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!

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549 Properties

549 Featured Properties Available

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$1,730,000

Active

Single Family Home

5 Beds 3 Baths 2,901 SqFt

156 SIESTA DR, Sarasota, FL 34242

Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best ...

Listed by KW COASTAL LIVING III

4114 ROBERTS POINT CIR, Sarasota, FL 34242

$1,600,000

Active

Single Family Home

4 Beds 3 Baths 2,165 SqFt

4114 ROBERTS POINT CIR, Sarasota, FL 34242

Discover the chance to own a meticulously maintained 4-bedroom, 3-bathroom home in Roberts Point—one of North Siesta Key...

Listed by MICHAEL SAUNDERS & COMPANY

6157 MIDNIGHT PASS RD #G21, Sarasota, FL 34242

$399,000

Active

Condo

2 Beds 1 Bath 690 SqFt

6157 MIDNIGHT PASS RD #G21, Sarasota, FL 34242

Welcome to Bay Oaks Condominiums on world-famous Siesta Key, Florida—an island paradise on the Gulf of Mexico, home to t...

Listed by CORCORAN DWELLINGS REALTY

$8,995,000

Active

Single Family Home

5 Beds 6 Baths 6,455 SqFt

265 CEDAR PARK CIR, Sarasota, FL 34242

A truly exceptional waterfront retreat in one of Sarasota's most coveted enclaves—Cedar Park Circle on North Siesta Key—...

Listed by COMPASS FLORIDA LLC

1255 E PEPPERTREE DR #201, Sarasota, FL 34242

$560,000

Active

Condo

2 Beds 2 Baths 1,460 SqFt

1255 E PEPPERTREE DR #201, Sarasota, FL 34242

Move in ready AND priced to sell quickly! Don't miss the chance to own this beautifully updated turnkey furnished 2-bedr...

Listed by MICHAEL SAUNDERS & COMPANY

8776 MIDNIGHT PASS RD #C107, Sarasota, FL 34242

$6,000

Active

Condo

2 Beds 2 Baths 1,338 SqFt

8776 MIDNIGHT PASS RD #C107, Sarasota, FL 34242

Available for Annual Rental – Experience the best of Siesta Key living at the Island Reef Association on Turtle Beach. T...

Listed by SHOWTIME REALTY

$18,900,000

Active

Single Family Home

5 Beds 7 Baths 7,756 SqFt

8250 SANDERLING RD, Sarasota, FL 34242

Positioned on the white sands of Siesta Key, 8250 Sanderling Road is more than a residence; it is a bold statement in mo...

Listed by DOUGLAS ELLIMAN

$1,329,000

Active

Multi-Family

4 Beds 2 Baths 1,392 SqFt

1141 SUN N SEA DR, Sarasota, FL 34242

Exceptional Investment Opportunity Awaits! Just a two-minute stroll from the stunning white sands of Siesta Key Beach, S...

Listed by COMPASS FLORIDA LLC

$1,200,000

Active

Condo

2 Beds 2 Baths 1,363 SqFt

460 BEACH RD #B2, Sarasota, FL 34242

This beach front opportunity in spindrift does not come around often! With a prime Siesta beachfront unit within a three...

Listed by NORTHGROUP REAL ESTATE, INC

5600 BEACH WAY DR #304, Sarasota, FL 34242

$760,000

Active

Condo

2 Beds 2 Baths 1,182 SqFt

5600 BEACH WAY DR #304, Sarasota, FL 34242

Top-Floor Gulf View Retreat Where Coastal Comfort Meets Modern Living This fully renovated, top-floor condo in the hear...

Listed by EXP REALTY LLC

8779 MIDNIGHT PASS RD #401H, Sarasota, FL 34242

100

$595,000

Active

Condo

2 Beds 2 Baths 1,485 SqFt

8779 MIDNIGHT PASS RD #401H, Sarasota, FL 34242

Reserve your place in the sun for this Winter and years to come! ENJOY THE BAY VIEWS FROM THIS UPDATED HOME! Kitchen wit...

Listed by MICHAEL SAUNDERS & COMPANY

5830 MIDNIGHT PASS RD #46, Sarasota, FL 34242

$559,000

Price Dropped by $36K

Condo

1 Bed 1 Bath 728 SqFt

5830 MIDNIGHT PASS RD #46, Sarasota, FL 34242

Welcome to your ultimate coastal retreat! This stunning 1-bedroom, 1-bathroom ground floor condo has been completely ren...

Listed by KELLER WILLIAMS ON THE WATER S

6157 MIDNIGHT PASS RD #A51, Sarasota, FL 34242

$365,000

Price Dropped by $30K

Condo

2 Beds 1 Bath 690 SqFt

6157 MIDNIGHT PASS RD #A51, Sarasota, FL 34242

This charming updated ground floor condo features 2 bedrooms and 1 bathroom and is the lowest priced unit in the Bay Oak...

Listed by TAM BAY REALTY LLC

8776 MIDNIGHT PASS RD #C307, Sarasota, FL 34242

$2,750

Active

Condo

2 Beds 2 Baths 1,338 SqFt

8776 MIDNIGHT PASS RD #C307, Sarasota, FL 34242

Available June 1 2026 at this time. <br>Experience the best of Beach to Bay Luxury Resort-Style Living in this beautif...

Listed by SHOWTIME REALTY

6006 MIDNIGHT PASS RD #51, Sarasota, FL 34242

$600,000

Active

Condo

1 Bed 1 Bath 600 SqFt

6006 MIDNIGHT PASS RD #51, Sarasota, FL 34242

Welcome to Casa Mar on Siesta Key. A weekly rental property that can serve you as an investment and a beach vacation gat...

Listed by KW COASTAL LIVING III

5855 MIDNIGHT PASS RD #314, Sarasota, FL 34242

$495,000

Active

Condo

1 Bed 1 Bath 751 SqFt

5855 MIDNIGHT PASS RD #314, Sarasota, FL 34242

Attention Boaters, Kayakers and Tennis players! Located in the heart of Siesta Key overlooking the Sarasota Little Bay, ...

Listed by FLORIDA & NEW YORK REAL ESTATE

4859 COMMONWEALTH DR, Sarasota, FL 34242

$1,250,000

Active

Multi-Family

3 Beds 3 Baths 2,222 SqFt

4859 COMMONWEALTH DR, Sarasota, FL 34242

INCOME-GENERATING TRIPLEX JUST MINUTES FROM WORLD-FAMOUS SIESTA KEY BEACH! <br>Located in the desirable Siesta Beach nei...

Listed by HARRY ROBBINS ASSOC INC

137 AVENIDA MESSINA #2, Sarasota, FL 34242

$4,500

Active

Condo

2 Beds 2 Baths 900 SqFt

137 AVENIDA MESSINA #2, Sarasota, FL 34242

Perfectly situated just one block from the heart of Siesta Key Village and a mere two blocks from the pristine white san...

Listed by COLDWELL BANKER REALTY

8897 MIDNIGHT PASS RD #105, Sarasota, FL 34242

100

$538,000

Active

Condo

2 Beds 2 Baths 1,233 SqFt

8897 MIDNIGHT PASS RD #105, Sarasota, FL 34242

Siesta Key! Sunrise Cove has beautifully maintained grounds. Pool and Bay views. Two bedroom, two bath! Kitchen with all...

Listed by MICHAEL SAUNDERS & COMPANY

6005 MIDNIGHT PASS RD #S4, Sarasota, FL 34242

$6,000

Active

Villa

2 Beds 2 Baths 1,210 SqFt

6005 MIDNIGHT PASS RD #S4, Sarasota, FL 34242

Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Be...

Listed by CONCESSION REAL ESTATE COMP.

1255 DOCKSIDE PL #211, Sarasota, FL 34242

$3,600

Active

Condo

3 Beds 2 Baths 1,737 SqFt

1255 DOCKSIDE PL #211, Sarasota, FL 34242

Welcome to your ideal Siesta Key retreat! This charming 2-bedroom, 2-bath condo comfortably sleeps up to 6 guests and is...

Listed by CONCESSION REAL ESTATE COMP.

8701 MIDNIGHT PASS RD #106A, Sarasota, FL 34242

$3,400

Active

Condo

2 Beds 2 Baths 1,357 SqFt

8701 MIDNIGHT PASS RD #106A, Sarasota, FL 34242

Prime Location! Prime Living! Whether you're a local professional or a traveling professional seeking a long-term home b...

Listed by KW COASTAL LIVING III

6150 MIDNIGHT PASS RD #Unit 10 A&B, Sarasota, FL 34242

$1,395,000

Active

Condo

4 Beds 3 Baths 1,962 SqFt

6150 MIDNIGHT PASS RD #Unit 10 A&B, Sarasota, FL 34242

A rare investment opportunity awaits with this proven income-producing property on world-renowned Siesta Key Beach. Loca...

Listed by RE/MAX ALLIANCE GROUP

$1,685,000

Price Dropped by $100K

Single Family Home

3 Beds 2 Baths 1,972 SqFt

5164 WINDWARD AVE, Sarasota, FL 34242

***SELLER FINANCING AVAILABLE*** Tucked away on a quiet dead-end street, this exceptional waterfront estate on Siesta K...

Listed by WILLIAM RAVEIS REAL ESTATE

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