SIESTA KEY ... The Perfect Blend of Lifestyle & Investment Opportunity

Siesta Key is a true paradise for those seeking the ideal beachfront lifestyle. With its pristine beaches, vibrant neighborhoods, eclectic village dining and entertainment scene, and lucrative investment opportunities (thanks to a thriving tourism industry!) this picturesque barrier island offers the perfect blend of tranquility and excitement.    

When it comes to lifestyle, Siesta Key has it all. Known for its powdery white sands, Siesta Beach consistently ranks among the top beaches in the world.  If you're a sunbather, avid swimmer, or beach volleyball enthusiast, the crystal-clear waters and warm sunshine are sure to bring joy to your everyday life.   Whether you're looking for a cozy cottage, luxury waterfront, condominium or single family, Siesta Key has somethin for every lifestyle!  
Filters Reset
Save Search
708 Properties

708 Featured Properties Available

Map
Grid
782 BIRDSONG LN, Sarasota, FL 34242
1/51 51

$879,900

Open Sun 12PM-4PM

Single Family Home

2 Beds 2 Baths 1,577 SqFt

782 BIRDSONG LN, Sarasota, FL 34242

Virtually Staged. Adorable 2 Bed 2 Bath Plus a BONUS ROOM/Office almost 1600SF living area and move in ready w/ NO HOA o...

Listed by Michelle Shiver KELLER WILLIAMS ON THE WATER S

6267 MIDNIGHT PASS RD #306, Sarasota, FL 34242
1/86 86

$650,137

Open Sun 9AM-12PM

Condo

2 Beds 2 Baths 1,387 SqFt

6267 MIDNIGHT PASS RD #306, Sarasota, FL 34242

Experience the ultimate island lifestyle in this beautifully appointed 2-bedroom, 2-bathroom condo on world-famous Siest...

Listed by Trish Wittmus BERKSHIRE HATHAWAY HOMESERVICE

603 TREMONT ST, Sarasota, FL 34242
1/100 100

$3,690,000

Pending

Single Family Home

4 Beds 5 Baths 3,996 SqFt

603 TREMONT ST, Sarasota, FL 34242

Under contract-accepting backup offers. Perfectly positioned in the heart of Siesta Key, this masterfully crafted New Co...

Listed by Faith Stutzman PHAM REALTY GROUP LLC

8800 MIDNIGHT PASS RD, Sarasota, FL 34242
1/89 89

$3,690,000

Open Sun 1PM-4PM

Single Family Home

4 Beds 5 Baths 3,676 SqFt

8800 MIDNIGHT PASS RD, Sarasota, FL 34242

With gulf sunset views, and walkable private beach access, this New Construction Modern Beach House on Siesta Key mixes ...

Listed by Faith Stutzman PHAM REALTY GROUP LLC

5673 MIDNIGHT PASS RD #201, Sarasota, FL 34242
1/39 39

$460,000

Open 7/4 12:30PM-2PM

Condo

2 Beds 2 Baths 1,012 SqFt

5673 MIDNIGHT PASS RD #201, Sarasota, FL 34242

Welcome to Unit 201 at White Sands Condominium — a bright, airy coastal retreat perfectly positioned on iconic Midnight ...

Listed by Ed French COLDWELL BANKER REALTY

8977 MIDNIGHT PASS RD #519, Sarasota, FL 34242
1/100 100

$585,900

Open Sat 1PM-4PM

Condo

2 Beds 2 Baths 1,233 SqFt

8977 MIDNIGHT PASS RD #519, Sarasota, FL 34242

Wake Up Above Sarasota Bay — Penthouse Views, Coastal Living, and Endless Horizons! <br>Imagine beginning each day from ...

Listed by Amy DiSalvo KELLER WILLIAMS ON THE WATER S

5880 MIDNIGHT PASS RD #907, Sarasota, FL 34242
1/71 71

$1,850,000

Open Sun 1PM-3PM

Condo

3 Beds 2 Baths 2,165 SqFt

5880 MIDNIGHT PASS RD #907, Sarasota, FL 34242

TOP FLOOR. TOP BEACH. TOP NOTCH. This Siesta Key condo checks ALL the hard to find boxes — THREE bedrooms. PRIVATE Beach...

Listed by Christa Spalding COLDWELL BANKER REALTY

1257 S PORTOFINO DR #104, Sarasota, FL 34242
1/96 96

$449,900

Open Sun 1PM-3PM

Condo

1 Bed 2 Baths 780 SqFt

1257 S PORTOFINO DR #104, Sarasota, FL 34242

Bring your boat and dock steps from your back door.. Turnkey living in Siesta Harbor, a 55+ waterfront community, with b...

Listed by Suzy Kolaz KELLER WILLIAMS ON THE WATER S

1224 MOONMIST CIR #S-3, Sarasota, FL 34242
1/46 46

$749,000

Open Sun 12PM-3PM

Condo

3 Beds 3 Baths 1,949 SqFt

1224 MOONMIST CIR #S-3, Sarasota, FL 34242

Outstanding remodeled and updated freestanding 3/3 villa in private and beautiful Polynesian Gardens. New ceramic tile f...

Listed by Stephen Clementi COLDWELL BANKER REALTY

611 VENICE LN, Sarasota, FL 34242
3D

$1,050,000

Open Sun 2PM-4PM

Single Family Home

3 Beds 2 Baths 2,168 SqFt

611 VENICE LN, Sarasota, FL 34242

Island living meets easy everyday comfort in this turnkey furnished Siesta Key pool home. With 3 bedrooms, 2 bathrooms, ...

Listed by Christine Pope MICHAEL SAUNDERS & COMPANY

8635 MIDNIGHT PASS RD #201C, Sarasota, FL 34242
1/47 47

$599,999

Open Sun 11AM-1PM

Condo

2 Beds 2 Baths 1,160 SqFt

8635 MIDNIGHT PASS RD #201C, Sarasota, FL 34242

PRICE REDUCTION! This beautifully FULLY FURNISHED END-UNIT condo is a true gem, offering an abundance of natural light a...

Listed by Justin Piccillo KW COASTAL LIVING III

101 WHISPERING SANDS DR #105, Sarasota, FL 34242
3D

$679,000

Open Sun 1PM-3PM

Condo

2 Beds 2 Baths 1,271 SqFt

101 WHISPERING SANDS DR #105, Sarasota, FL 34242

INCREDIBLE VIEWS!.....INCREDIBLE LOCATION!.....INCREDIBLE COMMUNITY!....You will be Impressed by this Special & Rare Opp...

Listed by Mike Martino KELLER WILLIAMS ON THE WATER S

5790 MIDNIGHT PASS RD #506, Sarasota, FL 34242
1/35 35

$1,170,000

Open Sun 1PM-4PM

Condo

2 Beds 2 Baths 1,335 SqFt

5790 MIDNIGHT PASS RD #506, Sarasota, FL 34242

Gulf-front views at the Gulf & Bay Club, resort living on Siesta Key! Ideally on the fifth floor of the A Building in Gu...

Listed by Lisa Gullick PREMIER SOTHEBY'S INTERNATIONAL REALTY

6287 MIDNIGHT PASS RD #103, Sarasota, FL 34242
1/36 36

$685,000

Open Sun 11:30AM-2:30PM

Condo

2 Beds 2 Baths 1,550 SqFt

6287 MIDNIGHT PASS RD #103, Sarasota, FL 34242

Welcome to your sunny slice of paradise on Siesta Key. This bright and inviting south-facing condominium offers a great ...

Listed by Peg Davant PREMIER SOTHEBY'S INTERNATIONAL REALTY

5507 CONTENTO DR, Sarasota, FL 34242
1/91 91

$1,725,000

Open Sun 1PM-4PM

Single Family Home

3 Beds 3 Baths 1,788 SqFt

5507 CONTENTO DR, Sarasota, FL 34242

A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000l...

Listed by Livya Hament PREFERRED SHORE LLC

4708 OCEAN BLVD #E7, Sarasota, FL 34242
1/39 39

$2,299,000

Open Sun 1PM-4PM

Condo

3 Beds 3 Baths 2,277 SqFt

4708 OCEAN BLVD #E7, Sarasota, FL 34242

Experience refined coastal living in North Siesta Key at 4708 Ocean Boulevard, a fully renovated 2025 corner residence i...

Listed by Stacey King MICHAEL SAUNDERS & COMPANY

137 AVENIDA MESSINA #3, Sarasota, FL 34242
1/36 36

$625,000

Open Thu 1PM-4PM

Condo

2 Beds 2 Baths 900 SqFt

137 AVENIDA MESSINA #3, Sarasota, FL 34242

Discover this beautiful upstairs furnished condo in a highly desirable complex that is ideally situated in the Mira Mar ...

Listed by Jackie de Manio Eberley COLDWELL BANKER REALTY

4508 WOODSIDE RD, Sarasota, FL 34242
3D

$2,450,000

Open Sun 1PM-4PM

Single Family Home

3 Beds 2 Baths 2,341 SqFt

4508 WOODSIDE RD, Sarasota, FL 34242

The Fastest Open-Water Access Available on Siesta Key Under $2.5 Million <br>Less than 3 minutes to Sarasota Bay, 95 fee...

Listed by Derek Edwards KELLER WILLIAMS ON THE WATER S

1035 SEASIDE DR #404, Sarasota, FL 34242
1/44 44

$2,600,000

Open Sun 12PM-3PM

Condo

2 Beds 3 Baths 1,646 SqFt

1035 SEASIDE DR #404, Sarasota, FL 34242

Experience beachfront ownership that works for you. Residence 404 at Ten35 Seaside offers a rare opportunity to own a fu...

Listed by Jeff Lauer EXP REALTY LLC

6144 MIDNIGHT PASS RD #2N, Sarasota, FL 34242
1/53 53

$1,699,000

Open Sun 12PM-2PM

Condo

2 Beds 2 Baths 1,204 SqFt

6144 MIDNIGHT PASS RD #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 livin...

Listed by Susan Keal MICHAEL SAUNDERS & COMPANY

300 GARDEN LN, Sarasota, FL 34242
1/26 26

$2,790,000

Open Sun 9AM-5PM

Single Family Home

4 Beds 4 Baths 3,256 SqFt

300 GARDEN LN, Sarasota, FL 34242

A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! <br> <br>D...

Listed by Holly Parry WILLIAM RAVEIS REAL ESTATE

1350 N PORTOFINO DR #107, Sarasota, FL 34242
1/55 55

$373,900

Open Sun 1PM-3PM

Condo

1 Bed 2 Baths 780 SqFt

1350 N PORTOFINO DR #107, Sarasota, FL 34242

SIESTA HARBOR...55+...BEAUTIFUL CANAL & Intercoastal Water Way VISTAS with boats slowly IDILYING By and YOU HAVE BEACH A...

Listed by Scotty Ledford VUE REALTY, LLC

6285 MIDNIGHT PASS RD #403, Sarasota, FL 34242
1/51 51

$639,000

Open Sun 1PM-4PM

Condo

2 Beds 2 Baths 1,306 SqFt

6285 MIDNIGHT PASS RD #403, Sarasota, FL 34242

PRICE REDUCTION for this bright and airy south-facing penthouse! <br>Coveted for its soaring ceilings and the opportuni...

Listed by Joan Winters EXIT KING REALTY

521 CUMMINGS ST, Sarasota, FL 34242
1/56 56

$1,450,000

New

Single Family Home

3 Beds 3 Baths 2,500 SqFt

521 CUMMINGS ST, Sarasota, FL 34242

Tucked away on a quiet cul-de-sac on north Siesta Key, this Key West-inspired canal-front retreat captures the ease of c...

Listed by Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 1
  • 2
  • 3
  • 4
  • 5
  • ...
  • 30
Quick Search