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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808 Properties

808 Featured Properties Available

Name: Open House - 12AM-3PM
Start: 2026-05-23T00:00:00.000Z
End: 2026-05-23T15:00:00.000Z
Location: 1257 S PORTOFINO DR #104, Sarasota, FL 34242

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1257 S PORTOFINO DR #104, Sarasota, FL 34242

$449,900

Open Sat 12AM-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

6480 MIDNIGHT PASS RD #503, Sarasota, FL 34242

$1,199,000

Open Sat 6PM-8PM

Condo

2 Beds 2 Baths 1,265 SqFt

6480 MIDNIGHT PASS RD #503, Sarasota, FL 34242

Turnkey-furnished and move-in ready, experience the ultimate coastal lifestyle in this beautifully maintained beachfront...

Listed by Heather Lakeman EXIT KING REALTY

5760 MIDNIGHT PASS RD ##209D, Sarasota, FL 34242

$1,175,000

Open Sun 1PM-4PM

Condo

2 Beds 2 Baths 1,361 SqFt

5760 MIDNIGHT PASS RD ##209D, Sarasota, FL 34242

Welcome home to Gulf & Bay Club, the premier condominium community on Siesta Key Beach. Enjoy stunning views of the fres...

Listed by Tina Johns COLDWELL BANKER REALTY

1215 S PORTOFINO DR #406, Sarasota, FL 34242

$435,000

Open Sun 1PM-3PM

Condo

2 Beds 2 Baths 929 SqFt

1215 S PORTOFINO DR #406, Sarasota, FL 34242

Escape the winter chill and step into your endless summer at this meticulously maintained, fully turn-key furnished 2-be...

Listed by Miao Whiteside BERKSHIRE HATHAWAY HOMESERVICE

$3,500,000

Open Sat 1PM-4PM

Single Family Home

5 Beds 4 Baths 3,446 SqFt

765 SIESTA KEY CIR, Sarasota, FL 34242

Hidden behind an expansive 250-foot circular driveway, the residence is designed for those who appreciate luxury waterfr...

Listed by Taylor Brady RE/MAX PALM REALTY

$2,350,000

Open Sat 12AM-2PM

Single Family Home

4 Beds 4 Baths 2,977 SqFt

7345 PINE NEEDLE RD, Sarasota, FL 34242

Beautifully renovated 4-bedroom, 4-bath pool home tucked behind the gates of the exclusive Sanderling Club. Surrounded b...

Listed by Amy Nadell COLDWELL BANKER REALTY

$1,072,000

Open Sat 12PM-2PM

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

1080 W PEPPERTREE LN #305A, Sarasota, FL 34242

$1,135,000

Open Sat 12PM-3PM

Condo

2 Beds 2 Baths 1,365 SqFt

1080 W PEPPERTREE LN #305A, Sarasota, FL 34242

Rarely available beach-view residence with deeded access to the renowned shores of Siesta Key Beach. Located on the thir...

Listed by Eliza Miller PEPPERTREE BAY REALTY INC

5740 MIDNIGHT PASS RD #403, Sarasota, FL 34242

$1,950,000

Open Sun 1PM-3PM

Condo

2 Beds 2 Baths 1,449 SqFt

5740 MIDNIGHT PASS RD #403, Sarasota, FL 34242

A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-k...

Listed by Drew Jacobsen COMPASS FLORIDA LLC

6140 MIDNIGHT PASS RD #904, Sarasota, FL 34242

$2,450,000

Open Sat 1PM-4PM

Condo

2 Beds 2 Baths 1,940 SqFt

6140 MIDNIGHT PASS RD #904, Sarasota, FL 34242

Experience the pinnacle of island living in this 9th-floor, west-facing penthouse offering sweeping, unobstructed Gulf a...

Listed by Suki Scollo COLDWELL BANKER REALTY

6140 MIDNIGHT PASS RD #501, Sarasota, FL 34242

$1,895,000

Open Sat 1PM-4PM

Condo

3 Beds 2 Baths 1,798 SqFt

6140 MIDNIGHT PASS RD #501, Sarasota, FL 34242

Spacious and inviting, this TRUE 3-bedroom, 5th-floor end-unit condominium is located directly on Siesta Key's world-ren...

Listed by Suki Scollo COLDWELL BANKER REALTY

$1,800,000

Open Sat 12PM-3PM

Single Family Home

4 Beds 3 Baths 2,233 SqFt

3515 LA PALOMA AVE, Sarasota, FL 34242

Elevated Coastal Living Meets TURNKEY Income on Siesta Key <br> <br>Welcome to 3515 La Paloma Ave, a fully reimagined co...

Listed by Derek Edwards KELLER WILLIAMS ON THE WATER S

6140 MIDNIGHT PASS RD #603, Sarasota, FL 34242

$1,225,000

Open Sat 1PM-4PM

Condo

2 Beds 2 Baths 1,521 SqFt

6140 MIDNIGHT PASS RD #603, Sarasota, FL 34242

Perched on the 6th floor with sweeping, unobstructed western views of the Gulf and world famous Crescent Beach, this spe...

Listed by Suki Scollo COLDWELL BANKER REALTY

$1,250,000

Open Sun 1PM-4PM

Single Family Home

3 Beds 2 Baths 1,796 SqFt

528 RALPH ST, Siesta Key, FL 34242

TURNKEY WATERFRONT INVESTMENT PROPERTY – Ideal for Short-Term Rental <br>Exceptional opportunity to acquire a fully prep...

Listed by Brian Rice EPIQUE REALTY, INC.

$5,395,000

Open 5/20 1PM-4PM

Single Family Home

9 Beds 8 Baths 4,055 SqFt

332 AVENIDA DE MAYO, Sarasota, FL 34242

~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautif...

Listed by Sabrina Ullmann RE/MAX ALLIANCE GROUP

5880 MIDNIGHT PASS RD #511, Sarasota, FL 34242

$2,490,000

Open Sat 11AM-2PM

Condo

3 Beds 4 Baths 2,481 SqFt

5880 MIDNIGHT PASS RD #511, Sarasota, FL 34242

You will be WOWED! by this Furnished 2400+ Sq Ft of Elegant BEACHSIDE LIVING with (3) Generously Sized Bedrooms & (3.5) ...

Listed by Mike Martino KELLER WILLIAMS ON THE WATER S

6415 MIDNIGHT PASS RD #705, Sarasota, FL 34242

$584,500

Open Sun 11AM-2PM

Condo

2 Beds 2 Baths 1,287 SqFt

6415 MIDNIGHT PASS RD #705, Sarasota, FL 34242

Welcome to the best location on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. ...

Listed by Anthony DeLuca DELUCA REALTY INC

6140 MIDNIGHT PASS RD #101, Sarasota, FL 34242

$875,000

Open Sat 1PM-4PM

Condo

1 Bed 1 Bath 1,041 SqFt

6140 MIDNIGHT PASS RD #101, Sarasota, FL 34242

Experience the ultimate Siesta Key beach get-away in your TURNKEY FURNISHED, west-facing condo at Horizons West and just...

Listed by Suki Scollo COLDWELL BANKER REALTY

5201 AVENIDA DEL MARE, Sarasota, FL 34242

$1,450,000

Open Fri 10AM-2PM

Single Family Home

4 Beds 4 Baths 2,802 SqFt

5201 AVENIDA DEL MARE, Sarasota, FL 34242

WELCOME to one of Siesta Key's hidden gems. From this Key West style home, you can walk or bike ride to the soft, quartz...

Listed by Mary Kassen PREFERRED SHORE LLC

137 AVENIDA MESSINA #3, Sarasota, FL 34242

$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

5661 MIDNIGHT PASS RD #401, Sarasota, FL 34242

$469,900

Open Fri 11:30AM-1PM

Condo

2 Beds 2 Baths 1,012 SqFt

5661 MIDNIGHT PASS RD #401, Sarasota, FL 34242

Welcome to coastal living at its best in White Sands Village, a desirable waterfront community ideally located in the mi...

Listed by Lisa Blakeney COLDWELL BANKER REALTY

6063 E PEPPERTREE WAY #111, Sarasota, FL 34242

$825,000

Open Sat 12PM-3PM

Condo

2 Beds 2 Baths 1,115 SqFt

6063 E PEPPERTREE WAY #111, Sarasota, FL 34242

First-Floor Bayfront | No Stairs | Full Bay Views | Outdoor Patio. <br>Enjoy effortless coastal living in this like-new,...

Listed by Eliza Miller PEPPERTREE BAY REALTY INC

$2,450,000

Open Fri 12PM-3PM

Single Family Home

3 Beds 2 Baths 2,276 SqFt

4508 WOODSIDE RD, Sarasota, FL 34242

Welcome to one of Siesta Key's best deep-water boating opportunities, offering quick access to Sarasota Bay and open wat...

Listed by Derek Edwards KELLER WILLIAMS ON THE WATER S

9011 MIDNIGHT PASS RD #426, Sarasota, FL 34242

$569,000

Open Sat 12PM-3PM

Condo

2 Beds 2 Baths 1,093 SqFt

9011 MIDNIGHT PASS RD #426, Sarasota, FL 34242

Location! Location! Location! Great Investment Property, Rent 12 times a year with a 30 day minimum and an onsite manage...

Listed by Sheryl O'Keefe MEDWAY REALTY

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