9,352

Siesta Key, FL Homes

Section Image
  • /40

    $1,250,000

    Pending
    • 4 Beds
    • 4 Baths
    • 2,173 Sq Ft

    604 Avenida de Mayo, Sarasota, FL 34242

    Back on the market! Beautiful triplex that went through a total renovation 2024. A re-roof project was completed in 2022 and is under a transferable warranty. Property can be rented as 3 separate units - Studio, One Bedroom, Three Bedroom. Property could easily be converted to a duplex (2 BR / 1 BA + 3 BR / 2 BA) in the event the owner prefers to live in one unit and rent the other. Just a few

    Dan DeSoto, Jr MICHAEL SAUNDERS & COMPANY

    604 Avenida de Mayo, Sarasota, FL 34242
  • /23

    $6,900 Per Month

    • 2 Beds
    • 2 Baths
    • 959 Sq Ft
    • Condo for Rent

    1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242

    This fabulous, updated, one-bedroom PLUS separate sleeping den easily sleeps four guests. The den has a queen size bed for additional sleeping space - Complete with a closet and door for privacy.Relax in the spacious living area or enjoy a glass of wine on the lanai where you can enjoy watching the multitude of birds who visit each day.The condo is turnkey furnished including a

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242
  • /2

    $2,200,000

    Sold Jun 22, 2026

    467 Canal Rd Unit 467, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 3,228 Sq Ft
    • Built 2005

    Last Sold Summary

    • 30% Below List Price
    • $682/SF
    • 542 Days On Market

    Current Estimated Value $2,098,374

    Last Listing Agent Dan Miller PREFERRED SHORE LLC

    467 Canal Rd Unit 467, Sarasota, FL 34242
    • /73

      Est $568,240

      Not Listed For Sale

      1500 Cove II Place Unit 532, Sarasota, FL 34242

      • 2 Beds
      • 1.5 Baths
      • 860 Sq Ft
      • Built 1979
      1500 Cove II Place Unit 532, Sarasota, FL 34242

      Last Sold Summary

      • 41 Days On Market

  • /84

    $1,600,000

    • 3 Beds
    • 2.5 Baths
    • 2,557 Sq Ft

    5231 Siesta Cove Dr, Sarasota, FL 34242

    Tucked inside the private enclave of Siesta Cove, this beautifully updated island home offers that rare blend of privacy, space, and an easy walk to world-famous Siesta Key Beach. Set on an oversized 0.35-acre lot, the property features 3 bedrooms, 2.5 baths, and more than 2,500 square feet of bright, open living space designed for both everyday comfort and effortless entertaining. Vaulted

    Natalie Gutwein MICHAEL SAUNDERS & COMPANY

    5231 Siesta Cove Dr, Sarasota, FL 34242
  • /9

    $6,930 Per Month

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • House for Rent

    6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242

    Villa A18 is updated and upgraded with all the amenities to enjoy your home away from home vacation stay! Just steps to the beach voted #1 twice by Dr. Beach. This villa allows up to 6 occupants. You can also enjoy the Florida sunshine just steps away from one of the largest pools located on Siesta Key! Located on the free trolley line you can take a ride into Siesta Key village or south to

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 18, Sarasota, FL 34242
  • /2

    $600,000

    Sold Aug 29, 2025

    4522 Banan Place, Sarasota, FL 34242

    • 2 Beds
    • 2 Baths
    • 978 Sq Ft
    • Built 1962

    Last Sold Summary

    • 17% Below List Price
    • $613/SF
    • 191 Days On Market

    Current Estimated Value $685,600

    Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

    4522 Banan Place, Sarasota, FL 34242
    • /79

      Est $695,262

      Not Listed For Sale

      1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,139 Sq Ft
      • Built 1975
      1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

      Last Sold Summary

      • 48 Days On Market

  • /31

    $950,000

    $45K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,122 Sq Ft

    757 Beach Rd Unit 310, Sarasota, FL 34242

    Front row view of the world-renowned Siesta Key Beach. This unit is situated right across from the public beach and is withing 0.9 miles/3 minutes to the village. This turnkey fully furnished and equipped unit is move in ready. Right thru the front door you are greeted with an open floor plan overlooking the beach and the gulf water views. Smell the salt air as you lounge or dine on your large

    Shirley LaGrange COLDWELL BANKER REALTY

    757 Beach Rd Unit 310, Sarasota, FL 34242
  • /24

    $6,300 Per Month

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

    6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242

    Starting at $210/night! Escape to coastal comfort in this charming 2-bedroom villa just steps from the beach. This beautifully furnished retreat boasts a bright and airy living space with vaulted ceilings, exposed wood beams, and abundant natural light. The open-concept living area features cozy seating, a large flat-screen TV, and stylish coastal décor that perfectly blends comfort with

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242
  • /2

    $5,600,000

    Sold Jan 22, 2026

    251 Cedar Park Cir, Sarasota, FL 34242

    • 4 Beds
    • 3.5 Baths
    • 3,446 Sq Ft
    • Built 2013

    Last Sold Summary

    • 7% Below List Price
    • $1,625/SF
    • 20 Days On Market

    Current Estimated Value $5,532,024

    Last Listing Agent Steve Wexler PREMIER SOTHEBY'S INTERNATIONAL REALTY

    251 Cedar Park Cir, Sarasota, FL 34242
    • /79

      Est $809,842

      Not Listed For Sale

      1600 Cove II Place Unit 424, Sarasota, FL 34242

      • 3 Beds
      • 2.5 Baths
      • 1,720 Sq Ft
      • Built 1979
      1600 Cove II Place Unit 424, Sarasota, FL 34242

      Last Sold Summary

      • 28 Days On Market

  • /32

    $1,350,000

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

    6300 Midnight Pass Rd Unit 708, Sarasota, FL 34242

    Rising gracefully along the shores of Siesta Key, Crystal Sands is one of the island’s most recognizable Gulf-front landmarks, celebrated for its soft architectural curves and commanding 12-story presence at the water’s edge. This7th-floor, two-bedroom, two-bath residence in desirable Stack 8 captures sweeping northwest views and unforgettable sunsets stretching across the horizon. Inside, the

    Rudy Dudon MICHAEL SAUNDERS & COMPANY

    6300 Midnight Pass Rd Unit 708, Sarasota, FL 34242
  • /73

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Condo for Rent

    5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242

    Welcome to Gulf Horizon, your luxurious coastal escape at the Gulf & Bay Club in beautiful Siesta Key. Professionally managed by Gulf Coast Vacations, this stunning 2-bedroom, 2-bathroom sixth-floor gulf-view condo offers the ultimate blend of elegance, comfort, and breathtaking scenery in one of the island’s most exclusive beachfront communities.From the moment you step into the elegant

    Andy Moore GULF COAST REALTY & MANAGEMENT

    5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
  • /2

    $1,950,000

    Sold Dec 18, 2025

    5430 Avenida Del Mare, Sarasota, FL 34242

    • 3 Beds
    • 2 Baths
    • 2,010 Sq Ft
    • Built 1951

    Last Sold Summary

    • 22% Below List Price
    • $970/SF
    • 225 Days On Market

    Current Estimated Value $1,886,096

    Last Listing Agent Jonathan Minerick HOMECOIN.COM

    5430 Avenida Del Mare, Sarasota, FL 34242
    • /61

      Est $971,104

      Not Listed For Sale

      1319 Dockside Place Unit 221, Sarasota, FL 34242

      • 3 Beds
      • 3 Baths
      • 1,827 Sq Ft
      • Built 1982
      1319 Dockside Place Unit 221, Sarasota, FL 34242

      Last Sold Summary

      • 141 Days On Market

  • /37

    $2,500,000

    $195K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1248 Northport Dr, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. Siesta Key, island living at its best. Welcome to your waterside home where you’ll enjoy a carefree, tropical lifestyle all year long. This home has been nicely maintained along with an extensive addition completed in 2015. The original home included two guest bedrooms with adjoining Jack and Jill bath plus a primary suite. The 1,200-square-foot

    Peg Davant PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1248 Northport Dr, Sarasota, FL 34242
  • /78

    $2,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 860 Sq Ft
    • Condo for Rent

    1700 Cove II Place Unit 310, Sarasota, FL 34242

    Available 2950.00 Monthly - April 20th 2026 through December 31st 2026... Not Available 2027 Jan through April 15th 2027 Stunning Water Views & Deeded Beach Access | Siesta Key plus taxes and fees. Live your Dream on Siesta Key for the Summer...Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the

    Robert Bevington SHOWTIME REALTY

    1700 Cove II Place Unit 310, Sarasota, FL 34242
  • /2

    $4,095,000

    Sold Jan 26, 2026

    5078 Sandy Beach Ave, Sarasota, FL 34242

    • 4 Beds
    • 4 Baths
    • 3,164 Sq Ft
    • Built 2024

    Last Sold Summary

    • 5% Below List Price
    • $1,294/SF
    • 2 Days On Market

    Current Estimated Value $3,986,851

    Last Listing Agent Darlene Gamble FINE PROPERTIES

    5078 Sandy Beach Ave, Sarasota, FL 34242
    • /30

      Not Listed For Sale

      5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,270 Sq Ft
      • Built 1974
      5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

      Last Sold Summary

      • 66 Days On Market

  • /34

    $2,240,000

    $352K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,670 Sq Ft

    462 Island Cir, Sarasota, FL 34242

    Beaches, Boating & Bistros. This 3 bedroom, 3 bathroom home has it all. Beaches: Located on Palm Island, an Island on an Island only a 2-minute walk to the world-famous cool quartz sands of Siesta Beach (Beach Access #10). You can walk for miles along the sparkling Gulf waters and watch the dolphins play. Kick back on the white sand, go swimming in the clear water, or simply admire the sunset —

    Dan Miller PREFERRED SHORE LLC

    462 Island Cir, Sarasota, FL 34242
  • /37

    $10,000 Per Month

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

    1125 W Peppertree Dr Unit 102, Sarasota, FL 34242

    A 3 month stay is preferred but will accept a 2 month stay, possible 1 month. Call the office for details.Luxuriously remodeled 2 bedroom 2 full bath unit on the first floor in a gulf side high-rise building.The unit has updated wood tiles throughout, ceiling fans in each room, recessed and updated lighting.The kitchen is fully updated with stainless steel appliances, gorgeous counter

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 102, Sarasota, 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 $735,563

    Last Listing Agent Justin Harris REAL BROKER, LLC

    5223 Shadow Lawn Dr, Sarasota, FL 34242
    • /30

      Est $567,872

      Not Listed For Sale

      5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1976
      5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242

      Last Sold Summary

      • 368 Days On Market

  • /67

    $1,250,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft

    5569 Shadow Lawn Dr, Sarasota, FL 34242

    Under contract-accepting backup offers. NEW SOD AND LANDSCAPING JUST INSTALLED, and a brand-new irrigation system was installed as well to keep everything to paradise standards! Welcome to the heart of world-renowned Siesta Key, where coastal living meets modern luxury. This fully renovated, solidly constructed home offers exceptional quality and thoughtful upgrades throughout, including PGT

    Brittany McCord IRONGATE REALTY INC

    5569 Shadow Lawn Dr, Sarasota, FL 34242
  • /38

    $8,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • Condo for Rent

    1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242

    Welcome to this stunning second-level condo nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this meticulously designed residence offers the epitome of luxurious coastal living.As you step inside, you are greeted by an inviting ambiance that seamlessly blends modern elegance with coastal

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1275 Siesta Bayside Dr Unit 1275B, 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 $660,543

    Last Listing Agent Cindy Furtado WATERSIDE REALTY LLC

    5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242
    • /46

      Est $604,611

      Not Listed For Sale

      141 Avenida Messina Unit 1, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 900 Sq Ft
      • Built 1966
      141 Avenida Messina Unit 1, Sarasota, FL 34242

      Last Sold Summary

      • 119 Days On Market

  • /39

    $1,350,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,498 Sq Ft

    5880 Midnight Pass Rd Unit 804, Sarasota, FL 34242

    An unusual price for an unusual seaside residence. Completely renovated with stunning views from every window. Enjoy your morning coffee on the lanai and relish the downtown skyline as well as the Gulf of Mexico and Siesta Beach. Renovations include completely repainted, impact resistance windows, new interior doors, closet organizers and new front door. Casarina amenities include heated

    Maurice Menager MICHAEL SAUNDERS & COMPANY

    5880 Midnight Pass Rd Unit 804, Sarasota, FL 34242
  • /20

    $3,150 Per Month

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft
    • Condo for Rent

    1250 N Portofino Dr Unit 302, Sarasota, FL 34242

    55+ Harbor View Haven on Siesta Key w/beach access!Discover relaxation and adventure at our Siesta Harbor condo on Siesta Key. This bright 2 bedroom unit offers modern comfort and stunning harbor views from the screened porch. Enjoy deeded beach access and watch breathtaking sunsets. You'll have access to amenities like a fishing pier, boat slips, a pool, and clubhouse activities. Whether

    Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

    1250 N Portofino Dr Unit 302, Sarasota, 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 $990,991

    Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

    19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242
    • /33

      Est $570,518

      Not Listed For Sale

      137 Avenida Messina Unit 2, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 900 Sq Ft
      • Built 1966
      137 Avenida Messina Unit 2, Sarasota, FL 34242

      Last Sold Summary

      • 42 Days On Market

  • /35

    $714,000

    $45K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft

    1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242

    Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized

    Roger Pettingell COLDWELL BANKER REALTY

    1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
  • /38

    $3,300 Per Month

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

    4660 Ocean Blvd Unit G1, Sarasota, FL 34242

    Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added

    Beth Dilley ASCENDIA REAL ESTATE

    4660 Ocean Blvd Unit G1, 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 $1,596,443

    Last Listing Agent Mark Coppens EXP REALTY LLC

    5121 Oxford Dr, Sarasota, FL 34242
    • /62

      Est $697,860

      Not Listed For Sale

      6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242

      • 2 Beds
      • 2 Baths
      • 1,212 Sq Ft
      • Built 1968
      6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242

      Last Sold Summary

      • 115 Days On Market

  • /71

    $699,000

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

    101 Whispering Sands Dr Unit 105, Sarasota, FL 34242

    INCREDIBLE VIEWS!.....INCREDIBLE LOCATION!.....INCREDIBLE COMMUNITY!....You will be Impressed by this Special & Rare Opportunity for TURNKEY FURNISHED Residence with FULL WATER VIEWS throughout all Living Areas!..... Located in the Whispering Sands Community you will be able to WALK to the adjacent Village as well as ENJOY over 800' of PRIVATE deeded "white baby powder quartz sands" Beach Access;

    Michael A Martino KELLER WILLIAMS ON THE WATER S

    101 Whispering Sands Dr Unit 105, Sarasota, FL 34242
  • /31

    $6,000 Per Month

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

    1125 W Peppertree Dr Unit 605, Sarasota, FL 34242

    2 BR - 2 BA - 6 Person Max - Pond View - Gulf-side High-rise - Approx. 150 yards from beachThis property is a 30 night minimum.Unit 1125-605 offers assigned covered parking under the building.The master bedroom offers a King bed and a walk-in glass door shower with 2 vanities.The guest bedroom offers 2 twin beds and a walk-in glass door shower with one vanity.Enjoy the futon

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1125 W Peppertree Dr Unit 605, 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 $4,037,486

      Not Listed For Sale

      5310 Avenida Del Mare, Siesta Key, FL 34242

      • 5 Beds
      • 8 Baths
      • 3,759 Sq Ft
      • Built 2023
      5310 Avenida Del Mare, Siesta Key, FL 34242

      Last Sold Summary

      • 132 Days On Market

Showing Results 201 - 240, Page 6 of 18

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