9,352

Siesta Key, FL Homes

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  • /54

    $745,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    5855 Midnight Pass Rd Unit 420, Sarasota, FL 34242

    Location, location & views! Enjoy and experience luxury living at the Harbor Towers located just steps away from the world-famous Siesta Key beach. Highly desirable 4th floor unit, 2BR/2BTH with spectacular Gulf of America views from every room. Fully updated unit with new windows, new pipes, quartz countertops, new kitchen cabinets doors, new bathrooms and luxury vinyl flooring throughout. This

    Mihaela Dragan FINE PROPERTIES

    5855 Midnight Pass Rd Unit 420, Sarasota, FL 34242
  • /52

    $5,525 Per Month

    • 3 Beds
    • 2 Baths
    • 1,822 Sq Ft
    • House for Rent

    726 Birdsong Ln, Sarasota, FL 34242

    AVAILABLE after June 1, 2026! Enjoy your own slice of paradise on World Famous Siesta Key! This beautifully renovated turnkey 3-bedroom, 2-bath heated pool home is just a short distance from the #1-rated beaches and the charming shops and restaurants of Siesta Key Village. Whether you're here for million-dollar sunsets, endless watersports, the famous Sunday Drum Circle, or simply peaceful days

    Scott Nold TNG REAL ESTATE

    726 Birdsong Ln, 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 $1,322,798

    Last Listing Agent Frank Golio LEGACY BAY PARTNERS

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

      Est $1,171,426

      Not Listed For Sale

      615 Avenida Del Norte, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1962
      615 Avenida Del Norte, Sarasota, FL 34242

      Last Sold Summary

      • 90 Days On Market

  • /62

    $1,600,000

    $950K PRICE DROP Pending
    • Land
    • 25,264 Sq Ft
    • $2,758,621 per Acre

    0 Ocean Blvd, Sarasota, FL 34242

    Under contract-accepting backup offers. Future Land Use: Residential. Now positioned at market for immediate sale - build your dream home on this waterfront estate homesite. PRICED TO SELL! Recently reduced by $550,000, this 0.58-acre Siesta Key homesite with canal frontage now represents one of the most compelling values on the market! Cleared - .58 acre homesite. Rare Canal-Front Opportunity on

    Lisa Shepard BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

    0 Ocean Blvd, Sarasota, FL 34242
  • /11

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242

    Villa 38 at Aloha Kai offers a spacious living area that opens onto an enclosed porch—perfect for enjoying your morning coffee. Its unique design features beamed ceilings and eclectic furnishings, creating a charming beach bungalow atmosphere. The fully equipped kitchen has everything you need to prepare meals to enjoy on the patio, and a convenient walk-in shower adds to your comfort. Located on

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 38, 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 $625,314

    Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

    113 Whispering Sands Dr Unit V47, Sarasota, FL 34242
    • /47

      Est $1,812,248

      Not Listed For Sale

      615 Calle Del Otono, Sarasota, FL 34242

      • 3 Beds
      • 3.5 Baths
      • 2,616 Sq Ft
      • Built 2022
      615 Calle Del Otono, Sarasota, FL 34242

      Last Sold Summary

      • 69 Days On Market

  • /46

    $3,195,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,803 Sq Ft

    527 Beach Rd, Sarasota, FL 34242

    Discover an exceptional income-generating property in the heart of coveted Siesta Key right on Beach Road! This fully renovated raised multi-unit compound features a spacious 2-bedroom, 2-bathroom unit and a 2-bedroom, 1-bathrooom unit (side by side). An impressive gross income in 2023 and n 2024 (despite hurricane-related downtime), this turnkey investment provides immediate cash flow. Note:

    Steven Koleno BEYCOME OF FLORIDA LLC

    527 Beach Rd, Sarasota, FL 34242
  • /28

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

    Starting at $179/night! Step into luxury and comfort at our newly renovated 2-bedroom, 1.5-bathroom condo, perfectly designed for your next getaway. This vibrant space features a fully equipped kitchen ready for your culinary adventures and a private carport just steps from the unit for hassle-free parking. Recently updated in Summer 2023, the condo comfortably accommodates up to six guests with

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
  • /2

    $1,259,000

    Sold Jul 16, 2025

    20 Whispering Sands Dr Unit 406, Sarasota, FL 34242

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

    Last Sold Summary

    • 10% Below List Price
    • $982/SF
    • 61 Days On Market

    Current Estimated Value $1,215,172

    Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

    20 Whispering Sands Dr Unit 406, Sarasota, FL 34242
    • /68

      Est $2,876,082

      Not Listed For Sale

      5132 Sandy Shore Ave, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,950 Sq Ft
      • Built 2016
      5132 Sandy Shore Ave, Sarasota, FL 34242

      Last Sold Summary

      • 65 Days On Market

  • /71

    $500,000

    $99K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft

    6157 Midnight Pass Rd Unit B12, Sarasota, FL 34242

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Waterfront Siesta Key condo with breathtaking Sarasota Bay intracoastal views and weekly rentals allowed. This rare 2BR/2.5BA Bay Oaks residence is a remarkable opportunity for a buyer with vision to transform a diamond in the rough into a spectacular waterfront getaway, full-time residence, or investment

    Jessica Burdick LOYD ROBBINS & CO. LLC

    6157 Midnight Pass Rd Unit B12, Sarasota, FL 34242
  • /10

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242

    This is a fun tropically decorated beach villa that will put a smile on your face when you walk in!! This unit can easily occupy up to 6. We have recently remodeled the kitchen and both bathrooms. The master bedroom features a king size bed with a new pillow top mattress. The master bath is new with a roman walk in shower. There is an LCD TV, DVD player and a nice closet. The second bedroom has a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 13, 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 $724,074

    Last Listing Agent Albert Wooster ALBERT WOOSTER & COMPANY

    4637 Ocean Blvd, Sarasota, FL 34242
    • /50

      Est $487,217

      Not Listed For Sale

      5667 Midnight Pass Rd Unit 304, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,012 Sq Ft
      • Built 1975
      5667 Midnight Pass Rd Unit 304, Sarasota, FL 34242

      Last Sold Summary

      • 88 Days On Market

  • /69

    $3,675,000

    $100K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,788 Sq Ft

    3939 Higel Ave, Sarasota, FL 34242

    Now Offered At a Refined Price — Modern Siesta Key Living. Set on the north end of Siesta Key, this striking modernist residence offers the rare balance of island serenity and seamless access to the mainland, placing vibrant downtown Sarasota, Southside Village, and the area’s cultural and dining destinations just minutes away—while the azure waters of the Gulf of Mexico and Siesta Key’s

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    3939 Higel Ave, Sarasota, FL 34242
  • /39

    $3,995 Per Month

    • 2 Beds
    • 1.5 Baths
    • 981 Sq Ft
    • Townhouse for Rent

    Unlisted Address

    Welcome to this Siesta Key Florida fully furnished town house for rent, located on the barrier island of Siesta Key Florida #1 beach in USA, made famous for its pure quartz sugar sand. A truly tropical beach front community Sandy Cove in Siesta Key with private fishing pier, small private beach and beautiful ocean view, and only one block from Siesta Key Village. A rarely available 2 bedroom two

    Matthew fehniger JJF REALTY INC

    Unlisted Address
  • /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 $914,710

    Last Listing Agent Brittany McCord IRONGATE REALTY INC

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

      Est $1,188,051

      Not Listed For Sale

      1260 Dolphin Bay Way Unit 402, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,915 Sq Ft
      • Built 1997
      1260 Dolphin Bay Way Unit 402, Sarasota, FL 34242

      Last Sold Summary

      • 14 Days On Market

  • /43

    $515,000

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

    5619 Midnight Pass Rd Unit 503, Sarasota, FL 34242

    Welcome to White Sands. Whether you're searching for a profitable investment opportunity or your own private island retreat, this property offers the best of both worlds. Ideally located directly across from world-famous Siesta Key Beach where you will conveniently find pickleball, tennis, volleyball and a playground. This turn-key, pet-friendly furnished completely remodeled 2/2 condominium

    Kadie Nolan PREFERRED SHORE LLC

    5619 Midnight Pass Rd Unit 503, Sarasota, FL 34242
  • /27

    $5,700 Per Month

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

    1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242

    Steps from beautiful Crescent Beach, this fully renovated 2 bedroom 2 full bathroom unit is located in Gulf-side High-rise on the 8th floor. Step into the extended living lanai area to experience wrap around views of the gulf. Enjoy a window bench, choice of comfy loveseats, or dine with a view of the blue waters and white sand.An updated kitchen with stainless steel appliances peeks through

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 802AA, 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 $643,220

    Last Listing Agent Linda Stowe MICHAEL SAUNDERS & COMPANY

    6150 Midnight Pass Rd Unit 26, Sarasota, FL 34242
    • /2

      Est $755,590

      Not Listed For Sale

      5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 925 Sq Ft
      • Built 1971
      5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242

      Last Sold Summary

      • 72 Days On Market

  • /15

    $970,000

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft

    1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

    Experience coastal living and investment potential in this beautifully appointed 3-bedroom, 2-bathroom townhome, ideally located in the highly sought-after Gulf and Bay Club Bayside community on Siesta Key. Just minutes from the world-renowned beaches and Siesta Key Village, this property offers the perfect blend of relaxation and convenience to shopping, dining and entertainment. This turn-key

    Amy Nadell COLDWELL BANKER REALTY

    1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
  • /15

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,071 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242

    Welcome to the newly renovated A04 Villa! Private entrance leads to the screened in lanai and open air space which includes the kitchen, dining area and comfortable seating to enjoy the large flat screen tv. The villa sleeps up to 6. 2 queen beds in the primary bedroom and 2 twin beds in the guest bedroom. Both bedrooms are also equipped with flat screen TVs. This large villa features 2

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242
  • /2

    $1,700,000

    Sold Aug 21, 2025

    1031 Contento St, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,853 Sq Ft
    • Built 1971

    Last Sold Summary

    • 3% Below List Price
    • $917/SF
    • 24 Days On Market

    Current Estimated Value $1,701,032

    Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1031 Contento St, Sarasota, FL 34242
    • /2

      Est $1,009,840

      Not Listed For Sale

      4439 Ocean Blvd, Sarasota, FL 34242

      • 1 Bed
      • 1 Bath
      • 3,042 Sq Ft
      • Built 1951
      4439 Ocean Blvd, Sarasota, FL 34242

      Last Sold Summary

      • 67 Days On Market

  • /44

    $581,000

    $18K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 753 Sq Ft

    915 Beach Rd Unit 318, Sarasota, FL 34242

    BEACH VIEWS, RENTAL FLEXIBILITY, AND THE ULTIMATE SIESTA KEY LIFESTYLE! Welcome to La Siesta Condominiums, where the sugar-white sands of Siesta Key Beach are quite literally across the street and every day feels like a vacation. Perched on the third floor, this beautifully furnished and move-in ready 2-bedroom, 1-bath condo enjoys sweeping views of the Gulf, beach, and resort-style community

    Laura Millslagle PREFERRED SHORE LLC

    915 Beach Rd Unit 318, Sarasota, FL 34242
  • /19

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,264 Sq Ft
    • House for Rent

    143 Whispering Sands Dr, Sarasota, FL 34242

    Available for season 2027! This 2 bedroom 2 bath villa with easy ground floor entry features tile flooring in the main living areas and plush new carpeting in the bedrooms. The stylish galley kitchen has been fully updated with custom white cabinetry, granite countertops and backsplash, recessed lighting, and brand-new GE appliances, perfect for preparing meals after a day at the beach.Enjoy

    Maureen Plichta STRINGER MANAGEMENT INC

    143 Whispering Sands Dr, 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 $662,716

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

    1131 Lake House Cir Unit C114, Sarasota, FL 34242
    • /76

      Est $2,884,827

      Not Listed For Sale

      238 Island Cir, Sarasota, FL 34242

      • 4 Beds
      • 4 Baths
      • 2,854 Sq Ft
      • Built 1965
      238 Island Cir, Sarasota, FL 34242

      Last Sold Summary

      • 22 Days On Market

  • /37

    $7,950,000

    New Construction $2M PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 6,206 Sq Ft

    84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Experience luxury living at its finest in this breathtaking one-of-a-kind new construction condominium nestled directly on the pristine shores of world famous Siesta Beach. Spanning over 6200 square feet, this exclusive residence offers unparalleled opulence and panoramic views of the azure waters and fiery sunsets. Elegance meets convenience with a

    Thomas Cail RE/MAX ALLIANCE GROUP

    84 Avenida Veneccia Unit 202 & 203, Sarasota, FL 34242
  • /25

    $8,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    1125 W Peppertree Dr Unit 707, Sarasota, FL 34242

    2 BR - 2 BA - 4 Person Max - Gulf side - Mid-Rise - Approx.150 yards from beach This property is a 30 night minimum.This 2-bedroom, 2 bath located on the gulf side is approx. 150 yards from the beach. This unit is on the 7th floor, accessible via elevator or stairs. Plenty of room for dining at the 6-service dining table. Couches, a ceiling fan, and TV in the living room for

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 707, 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 $905,133

    Last Listing Agent Carol Thomas MICHAEL SAUNDERS & COMPANY

    5780 Midnight Pass Rd Unit 710, Sarasota, FL 34242
    • /77

      Est $1,455,445

      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

  • /94

    $1,349,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 2,691 Sq Ft

    3942 Hamilton Club Cir Unit 13, Sarasota, FL 34242

    Siesta Key, exclusive gated community of only 18 homes with Marina, pool and tennis all within a private, lush, tropical paradise . Walking paths around the lagoon as well as the beautiful Marina make Hamilton Club a truly unique lifestyle. Inspired by the architcture of Bermuda with its close ties to 17th Century Great Britian is recognised by its striking pastel colored walls and "welcoming

    Barbara Dumbaugh MICHAEL SAUNDERS & COMPANY

    3942 Hamilton Club Cir Unit 13, Sarasota, FL 34242
  • /9

    $10,770 Per Month

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

    6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242

    We welcome you to stay in our updated oceanfront condo on Siesta Key Crescent Beach - the best beach in Florida! Our spacious 2 bed/2 bath oceanfront home is 1080 square feet with an ocean view that cannot be beat! Unit #206 is part of the Casa Blanca Vacation Beach Resort, and the crystal white sand is steps away! Remodeled in 2023, fully equipped kitchen with quiet dishwasher, spacious living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 206, 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 $1,557,077

    Last Listing Agent Estela Ziu COMPASS FLORIDA, LLC

    557 Venice Ln, Sarasota, FL 34242
    • /2

      Est $1,172,650

      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

Showing Results 521 - 560, Page 14 of 18

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