9,261

Siesta Key, FL Homes

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  • /48

    $669,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,120 Sq Ft

    1128 W Peppertree Ln Unit 111, Siesta Key, FL 34242

    Under contract-accepting backup offers. Experience the ultimate Siesta Key lifestyle in this beautifully updated Gulf side first-floor, turnkey furnished 2-bedroom, 1.5-bath condo with tranquil pond views and deeded beach access to the #1 beach in the USA. Thoughtfully renovated and move-in ready, this charming residence features large-format porcelain tile flooring, crown molding, fresh paint,

    Cheryl Santelli PEPPERTREE BAY REALTY INC

    1128 W Peppertree Ln Unit 111, Siesta Key, FL 34242
  • /27

    $12,600 Per Month

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

    301 Avenida Madera Unit A, Sarasota, FL 34242

    If you’re searching for the perfect location for your next vacation, your search ends here!This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid

    Robert Bevington SHOWTIME REALTY

    301 Avenida Madera Unit A, Sarasota, FL 34242
  • /2

    $650,000

    Sold Nov 25, 2025

    5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Built 1974

    Last Sold Summary

    • 21% Below List Price
    • $650/SF
    • 199 Days On Market

    Current Estimated Value $652,121

    Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY

    5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242
    • /77

      Est $1,511,393

      Not Listed For Sale

      5319 Siesta Cove Dr, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,740 Sq Ft
      • Built 1989
      5319 Siesta Cove Dr, Sarasota, FL 34242

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Tammy Garner COLDWELL BANKER REALTY

  • /56

    $1,450,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,500 Sq Ft

    521 Cummings St, Sarasota, FL 34242

    Under contract-accepting backup offers. Tucked away on a quiet cul-de-sac on north Siesta Key, this Key West-inspired canal-front retreat captures the ease of casual island living with boating water, inviting outdoor spaces and easy access to Siesta Village, the famous white quartz sands of Siesta Beach and the azure waters of the Gulf. Set along 95 feet of private canal frontage just off the

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    521 Cummings St, Sarasota, FL 34242
  • /13

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 32, Sarasota, FL 34242

    Villa 32 at Aloha Kai is ideally located on Siesta Key, a beloved barrier island along Florida’s beautiful West Coast. This cozy unit features 1 bedroom, 1 bathroom, and includes the convenience of an in-unit washer and dryer. Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—consistently ranked the number one beach in the continental United States.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 32, Sarasota, FL 34242
  • /2

    $1,125,000

    Sold Mar 31, 2026

    6342 Midnight Pass Rd Unit 423, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,214 Sq Ft
    • Built 1977

    Last Sold Summary

    • 13% Below List Price
    • $927/SF
    • 49 Days On Market

    Current Estimated Value $1,126,109

    Last Listing Agent Jan Jordan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

    6342 Midnight Pass Rd Unit 423, Sarasota, FL 34242
    • /2

      Est $1,260,900

      Not Listed For Sale

      5239 Siesta Cove Dr, Sarasota, FL 34242

      • 4 Beds
      • 4 Baths
      • 2,333 Sq Ft
      • Built 1983
      5239 Siesta Cove Dr, Sarasota, FL 34242

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Christopher Grant GRANT TEAM REAL ESTATE, LLC

  • /53

    $485,999

    • 1 Bed
    • 1 Bath
    • 513 Sq Ft

    5950 Midnight Pass Rd Unit 101, Sarasota, FL 34242

    An exceptional opportunity to own a beautifully updated and turn-key beach condominium in the heart of Siesta Key, offering the flexibility of a strong rental investment, seasonal getaway, or your own private coastal retreat. Located within Siesta Beach House Condominiums, this residence places you just a short walk to both Siesta Beach and Crescent Beach, while also offering the rare advantage

    Rachel Tritschler RE/MAX ALLIANCE GROUP

    5950 Midnight Pass Rd Unit 101, Sarasota, FL 34242
  • /15

    $5,070 Per Month

    • 1 Bath
    • 420 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 2, Sarasota, FL 34242

    Starting at $154/night! Escape to the perfect beachside retreat at our charming and cozy studio on beautiful Siesta Key. Just steps from the world-renowned white sands of Siesta Beach, this inviting space is ideal for couples or solo travelers looking to unwind in comfort. The studio features two plush queen-size beds, a relaxed seating area, and a flat-screen TV for your entertainment. Prepare

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

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

    $325,000

    Sold Dec 31, 2025

    101 Whispering Sands Dr Unit 205, Sarasota, FL 34242

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

    Last Sold Summary

    • 19% Below List Price
    • $256/SF
    • 25 Days On Market

    Current Estimated Value $473,846

    Last Listing Agent Julie Froeschle BERKSHIRE HATHAWAY HOMESERVICE

    101 Whispering Sands Dr Unit 205, Sarasota, FL 34242
    • /78

      Est $637,367

      Not Listed For Sale

      105 Whispering Sands Dr Unit V48, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1970
      105 Whispering Sands Dr Unit V48, Sarasota, FL 34242

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

  • /70

    $719,000

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft

    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242

    A first-floor 2-bedroom, 2-bath residence in Gulf and Bay Club Bayside with no unit above, offering added privacy and direct access. An optional second garage is available for purchase under a separate bill of sale. Located on Siesta Key, an eight-mile barrier island consistently recognized among the top beach destinations in the United States and globally, Siesta Beach has been ranked the #1

    Tiffany Nisbet RE/MAX ALLIANCE GROUP

    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
  • /10

    $8,370 Per Month

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

    6154 Midnight Pass Rd Unit C08, 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 C08, Sarasota, FL 34242
  • /2

    $8,000,000

    Sold Jun 24, 2026

    4105 Shell Rd, Sarasota, FL 34242

    • Land
    • 1.2 Acres
    • $6,666,667 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 649 Days On Market

    Current Estimated Value $5,601,270

    Last Listing Agent Michael Hays MICHAEL SAUNDERS & COMPANY

    4105 Shell Rd, Sarasota, FL 34242
    • /51

      Est $1,122,354

      Not Listed For Sale

      115 Sand Dollar Ln, Sarasota, FL 34242

      • 3 Beds
      • 3.5 Baths
      • 3,320 Sq Ft
      • Built 1982
      115 Sand Dollar Ln, Sarasota, FL 34242

      Last Sold Summary

      • 324 Days On Market

      Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /3

    $1,250,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,195 Sq Ft

    5924 Midnight Pass Rd Unit 507, Sarasota, FL 34242

    An exceptional opportunity to secure a Gulf-front residence in the highly sought-after Sarasota Surf & Racquet Club on Siesta Key. Positioned on the 5th floor, this two-bedroom, two-bath condominium offers sweeping, unobstructed views of the Gulf of Mexico?the kind of breathtaking backdrop that defines true beachfront living.With 1,195 square feet of interior space plus an expansive

    Rudy Dudon MICHAEL SAUNDERS & COMPANY

    5924 Midnight Pass Rd Unit 507, Sarasota, FL 34242
  • /13

    $8,370 Per Month

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

    6020 Midnight Pass Rd Unit 3, Sarasota, FL 34242

    Enjoy a relaxing getaway in Villa 3 at Aloha Kai, a cozy beach villa beautifully decorated with casual coastal charm. The screened porch provides the perfect spot for morning coffee, unwinding with a good book, or entertaining guests in the evening with a meal or cocktail. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 3, Sarasota, FL 34242
  • /2

    $1,340,900

    Sold May 15, 2026

    19 Whispering Sands Dr Unit 302, Sarasota, FL 34242

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

    Last Sold Summary

    • 1% Below List Price
    • $916/SF
    • 26 Days On Market

    Current Estimated Value $1,280,547

    Last Listing Agent Frank Golio LEGACY BAY PARTNERS

    19 Whispering Sands Dr Unit 302, Sarasota, FL 34242
    • /2

      Est $3,077,428

      Not Listed For Sale

      850 Siesta Key Cir, Sarasota, FL 34242

      • 5 Beds
      • 5 Baths
      • 3,647 Sq Ft
      • Built 2005
      850 Siesta Key Cir, Sarasota, FL 34242

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Mark McCann, PA MICHAEL SAUNDERS & COMPANY

  • /35

    $625,000

    • 2 Beds
    • 1.5 Baths
    • 834 Sq Ft

    6020 Midnight Pass Rd Unit 49, Sarasota, FL 34242

    Turn-Key Furnished Villa in Aloha Kai – One of Siesta Key's Premier Beachfront Communities! Just steps from world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 1.5-bath villa offers the perfect combination of coastal living, rental potential, and investment opportunity. Whether you're searching for a vacation home, seasonal retreat, full-time residence, or income-producing

    Rex Glasson DOUGLAS ELLIMAN

    6020 Midnight Pass Rd Unit 49, Sarasota, FL 34242
  • /18

    $8,970 Per Month

    • 1 Bath
    • 435 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242

    Starting at $299/night! Explore a luxurious studio-style condominium at Casa Mar, featuring one bathroom and a queen-sized murphy bed. This elegant retreat boasts a fully equipped kitchen that flows into a spacious dining area, ideal for hosting guests. Benefit from the convenience of a private carport just a few steps away from your residence. Casa Mar offers an impressive range of amenities,

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242
  • /2

    $600,000

    Sold Jun 09, 2026

    113 Whispering Sands Dr Unit V47, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1968

    Last Sold Summary

    • 14% Below List Price
    • $446/SF
    • 87 Days On Market

    Current Estimated Value $602,928

    Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

    113 Whispering Sands Dr Unit V47, Sarasota, FL 34242
    • /64

      Est $1,411,587

      Not Listed For Sale

      5125 Oakmont Place, Sarasota, FL 34242

      • 4 Beds
      • 4.5 Baths
      • 3,206 Sq Ft
      • Built 1977
      5125 Oakmont Place, Sarasota, FL 34242

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /31

    $595,000

    $30K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 836 Sq Ft

    6154 Midnight Pass Rd Unit A-05, Sarasota, FL 34242

    PRICE IMPROVEMENT! Now the lowest priced 2 bed/2 bath on the Gulf side of Midnight Pass plus the added bonus of in-unit laundry, this Siesta Key condo offers unmatched value! Casa Blanca is a charming Gulf-side community with a mix of cozy villas and a three-story beachfront building overlooking the Siesta Key’s world famous Crescent Beach. This residence features 2 bedrooms and 1.5 beautifully

    Rudy Dudon MICHAEL SAUNDERS & COMPANY

    6154 Midnight Pass Rd Unit A-05, Sarasota, FL 34242
  • /13

    $8,700 Per Month

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

    6020 Midnight Pass Rd Unit 35, Sarasota, FL 34242

    Toes in the sand and sunshine on your shoulder—welcome home to the spacious one-bedroom Villa 35 at Aloha Kai. This beautifully updated villa features granite countertops in both the kitchen and bath, while the bedroom offers ample space and a large closet. The open-concept layout extends to a front porch enclosed with windows and blinds, providing additional living space and privacy. Located on

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 35, Sarasota, FL 34242
  • /2

    $1,350,000

    Sold Aug 07, 2026

    0 Ocean Blvd, Sarasota, FL 34242

    • Land
    • 25,264 Sq Ft
    • $2,327,586 per Acre

    Last Sold Summary

    • 47% Below List Price
    • 402 Days On Market

    Last Listing Agent Lisa Shepard BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

    0 Ocean Blvd, Sarasota, FL 34242
    • /36

      Est $1,214,228

      Not Listed For Sale

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

      • 3 Beds
      • 2 Baths
      • 1,835 Sq Ft
      • Built 1988
      1345 Siesta Bayside Dr Unit 1345F, Sarasota, FL 34242

      Last Sold Summary

      • 93 Days On Market

      Last Listing Agent Victoria Chartrand COLDWELL BANKER REALTY

  • /70

    $4,400,000

    $500K PRICE DROP
    • 9 Beds
    • 11 Baths
    • 4,437 Sq Ft

    5322 Calle de La Siesta, Sarasota, FL 34242

    5.9% Seller Financing and Nightly rentals, a unicorn. This 7-unit investment property is unique in that it operates more similar to hotel than a single family vacation rental. It has years of returning guests and it's one of very few elevated properties allowing the former mentioned, nightly rentals. 2-studios, 2-1 bedrooms, 2-2 bedrooms, and a penthouse suite with wrap around balcony. Your

    Jason Skowronski COMPASS FLORIDA LLC

    5322 Calle de La Siesta, Sarasota, FL 34242
  • /20

    $5,070 Per Month

    • 1 Bath
    • 435 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242

    Starting at $169/night. Discover the perfect beach getaway at our charming studio, ideally located on the beautiful Siesta Key. Just steps from the pristine white sands of Siesta Beach, this cozy, well-appointed retreat is perfect for couples or solo travelers seeking a relaxing escape. The studio features a comfortable queen-size bed, a cozy seating area, and a flat-screen TV for your

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242
  • /2

    $440,000

    Sold Jun 26, 2026

    6157 Midnight Pass Rd Unit B12, Sarasota, FL 34242

    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft
    • Built 1974

    Last Sold Summary

    • 27% Below List Price
    • $330/SF
    • 136 Days On Market

    Current Estimated Value $552,704

    Last Listing Agent Jessica Burdick LOYD ROBBINS & CO. LLC

    6157 Midnight Pass Rd Unit B12, Sarasota, FL 34242
    • /2

      Est $1,906,064

      Not Listed For Sale

      5598 Siesta Estates Ct, Sarasota, FL 34242

      • 6 Beds
      • 5.5 Baths
      • 3,924 Sq Ft
      • Built 2000
      5598 Siesta Estates Ct, Sarasota, FL 34242

      Last Sold Summary

      • 353 Days On Market

      Last Listing Agent Darren Duffy RE/MAX PALM REALTY

  • /88

    $499,000

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

    6157 Midnight Pass Rd Unit E12, Sarasota, FL 34242

    New Listing Photos now attached! Weekly rentals, prime Siesta Key location, and immediate income potential—this is the beach investment opportunity buyers wait for. Welcome to Bay Oaks, where island living meets exceptional rental flexibility in one of the most desirable communities on Siesta Key.This beautifully updated 2-bedroom, 2-bath condo is being offered fully turn-key furnished,

    Jason Wood CORCORAN DWELLINGS REALTY

    6157 Midnight Pass Rd Unit E12, Sarasota, FL 34242
  • /21

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 71, Sarasota, FL 34242

    Starting at $179/night! Welcome to your vibrant beachside retreat! This charming ground-level condo features a spacious bedroom with a king bed, a sleeper sofa in the living room, and a full bathroom—perfect for relaxation and adventure. Whip up delicious meals in the fully equipped kitchen and enjoy them in the cozy dining area nearby. Convenience is at your fingertips with your own private

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 71, Sarasota, FL 34242
  • /2

    $700,000

    Sold Dec 08, 2025

    4637 Ocean Blvd, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 2,065 Sq Ft
    • Built 1952

    Last Sold Summary

    • 20% Below List Price
    • $339/SF
    • 73 Days On Market

    Current Estimated Value $710,524

    Last Listing Agent Albert Wooster ALBERT WOOSTER & COMPANY

    4637 Ocean Blvd, Sarasota, FL 34242
    • /59

      Est $692,430

      Not Listed For Sale

      5860 Midnight Pass Rd Unit 19, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,241 Sq Ft
      • Built 1971
      5860 Midnight Pass Rd Unit 19, Sarasota, FL 34242

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Suki Scollo COLDWELL BANKER REALTY

  • /48

    $589,000

    $50K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 532 Sq Ft

    22 Sandy Cove Rd Unit 203, Sarasota, FL 34242

    A MUST SEE with a $40,000 PRICE REDUCTION! The market is starting to normalize, Strike Now! Come see this 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

    Beth Dilley ASCENDIA REAL ESTATE

    22 Sandy Cove Rd Unit 203, Sarasota, FL 34242
  • /26

    $9,225 Per Month

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

    1125 W Peppertree Dr Unit 402, Sarasota, FL 34242

    Stylish 2-Bedroom, 2-Bathroom Condo in Peppertree Bay - Siesta Key, FLLooking for the perfect vacation getaway? This stunning 2-bedroom, 2-bathroom condo in the desirable Peppertree Bay community is just what you need! Nestled on the fourth floor, this high-rise retreat offers tranquil pond views and a serene atmosphere.The unit features assigned covered parking under the building for

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 402, Sarasota, FL 34242
  • /2

    $933,000

    Sold Jun 01, 2026

    5353 Shadow Lawn Dr, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • Built 1960

    Last Sold Summary

    • $585/SF
    • 1 Day On Market

    Current Estimated Value $918,057

    Last Listing Agent Brittany McCord IRONGATE REALTY INC

    5353 Shadow Lawn Dr, Sarasota, FL 34242
    • /2

      Est $2,056,221

      Not Listed For Sale

      5531 Contento Dr, Sarasota, FL 34242

      • 5 Beds
      • 4 Baths
      • 3,653 Sq Ft
      • Built 1966
      5531 Contento Dr, Sarasota, FL 34242

      Last Sold Summary

      • 212 Days On Market

      Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

Showing Results 521 - 560, Page 14 of 18

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