9,352

Siesta Key, FL Homes

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  • /48

    $629,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 532 Sq Ft

    22 Sandy Cove Rd Unit 203, Sarasota, FL 34242

    $10,000 Price Reduction! Introducing a charming one-bedroom, one-bathroom condo in the heart of Siesta Key, where Old Florida charm meets modern coastal living. This elevated second-floor unit offers a bright, inviting living space set within a secluded, tropical oasis designed by the renowned Frank Folsm Smith of the Sarasota School of Architecture. Enjoy peace of mind with no history of storm

    Beth Dilley ASCENDIA REAL ESTATE

    22 Sandy Cove Rd Unit 203, Sarasota, FL 34242
  • /17

    $8,400 Per Month

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

    1200 E Peppertree Ln Unit 206, Sarasota, FL 34242

    his property is a 30-night minimum.This 2-bedroom, 2 bath has benefits of both sides being located on the bay side with beach access and on the second floor.The master bedroom has a king bed with a 50 inch flat screen TV, a ceiling fan, and access to the lanai. The master bathroom is a walk-in shower with a glass door and a grab bar.The guest bedroom has a king size bed with a 32 inch

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1200 E Peppertree Ln Unit 206, Sarasota, FL 34242
  • /2

    $1,200,000

    Sold Aug 29, 2025

    5740 Midnight Pass Rd Unit 402, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft
    • Built 1986

    Last Sold Summary

    • 17% Below List Price
    • $898/SF
    • 180 Days On Market

    Current Estimated Value $1,195,458

    Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

    5740 Midnight Pass Rd Unit 402, Sarasota, FL 34242
    • /30

      Est $567,040

      Not Listed For Sale

      901 Beach Rd Unit 202, Sarasota, FL 34242

      • 2 Beds
      • 1 Bath
      • 753 Sq Ft
      • Built 1972
      901 Beach Rd Unit 202, Sarasota, FL 34242

      Last Sold Summary

      • 16 Days On Market

  • /92

    $4,485,000

    New Construction $165K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,132 Sq Ft

    558 Venice Ln, Sarasota, FL 34242

    Newly completed and move-in ready, this Coastal Contemporary waterfront residence on Siesta Key by award-winning Heritage Builders offers 4,132 sq ft with 5 bedrooms, 4.5 baths, a private study, loft, and elevator—perfectly blending luxury, functionality, and coastal living. The main level features white oak wood floors, soaring beamed ceilings, and a bright open-concept layout designed for both

    Andrew Haddad COMPASS FLORIDA LLC

    558 Venice Ln, Sarasota, FL 34242
  • /18

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 14A, Sarasota, FL 34242

    A wonderful beach vacation awaits you at Villa 14A at Aloha Kai, an updated villa just steps from the beach. Featuring two double beds, it’s an ideal spot for a girlfriend getaway. Start your day with a leisurely walk along the shore, then spend the afternoon relaxing on the front porch or back patio. For a perfect evening, visit a local waterfront restaurant to enjoy a sunset cocktail and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 14A, Sarasota, FL 34242
  • /2

    $595,000

    Sold May 12, 2026

    5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242

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

    Last Sold Summary

    • 8% Below List Price
    • $516/SF
    • 8 Days On Market

    Current Estimated Value $637,356

    Last Listing Agent Anna Williams SHOWTIME REALTY

    5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242
    • /90

      Est $2,164,138

      Not Listed For Sale

      5420 Azure Way, Sarasota, FL 34242

      • 4 Beds
      • 4.5 Baths
      • 4,105 Sq Ft
      • Built 1978
      5420 Azure Way, Sarasota, FL 34242

      Last Sold Summary

      • 108 Days On Market

  • /87

    $3,249,000

    Pending
    • 6 Beds
    • 4 Baths
    • 2,328 Sq Ft

    5319 Calle de La Siesta, Sarasota, FL 34242

    Under contract-accepting backup offers. Introducing 5319 Calle De La Siesta, a coastal haven that effortlessly fuses opulence, convenience, and serenity. Revel in the sophistication of this remarkable residence, featuring an exclusive heated pool, ideally situated just a 3-minute stroll from Siesta Key Village and a mere 1-minute amble to the pristine Siesta Key Beach – your ultimate sanctuary.

    Curtis Ware KW COASTAL LIVING III

    5319 Calle de La Siesta, Sarasota, FL 34242
  • /23

    $3,600 Per Month

    • 3 Beds
    • 2 Baths
    • 1,737 Sq Ft
    • Condo for Rent

    1255 Dockside Place Unit 211, Sarasota, FL 34242

    Welcome to your ideal Siesta Key retreat! This charming 2-bedroom, 2-bath condo comfortably sleeps up to 6 guests and is just a short walk from the world-famous Siesta Key Beach. Whether you’re looking to relax or stay active, this inviting property offers everything you need for an unforgettable vacation.The Space:Step inside this peaceful condo featuring a spacious main bedroom with

    Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

    1255 Dockside Place Unit 211, Sarasota, FL 34242
  • /2

    $750,000

    Sold May 21, 2026

    4822 Ocean Blvd Unit 2A, Sarasota, FL 34242

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

    Last Sold Summary

    • 12% Below List Price
    • $523/SF
    • 175 Days On Market

    Current Estimated Value $830,420

    Last Listing Agent Beth Dilley ASCENDIA REAL ESTATE

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

      Est $1,174,222

      Not Listed For Sale

      420 Beach Rd Unit 305, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1980
      420 Beach Rd Unit 305, Sarasota, FL 34242

      Last Sold Summary

      • 393 Days On Market

  • /38

    $2,199,000

    $91K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,277 Sq Ft

    4708 Ocean Blvd Unit E4, Sarasota, FL 34242

    Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz

    Mina Johnson MICHAEL SAUNDERS & COMPANY

    4708 Ocean Blvd Unit E4, Sarasota, FL 34242
  • /18

    $7,367 Per Month

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

    6020 Midnight Pass Rd Unit 7, Sarasota, FL 34242

    ife is good at the beach! This light, bright, and beautifully maintained 2-bedroom, 1-bath villa at Aloha Kai is ready for your arrival—just drop your bags and head straight to the pool or beach. Featuring stainless steel appliances, an open-concept floor plan, and a screened porch, the villa offers the perfect blend of comfort and style. Located on Siesta Key, a renowned barrier island on

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 7, Sarasota, FL 34242
  • /2

    $1,050,000

    Sold Mar 31, 2026

    6208 Midnight Pass Rd Unit 202, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft
    • Built 1979

    Last Sold Summary

    • $913/SF
    • 0 Days On Market

    Current Estimated Value $1,048,951

    Last Listing Agent Stacy Liljeberg MICHAEL SAUNDERS & COMPANY

    6208 Midnight Pass Rd Unit 202, Sarasota, FL 34242
    • /2

      Est $684,642

      Not Listed For Sale

      1155 Lake House Cir Unit C119, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 1981
      1155 Lake House Cir Unit C119, Sarasota, FL 34242

      Last Sold Summary

      • 8 Days On Market

  • /86

    $1,299,000

    $151K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,334 Sq Ft

    5920 Midnight Pass Rd Unit 406, Sarasota, FL 34242

    TOWER RESIDENCE IN SARASOTA SURF AND RACQUET CLUB. 2BR/2BA in a Gulf & Beach Front Community – Resort Style Amenities – Proven Vacation Rental – Move In Ready - Enjoy the island lifestyle in one of Siesta Key’s most desirable beach front communities, located directly on Crescent Beach, the powdery white sand shoreline that makes Siesta Key world-famous. This beautifully appointed 4th-floor

    Greg Hudson COLDWELL BANKER REALTY

    5920 Midnight Pass Rd Unit 406, Sarasota, FL 34242
  • /34

    $8,100 Per Month

    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Condo for Rent

    1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242

    Welcome to your Gulf & Bay Club Bayside sanctuary in the heart of Siesta Key, FL! This second-story bay front condo offers a blissful retreat with breathtaking views of the azure waters. With two bedrooms and two bathrooms, this meticulously designed residence seamlessly blends coastal elegance with modern comfort.Step into a sunlit living space adorned with coastal-inspired décor,

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242
  • /2

    $590,000

    Sold Jun 05, 2026

    1169 W Peppertree Dr Unit 118A, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,083 Sq Ft
    • Built 1974

    Last Sold Summary

    • 9% Below List Price
    • $545/SF
    • 64 Days On Market

    Current Estimated Value $632,958

    Last Listing Agent Brian Ward WATERSIDE REALTY LLC

    1169 W Peppertree Dr Unit 118A, Sarasota, FL 34242
    • /2

      Est $1,735,453

      Not Listed For Sale

      5536 Contento Dr, Sarasota, FL 34242

      • 4 Beds
      • 2.5 Baths
      • 2,527 Sq Ft
      • Built 1969
      5536 Contento Dr, Sarasota, FL 34242

      Last Sold Summary

      • 32 Days On Market

  • /46

    $1,195,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,433 Sq Ft

    5790 Midnight Pass Rd Unit 208, Sarasota, FL 34242

    Experience, luxury gulf front living at its best in this beautiful move in ready beachfront condo on world famous Siesta Key Beach in Sunny Sarasota, Florida. Perfectly located to enjoy breathtaking views of the Gulf Waters, powdery white quartz sand and beautiful evening sunsets. This turnkey, tastefully furnished residence is the ultimate coastal paradise either as a primary residence, vacation

    Andy McDonald ESLINGER REALTY INC

    5790 Midnight Pass Rd Unit 208, Sarasota, FL 34242
  • /10

    $6,900 Per Month

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

    6154 Midnight Pass Rd Unit B05, Sarasota, FL 34242

    The owners have just replaced the carpet in this beautifully appointed 2 bedroom one and one half bathroom unit. There is private wireless for your enjoyment, while being just steps away from the refreshing pool and a short walk to the beach this unit is waiting for you. Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually owned.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit B05, Sarasota, FL 34242
  • /2

    $1,835,000

    Sold Jan 29, 2026

    5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242

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

    Last Sold Summary

    • 6% Below List Price
    • $1,071/SF
    • 23 Days On Market

    Current Estimated Value $1,786,046

    Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

    5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242
    • /85

      Est $3,017,885

      Not Listed For Sale

      5330 Siesta Cove Dr, Sarasota, FL 34242

      • 4 Beds
      • 4 Baths
      • 4,680 Sq Ft
      • Built 1977
      5330 Siesta Cove Dr, Sarasota, FL 34242

      Last Sold Summary

      • 95 Days On Market

  • /4

    $4,795,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,523 Sq Ft

    5572 Shadow Lawn Dr, Sarasota, FL 34242

    Under Construction. An exceptional opportunity to own a brand-new waterfront residence in the highly sought-after Siesta Isles community. Expertly crafted by Nutter Custom Construction, this British West Indies-inspired custom home offers 3,568 square feet of air-conditioned living space and 5,725 total square feet designed for luxurious coastal living. Situated on a 14,300-square-foot lot with

    Morgan Marziali NCC PROPERTIES LLC

    5572 Shadow Lawn Dr, Sarasota, FL 34242
  • /10

    $6,900 Per Month

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

    6154 Midnight Pass Rd Unit 12, Sarasota, FL 34242

    Villa C12 is a beautiful 2 bedrooms, 1 bathroom beach accommodation located in the exclusive Casa Blanca beachside condos on the pristine shores of Siesta Key's coveted Crescent Beach rated as one of the top ten beaches in the USA. The kitchen is fully equipped for all your food preparation needs. You'll love dining al fresco or sipping a cocktail in the screened lanai. It is located a few short

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 12, Sarasota, FL 34242
  • /2

    $630,000

    Sold Jan 07, 2026

    753 Tropical Cir, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,695 Sq Ft
    • Built 1979

    Last Sold Summary

    • 21% Below List Price
    • $372/SF
    • 82 Days On Market

    Current Estimated Value $719,711

    Last Listing Agent Patrick Ritchey RE/MAX ALLIANCE GROUP

    753 Tropical Cir, Sarasota, FL 34242
    • /2

      Est $1,111,531

      Not Listed For Sale

      627 Avenida Del Norte, Sarasota, FL 34242

      • 3 Beds
      • 4 Baths
      • 1,713 Sq Ft
      • Built 1949
      627 Avenida Del Norte, Sarasota, FL 34242

      Last Sold Summary

      • 22 Days On Market

  • /33

    $499,000

    $4K PRICE INCREASE
    • 1 Bed
    • 1 Bath
    • 748 Sq Ft

    6157 Midnight Pass Rd Unit E22, Sarasota, FL 34242

    BEAUTIFUL 1 BEDROOM 1 BATH UNIT IN BAY OAKS on SIESTA KEY ** TURNKEY FURNISHED ** 1 WEEK RENTALS ALLOWED ** The waves crash, the sand is sugar-coated and the sunsets are striking on Siesta Key.. There is no better location to invest in a 2nd home or investment property. This condo is located on the 2nd floor of building E in Bay Oaks. You will love the large open kitchen and expansive design of

    Justin Shirley SHIRLEY INTERNATIONAL REALTY

    6157 Midnight Pass Rd Unit E22, Sarasota, FL 34242
  • /73

    $10,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,030 Sq Ft
    • House for Rent

    5628 Cape Leyte Dr, Sarasota, FL 34242

    Your cozy getaway awaits in Siesta Key at this terrific house. With three bedrooms featuring a king, queen, and full bed, guests find plenty of space to relax. The large heated pool gives you an amazing space for relaxing after a day at the beach which is just steps away. You also have a large gazebo adjacent to the pool to get out of the sun and showcase you BBQ skills. Whether you’re unwinding

    Troy Jenkins REALTY EXECUTIVES GALLERY

    5628 Cape Leyte Dr, Sarasota, FL 34242
  • /2

    $660,000

    Sold Sep 17, 2025

    6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Built 1975

    Last Sold Summary

    • 12% Below List Price
    • $512/SF
    • 187 Days On Market

    Current Estimated Value $670,958

    Last Listing Agent Crystal Saly RE/MAX PALM

    6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242
    • /2

      Est $1,056,173

      Not Listed For Sale

      5159 Oakmont Place, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,953 Sq Ft
      • Built 1977
      5159 Oakmont Place, Sarasota, FL 34242

      Last Sold Summary

      • 47 Days On Market

  • /68

    $595,000

    • 2 Beds
    • 2 Baths
    • 1,182 Sq Ft

    5600 Beach Way Dr Unit 210, Sarasota, FL 34242

    This newly listed condominium presents a distinguished opportunity to own a fully furnished residence directly across the street from the number one ranked beach in the world. Situated across the street from Siesta Key public beach, this property offers an exceptional blend of coastal elegance and investment potential. The two-bedroom, two-bathroom split floor plan provides both privacy and

    Dion Souza SARABAY REAL ESTATE INC

    5600 Beach Way Dr Unit 210, Sarasota, FL 34242
  • /24

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 65, 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 offers a fully equipped kitchen adjacent to a spacious dining area, ideal for entertaining. A convenient stackable washer and dryer is located within the unit, adding to your comfort and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 65, Sarasota, FL 34242
  • /2

    $801,000

    Sold Jun 18, 2026

    1700 Cove II Place Unit 324, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft
    • Built 1979

    Last Sold Summary

    • 6% Below List Price
    • $466/SF
    • 63 Days On Market

    Current Estimated Value $852,414

    Last Listing Agent Kim Sheridan WATERSIDE REALTY LLC

    1700 Cove II Place Unit 324, Sarasota, FL 34242
    • /50

      Est $542,332

      Not Listed For Sale

      Unlisted Address

      • 2 Beds
      • 2 Baths
      • 1,010 Sq Ft
      • Built 1979
      Unlisted Address

      Last Sold Summary

      • 10 Days On Market

  • /47

    $1,399,000

    $496K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,124 Sq Ft

    5560 Shadow Lawn Dr, Sarasota, FL 34242

    Under contract-accepting backup offers. One of the lowest priced homes on Siesta Key's deep boating water and only 3 blocks to the white quartz sand and aqua Gulf waters! An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this well-maintained residence is ideally positioned just minutes from the powdery white sands of world-famous Siesta Beach and the turquoise waters of

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    5560 Shadow Lawn Dr, Sarasota, FL 34242
  • /16

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 24, Sarasota, FL 34242

    Starting at $179/night! Step into your perfect beach getaway with this charming ground-floor 1-bedroom unit located in the sought-after Casa Mar complex, just off Midnight Pass Road and only steps from the sand. Relax on the screened lanai overlooking a peaceful courtyard, where two sparkling pools invite you to unwind in the Florida sunshine. A short stroll along the sidewalk brings you directly

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 24, Sarasota, FL 34242
  • /2

    $500,000

    Sold Feb 13, 2026

    5219 Calle de Rio, Siesta Key, FL 34242

    • Land
    • 6,969 Sq Ft
    • $3,125,000 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 405 Days On Market

    Current Estimated Value $502,747

    Last Listing Agent Robert Bevington SHOWTIME REALTY

    5219 Calle de Rio, Siesta Key, FL 34242
    • /2

      Est $1,775,744

      Not Listed For Sale

      4820 Higel Ave, Sarasota, FL 34242

      • 4 Beds
      • 3 Baths
      • 2,672 Sq Ft
      • Built 1972
      4820 Higel Ave, Sarasota, FL 34242

      Last Sold Summary

      • 23 Days On Market

Showing Results 641 - 680, Page 17 of 18

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