9,260

Siesta Key, FL Homes

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  • /56

    $1,135,000

    • 2 Beds
    • 2 Baths
    • 1,365 Sq Ft

    1080 W Peppertree Ln Unit 305A, Sarasota, FL 34242

    This is the one! Rarely available beach-view residence with deeded access to the renowned shores of Siesta Key Beach. Located on the third floor, this bright and inviting unit features a versatile layout, including a pull-out sofa on the lanai with a privacy partition—perfect for creating a comfortable third sleeping area for guests.The well-designed split floor plan offers a spacious dining

    Eliza Miller PEPPERTREE BAY REALTY INC

    1080 W Peppertree Ln Unit 305A, Sarasota, FL 34242
  • /20

    $7,783

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft
    • Condo for Rent

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242

    The advertised rate of $7,783/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
  • /2

    $700,000

    Sold Dec 22, 2025

    5223 Shadow Lawn Dr, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 1,459 Sq Ft
    • Built 1967

    Last Sold Summary

    • 30% Below List Price
    • $480/SF
    • 161 Days On Market

    Current Estimated Value $746,851

    Last Listing Agent Justin Harris REAL BROKER, LLC

    5223 Shadow Lawn Dr, Sarasota, FL 34242
    • /2

      Est $3,507,972

      Not Listed For Sale

      317 Beach Rd, Sarasota, FL 34242

      • 4 Beds
      • 3.5 Baths
      • 3,362 Sq Ft
      • Built 2009
      317 Beach Rd, Sarasota, FL 34242

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  • /69

    $1,300,000

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft

    420 Beach Rd Unit 508, Sarasota, FL 34242

    Virtually Staged. Rarely available 5th-floor residence in Siesta Gulf View’s coveted 08 stack. This exceptional beach retreat showcases an extended wrap balcony with unobstructed west and south panoramic views of Siesta Key’s white-sand beaches and glowing Gulf sunsets. Bathed in natural light, the spacious split-bedroom layout offers walk-in closets in both bedrooms, motorized storm shutters, an

    Suki Scollo COLDWELL BANKER REALTY

    420 Beach Rd Unit 508, Sarasota, FL 34242
  • /16

    $9,000 Per Month

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

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242

    Beach or pool today? Or perhaps you'd rather stay in and enjoy a good book on the charming porch of Villa 53 at Aloha Kai. This beautifully remodeled retreat features an updated kitchen and bath, paired perfectly with coastal-inspired furnishings that create a relaxing home away from home. The spacious bedroom offers generous closet space, ensuring comfort and convenience during your stay.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
  • /2

    $655,000

    Sold Jun 12, 2026

    5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 921 Sq Ft
    • Built 1970

    Last Sold Summary

    • 3% Below List Price
    • $711/SF
    • 16 Days On Market

    Current Estimated Value $648,180

    Last Listing Agent Cindy Furtado WATERSIDE REALTY LLC

    5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242
    • /100

      Est $7,557,958

      Not Listed For Sale

      4300 Higel Ave, Sarasota, FL 34242

      • 6 Beds
      • 9 Baths
      • 8,615 Sq Ft
      • Built 2008
      4300 Higel Ave, Sarasota, FL 34242

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Mark Coppens EXP REALTY LLC

  • /40

    $549,900

    Open Sat 11AM - 2PM
    • 2 Beds
    • 1.5 Baths
    • 860 Sq Ft

    1500 Cove II Place Unit 531, Sarasota, FL 34242

    Experience the ultimate Siesta Key lifestyle in this turnkey-furnished condominium at Midnight Cove II, ideally situated on beautiful Crescent Beach. Enjoy stunning water and pool views from your private balcony while taking advantage of the community's highly sought after weekly rental program, making this an exceptional investment opportunity, vacation retreat, or personal getaway.The open

    Kimberly Eudy RE/MAX PALM REALTY OF VENICE

    1500 Cove II Place Unit 531, Sarasota, FL 34242
  • /36

    $2,395 Per Month

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

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242

    SIESTA KEY LIVING!! This unfurnished 2 bed/2 bath residence has a remodeled kitchen with faux granite countertops, a new microwave, dishwasher, fans throughout, tile floors throughout, and a screened porch. Enjoy the beautifully manicured 7 acres with live oaks, palm trees, tropical flowers, and flowering shrubs. A courtyard path leads to boat docks in a sheltered marina that connects to the

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
  • /2

    $965,000

    Sold Jun 01, 2026

    19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242

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

    Last Sold Summary

    • 18% Below List Price
    • $753/SF
    • 69 Days On Market

    Current Estimated Value $973,654

    Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

    19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242
    • /2

      Est $1,823,169

      Not Listed For Sale

      3928 Roberts Point Rd, Sarasota, FL 34242

      • 3 Beds
      • 2.5 Baths
      • 1,839 Sq Ft
      • Built 1951
      3928 Roberts Point Rd, Sarasota, FL 34242

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Wayne Cherry PROGRAM REALTY, LLC

  • /50

    $3,990,000

    • 6 Beds
    • 6 Baths
    • 3,888 Sq Ft

    104 Avenida Veneccia Unit 171, Sarasota, FL 34242

    Six fully renovated, individually rentable units come together in this turnkey Siesta Key investment property, currently operating as an established vacation rental just steps from the world-famous shores of Siesta Key Beach. Offered fully furnished, the property presents a unique opportunity to acquire an established income-producing property with six private one-bedroom, one-bath units in one

    Curtis Ware KW COASTAL LIVING III

    104 Avenida Veneccia Unit 171, Sarasota, FL 34242
  • /25

    $12,296 Per Month

    • 2 Beds
    • 2 Baths
    • 1,319 Sq Ft
    • House for Rent

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

    Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience. Step into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242
  • /2

    $1,595,000

    Sold Sep 02, 2025

    5121 Oxford Dr, Sarasota, FL 34242

    • 3 Beds
    • 3 Baths
    • 2,270 Sq Ft
    • Built 1983

    Last Sold Summary

    • $703/SF
    • 1 Day On Market

    Current Estimated Value $1,599,333

    Last Listing Agent Mark Coppens EXP REALTY LLC

    5121 Oxford Dr, Sarasota, FL 34242
    • /2

      Est $511,382

      Not Listed For Sale

      6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,101 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Kristin Gilardi EXP REALTY LLC

  • /35

    $1,395,000

    • 3 Beds
    • 2.5 Baths
    • 2,041 Sq Ft

    306 Beach Rd Unit 306, Sarasota, FL 34242

    EXCEPTIONAL WEEKLY RENTAL TOWNHOME JUST STEPS FROM SIESTA KEY VILLAGE!An exceptional opportunity to enjoy a turnkey-furnished, three-bedroom townhome in ahighly desirable location on the beach side of the road, just steps from the vibrantatmosphere of Siesta Key Village. With weekly rentals, pet-friendly accommodations, atwo-car garage, and gated access to world-renowned Siesta

    Ethel Lovelace MICHAEL SAUNDERS & COMPANY

    306 Beach Rd Unit 306, Sarasota, FL 34242
  • /51

    $1,875 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    6327 Midnight Pass Rd, Sarasota, FL 34242

    **DON’T MISS THIS OPPORTUNITY TO LIVE ON WORLD-FAMOUS SIESTA KEY!**ALL UTILITIES & WIFI INCLUDED**Welcome to Midnight Cove II—an impeccably maintained community on Siesta Key, just moments from the powdery white sands of Crescent Beach and minutes from iconic Siesta Beach. A quick ride brings you to Siesta Key Village, where you can enjoy boutique shopping, great dining, cocktails, live music,

    6327 Midnight Pass Rd, Sarasota, FL 34242
  • /2

    $20,000

    Sold Mar 03, 2026

    915 Seaside Dr Unit 511, Weeks 2-3, Sarasota, FL 34242

    • 4 Beds
    • 4 Baths
    • 2,625 Sq Ft
    • Built 2009

    Last Sold Summary

    • 43% Below List Price
    • $8/SF
    • 51 Days On Market

    Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

    915 Seaside Dr Unit 511, Weeks 2-3, Sarasota, FL 34242
    • /2

      Est $531,309

      Not Listed For Sale

      6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,101 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Frank Harris COAST 2 COAST HOME REALTY, PLLC

  • /20

    $646,000

    Under Contract
    • Land
    • 6,098 Sq Ft
    • $4,614,286 per Acre

    643 Calle de Peru, Sarasota, FL 34242

    Under contract-accepting backup offers. Opportunity to build your dream home and/or income producing property near world famous Siesta Beach!Being sold for lot value only. The present structure is a tear down due to roof leaks during past hurricane. Optional plans are available for a custom "to be built" home with a pool for $1,996,000.

    Rachelle Tirey PREFERRED SHORE LLC

    643 Calle de Peru, Sarasota, FL 34242
  • /41

    $7,600 Per Month

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

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

    Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
  • /2

    $690,000

    Sold Nov 24, 2025

    114 Whispering Sands Dr Unit V21, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,387 Sq Ft
    • Built 1968

    Last Sold Summary

    • 5% Below List Price
    • $497/SF
    • 0 Days On Market

    Current Estimated Value $691,091

    Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

    114 Whispering Sands Dr Unit V21, Sarasota, FL 34242
    • /2

      Est $521,850

      Not Listed For Sale

      6157 Midnight Pass Rd Unit E42, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,101 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit E42, Sarasota, FL 34242

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Robin Jones EXIT KING REALTY

  • /76

    $1,100,000

    Open Sat 1PM - 4PM $75K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft

    5760 Midnight Pass Rd Unit 209, Sarasota, FL 34242

    Welcome home to Gulf & Bay Club, the premier condominium community on Siesta Key Beach. Enjoy stunning views of the freshwater lake, fountains, island lagoon, swimming pools, sandy beach, and the Gulf of America from your private lanai. Step into this beautifully remodeled Turnkey Furnished, 2-bed, 2-bath condo offering modern finishes and thoughtful upgrades throughout. The kitchen features

    Tina Johns COLDWELL BANKER REALTY

    5760 Midnight Pass Rd Unit 209, Sarasota, FL 34242
  • /36

    $2,395 Per Month

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

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242

    SIESTA KEY LIVING!! This unfurnished 2 bed/2 bath residence has a remodeled kitchen with faux granite countertops, a new microwave, dishwasher, fans throughout, tile floors throughout, and a screened porch. Enjoy the beautifully manicured 7 acres with live oaks, palm trees, tropical flowers, and flowering shrubs. A courtyard path leads to boat docks in a sheltered marina that connects to the

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
  • /2

    $895,000

    Sold Jun 05, 2026

    635 Tropical Cir, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 2,255 Sq Ft
    • Built 1983

    Last Sold Summary

    • 31% Below List Price
    • $397/SF
    • 163 Days On Market

    Current Estimated Value $1,014,402

    Last Listing Agent Tami Cashi COLDWELL BANKER REALTY

    635 Tropical Cir, Sarasota, FL 34242
    • /71

      Est $391,115

      Not Listed For Sale

      6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

      • 2 Beds
      • 1 Bath
      • 690 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Babette Paige COLDWELL BANKER REALTY

  • /58

    $2,100,000

    • 3 Beds
    • 3.5 Baths
    • 2,922 Sq Ft

    471 Island Cir, Sarasota, FL 34242

    Offered for the first time, 471 Island Circle is a private contemporary coastal retreat designed for modern luxury, effortless living and the ease of a low-maintenance Siesta Key lifestyle. Ideally positioned in the community of Palm Island, close to Siesta Beach and the charm of Siesta Village, this three-level residence offers a rare blend of privacy, quality construction and everyday comfort

    Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

    471 Island Cir, Sarasota, FL 34242
  • /72

    $5,000 Per Month

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft
    • Condo for Rent

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242

    Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

    Margaret Young JENNETTE PROPERTIES, INC.

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
  • /2

    $1,425,000

    Sold May 20, 2026

    704 Tropical Cir, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 2,073 Sq Ft
    • Built 1976

    Last Sold Summary

    • 4% Above List Price
    • $687/SF
    • 7 Days On Market

    Current Estimated Value $1,384,135

    Last Listing Agent Jeffrey Hinrichs MICHAEL SAUNDERS & COMPANY

    704 Tropical Cir, Sarasota, FL 34242
    • /82

      Est $547,435

      Not Listed For Sale

      6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

      • 2 Beds
      • 2.5 Baths
      • 1,332 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Suki Scollo COLDWELL BANKER REALTY

  • /93

    $2,995,000

    • 3 Beds
    • 3 Baths
    • 2,755 Sq Ft

    5178 Oakmont Place, Sarasota, FL 34242

    For the buyer who believes the best of Siesta Key is experienced by boat, 5178 Oakmont Place delivers an exceptional combination of deep-water canal frontage, estate-sized privacy, refined island living, and effortless access to Sarasota Bay. Set on more than half an acre along Siesta Key’s coveted Grand Canal, this tastefully updated custom residence pairs Caribbean-inspired architecture with 93

    Adnan Dedic COMPASS FLORIDA LLC

    5178 Oakmont Place, Sarasota, FL 34242
  • /21

    $2,200 Per Month

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

    212 Pass Key Rd, Siesta Key, FL 34242

    Oceanview unit in Siesta Key

    212 Pass Key Rd, Siesta Key, FL 34242
  • /2

    $1,175,000

    Sold Feb 10, 2026

    19 Whispering Sands Dr Unit 1204, Sarasota, FL 34242

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

    Last Sold Summary

    • 9% Below List Price
    • $917/SF
    • 9 Days On Market

    Current Estimated Value $1,178,679

    Last Listing Agent Chelsa Vahtomin COLDWELL BANKER REALTY

    19 Whispering Sands Dr Unit 1204, Sarasota, FL 34242
    • /26

      Est $602,150

      Not Listed For Sale

      6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

      • 2 Beds
      • 2.5 Baths
      • 1,332 Sq Ft
      • Built 1974
      6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

      Last Sold Summary

      • 205 Days On Market

      Last Listing Agent Mark Zervos PLATINUM REAL ESTATE

  • /59

    $699,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    4660 Ocean Blvd Unit F1, Sarasota, FL 34242

    Views, views, and more views. Stunning FULL GULF views, dolphin views, manatee views, pelican views, eagle views, pool views and spectacular sunset views that will take your breath away! If a picture is worth a thousand words, this turnkey furnished Sea Village Ocean Blvd beauty will write a book with it's truly one of a kind ocean views! Experience the top finishes, including plantation

    Tera Kiger TERA KIGER, LICENSED REAL ESTATE BROKER

    4660 Ocean Blvd Unit F1, Sarasota, FL 34242
  • /31

    $7,000 Per Month

    • 2 Beds
    • 11 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242

    This property is a 30 night minimum.1200-303 is a Bay side Mid-rise unit, located approximately 150 yards away from the Bay.Newly remodeled kitchen with stainless steel appliances. Grab bars located in both bathrooms. Guest bedroom T.V is mounted on the wall. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding:

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
  • /2

    $1,120,000

    Sold Apr 23, 2026

    5790 Midnight Pass Rd Unit 406, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 1,433 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $782/SF
    • 3 Days On Market

    Current Estimated Value $1,137,775

    Last Listing Agent linda duquette ENGEL & VOELKERS VENICE DOWNTOWN

    5790 Midnight Pass Rd Unit 406, Sarasota, FL 34242
    • /2

      Est $3,413,669

      Not Listed For Sale

      722 Siesta Key Cir, Sarasota, FL 34242

      • 4 Beds
      • 4.5 Baths
      • 3,488 Sq Ft
      • Built 2024
      722 Siesta Key Cir, Sarasota, FL 34242

      Last Sold Summary

      • 311 Days On Market

      Last Listing Agent Karen Greco GRECO REAL ESTATE

Showing Results 241 - 280, Page 7 of 18

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