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Siesta Key

Siesta Key is an eight-mile-long barrier island connected to Sarasota by bridges on the north and south ends of the key. Although within easy driving distance of downtown Sarasota’s shopping, dining and culture, Siesta Key offers residents privacy and stunningly gorgeous natural surroundings.

Siesta Beach is renowned for having the world’s finest, whitest sand. Both public and private beach access makes Siesta Key an ocean lover’s dream.  An a given day, dolphins, manatees and rare island birds find a safe habitat among the island’s wild sea oats and mangroves.

Siesta Key

All Listings $100,000 - $200,000 $200,000 - $300,000
$300,000 - $400,000 $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $700,000 - $800,000 $800,000 - $900,000
$900,000 - $1,000,000 Over $1,000,000
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Sort listings by:New Listings First
Photo of Listing #A4429163

124 Whispering Sands Cir #v-17, Sarasota, FL - $450,000

Residential, Villa
  • 3 Beds
  • 2 Baths
  • 1,327 SQFT
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Welcome To One Level Living Just Steps From The Sunset Over The Spectacular Gulf Of Mexico! Nestled In The Amenity Rich, Gulf Front Community Of Whispering Sands, This Spacious, Free Standing, 3 Bedroom Villa Features A Highly Desirable 1 Car Gar...

Photo of Listing #A4432989

925 Beach Rd #308, Sarasota, FL - $415,000

Residential, Condo
  • 2 Beds
  • 1 Baths
  • 753 SQFT
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La Siesta Is Located Directly Across The Street From The World Famous Siesta Key Beach. Enjoy The Beautiful Turquoise Gulf Water Views From This 2 Bedroom/1 Bath 3rd Floor Condo. This Unit Offers An Open Floor With Light And Bright Colors, And Is ...

Photo of Listing #A4433821

3955 Roberts Point Rd, Sarasota, FL - $1,500,000

Residential, Single Family Home
  • 5 Beds
  • 4 Baths
  • 2,952 SQFT
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Priced At Dirt Value! Come Build The Home Of Your Dreams Or Bring Your Imagination And Update The 1965 Built, 2,952 Sq/ft Home On An Extremely Rare ½ Acre Lot On Siesta Key With Water On 2 Sides! A Boaters Dream Come True! With No Bridges To Bay, ...

Photo of Listing #A4429107

1125 W Peppertree Dr #703, Sarasota, FL - $749,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,200 SQFT
  • 1 DOM
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Complete Renovation! Stunning Gulf View! This Luxurious Condo Has Been Professionally Remodeled. Enjoy The Views Of The Gulf Of Mexico And The Peppertree Pond View From The Lanai. This 2 Bedroom 2 Bath Condo Features A Spacious Open Plan, Granite ...

Photo of Listing #A4433729

1308 Old Stickney Point Rd #w34, Sarasota, FL - $995,000

Residential, Condo
  • 3 Beds
  • 3 Baths
  • 2,512 SQFT
  • 1 DOM
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Looking For A Siesta Key Condo That Lives Like A Home? How’s 3 Bedrooms, 2 ½ Baths, 17 Years-young Boutique Complex, 2 Under Building Assigned Parking Spaces, Additional 2 Car Private Under Building Garage Available, Updated Kitchen That Opens To ...

Photo of Listing #A4429295

5750 Midnight Pass Rd #309, Sarasota, FL - $700,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,335 SQFT
  • 2 DOM
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Short Sale. Located On The #1 Rated Beaches And One Of The Most Desirable Shorelines In The World. Live The Florida Dream In This Siesta Key Beachfront Retreat. The Exclusive, Gated Gulf & Bay Club Presents An Incredibly Privileged Lifestyle, Ri...

Photo of Listing #A4433397

5110 Sandy Beach Ave, Sarasota, FL - $799,900

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,110 SQFT
  • 2 DOM
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Perfect, Mid-century Modern Style Home With Spacious Outdoor Lanai, Pool, Boat Slip And Davits! What An Outstanding Opportunity To Recreate The Simplistic Timeless Charm Of The 60’s! This Is The Last Wide Canal Before The Grand Canal In Sara Sands...

Photo of Listing #A4432688

1019 W Peppertree Dr #112, Sarasota, FL - $899,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 975 SQFT
  • 2 DOM
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Direct Beach Front Unit!!!! And What A View It Is. Downstairs Walk Out To The Famed Siesta Key Beach. Wake Up Each Morning And Have Your Cup Of Coffee With The Mezmorizing Sound Of Waves Hitting The Beach And Then Evening Comes And You Will Know...

Photo of Listing #A4432544

5750 Midnight Pass Rd #307, Sarasota, FL - $795,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,471 SQFT
  • 3 DOM
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And Here It Is! Absolutely Amazing Sunset Views, Full Gulf Views And Full Private Beach Views Can Be Seen From The Comfort Of This Spectacular 2 Bed/2bath Condo In The Highly Sought After E Building In The Renowned Gulf And Bay Club! This Unit Is ...

Photo of Listing #A4432840

5830 Midnight Pass Rd #87, Sarasota, FL - $449,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 921 SQFT
  • 3 DOM
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This Is Probably One Of The Best Values On Siesta Key!!! No Road To Cross To Get To The Gorgeous Siesta Key Beach!! This Rarely Available, Spacious And Well Appointed 2 Bedroom 2 Bath Villa Located In Beautifully Landscaped Jamaica Royale Is Now A...

Photo of Listing #A4433441

3525 White Ln, Sarasota, FL - $1,749,000

Residential, Single Family Home
  • 3 Beds
  • 2 Baths
  • 2,336 SQFT
  • 3 DOM
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A Tropical Waterfront Paradise On The Coveted North End Of Siesta Key- A Short Distance To Siesta Key Beach And Convenient To The Mainland And Downtown Sarasota. This Beautiful Arthur Rutenberg Home Boasts An Open Floor Plan With Abundant Natural ...

Photo of Listing #A4431472

5880 Midnight Pass Rd #708, Sarasota, FL - $795,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,562 SQFT
  • 5 DOM
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Experience Direct And Full Gulf Views From This Seventh-floor Delightful Residence. Enjoy Scenes Of Spectacular Sunsets. Welcome To A Home That Has Already Been Updated To Todays Style Kitchen And Baths. Move In Ready! Newer White Kitchen With Acc...

Photo of Listing #A4433162

1271 Siesta Bayside Dr #1271-a, Sarasota, FL - $540,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,130 SQFT
  • 5 DOM
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Gulf & Bay Club Bayside - This Beautifully Remodeled Key West-style 2 Bedroom, 2 Bath, 1 Car Garage, Turnkey Furnished Condo With Serene Pond View Has It All! Extremely Meticulously Maintained- Wood Cabinetry, Granite Counter Tops, Wood Floors, ...

Photo of Listing #A4433097

1302 Roberts Bay Ln, Sarasota, FL - $550,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,095 SQFT
  • 6 DOM
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Towering Ceilings Greet You When Entering The Foyer Opening To The Spacious Living Room With A Wood Burning Fireplace. The Dining Room Is Large Enough Accommodate Your Entertaining Needs And Plenty Of Space For Your Favorite Hutch And Dining Table...

Photo of Listing #A4433147

1030 Crescent St, Sarasota, FL - $1,400,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 2,087 SQFT
  • 6 DOM
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Amazing Townhouse Style Home, Just Steps From Crescent Beach At Point Of Rocks, With A Private Heated Pool And Spa. 3 Bedrooms, 3 And A Half Bathrooms And A 2 Car Garage Are Just The Basic Features. This Immaculate Home Is Loaded With Upgrades Suc...

Photo of Listing #A4433238

1201 Tree Bay Ln, Sarasota, FL - $1,990,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,596 SQFT
  • 6 DOM
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Paradise Awaits You In The Quiet Neighborhood Of Tortoise Estates On Siesta Key. Entering Through The Wrought Iron Gate, You Are Invited Into The Warmth & Charm This Italian Mediterranean Estate Residence Offers. The Lush, Ivy Covered Entrance, Le...

Photo of Listing #A4433299

6703 Midnight Pass Rd #115, Sarasota, FL - $358,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 964 SQFT
  • 6 DOM
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Beautifully Updated, Turnkey Furnished Condo In Siesta Key’s South Village! Truly An Ideal Location! Steps To Everything: The Sugary Sands Of Siesta Beach, Nearby Dining, Shopping, Nightlife, Boat & Bike Rentals, And Much More Within A Block Or Tw...

Photo of Listing #A4433205

1223 Mandalay Point Rd, Sarasota, FL - $1,599,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,156 SQFT
  • 6 DOM
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Stunning Bay Front Views From This Designer Remodeled Coastal Cottage On South Siesta Key. This Home Will Wow You From The Door With Gorgeous Wood Floors In The Formal Living And Cozy Slate Fireplace To Curl Up And Read A Book. The Open Kitchen Is...

Photo of Listing #A4432358

5860 Midnight Pass Rd #52, Sarasota, FL - $1,799,000

Residential, Condo
  • 3 Beds
  • 3 Baths
  • 2,160 SQFT
  • 7 DOM
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An Unrivaled Floor-to-ceiling View Of Crystal White Sand Beaches And Shimmering Blue Gulf Waters Will Leave You And Your Guests Speechless. This Is A Once In A Lifetime Opportunity To Own A Direct And On-the-sand Property In The Center Of Siesta ...

Photo of Listing #A4433150

8424 Midnight Pass Rd, Sarasota, FL - $3,995,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 3,760 SQFT
  • 7 DOM
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Home On Beautiful Heron Lagoon. Charming 3 Bedrooms, 2baths, And 2 1/2 Car Garage .gulf View From Upper Level

Photo of Listing #A4433164

627 Waterside Way, Sarasota, FL - $925,000

Residential, Single Family Home
  • 3 Beds
  • 2 Baths
  • 2,346 SQFT
  • 7 DOM
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Charming Home Located On One Of Siesta Key’s Most Desirable Cul-de-sac Streets, With Expansive Views Of The Grand Canal. This Well-built Quality Constructed Home Has Wood Floors, Built-in Cabinetry, And Recessed Lights. Kitchen Has Corian Counters...

Photo of Listing #A4433196

5855 Midnight Pass Rd #128, Sarasota, FL - $524,900

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,404 SQFT
  • 7 DOM
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Wow, Here Is A Condo That Is Dog Friendly And On The Ground Floor So No Elevator Rides To Take Your Best Friend Outside. This Condo Is Located On The Ground Level- Corner Unit With One Screened Lanai--and Two Outdoor Patios. One Patio With 3 Ste...

5424 Avenida Del Mare, Sarasota, FL - $1,199,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,444 SQFT
  • 8 DOM
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Enjoy This Great Grand Canal Location That Is Right Down The Street From The Best Beach In The Us. Situated On This Tropical Oasis Is A Key West Style Home That Is Move In Ready. The Open Floor Plan With Vaulted Ceilings Features A Metal Roo...

7223 Turnstone Rd, Sarasota, FL - $600,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 2,522 SQFT
  • 8 DOM
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Short Sale. Short Sale Subject To Third Party Approval! This Home Is A Candidate For A Tear Down. Excellent Location.

6157 Midnight Pass Rd #e45, Sarasota, FL - $349,900

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,101 SQFT
  • 8 DOM
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Top Floor Unit At Bay Oaks On Siesta Key. Unit Has East And West Views Of Intercoastal And Gulf Of Mexico. Watch The Sunsets From Your Front Balcony. Well Maintained 2 Bedroom, 2 Bath Condo. Great Rental!! Master Bedroom Has Walkin Closet And ...

5830 Midnight Pass Rd #204, Sarasota, FL - $725,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,285 SQFT
  • 8 DOM
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Opportunity Awaits, Just Steps From The Sand With This Beachfront Condo On The Second Floor Offering Elevator Access And A Popular Rental Program With Income Generating Weekly Rentals. Whether Your Desire Is To Redesign, Simply Settle In, Or Inve...

5880 Midnight Pass Rd #507, Sarasota, FL - $1,225,000

Residential, Condo
  • 3 Beds
  • 2 Baths
  • 2,037 SQFT
  • 8 DOM
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Paradise Found! A Rare 3 Bedroom, 2 Bath Fully Renovated Casarina Unit Will Delight All Buyers. Whether You Seek A Beach Sanctuary Offering Water Views And Salty Breezes From Your Patio, Or You Are An Entertainer Looking To Impress The Most Disc...

8779 Midnight Pass Rd #402h, Sarasota, FL - $489,900

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,303 SQFT
  • 8 DOM
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Tranquil Setting At This Gulf To Bay Community With Beach & Boat Docks. Spectacular Views Of Gentle Bay Waters. Every Day Is Like A Vacation With Two Heated Pools, Saunas, Two Lighted Tennis Courts, Pickle Ball, Billiards, Two Car Wash Areas, Two...

112 Whispering Sands Dr #v-23, Sarasota, FL - $585,000

Residential, Condo
  • 3 Beds
  • 2 Baths
  • 1,317 SQFT
  • 8 DOM
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Rarely Available Free Standing Villa With 2 Car Garage Located Within Steps To 800 Feet Of Private Beach Front! This Highly Desirable Detached Villa Lives Like A Single Family Home! The Kitchen Has Been Recently Updated With New Soft Close Drawer...

6415 Midnight Pass Rd #906, Sarasota, FL - $539,900

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,287 SQFT
  • 9 DOM
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Weekly Rentals, Beautiful Views, Easy Access On And Off The Key And Deeded Beach Access, What More Do You Need! This Turnkey Furnished Home Is Move In Ready So Pack Your Bags And Let’s Make A Deal. This Wonderful 9th Floor Unit Offers Spectacular...

626 Avenida De Mayo, Sarasota, FL - $1,160,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,285 SQFT
  • 10 DOM
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New 2018 Construction Custom Contemporary Beach Style Home! Island Living Awaits You In This Exquisitely Designed 3 Bedroom, 2.5 Bath Home Walking Distance To Siesta Key Village And Minutes To The #1 Siesta Key Beach! Great For Coastal Retreat/2nd...

1028 Crescent St, Sarasota, FL - $1,250,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 2,052 SQFT
  • 10 DOM
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Amazing Opportunity To Own An Income Producing Rental Property, Located On Siesta Key, Just Steps Away From Crescent Beach At Point Of Rocks. Sold Fully Furnished, This Home Boasts An Open Floorplan With A Private Pool And Spa. 3 Bedrooms, 3 Bathr...

8600 Midnight Pass Rd #701, Sarasota, FL - $2,100,000

Residential, Condo
  • 3 Beds
  • 4 Baths
  • 2,270 SQFT
  • 10 DOM
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Siesta Key - Hidden Lagoon Beach Club - Penthouse Unit - Full Panoramic Gulf Of Mexico Views. There Are Very Very Few Of These Properties On Siesta Key. A Real Seventh Floor Penthouse, End Unit, With Full South And West Panoramic "gulf Of Mexico" ...

5830 Midnight Pass Rd #13, Sarasota, FL - $479,000

Residential, Villa
  • 2 Beds
  • 2 Baths
  • 784 SQFT
  • 11 DOM
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Lovingly Cared For And Nicely Updated Villa In Popular Jamaica Royale On Glistening Siesta Key Beach. This Unit Has Been The Owner’s Winter Home For Many Years And As Such It Has Not Seen The Wear And Tear Of Rentals – It Does Not Have A Long Rent...

5830 Midnight Pass Rd #107, Sarasota, FL - $499,000

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 921 SQFT
  • 11 DOM
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Priced To Sell! Turnkey Furnished, Updated Two Bedroom, Two Bath Ground Floor Condo. This Residence Was Recently Updated With A New Open Concept Kitchen With Quality Custom Cabinets And Silestone Counter Tops. The Drawers Are Pull Out For Easy Ac...

8750 Midnight Pass Rd #203, Sarasota, FL - $499,900

Residential, Condo
  • 2 Beds
  • 2 Baths
  • 1,650 SQFT
  • 11 DOM
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This Is The Largest 2b/2b Open Floor Plan That Tortuga Offers. Beautifully Done With Granite Tile Counters And Wrap Around, Built In Cabinetry In The Living Room. This Unit Is Sold Turn Key Furnished And Ready To Go. So Move Right In And Start You...

3333 Higel Ave, Sarasota, FL - $2,100,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,956 SQFT
  • 12 DOM
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This Open Concept, Well Maintained, Beautiful Home Is On A Quiet Canopied Street At The North End Of Siesta Key. It Features A Double Lot With Colorful Landscaping And Mature Palms And Trees. It's A Wonderful Place To Entertain As There Are Expans...

146 Avenida Veneccia, Sarasota, FL - $1,399,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 1,438 SQFT
  • 12 DOM
View details More Photos Save

Siesta Key - Siesta Key Beach - Partial Gulf Viiews - Weekly / Daily Rental. This Property Has Many Living Options. Located On Siesta Key, Very Close To Siesta Key Village And Siesta Beach Access. Where To Begin; Built In 1967 This "sarasota Archi...

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on April 18th, 2019 at 9:15pm EDT.