 Days On Market

    Current Estimated Value $635,311

    Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

    141 Avenida Messina Unit 4, Sarasota, FL 34242
    • /2

      Est $3,479,172

      Not Listed For Sale

      317 Beach Rd, Sarasota, FL 34242

      • 4 Beds
      • 3.5 Baths
      • 3,362 Sq Ft
      • Built 2009
      317 Beach Rd, Sarasota, FL 34242

      Last Sold Summary

      • 14 Days On Market

  • /52

    $520,000

    $220K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 672 Sq Ft

    6020 Midnight Pass Rd Unit 63, Sarasota, FL 34242

    Welcome to Villa 63 at Aloha Kai, a beautifully renovated one-bedroom, one-bath villa located just steps from the world-famous quartz sands of Siesta Key Beach. This coastal retreat has been fully remodeled from top to bottom, offering the perfect combination of comfort, style, and income potential. From the moment you arrive, you’ll notice the fresh exterior with tropical landscaping, paver

    Natalie Gutwein MICHAEL SAUNDERS & COMPANY

    6020 Midnight Pass Rd Unit 63, Sarasota, FL 34242
  • /10

    $7,500 Per Month

    • 2 Beds
    • 1 Bath
    • 941 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit C05, Sarasota, FL 34242

    Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually owned. The minimum stay is 5 or 7 nights, depending on the owner. Every Unit at Casa Blanca is individually decorated and fully furnished including all cookware and linens including beach towels. They have individually controlled AC/Heating and color cable TVs, WIFI, telephones

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit C05, Sarasota, FL 34242
  • /2

    $690,000

    Sold Feb 06, 2026

    204 Hourglass Way Unit V9, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,327 Sq Ft
    • Built 1968

    Last Sold Summary

    • 8% Below List Price
    • $520/SF
    • 22 Days On Market

    Current Estimated Value $684,977

    Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

    204 Hourglass Way Unit V9, Sarasota, FL 34242
    • /100

      Est $7,463,896

      Not Listed For Sale

      4300 Higel Ave, Sarasota, FL 34242

      • 6 Beds
      • 9 Baths
      • 8,615 Sq Ft
      • Built 2008
      4300 Higel Ave, Sarasota, FL 34242

      Last Sold Summary

      • 4 Days On Market

  • /17

    $4,650,000

    New Construction $250K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,723 Sq Ft

    5174 Sandy Cove Ave, Sarasota, FL 34242

    Under Construction. Welcome to 5174 Sandy Cove Ave, a pinnacle of contemporary elegance nestled in the heart of Sarasota, Florida. Designed by architect Mark Sultana. This 3900 sq foot new construction home epitomizes the fusion of exquisite design and impeccable craftsmanship, promising an unparalleled sanctuary for its new owner. Positioned just minutes from Sarasota's pristine white sand

    Troy Jenkins REALTY EXECUTIVES GALLERY

    5174 Sandy Cove Ave, Sarasota, FL 34242
  • /15

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 2, Sarasota, FL 34242

    Villa 2 at Aloha Kai is beautifully situated on Siesta Key, a popular barrier island along Florida’s West Coast. This family-friendly, gated resort community is nestled in the heart of Crescent Beach, which is ranked as the number one beach in the continental United States. Known for its dazzling white quartz sand and vibrant emerald-green waters, Siesta Key is among Florida’s top vacation

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 2, Sarasota, FL 34242
  • /2

    $599,000

    Sold Nov 14, 2025

    5911 Midnight Pass Rd Unit 504, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,447 Sq Ft
    • Built 1984

    Last Sold Summary

    • 20% Below List Price
    • $414/SF
    • 314 Days On Market

    Current Estimated Value $626,838

    Last Listing Agent Katie Cintron COLDWELL BANKER REALTY

    5911 Midnight Pass Rd Unit 504, Sarasota, FL 34242
    • /2

      Est $1,805,642

      Not Listed For Sale

      3928 Roberts Point Rd, Sarasota, FL 34242

      • 3 Beds
      • 2.5 Baths
      • 1,839 Sq Ft
      • Built 1951
      3928 Roberts Point Rd, Sarasota, FL 34242

      Last Sold Summary

      • 2 Days On Market

  • /93

    $500,000

    $150K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,271 Sq Ft

    225 Hourglass Way Unit 103, Sarasota, FL 34242

    Virtually Staged. GREAT PRICE IMPROVEMENT! Welcome to this RARE, 2 bed/2 bath, double lanai corner residence with peaceful lagoon views in the premiere Gulf front property of Whispering Sands! Nestled in the desirable Sunset House building, this freshly painted, updated unit offers a quiet, private setting, with serene views of lush landscaping and the shimmering lagoon with its abundant fish,

    Harriet Stopher COLDWELL BANKER REALTY

    225 Hourglass Way Unit 103, Sarasota, FL 34242
  • /24

    $5,370 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 22, Sarasota, FL 34242

    Starting at $179/night. Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, where comfort and style meet just steps from the beach. The spacious primary suite features a king-sized bed, while the fully equipped kitchen flows seamlessly into a generous dining area and inviting living room, perfect for relaxing or entertaining. Step outside to enjoy a screened-in lanai furnished

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 22, Sarasota, FL 34242
  • /2

    $455,000

    Sold Aug 08, 2025

    1250 N Portofino Dr Unit 201, Sarasota, FL 34242

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

    Last Sold Summary

    • 27% Below List Price
    • $459/SF
    • 125 Days On Market

    Current Estimated Value $477,758

    Last Listing Agent Jessica Bow RE/MAX PALM

    1250 N Portofino Dr Unit 201, Sarasota, FL 34242
    • /2

      Est $504,539

      Not Listed For Sale

      6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,101 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

      Last Sold Summary

      • 23 Days On Market

  • /47

    $685,000

    $39K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    4900 Ocean Blvd Unit 201, Sarasota, FL 34242

    Enjoy coastal living in this updated 2-bedroom, 2-bath Siesta Key condo, just minutes from Siesta Key Village and the beach. The second-floor residence features a fresh coastal design and a kitchen remodeled in 2020 with granite countertops, stainless-steel appliances, and a washer/dryer. Natural light fills the space through large sliders that open to two spacious lanais with peaceful water and

    David Broecker PINPOINT REALTY GROUP LLC

    4900 Ocean Blvd Unit 201, Sarasota, FL 34242
  • /15

    $8,370 Per Month

    • 2 Beds
    • 1.5 Baths
    • 941 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit 14, Sarasota, FL 34242

    Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually owned. The minimum stay is 5 or 7 nights, depending on the owner. Every Unit at Casa Blanca is individually decorated and fully furnished including all cookware and linens including beach towels. They have individually controlled AC/Heating and color cable TVs, WIFI, telephones

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 14, Sarasota, FL 34242
  • /2

    $450,000

    Sold Nov 06, 2025

    5669 Midnight Pass Rd Unit 308, Sarasota, FL 34242

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

    Last Sold Summary

    • 9% Below List Price
    • $445/SF
    • 152 Days On Market

    Current Estimated Value $458,345

    Last Listing Agent David Anthony MICHAEL SAUNDERS & COMPANY

    5669 Midnight Pass Rd Unit 308, Sarasota, FL 34242
    • /71

      Est $397,269

      Not Listed For Sale

      6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

      • 2 Beds
      • 1 Bath
      • 690 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

      Last Sold Summary

      • 42 Days On Market

  • /52

    $699,000

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

    6012 W Peppertree Way Unit 227B, Sarasota, FL 34242

    Gulf-Side Condo on Siesta Key! Don’t miss this great opportunity to own a beautiful condo with a pool view and just steps from the beach. This spacious first-floor unit features 2 bedrooms and 2 bathrooms, high ceilings, and generously sized rooms that provide plenty of space for family and guests. The condo also includes a private garage and the convenience of an in-unit washer and dryer.

    Cheryl Santelli PEPPERTREE BAY REALTY INC

    6012 W Peppertree Way Unit 227B, Sarasota, FL 34242
  • /20

    $5,370 Per Month

    • 1 Bed
    • 1 Bath
    • 708 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 53, Sarasota, FL 34242

    Starting at $179/night! Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, featuring a king-sized bed in the primary suite and a comfortable sleeper sofa in the living area. This stylish retreat boasts a fully equipped kitchen adjoining a spacious dining area, ideal for entertaining or relaxing meals. Enjoy the convenience of a private carport just steps from your door, while

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 53, Sarasota, FL 34242
  • /2

    $913,500

    Sold Oct 10, 2025

    5385 Avenida Del Mare, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 2,956 Sq Ft
    • Built 1981

    Last Sold Summary

    • 39% Below List Price
    • $309/SF
    • 96 Days On Market

    Current Estimated Value $1,049,920

    Last Listing Agent Tracey Bodmer THE BREEZE REALTY GROUP INC

    5385 Avenida Del Mare, Sarasota, FL 34242
    • /82

      Est $559,355

      Not Listed For Sale

      6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

      • 2 Beds
      • 2.5 Baths
      • 1,332 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

      Last Sold Summary

      • 64 Days On Market

  • /72

    $2,795,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,201 Sq Ft

    5303 Hidden Harbor Rd, Sarasota, FL 34242

    Now is your opportunity to own this waterfront tropical oasis on Siesta Key in the highly sought after exclusive community of Hidden Harbor. Comprised of just 36 homes, Hidden Harbor located on the North end of Siesta Key, is one of the most unique developments in Sarasota with its tropical landscaping reminiscent of old Florida. Most known for its waterfront lots and brick paver streets shaded

    Walter Shepherd COLDWELL BANKER REALTY

    5303 Hidden Harbor Rd, Sarasota, FL 34242
  • /51

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft
    • Condo for Rent

    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242

    This luxury Siesta Key beachfront unit in the exclusive Gulf and Bay Club offers full panoramic views of the Gulf of Mexico and the #1 beach in the USA, Siesta Key! This beautifully updated 2-bedroom, 2-bathroom unit features hardwood floors, granite countertops, and an abundance of cabinet space. The bathrooms are elegantly updated with tile and granite counters, making this a truly turnkey

    Robert Bevington SHOWTIME REALTY

    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
  • /2

    $1,225,000

    Sold Mar 30, 2026

    6140 Midnight Pass Rd Unit 407, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,521 Sq Ft
    • Built 1967

    Last Sold Summary

    • 4% Below List Price
    • $805/SF
    • 25 Days On Market

    Current Estimated Value $1,273,885

    Last Listing Agent Brian Partie ENGEL + VOELKERS SARASOTA

    6140 Midnight Pass Rd Unit 407, Sarasota, FL 34242
    • /26

      Est $613,709

      Not Listed For Sale

      6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

      • 2 Beds
      • 2.5 Baths
      • 1,332 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

      Last Sold Summary

      • 205 Days On Market

  • /53

    $1,890,000

    $110K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,882 Sq Ft

    951 Contento St, Sarasota, FL 34242

    New low price and potential seller financing! Deep boating water on the Grand Canal and Siesta Key’s world-famous beaches just minutes away, experience the best of island living. This beautifully renovated three-bedroom, three-bath waterfront residence offers a peaceful island retreat with nearly 2,900 square feet of living space plus a private office, ideal for everyday living and entertaining.

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    951 Contento St, Sarasota, FL 34242
  • /32

    $8,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft
    • Condo for Rent

    1200 E Peppertree Ln Unit 402, Sarasota, FL 34242

    This condo is a 30-night minimum.Condo 1200-402 at Peppertree Bay on Siesta KeyThis 2 bedroom, 2 bathrooms recently remodeled, is only steps away from Crescent Beach and is located on the 4th floor.This condo comfortably sleeps 6 guests.The master King bedroom is equipped with a 43'' Smart TV for your entertainment and a ceiling fan. The master bathroom has a walk-in

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1200 E Peppertree Ln Unit 402, Sarasota, FL 34242
  • /2

    $985,000

    Sold Apr 22, 2026

    4822 Ocean Blvd Unit 9A, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • Built 1973

    Last Sold Summary

    • 21% Below List Price
    • $686/SF
    • 68 Days On Market

    Current Estimated Value $995,960

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    4822 Ocean Blvd Unit 9A, Sarasota, FL 34242
    • /2

      Est $3,382,718

      Not Listed For Sale

      722 Siesta Key Cir, Sarasota, FL 34242

      • 4 Beds
      • 4.5 Baths
      • 3,488 Sq Ft
      • Built 2024
      722 Siesta Key Cir, Sarasota, FL 34242

      Last Sold Summary

      • 311 Days On Market

  • /56

    $1,135,000

    • 2 Beds
    • 2 Baths
    • 1,365 Sq Ft

    1080 W Peppertree Ln Unit 305A, Sarasota, FL 34242

    Rarely available beach-view residence with deeded access to the renowned shores of Siesta Key Beach. Located on the third floor, this bright and inviting unit features a versatile layout, including a pull-out sofa on the lanai with a privacy partition—perfect for creating a comfortable third sleeping area for guests.The well-designed split floor plan offers a spacious dining area, an eat-in

    Eliza Miller PEPPERTREE BAY REALTY INC

    1080 W Peppertree Ln Unit 305A, Sarasota, FL 34242
  • /11

    $8,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,043 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit 201, Sarasota, FL 34242

    Welcome to this beautifully updated, Gulf-facing apartment located directly on the soft white sands of Crescent Beach. Designed for comfort and relaxation, this spacious unit offers sweeping views of the Gulf of Mexico and nightly sunsets that are nothing short of spectacular. Whether you're lounging in the tastefully decorated living room or enjoying a quiet moment on the private, screened-in

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 201, Sarasota, FL 34242
  • /2

    $2,850,000

    Sold Nov 24, 2025

    1216 Northport Dr, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 3,579 Sq Ft
    • Built 2014

    Last Sold Summary

    • $796/SF

    Current Estimated Value $2,957,569

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

    1216 Northport Dr, Sarasota, FL 34242
    • /2

      Est $613,176

      Not Listed For Sale

      915 Beach Rd Unit 419, Sarasota, FL 34242

      • 2 Beds
      • 1 Bath
      • 753 Sq Ft
      • Built 1972
      915 Beach Rd Unit 419, Sarasota, FL 34242

      Last Sold Summary

  • /45

    $949,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft

    1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242

    Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities.Spanning nearly

    Roger Pettingell COLDWELL BANKER REALTY

    1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
  • /45

    $11,000 Per Month

    • 3 Beds
    • 3 Baths
    • 3,324 Sq Ft
    • House for Rent

    681 Avenida de Mayo, Sarasota, FL 34242

    Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations. Step inside to find over-sized rooms that can be utilized for entertaining or simply

    Colette Jay HORIZON REALTY INTERNATIONAL

    681 Avenida de Mayo, Sarasota, FL 34242
  • /2

    $575,000

    Sold Mar 13, 2026

    5860 Midnight Pass Rd Unit 40, Sarasota, FL 34242

    • 1 Bed
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $553/SF
    • 10 Days On Market

    Current Estimated Value $574,342

    Last Listing Agent Keith Redding WILLIAM RAVEIS - FLORIDA LLC

    5860 Midnight Pass Rd Unit 40, Sarasota, FL 34242
    • /2

      Est $501,732

      Not Listed For Sale

      147 Whispering Sands Dr Unit V-29, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,264 Sq Ft
      • Built 1968
      147 Whispering Sands Dr Unit V-29, Sarasota, FL 34242

      Last Sold Summary

      • 52 Days On Market

Showing Results 281 - 320, Page 8 of 18

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