9,352

Siesta Key, FL Homes

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  • /2

    $3,800,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,200 Sq Ft

    5531 Calle Del Verano, Sarasota, FL 34242

    Pre-Construction. To be built. Brought to you by Noah Thomas Builders in a prime Siesta Key location. This contemporary coastal new construction at 5531 Calle del Verano showcases modern luxury paired with timeless island design—just ONE BLOCK from the powdery quartz sands of Siesta Key Beach, consistently ranked among the best beaches in the world. Thoughtfully engineered and built to FEMA’s

    Holly Wikfors 1ST CLASS REAL ESTATE SUNCOAST

    5531 Calle Del Verano, Sarasota, FL 34242
  • /34

    $7,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,282 Sq Ft
    • Condo for Rent

    19 Whispering Sands Dr Unit 106, Sarasota, FL 34242

    Still available for season January - April 2026l! Two bedroom 2 bath ground floor with view of the Gulf. Step outside and your on the sand! Escape the winter and be on the beach. Located in the heart of Siesta Key’s most desirable area, this property offers exceptional appeal with being just steps from the world-famous powdery white sand beach. Siesta Key Village is within easy walking distance,

    Maureen Plichta STRINGER MANAGEMENT INC

    19 Whispering Sands Dr Unit 106, 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 $424,754

    Last Listing Agent Dawn Lacey LACEY REALTY INC

    6006 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    • /78

      Est $699,662

      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

  • /25

    $1,945,000

    $155K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,996 Sq Ft

    814 Paradise Way, Sarasota, FL 34242

    Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island’s most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, the property provides privacy, scenic water views, and easy boating access to the Bay with only one higher bridge to navigate. A standout feature is

    Doug Addeo COMMUNITY REALTY ASSOCIATES

    814 Paradise Way, Sarasota, FL 34242
  • /41

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • House for Rent

    5577 Contento Dr, Sarasota, FL 34242

    This is a short term (weekly) rental. Listing reflects off season rate. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates

    Beth Dilley ASCENDIA REAL ESTATE

    5577 Contento Dr, 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 $606,113

    Last Listing Agent Shane Lewis MICHAEL SAUNDERS & COMPANY

    4189 Roberts Point Cir, Sarasota, FL 34242
    • /51

      Est $1,078,306

      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

  • /40

    $965,000

    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft

    1161 Coquille St Unit 206, Sarasota, FL 34242

    Welcome to coastal elegance and a rare opportunity to own one of only 27 townhomes in the highly sought-after Coquille community, nestled on the picturesque barrier island of Siesta Key, where you are steps to having your feet in the famous soft, white quartz sand that makes Siesta Beach famous. This spacious and light-filled, furnished 2-bedroom, 2-bathroom residence also includes a Florida room

    Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

    1161 Coquille St Unit 206, Sarasota, FL 34242
  • /30

    $7,000 Per Month

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

    1360 Siesta Bayside Dr, Sarasota, FL 34242

    This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The 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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1360 Siesta Bayside Dr, 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 $710,563

    Last Listing Agent Janell Stuckwisch EXP REALTY LLC

    5600 Beach Way Dr Unit 304, Sarasota, FL 34242
    • /67

      Est $1,069,060

      Not Listed For Sale

      1033 Shadow Lawn Way, Sarasota, FL 34242

      • 3 Beds
      • 2 Baths
      • 2,103 Sq Ft
      • Built 1960
      1033 Shadow Lawn Way, Sarasota, FL 34242

      Last Sold Summary

      • 69 Days On Market

  • /34

    $1,250,000

    $200K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,187 Sq Ft

    5400 Ocean Blvd Unit 6-4, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Virtually Staged. MAJOR PRICE REDUCTION! The lowest-priced 2-bedroom residence at Beach Terrace in over 8 years—this is the opportunity of the decade! Welcome to one of Siesta Key's most desirable addresses. This exceptional corner residence offers direct Gulf of Mexico frontage, perfectly positioned at the end of the village where luxury meets

    Mickey Kiernan MICHAEL SAUNDERS & COMPANY

    5400 Ocean Blvd Unit 6-4, Sarasota, FL 34242
  • /34

    $8,000 Per Month

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

    1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242

    Experience luxury waterfront living in this stunning 2-bedroom, 2-bathroom condo situated on the second level of Gulf & Bay Club Bayside in Siesta Key, Florida. Boasting breathtaking views of the bay, this meticulously designed residence boasts comfort. Step into a spacious living area adorned with coastal finishes and large windows that invite an abundance of natural light. The open-concept

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1382 Siesta Bayside Dr Unit 1382C, 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 $3,593,076

    Last Listing Agent Carol Thomas MICHAEL SAUNDERS & COMPANY

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

      Est $3,104,669

      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

  • /53

    $1,699,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft

    6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242

    It's all about THE VIEW and the Direct Beach Access!!! This first floor condominium has a Full Gulf View from the living room and glassed-in lanai. The water views are amazing, and the sunsets are gorgeous! You will walk out your front door right down to the sand to enjoy the warm Gulf water in minutes. There was no water intrusion and no water damage to this unit in past storms, as there are

    Susan Keal MICHAEL SAUNDERS & COMPANY

    6144 Midnight Pass Rd Unit 2N, Sarasota, FL 34242
  • /16

    $7,500 Per Month

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

    6020 Midnight Pass Rd Unit 29, Sarasota, FL 34242

    If the beach is calling your name, Villa 29 at Aloha Kai is the perfect retreat. Whether you’re grabbing a towel and heading to the shore or curling up with a good book by the pool, you’ll find plenty of sunshine and tranquility to enjoy. Unwind on your screened porch or sink into the comfort of a king-size bed as you rest and recharge. For your convenience, this villa also includes a washer and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 29, 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 $2,312,520

    Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

    222 Beach Rd Unit 7, Sarasota, FL 34242
    • /64

      Est $1,576,031

      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

  • /39

    $465,000

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

    5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242

    Seller is offering a $5,000 flex credit — apply it toward a mortgage rate buydown to lower your monthly payments, or use it as an appliance package credit. Your choice, your move. Welcome to Unit 201 at White Sands Condominium — a bright, airy coastal retreat perfectly positioned on iconic Midnight Pass Road, Siesta Key. This spacious 1,012 sq ft, two-bedroom, two-bathroom condo is your gateway

    Meredith French COLDWELL BANKER REALTY

    5673 Midnight Pass Rd Unit 201, Sarasota, FL 34242
  • /42

    $5,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft
    • Condo for Rent

    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

    Variable rent based on season

    Terry Dorrity INTEGRITY INVESTMENTS REALTY

    6157 Midnight Pass Rd Unit D32, 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

    Last Listing Agent Marcia Van Ginhoven REDFIN CORPORATION

    5964 Midnight Pass Rd Unit N-16 (AKA # 135), Sarasota, FL 34242
    • /36

      Est $1,243,640

      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

  • /67

    $619,000

    • 2 Beds
    • 1.5 Baths
    • 836 Sq Ft

    6154 Midnight Pass Rd Unit A 3, Sarasota, FL 34242

    Tucked along the sugar-white sands of world-renowned Siesta Key, this freestanding villa offers the rare combination of effortless ownership, strong rental potential, and immediate coastal enjoyment. With direct beach access just steps away, every day begins and ends with the Gulf as your backdrop. Thoughtfully and completely updated, the residence features easy-care terrazzo flooring, a

    Ryndie Brusco MICHAEL SAUNDERS & COMPANY

    6154 Midnight Pass Rd Unit A 3, Sarasota, FL 34242
  • /35

    $8,200 Per Month

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

    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242

    Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
  • /2

    $825,000

    Sold Sep 12, 2025

    514 Ralph St, Sarasota, FL 34242

    • 4 Beds
    • 3 Baths
    • 1,934 Sq Ft
    • Built 1957

    Last Sold Summary

    • 30% Below List Price
    • $427/SF
    • 169 Days On Market

    Current Estimated Value $884,353

    Last Listing Agent Tim Yocum, Sr COLDWELL BANKER REALTY

    514 Ralph St, Sarasota, FL 34242
    • /2

      Est $1,947,812

      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

  • /48

    $669,000

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

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

    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, updated plumbing, new impact-resistant

    Cheryl Santelli PEPPERTREE BAY REALTY INC

    1128 W Peppertree Ln Unit 111, Siesta Key, FL 34242
  • /26

    $10,230 Per Month

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

    6154 Midnight Pass Rd Unit 202, Sarasota, FL 34242

    Completely remodeled in 2019. Endless Gulf views from every room. TWO queen sized beds in Master, two twins in second bedroom means plenty of space for your family, and everything is new and sparkling clean! Additional Person fees may apply. Enjoy a dip in one of the largest pools on Siesta Key! This second floor apartment has direct gulf views for stunning sunsets of the only beach to be voted

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 202, Sarasota, FL 34242
  • /2

    $1,100,000

    Sold Mar 20, 2026

    6342 Midnight Pass Rd Unit 310, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 852 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Below List Price
    • $1,291/SF
    • 0 Days On Market

    Current Estimated Value $1,106,595

    Last Listing Agent Brian Livesey WATERSIDE REALTY LLC

    6342 Midnight Pass Rd Unit 310, Sarasota, FL 34242
    • /59

      Est $686,155

      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

  • /58

    $799,900

    $127K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,358 Sq Ft

    6415 Midnight Pass Rd Unit 211, Sarasota, FL 34242

    Huge opportunity to own a spacious 2,400 sq ft, 3 bedroom condo on Siesta Key with an aggressive, new price drop! Now being offered at $799,900 - an unbelievable $339.22 per square foot (vs recent SK sales average of $460 per square foot). This is a fabulous family investment with plenty of room to sleep 8 people (Note: a 4th bedroom could easily be added). This condo has brand new

    Mina Johnson MICHAEL SAUNDERS & COMPANY

    6415 Midnight Pass Rd Unit 211, Sarasota, FL 34242
  • /19

    $8,300 Per Month

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

    6020 Midnight Pass Rd Unit 39, Sarasota, FL 34242

    Paradise is found at Villa 39 at Aloha Kai! Meticulously renovated, this villa stands out with its beamed ceilings and open floor plan, creating a cozy and inviting atmosphere from the moment you step inside this exceptional beach retreat. The primary bedroom features relaxing coastal decor and a spa-like private bath, while guests will feel equally comfortable in the thoughtfully designed living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 39, Sarasota, FL 34242
  • /2

    $690,000

    Sold Aug 14, 2025

    6310 Midnight Pass Rd Unit 405N, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 894 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $772/SF
    • 10 Days On Market

    Current Estimated Value $701,572

    Last Listing Agent Halie Monde KW COASTAL LIVING III

    6310 Midnight Pass Rd Unit 405N, Sarasota, FL 34242
    • /2

      Est $2,054,257

      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

  • /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
  • /21

    $8,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Apartment for Rent

    5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242

    Newly remodeled and furnished “Bougie beach bungalow” on Siesta Key Island. This Condo will “wow” you from the first moment you enter. Just say Alexa turn lights on and your command will be answered. This condo is on the first floor and it’s just a few minutes walk from the siesta key public beach access. The community is very welcoming to all guest and has a heated pool year-round and also many

    Stephanie Fox EXP REALTY LLC

    5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242
  • /2

    $720,000

    Sold Feb 05, 2026

    312 Avenida Leona, Siesta Key, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 1,824 Sq Ft
    • Built 2026

    Last Sold Summary

    • 58% Below List Price
    • $395/SF
    • 161 Days On Market

    Current Estimated Value $793,000

    Last Listing Agent Ron Pepka KW SUNCOAST

    312 Avenida Leona, Siesta Key, FL 34242
    • /7

      Est $1,152,552

      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

Showing Results 561 - 600, Page 15 of 18

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