9,260

Siesta Key, FL Homes

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  • /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
  • /24

    $7,600 Per Month

    • 2 Beds
    • 1 Bath
    • 959 Sq Ft
    • Condo for Rent

    1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242

    Gulf and Bay Club Bayside is one of the most attractive condominium units on Siesta Key. This beautifully remodeled unit offers luxury accommodations at a reasonable cost. Offering a beautiful lake view and steps to the resort-style pool. You will enjoy your stay every minute.Enjoy all of the luxurious amenities this unit has to offer, from comfortable King size bed to the comfy

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
  • /2

    $625,000

    Sold Feb 20, 2026

    6150 Midnight Pass Rd Unit 26, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,101 Sq Ft
    • Built 1967

    Last Sold Summary

    • 11% Below List Price
    • $568/SF
    • 54 Days On Market

    Current Estimated Value $632,610

    Last Listing Agent Linda Stowe MICHAEL SAUNDERS & COMPANY

    6150 Midnight Pass Rd Unit 26, Sarasota, FL 34242
    • /7

      Est $1,191,831

      Not Listed For Sale

      4929 Peaceable Way, Sarasota, FL 34242

      • 4 Beds
      • 2 Baths
      • 1,989 Sq Ft
      • Built 1974
      4929 Peaceable Way, Sarasota, FL 34242

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kristine Niehaus COLDWELL BANKER REALTY

  • /86

    $1,200,000

    $250K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,334 Sq Ft

    5920 Midnight Pass Rd Unit 406, Sarasota, FL 34242

    Under contract-accepting backup offers. PRICE DROP!! NOW A BEST BUY! TOWER RESIDENCE IN SARASOTA SURF AND RACQUET CLUB is a best buy for HUGE RENTAL INCOME and Siesta favorite for family vacations!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

    Greg Hudson COLDWELL BANKER REALTY

    5920 Midnight Pass Rd Unit 406, Sarasota, FL 34242
  • /21

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,122 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 20, Sarasota, FL 34242

    Lush tropical landscaping surrounds the screened-in porch of Villa 10 at Aloha Kai, offering endless hours of relaxation in a serene setting. This one-bedroom, one-bath villa also features a private patio for your enjoyment. The kitchen is bright, well-appointed, and equipped with everything you need for cooking and dining. The spacious bedroom provides ample closet space for your comfort. Known

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 20, Sarasota, FL 34242
  • /2

    $660,000

    Sold Feb 26, 2026

    1131 Lake House Cir Unit C114, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Built 1981

    Last Sold Summary

    • $488/SF

    Current Estimated Value $659,824

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

    1131 Lake House Cir Unit C114, Sarasota, FL 34242
    • /2

      Est $792,806

      Not Listed For Sale

      5211 Avenida de Cortez, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,272 Sq Ft
      • Built 1960
      5211 Avenida de Cortez, Sarasota, FL 34242

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Esti Baughen COLDWELL BANKER REALTY

  • /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
  • /15

    $6,900 Per Month

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

    6154 Midnight Pass Rd Unit B07, Sarasota, FL 34242

    Welcome to Villa B07! This unit has been completely renovated with all new flooring, walls, windows, doors, kitchen cabinets, granite countertop, state-of-the-art stainless-steel appliances, a new full bath with walk-in shower and new vanity, new half bath with new vanity, and a new hot/cold shower on the outside of the villa. The two bedrooms sleep 4 comfortably but there is a queen-sized

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit B07, Sarasota, FL 34242
  • /2

    $875,000

    Sold Sep 25, 2025

    5780 Midnight Pass Rd Unit 710, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Built 1979

    Last Sold Summary

    • 20% Below List Price
    • $643/SF
    • 493 Days On Market

    Current Estimated Value $905,010

    Last Listing Agent Carol Thomas MICHAEL SAUNDERS & COMPANY

    5780 Midnight Pass Rd Unit 710, Sarasota, FL 34242
    • /69

      Est $1,400,628

      Not Listed For Sale

      5310 Hidden Harbor Rd, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 2,295 Sq Ft
      • Built 1977
      5310 Hidden Harbor Rd, Sarasota, FL 34242

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Julie Larson WHITE SANDS REALTY GROUP FL

  • /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
  • /30

    $8,970 Per Month

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

    6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242

    Villa 1 at Aloha Kai is ideally situated on Siesta Key, a popular barrier island along Florida’s West Coast. Nestled within the family-friendly, gated resort community of Aloha Kai, it lies in the heart of Crescent Beach—ranked the number one beach in the continental United States. Renowned for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 1, Sarasota, FL 34242
  • /2

    $1,550,000

    Sold Mar 16, 2026

    557 Venice Ln, Sarasota, FL 34242

    • 5 Beds
    • 4 Baths
    • 3,213 Sq Ft
    • Built 1979

    Last Sold Summary

    • 13% Below List Price
    • $482/SF
    • 15 Days On Market

    Current Estimated Value $1,556,544

    Last Listing Agent Estela Ziu COMPASS FLORIDA, LLC

    557 Venice Ln, Sarasota, FL 34242
    • /45

      Est $1,560,605

      Not Listed For Sale

      395 Avenida Milano, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,143 Sq Ft
      • Built 1962
      395 Avenida Milano, Sarasota, FL 34242

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Jonathan Abrams MICHAEL SAUNDERS & COMPANY

  • /38

    $1,795,000

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

    6300 Midnight Pass Rd Unit 809, Sarasota, FL 34242

    From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renowned white-sand shoreline. Completely renovated in 2022, this two-bedroom beachfront retreat pairs sophisticated coastal interiors with an expansive screened Gulf-front terrace, storm-rated windows and sliding glass doors, and an

    Roger Pettingell COLDWELL BANKER REALTY

    6300 Midnight Pass Rd Unit 809, Sarasota, FL 34242
  • /31

    $9,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft
    • Condo for Rent

    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242

    Relax in this spacious two bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private, walking beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key*Taxes and fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
  • /2

    $425,000

    Sold Mar 13, 2026

    6006 Midnight Pass Rd Unit 4, Sarasota, FL 34242

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Built 1960

    Last Sold Summary

    • 6% Below List Price
    • $708/SF
    • 5 Days On Market

    Current Estimated Value $421,512

    Last Listing Agent Dawn Lacey LACEY REALTY INC

    6006 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    • /2

      Est $485,324

      Not Listed For Sale

      5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,012 Sq Ft
      • Built 1975
      5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Linda Williams GULF SHORES REALTY ERA POWERED

  • /68

    $580,000

    $15K PRICE DROP
    • 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

    Dion Souza SARABAY REAL ESTATE INC

    5600 Beach Way Dr Unit 210, Sarasota, FL 34242
  • /52

    $5,000 Per Month

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

    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

    Beachfront Bliss at Casa Mar – Siesta Key Dreaming of a Siesta Key getaway? Welcome to Unit 15 at Casa Mar, a charming 1BR/1BA beachfront condo that offers the perfect mix of relaxation and resort-style fun. Step outside and enjoy exclusive access to Casa Mar’s private stretch of quartz-whit e sand, complete with lounge chairs for sunbathing and unforgettable Gulf views. Cool off with a swim in

    Robert Bevington SHOWTIME REALTY

    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
  • /2

    $500,000

    Sold Nov 21, 2025

    4189 Roberts Point Cir, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,757 Sq Ft
    • Built 1930

    Last Sold Summary

    • 38% Below List Price
    • $285/SF
    • 315 Days On Market

    Current Estimated Value $603,257

    Last Listing Agent Shane Lewis MICHAEL SAUNDERS & COMPANY

    4189 Roberts Point Cir, Sarasota, FL 34242
    • /72

      Est $1,690,324

      Not Listed For Sale

      4926 Commonwealth Dr, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,968 Sq Ft
      • Built 1987
      4926 Commonwealth Dr, Sarasota, FL 34242

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Karen Nasello EXP REALTY LLC

  • /86

    $650,137

    • 2 Beds
    • 2 Baths
    • 1,387 Sq Ft

    6267 Midnight Pass Rd Unit 306, Sarasota, FL 34242

    Experience the ultimate island lifestyle in this beautifully appointed 2-bedroom, 2-bathroom condo on world-famous Siesta Key.Located just steps away from the powdery white quartz sands of Siesta Beach, this property grants you your own private deeded beach access where loungers are waiting for you. With the vibrant dining and shopping of the Village, this location cannot be beat.You can

    Trish Wittmus BERKSHIRE HATHAWAY HOMESERVICE

    6267 Midnight Pass Rd Unit 306, Sarasota, FL 34242
  • /14

    $8,370 Per Month

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

    6020 Midnight Pass Rd Unit 54, Sarasota, FL 34242

    Villa 54 at Aloha Kai is your ideal beach retreat, spacious, sun-filled, and designed for total relaxation. This corner villa features an open floor plan with abundant natural light, custom cabinetry, and thoughtful upgrades throughout. The updated kitchen includes stainless steel appliances and is fully equipped to make meal prep easy, while the in-unit washer and dryer add everyday convenience

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 54, Sarasota, FL 34242
  • /2

    $712,000

    Sold Nov 21, 2025

    5600 Beach Way Dr Unit 304, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 1970

    Last Sold Summary

    • 6% Below List Price
    • $602/SF
    • 72 Days On Market

    Current Estimated Value $703,585

    Last Listing Agent Janell Stuckwisch EXP REALTY LLC

    5600 Beach Way Dr Unit 304, Sarasota, FL 34242
    • /2

      Est $2,124,601

      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

      Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  • /52

    $1,559,000

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

    5400 Ocean Blvd Unit 17-04, Sarasota, FL 34242

    The iconic Terrace building is a masterpiece designed by renowned architect Frank Folsom Smith. This modernist building, built of poured concrete exudes strength and durability. Situated directly on Siesta Key Beach, and built with walls of sliding glass doors in every room to take advantage of the diverse, magnificent views in all directions. This is the penthouse being offered turnkey

    Carol Thomas MICHAEL SAUNDERS & COMPANY

    5400 Ocean Blvd Unit 17-04, Sarasota, FL 34242
  • /26

    $9,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242

    Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom vacation rental condo. The condo offers a relaxing lake, pool and tennis court view from the lanai. A few of your amenities include your own private garage, a washer and dryer IN THE CONDO, and a fully-equipped kitchen The community offers BBQ grills (6), two tennis courts,

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
  • /2

    $3,600,000

    Sold Mar 10, 2026

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

    • 3 Beds
    • 3 Baths
    • 2,374 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $1,516/SF
    • 92 Days On Market

    Current Estimated Value $3,488,950

    Last Listing Agent Carol Thomas MICHAEL SAUNDERS & COMPANY

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

      Est $743,757

      Not Listed For Sale

      1200 E Peppertree Ln Unit 407, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,460 Sq Ft
      • Built 1973
      1200 E Peppertree Ln Unit 407, Sarasota, FL 34242

      Last Sold Summary

      • 179 Days On Market

      Last Listing Agent Eliza Miller PEPPERTREE BAY REALTY INC

  • /31

    $529,000

    $100K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 940 Sq Ft

    925 Beach Rd Unit 107, Sarasota, FL 34242

    Under contract-accepting backup offers. Offered at $529,000, this 2-bedroom, 2-bath residence represents one of the most competitively priced opportunities to own directly across the street from Siesta Key Beach. Enjoy effortless access to the sugar-white sand and turquoise waters with an easy five-minute walk—no driving, no searching for parking, just the relaxed coastal lifestyle that makes

    Lisa Garcia COLDWELL BANKER REALTY

    925 Beach Rd Unit 107, Sarasota, FL 34242
  • /21

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 10, Sarasota, FL 34242

    Lush tropical landscaping surrounds the screened-in porch of Villa 10 at Aloha Kai, offering endless hours of relaxation in a serene setting. This one-bedroom, one-bath villa also features a private patio for your enjoyment. The kitchen is bright, well-appointed, and equipped with everything you need for cooking and dining. The spacious bedroom provides ample closet space for your comfort. Known

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 10, Sarasota, FL 34242
  • /2

    $2,200,000

    Sold Feb 27, 2026

    222 Beach Rd Unit 7, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 2,952 Sq Ft
    • Built 1980

    Last Sold Summary

    • 33% Below List Price
    • $745/SF
    • 224 Days On Market

    Current Estimated Value $2,289,901

    Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

    222 Beach Rd Unit 7, Sarasota, FL 34242
    • /2

      Est $1,234,856

      Not Listed For Sale

      3911 Roberts Point Rd, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,731 Sq Ft
      • Built 2015
      3911 Roberts Point Rd, Sarasota, FL 34242

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Barbara May MICHAEL SAUNDERS & COMPANY

  • /48

    $399,900

    $15K PRICE DROP
    • 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
  • /31

    $7,500 Per Month

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

    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242

    Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The condo is in a Gulf-side High-rise building on the 5th floor. Assigned covered parking located in the parking garage under the building.A luxurious dining area greets you as you enter, that flows through to the living room and out to the lanai. The lanai works as an extended living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
  • /2

    $650,000

    Sold Oct 03, 2025

    5964 Midnight Pass Rd Unit N-16 (AKA # 135), Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,268 Sq Ft
    • Built 1975

    Last Sold Summary

    • 8% Above List Price
    • $513/SF
    • 10 Days On Market

    Current Estimated Value $656,765

    Last Listing Agent Marcia Van Ginhoven REDFIN CORPORATION

    5964 Midnight Pass Rd Unit N-16 (AKA # 135), Sarasota, FL 34242
    • /46

      Est $758,640

      Not Listed For Sale

      6300 Midnight Pass Rd Unit 4, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,253 Sq Ft
      • Built 1969
      6300 Midnight Pass Rd Unit 4, Sarasota, FL 34242

      Last Sold Summary

      • 261 Days On Market

      Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

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