9,352

Siesta Key, FL Homes

Section Image
  • /76

    $1,299,900

    • 2 Beds
    • 2 Baths
    • 1,915 Sq Ft

    1260 Dolphin Bay Way Unit 403, Sarasota, FL 34242

    Experience coastal luxury in this beautifully updated 2BR/2BA condo in the gated, waterfront community of Dolphin Bay on Siesta Key. This exceptional 4th floor residence blends modern sophistication with breathtaking Intracoastal Waterway views, creating a serene yet elevated island lifestyle. A charming front porch welcomes you—perfect for relaxing with a favorite beverage while grilling and

    Stacey Andrews ANDREWS & ASSOCIATES REALTY

    1260 Dolphin Bay Way Unit 403, 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

    $2,050,000

    Sold May 04, 2026

    513 Venice Ln, Sarasota, FL 34242

    • 5 Beds
    • 3.5 Baths
    • 3,009 Sq Ft
    • Built 1993

    Last Sold Summary

    • 10% Below List Price
    • $681/SF
    • 118 Days On Market

    Current Estimated Value $2,099,750

    Last Listing Agent Curtis Ware KW COASTAL LIVING III

    513 Venice Ln, Sarasota, FL 34242
    • /2

      Est $661,609

      Not Listed For Sale

      1137 Lake House Cir Unit C215, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 1981
      1137 Lake House Cir Unit C215, Sarasota, FL 34242

      Last Sold Summary

      • 37 Days On Market

  • /44

    $1,150,000

    $450K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,165 Sq Ft

    4114 Roberts Point Cir, Sarasota, FL 34242

    Virtually Staged. Seller is motivated! Discover the chance to own a meticulously maintained 4-bedroom, 3-bathroom home in Roberts Point—one of North Siesta Key’s most sought-after neighborhoods. This versatile two-story property is ready for you to move in, renovate, or rebuild into your dream retreat. Designed with entertaining in mind, the home offers multiple outdoor decks and living spaces,

    Kelley Callaway MICHAEL SAUNDERS & COMPANY

    4114 Roberts Point Cir, 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

    $875,000

    Sold Jan 15, 2026

    757 Beach Rd Unit 300, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,181 Sq Ft
    • Built 1970

    Last Sold Summary

    • $741/SF

    Current Estimated Value $869,391

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

    757 Beach Rd Unit 300, Sarasota, FL 34242
    • /2

      Est $458,065

      Not Listed For Sale

      5855 Midnight Pass Rd Unit 201, Sarasota, FL 34242

      • 1 Bed
      • 1 Bath
      • 751 Sq Ft
      • Built 1976
      5855 Midnight Pass Rd Unit 201, Sarasota, FL 34242

      Last Sold Summary

      • 22 Days On Market

  • /49

    $1,000,000

    $500K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,996 Sq Ft

    1374 Moonmist Dr Unit B1, Sarasota, FL 34242

    A $500K price reduction - don't wait! A rarely available bayfront opportunity to create your dream retreat on Siesta Key. Experience the allure of waterfront living in this detached bayfront villa, poised for a fresh vision in the desirable Polynesian Gardens community on Siesta Key. One of only 11 exclusive bayfront residences, this end-unit villa offers sweeping, unobstructed views of the

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1374 Moonmist Dr Unit B1, Sarasota, FL 34242
  • /11

    $7,470 Per Month

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

    6154 Midnight Pass Rd Unit B03, 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 B03, Sarasota, FL 34242
  • /2

    $1,125,000

    Sold Feb 19, 2026

    5916 Midnight Pass Rd Unit 102, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,173 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $959/SF
    • 6 Days On Market

    Current Estimated Value $1,126,374

    Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

    5916 Midnight Pass Rd Unit 102, Sarasota, FL 34242
    • /34

      Est $1,122,724

      Not Listed For Sale

      5579 Cape Aqua Dr, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,557 Sq Ft
      • Built 1973
      5579 Cape Aqua Dr, Sarasota, FL 34242

      Last Sold Summary

      • 8 Days On Market

  • /48

    $570,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 753 Sq Ft

    915 Beach Rd Unit 215, Sarasota, FL 34242

    This turnkey condo sits right across the street from one of the #1 beaches in America! The 2 bedroom 1 bathroom condo with open floor plan overlooking the pool and courtyard, is perfect for your new home or investment opportunity near the beach. The recent updates include, new carpet, light fixtures, furniture, lanai furniture and decor. New HVAC installed 11/2025! La Siesta has on site

    Amber Moss RE/MAX Realty Team

    915 Beach Rd Unit 215, Sarasota, FL 34242
  • /34

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Condo for Rent

    420 Beach Rd Unit 502, Sarasota, FL 34242

    Turnkey furnished beachfront retreat on Siesta Key, one-month minimum rental. Greet each morning to the sound of the Gulf and close every evening beneath a glowing horizon and dazzling sunset from this gulf-front residence at Siesta Gulf View. Two bedrooms and two baths, this home opens onto a 31-foot screened and glass-enclosed lanai that runs the full width of the unit, framing an uninterrupted

    Joanna Benante MICHAEL SAUNDERS & COMPANY

    420 Beach Rd Unit 502, Sarasota, FL 34242
  • /2

    $450,000

    Sold Dec 19, 2025

    1350 N Portofino Dr Unit 208, Sarasota, FL 34242

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

    Last Sold Summary

    • 18% Below List Price
    • $484/SF
    • 188 Days On Market

    Current Estimated Value $453,274

    Last Listing Agent Maurice Menager MICHAEL SAUNDERS & COMPANY

    1350 N Portofino Dr Unit 208, Sarasota, FL 34242
    • /55

      Est $861,922

      Not Listed For Sale

      777 Beach Rd Unit 5A, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,166 Sq Ft
      • Built 1970
      777 Beach Rd Unit 5A, Sarasota, FL 34242

      Last Sold Summary

      • 42 Days On Market

  • /54

    $3,100,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft

    276 Island Cir, Sarasota, FL 34242

    Certificate of Occupancy received 5/27/2026 *Call today to schedule your private showing! Welcome to 276 Island Circle, an exceptional waterfront retreat nestled on an oversized lot in the highly sought-after Palm Island neighborhood of Siesta Key. Perfectly positioned along the Grand Canal and just a half-mile from the world-famous shores of Siesta Key Beach, this beautifully designed 4-bedroom,

    Michael Cella CELLA'S REAL ESTATE INC

    276 Island Cir, Sarasota, FL 34242
  • /84

    $9,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • House for Rent

    327 Avenida Milano, Sarasota, FL 34242

    Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

    Chrissie Cummings JENNETTE PROPERTIES INC

    327 Avenida Milano, Sarasota, FL 34242
  • /2

    $3,600,000

    Sold May 12, 2026

    329 Beach Rd Unit B, Sarasota, FL 34242

    • 5 Beds
    • 7 Baths
    • 4,563 Sq Ft
    • Built 2020

    Last Sold Summary

    • 9% Below List Price
    • $789/SF
    • 58 Days On Market

    Current Estimated Value $3,867,979

    Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

    329 Beach Rd Unit B, Sarasota, FL 34242
    • /2

      Est $684,754

      Not Listed For Sale

      1113 Lake House Cir Unit C110, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 1981
      1113 Lake House Cir Unit C110, Sarasota, FL 34242

      Last Sold Summary

      • 23 Days On Market

  • /45

    $620,000

    Open Fri 11AM - 1PM $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 836 Sq Ft

    6154 Midnight Pass Rd Unit 7, Sarasota, FL 34242

    Positioned along the powdery white sands of Siesta Key’s renowned Crescent Beach, this villa residence within Casa Blanca Beach Resort presents an exceptional opportunity to own in one of Sarasota’s most iconic Gulf-front communities. Casa Blanca is a unique collection of individually owned villas and apartments, each thoughtfully furnished and appointed for effortless coastal living or

    Joel Schemmel DOUGLAS ELLIMAN

    6154 Midnight Pass Rd Unit 7, Sarasota, FL 34242
  • /27

    $12,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242

    Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private 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

    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
  • /2

    $925,000

    Sold Jun 22, 2026

    625 Beach Rd Unit 602, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Built 1975

    Last Sold Summary

    • 29% Below List Price
    • $809/SF
    • 176 Days On Market

    Current Estimated Value $976,088

    Last Listing Agent Susanne Losso COLDWELL BANKER REALTY

    625 Beach Rd Unit 602, Sarasota, FL 34242
    • /44

      Est $1,130,323

      Not Listed For Sale

      1137 Coquille St Unit 107, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,071 Sq Ft
      • Built 1983
      1137 Coquille St Unit 107, Sarasota, FL 34242

      Last Sold Summary

      • 36 Days On Market

  • /93

    $499,000

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

    225 Hourglass Way Unit 303, Sarasota, FL 34242

    3RD FLOOR FLOODPROOF CORNER UNIT TOP FLOOR PENTHOUSE PRIVATE BEACH RESORT APPROX.1,665 sf. The Treehouse at Beautiful Whispering Sands Siesta Key the World's Finest White Sand Beach. This is a unique opportunity to own a rare corner unit on the green belt Not a Parking Lot View, double Lanai flood proof no damage from Hurricanes. The breeze you get going through this condo is incredible, also

    Jonathan Minerick HOMECOIN.COM

    225 Hourglass Way Unit 303, Sarasota, FL 34242
  • /98

    $18,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • House for Rent

    345 Avenida Leona, Sarasota, FL 34242

    Listing reflects peak season rate. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a bright, coastal-styled haven designed for relaxation and comfort. The spacious primary

    Beth Dilley ASCENDIA REAL ESTATE

    345 Avenida Leona, Sarasota, FL 34242
  • /2

    $810,000

    Sold Nov 21, 2025

    1080 W Peppertree Ln Unit 506A, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft
    • Built 1974

    Last Sold Summary

    • 25% Below List Price
    • $696/SF
    • 264 Days On Market

    Current Estimated Value $839,478

    Last Listing Agent Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1080 W Peppertree Ln Unit 506A, Sarasota, FL 34242
    • /48

      Est $1,227,047

      Not Listed For Sale

      5750 Midnight Pass Rd Unit 309, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,335 Sq Ft
      • Built 1984
      5750 Midnight Pass Rd Unit 309, Sarasota, FL 34242

      Last Sold Summary

      • 40 Days On Market

  • /41

    $1,160,000

    • 3 Beds
    • 2 Baths
    • 2,272 Sq Ft

    5345 Siesta Ct, Sarasota, FL 34242

    Welcome to Siesta Cove on Siesta Key, just minutes from world famous Siesta Key Beach. This bright, well maintained home offers comfortable island living in one of the area’s most desirable neighborhoods. The layout provides excellent flexibility with both a living room and a separate family room, giving you plenty of space to relax or entertain guests. Oversized windows throughout the home bring

    Fred Sassen MICHAEL SAUNDERS & COMPANY

    5345 Siesta Ct, Sarasota, FL 34242
  • /25

    $7,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242

    Starting at $255/night! Experience the ultimate beachfront getaway at Villa 40, a beautifully appointed 2-bedroom, 2-bathroom condo at Casa Mar, thoughtfully designed to accommodate up to six guests in comfort and style. This spacious retreat features a king bed in the primary bedroom, two twin beds in the second bedroom, and a queen air mattress for added flexibility. The fully equipped kitchen

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
  • /2

    $900,000

    Sold Aug 29, 2025

    5108 Saint Albans Ave, Sarasota, FL 34242

    • 3 Beds
    • 3.5 Baths
    • 1,767 Sq Ft
    • Built 1968

    Last Sold Summary

    • 20% Below List Price
    • $509/SF
    • 57 Days On Market

    Current Estimated Value $932,191

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5108 Saint Albans Ave, Sarasota, FL 34242
    • /2

      Est $343,967

      Not Listed For Sale

      1300 N Portofino Dr Unit 205, Sarasota, FL 34242

      • 1 Bed
      • 2 Baths
      • 780 Sq Ft
      • Built 1969
      1300 N Portofino Dr Unit 205, Sarasota, FL 34242

      Last Sold Summary

      • 217 Days On Market

  • /27

    $598,000

    $41K PRICE DROP Pending
    • 1 Bed
    • 1.5 Baths
    • 728 Sq Ft

    5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242

    Under contract-accepting backup offers. Experience the best of Gulf-side living in this beautifully renovated 1-bed, 1.5-bath condo on Siesta Key — just steps from the world-famous quartz-sand beaches of Siesta Key. Completely updated from top to bottom, this turnkey coastal retreat features brand-new designer furniture and appliances, making it move-in or rental-ready from the moment you arrive.

    Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

    5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242
  • /26

    $6,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Apartment for Rent

    1125 W Peppertree Dr Unit 705, Sarasota, FL 34242

    This property is a 30 night minimum.1125 - 705 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx.175 yards away from Crescent beach.Open kitchen floor plan. Newly remodeled kitchen with stainless steel appliances. Dual sink vanity in the Master bathroom. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai). Condo

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
  • /2

    $800,000

    Sold May 28, 2026

    0 Midnight Pass Rd Unit MFRA4692398, Sarasota, FL 34242

    • Land
    • 8,276 Sq Ft
    • $4,210,526 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

    0 Midnight Pass Rd Unit MFRA4692398, Sarasota, FL 34242
    • /68

      Est $1,184,200

      Not Listed For Sale

      6236 Midnight Pass Rd Unit 407, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 1,924 Sq Ft
      • Built 1979
      6236 Midnight Pass Rd Unit 407, Sarasota, FL 34242

      Last Sold Summary

      • 7 Days On Market

  • /76

    $689,000

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

    5855 Midnight Pass Rd Unit 510, Sarasota, FL 34242

    **Resort Style Living in the Heart of Siesta Key, For Those Who Desire The Active Life Style** Experience the best of Siesta Key living at Harbor Towers Yacht & Racquet Club, a premier waterfront community overlooking Little Sarasota Bay with one of the lowest HOA's on the Key. This beautifully maintained turn-key furnished **2-bedroom, 2-bath residence** features a desirable **split floor plan**

    Julie Kell COLDWELL BANKER REALTY

    5855 Midnight Pass Rd Unit 510, Sarasota, FL 34242
  • /33

    $6,000 Per Month

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

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

    Welcome to your slice of paradise in Gulf & Bay Club Bayside, a highly sought-after community located on beautiful Siesta Key, Florida. Professionally managed by Gulf Coast Vacation rentals, this first-floor 2-bedroom, 2-bathroom lakefront condo offers the perfect blend of coastal charm and resort-style living. From the moment you step inside, you’ll be greeted by a beachy, relaxed vibe that

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
  • /2

    $925,000

    Sold Dec 08, 2025

    396 Avenida Madera, Sarasota, FL 34242

    • 3 Beds
    • 3 Baths
    • 1,964 Sq Ft
    • Built 1958

    Last Sold Summary

    • 20% Below List Price
    • $471/SF
    • 148 Days On Market

    Current Estimated Value $958,696

    Last Listing Agent Michael Nogueira LUXURY & BEACH REALTY INC

    396 Avenida Madera, Sarasota, FL 34242
    • /58

      Est $1,579,183

      Not Listed For Sale

      4712 Ocean Blvd Unit W3, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 2,277 Sq Ft
      • Built 1981
      4712 Ocean Blvd Unit W3, Sarasota, FL 34242

      Last Sold Summary

      • 20 Days On Market

Showing Results 441 - 480, Page 12 of 18

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