9,352

Siesta Key, FL Homes

Section Image
  • /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
  • /23

    $8,550 Per Month

    • 2 Beds
    • 1 Bath
    • 1,014 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242

    Welcome to Villa #27, your home away from home on beautiful Crescent Beach, Siesta Key. As one of Aloha Kai’s closest villas to the Gulf of Mexico, you are just steps away from the top-rated beach in the United States. The villa’s décor is comfy and casual, featuring two sofas, a dining table that seats six, and an open kitchen—perfect for relaxing evenings in. Kick back and enjoy a late-night

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242
  • /2

    $2,700,000

    Sold May 04, 2026

    915 Seaside Dr Unit 407, Sarasota, FL 34242

    • 3 Beds
    • 3.5 Baths
    • 2,255 Sq Ft
    • Built 2009

    Last Sold Summary

    • 7% Below List Price
    • $1,197/SF
    • 119 Days On Market

    Current Estimated Value $2,793,304

    Last Listing Agent Brian Ward WATERSIDE REALTY LLC

    915 Seaside Dr Unit 407, Sarasota, FL 34242
    • /2

      Est $818,829

      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

  • /14

    $725,000

    $25K PRICE DROP
    • Land
    • 8,712 Sq Ft
    • $3,625,000 per Acre

    5302 La Rosas, Sarasota, FL 34242

    Welcome to Palm Island, the Heart of Siesta Key!! Palm Island is an Island on an Island, located a short walk to World Famous Sugery Sands of Siesta Key Beach (Beach Access 10) and Siesta Village. With only one small humpback bridge on & off, this beachy neighborhood is a quiet oasis that is close the beach, restaurants and nightlife that makes this area so desirable. Great opportunity to build

    Dan Miller PREFERRED SHORE LLC

    5302 La Rosas, Sarasota, FL 34242
  • /58

    $8,000 Per Month

    • 3 Beds
    • 3 Baths
    • 1,835 Sq Ft
    • Condo for Rent

    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242

    Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
  • /2

    $585,000

    Sold Dec 01, 2025

    1080 W Peppertree Ln Unit 602A, Sarasota, FL 34242

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

    Last Sold Summary

    • 16% Below List Price
    • $503/SF
    • 142 Days On Market

    Current Estimated Value $614,823

    Last Listing Agent Lisa Beach WATERSIDE REALTY LLC

    1080 W Peppertree Ln Unit 602A, Sarasota, FL 34242
    • /69

      Est $1,411,540

      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

  • /13

    $9,400,000

    New Construction Pending
    • 3 Beds
    • 4 Baths
    • 4,510 Sq Ft

    70 Avenida Veneccia Unit 402, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Pre-Construction. To be built. Introducing Sunset Beach, the premier boutique condominium on Siesta Key, offering refined beachfront living with breathtaking Gulf views. This exclusive collection features 11 residences with open-concept, flow-through floor plans and expansive glass walls. The spacious terraces and thoughtfully designed great room

    David Lehrman THE SARASOTA REAL ESTATE COMP.

    70 Avenida Veneccia Unit 402, Sarasota, FL 34242
  • /13

    $6,972 Per Month

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

    6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242

    New photos coming soon! Villa 36 at Aloha Kai is perfectly situated on Siesta Key, a popular barrier island on Florida’s West Coast. Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
  • /2

    $1,000,000

    Sold Jan 30, 2026

    5036 Higel Ave, Sarasota, FL 34242

    • Land
    • 15,246 Sq Ft
    • $2,857,143 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 8 Days On Market

    Current Estimated Value $1,019,778

    Last Listing Agent Diana Pomarico PALERMO REAL ESTATE PROF. INC.

    5036 Higel Ave, Sarasota, FL 34242
    • /45

      Est $1,628,838

      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

  • /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
  • /26

    $6,900 Per Month

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

    1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242

    This lovely well-maintained and upgraded condo in a gated community, is located on the ground floor and offers one bedroom plus an additional den furnished as a small guest bedroom. The condo is turnkey furnished including washer /dryer and private garage, an approximate 5-minute walk, via deeded, walking access across the street, to the #1 beach in the U.S.A., Siesta Key! Choose to enjoy two

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
  • /2

    $2,050,000

    Sold Apr 01, 2026

    518 Venice Ln, Sarasota, FL 34242

    • 3 Beds
    • 3 Baths
    • 2,676 Sq Ft
    • Built 1971

    Last Sold Summary

    • 11% Below List Price
    • $766/SF
    • 103 Days On Market

    Current Estimated Value $2,056,538

    Last Listing Agent Pamela Pileggi PREFERRED SHORE LLC

    518 Venice Ln, Sarasota, FL 34242
    • /2

      Est $486,419

      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

  • /57

    $669,000

    $30K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,466 Sq Ft

    1200 E Peppertree Ln Unit 307, Sarasota, FL 34242

    Under contract-accepting backup offers. Set within Peppertree Bay on Siesta Key, 1200 E Peppertree Lane #307 offers a well-proportioned, turnkey, move-in ready two-bedroom, two-bath residence encompassing 1,466 square feet. The interior presents a bright, open layout anchored by a spacious great room, where crown molding, tile flooring throughout, and an expansive wall of impact glass windows

    Sharon Chiodi DOUGLAS ELLIMAN

    1200 E Peppertree Ln Unit 307, Sarasota, FL 34242
  • /28

    $8,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,552 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242

    Let’s all go to the beach! Villa 52S at Aloha Kai is a spacious and bright 3-bedroom, 2-bath getaway with plenty of room for everyone to relax and enjoy. The large, open kitchen is perfect for gathering with friends and family to prepare drinks, snacks, or full meals to enjoy in the dining room or on your private rooftop patio. For added convenience, this villa also includes a washer and dryer.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242
  • /2

    $1,895,000

    Sold Mar 10, 2026

    5165 Sandy Cove Ave, Sarasota, FL 34242

    • 3 Beds
    • 2.5 Baths
    • 2,216 Sq Ft
    • Built 1964

    Last Sold Summary

    • 5% Below List Price
    • $855/SF
    • 72 Days On Market

    Current Estimated Value $1,887,675

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    5165 Sandy Cove Ave, Sarasota, FL 34242
    • /72

      Est $1,596,091

      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

  • /31

    $625,000

    • 2 Beds
    • 1.5 Baths
    • 836 Sq Ft

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

    Welcome home to Casa Blanca on Siesta Key, a beloved Gulf-side community known for its charming villas and laid-back beach lifestyle. With a mix of cozy residences and a three-story beachfront building, Casa Blanca offers a more convenient way to enjoy one of the most sought-after stretches of sand on Florida’s Gulf Coast. This villa features 2 bedrooms and 1.5 beautifully renovated baths,

    Rudy Dudon MICHAEL SAUNDERS & COMPANY

    6154 Midnight Pass Rd Unit A-05, Sarasota, FL 34242
  • /34

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,210 Sq Ft
    • House for Rent

    6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242

    Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Beach, just steps away, where sun and surf await. Relax by Siesta Key’s largest heated pool or unwind in the lush, park-like setting with peaceful bay views. Explore the nearby vibrant Village on Siesta Key, filled with diverse dining, unique shops, and lively events. With

    Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

    6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242
  • /2

    $450,000

    Sold Apr 29, 2026

    24 Sandy Cove Rd Unit A6-D, Sarasota, FL 34242

    • 1 Bed
    • 1 Bath
    • 561 Sq Ft
    • Built 1968

    Last Sold Summary

    • 10% Below List Price
    • $802/SF
    • 55 Days On Market

    Current Estimated Value $458,565

    Last Listing Agent Bev Murray BERKSHIRE HATHAWAY HOMESERVICE

    24 Sandy Cove Rd Unit A6-D, Sarasota, FL 34242
    • /2

      Est $739,835

      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

  • /91

    $565,000

    $30K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 820 Sq Ft

    4822 Ocean Blvd Unit 10E, Sarasota, FL 34242

    Experience penthouse-level living in this fully renovated, 10th-floor, condominium. This turnkey Siesta Key oceanfront property offers panoramic views of the Gulf, Sarasota Bay, and the skyline. Masterfully modernized, it blends luxurious coastal design with everyday resort-style convenience. Sweeping, unobstructed sights of dolphins, Big Pass, and vivid Gulf sunsets. A substantial great room

    Darren Beddoe COLDWELL BANKER REALTY

    4822 Ocean Blvd Unit 10E, Sarasota, FL 34242
  • /27

    $9,900 Per Month

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

    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242

    Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park your car and store all the beach equipment you will need for the beach. It's only a short 10 min. walk down the private deeded beach access to the beautiful white sands of Siesta Key beach. We share

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
  • /2

    $2,000,000

    Sold Nov 14, 2025

    0 Solymar Dr, Siesta Key, FL 34242

    • Land
    • 18,730 Sq Ft
    • $4,651,163 per Acre

    Last Sold Summary

    • 71% Below List Price
    • 238 Days On Market

    Last Listing Agent Curtis Ware KW COASTAL LIVING III

    0 Solymar Dr, Siesta Key, FL 34242
    • /2

      Est $1,195,337

      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

  • /40

    $1,200,000

    $15M PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,961 Sq Ft

    618 Avenida de Mayo, Sarasota, FL 34242

    Welcome to Old World Siesta Key...this 1940s Bungalow Home was converted approx 40 years ago into a Triplex and a Cottage was added at the rear of the property. Siesta Key is World Renown for it's White Powdery Sand Beaches and is so convenient to the Mainland and all the Attractions Sarasota has to offer such as the Arts, St Armands and Unbelievable Shopping. The Property is located

    Lisa Blakeley BLAKELEY & ASSOCIATES REALTY

    618 Avenida de Mayo, Sarasota, FL 34242
  • /53

    $8,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,346 Sq Ft
    • House for Rent

    431 Island Cir, Sarasota, FL 34242

    This is a short term rental. Listing reflects off season rate. New to the rental market! Whether you’re seeking a relaxing beach escape or an adventure-filled vacation, Island Retreat offers the perfect home base. Its prime location, luxurious amenities, and proximity to both the beach and Siesta Key Village make it an exceptional choice for creating unforgettable memories. Featuring 5

    Beth Dilley ASCENDIA REAL ESTATE

    431 Island Cir, Sarasota, FL 34242
  • /2

    $629,900

    Sold Aug 25, 2025

    925 Beach Rd Unit 408, Sarasota, FL 34242

    • 2 Beds
    • 1 Bath
    • 753 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $837/SF
    • 22 Days On Market

    Current Estimated Value $634,526

    Last Listing Agent Debbie Hering DEBBIE HERING REALTY & ASSOC.

    925 Beach Rd Unit 408, Sarasota, FL 34242
    • /46

      Est $759,807

      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

  • /28

    $2,680,950

    New Construction $1M PRICE INCREASE Pending
    • 4 Beds
    • 3.5 Baths
    • 2,750 Sq Ft

    105 Island Cir, Sarasota, FL 34242

    Under contract-accepting backup offers. Pre-Construction. To be built. Pre-Construction. To be built. IMAGINE a Custom Coastal Contemporary Home on Palm Island, Siesta Key. Picture a thoughtfully designed residence offering 2,750 sf of indoor living space and 3,467 sf of total indoor/outdoor space. E/M Custom Homes is renowned for their impeccable craftsmanship and modern coastal design creating

    Linda Scheller COLDWELL BANKER REALTY

    105 Island Cir, Sarasota, FL 34242
  • /27

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft
    • Condo for Rent

    6052 W Peppertree Way Unit 235B, Sarasota, FL 34242

    This property is a 30 night minimum. 6052 WPW is a Large Garden condo, located approximately 50 yards away from Crescent BeachOpen porch lanai with a 6 person table. Recessed lighting in both bathrooms. Master bathroom has a seat. Recessed lighting in the kitchen. This unit has access to a private garageApprox. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6052 W Peppertree Way Unit 235B, Sarasota, FL 34242
  • /2

    $585,000

    Sold May 12, 2026

    6154 Midnight Pass Rd Unit A13, Sarasota, FL 34242

    • 2 Beds
    • 1 Bath
    • 875 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $669/SF
    • 46 Days On Market

    Current Estimated Value $607,431

    Last Listing Agent Linda Holley WILLIAM RAVEIS - FLORIDA LLC

    6154 Midnight Pass Rd Unit A13, Sarasota, FL 34242
    • /38

      Est $3,377,483

      Not Listed For Sale

      5212 Siesta Cove Dr, Sarasota, FL 34242

      • 5 Beds
      • 6.5 Baths
      • 5,133 Sq Ft
      • Built 1979
      5212 Siesta Cove Dr, Sarasota, FL 34242

      Last Sold Summary

      • 225 Days On Market

  • /70

    $4,900,000

    Pending
    • 9 Beds
    • 11 Baths
    • 4,437 Sq Ft

    5322 Calle de La Siesta, Sarasota, FL 34242

    Under contract-accepting backup offers. 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

    Jason Skowronski COMPASS FLORIDA LLC

    5322 Calle de La Siesta, Sarasota, FL 34242
  • /11

    $10,230 Per Month

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

    6154 Midnight Pass Rd Unit 102, Sarasota, FL 34242

    Wake up to views of the beautiful gulf and beach from every room. Walk out to the best beach in the world. End your day with a breathtaking sunset dinner on the lanai. 102 is a ground floor, beach front apartment with 2 bedrooms and 2 baths. It is an open floor plan with porcelain tile throughout, comfortable seating in the living area, a full kitchen with all cookware and service items, and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 102, Sarasota, FL 34242
  • /2

    $835,000

    Sold Mar 16, 2026

    625 Beach Rd Unit 407, Sarasota, FL 34242

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

    Last Sold Summary

    • 10% Below List Price
    • $730/SF
    • 96 Days On Market

    Current Estimated Value $858,024

    Last Listing Agent Toni Zarghami KW COASTAL LIVING III

    625 Beach Rd Unit 407, Sarasota, FL 34242
    • /28

      Est $702,677

      Not Listed For Sale

      6206 Midnight Pass Rd Unit 203, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,312 Sq Ft
      • Built 1979
      6206 Midnight Pass Rd Unit 203, Sarasota, FL 34242

      Last Sold Summary

      • 454 Days On Market

Showing Results 601 - 640, Page 16 of 18

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