Siesta Key, FL Homes

/65
$495,000
- 2 Beds
- 2 Baths
- 929 Sq Ft
1300 N Portofino Dr Unit 103, Sarasota, FL 34242

Welcome to your slice of paradise on world-renowned Siesta Key! Located just steps from the powdery white sands of the #1 beach in the U.S., this beautifully updated 2-bedroom, 2-bathroom condo in the highly desirable Siesta Harbor 55+ community is the ultimate coastal retreat. Bright, spacious, and thoughtfully designed, this residence features stylish luxury vinyl flooring, a beautifully

Rachelle Golden MICHAEL SAUNDERS & COMPANY

1300 N Portofino Dr Unit 103, Sarasota, FL 34242
/21
$5,370 per month
- 1 Bed
- 1 Bath
- 708 Sq Ft
- House for Rent
6006 Midnight Pass Rd Unit 71, Sarasota, FL 34242

Starting at $179/night! Welcome to your vibrant beachside retreat! This charming ground-level condo features a spacious bedroom with a king bed, a sleeper sofa in the living room, and a full bathroom—perfect for relaxation and adventure. Whip up delicious meals in the fully equipped kitchen and enjoy them in the cozy dining area nearby. Convenience is at your fingertips with your own private

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

6006 Midnight Pass Rd Unit 71, Sarasota, FL 34242
/2
$1,200,000 Sold Aug 29, 2025

5740 Midnight Pass Rd Unit 402, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,337 Sq Ft
- Built 1986
Last Sold Summary
- 17% Below List Price
- $898/SF
- 180 Days On Market
Current Estimated Value $1,164,881

Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

5740 Midnight Pass Rd Unit 402, Sarasota, FL 34242

/40
Est $1,544,030 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,156 Sq Ft
599 Commonwealth Ln, Sarasota, FL 34242

599 Commonwealth Ln, Sarasota, FL 34242

/76
$4,475,000
- 4 Beds
- 4.5 Baths
- 4,213 Sq Ft
750 Siesta Key Cir, Sarasota, FL 34242

A refined coastal contemporary waterfront residence, this light-filled 2013 custom home is gracefully positioned within the coveted Siesta Key Baypoint neighborhood. Thoughtfully designed and meticulously maintained, the property presents a rare opportunity to enjoy the benefits of modern construction and recent capital improvements without the cost, uncertainty, or extended timelines of new

Rich Polese COMPASS FLORIDA LLC

750 Siesta Key Cir, Sarasota, FL 34242
/34
$7,900 per month
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
- Condo for Rent
19 Whispering Sands Dr Unit 106, Sarasota, FL 34242

Still available for season January - April 2026l! Two bedroom 2 bath ground floor with view of the Gulf. Step outside and your on the sand! Escape the winter and be on the beach. Located in the heart of Siesta Key’s most desirable area, this property offers exceptional appeal with being just steps from the world-famous powdery white sand beach. Siesta Key Village is within easy walking distance,

Maureen Plichta STRINGER MANAGEMENT INC

19 Whispering Sands Dr Unit 106, Sarasota, FL 34242
/2
$882,500 Sold Mar 07, 2025

431 Island Cir, Sarasota, FL 34242
- 4 Beds
- 2.5 Baths
- 2,346 Sq Ft
- Built 1962
Last Sold Summary
- 9% Below List Price
- $376/SF
- 0 Days On Market
Current Estimated Value $950,810

Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

431 Island Cir, Sarasota, FL 34242

/32
Est $851,555 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,494 Sq Ft
4837 Higel Ave, Sarasota, FL 34242

4837 Higel Ave, Sarasota, FL 34242

/46
$369,999
- 2 Beds
- 1 Bath
- 690 Sq Ft
6157 Midnight Pass Rd Unit G21, Sarasota, FL 34242

SIESTA KEY GEM | from weekly rental income, beach access, turnkey furnished, community pool & bayside amenities - GREAT INVESTMENT. Bay Oaks on world-famous Siesta Key, where bayside tranquility meets unbeatable convenience. Just moments from the powdery white sands of America’s #1 Beach, this beautifully maintained first-floor 2-bedroom, 1-bath condo offers the ultimate blend of relaxation,

Shayla Twit CORCORAN DWELLINGS REALTY

6157 Midnight Pass Rd Unit G21, Sarasota, FL 34242
/51
$6,500 per month
- 2 Beds
- 2 Baths
- 1,337 Sq Ft
- Condo for Rent
5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242

This luxury Siesta Key beachfront unit in the exclusive Gulf and Bay Club offers full panoramic views of the Gulf of Mexico and the #1 beach in the USA, Siesta Key! This beautifully updated 2-bedroom, 2-bathroom unit features hardwood floors, granite countertops, and an abundance of cabinet space. The bathrooms are elegantly updated with tile and granite counters, making this a truly turnkey

Robert Bevington SHOWTIME REALTY

5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
/2
$1,835,000 Sold Jan 29, 2026

5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,713 Sq Ft
- Built 1982
Last Sold Summary
- 6% Below List Price
- $1,071/SF
- 23 Days On Market
Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

5880 Midnight Pass Rd Unit 910, Sarasota, FL 34242

/70
Est $1,787,733 Not Listed For Sale
- 6 Beds
- 5 Baths
- 4,223 Sq Ft
4099 Higel Ave, Sarasota, FL 34242

4099 Higel Ave, Sarasota, FL 34242

/48
$1,795,000 Pending
- 3 Beds
- 3 Baths
- 2,477 Sq Ft
5348 Shadow Lawn Dr, Sarasota, FL 34242

Under contract-accepting backup offers. Set along the Grand Canal in Siesta Isles, this inviting waterfront pool home offers an effortless blend of space, comfort and classic island living. Thoughtfully designed on a single level, the approximately 2,477-square-foot residence features a desirable three-way split floor plan with three private bedroom suites, three baths, a dedicated office or den,

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

5348 Shadow Lawn Dr, Sarasota, FL 34242
/54
$4,500 per month
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Condo for Rent
137 Avenida Messina Unit 2, Sarasota, FL 34242

Flexible lease options available: 12-month annual lease at list price, or 2 plus months stays available for additional fees—perfect whether you're seeking a year-round island home or an extended winter escape. Discover the ultimate Siesta Key lifestyle in this beautifully renovated ground-floor retreat, perfectly positioned less than one block from the heart of Siesta Key Village and two blocks

Laura Rode KELLER WILLIAMS ON THE WATER S

137 Avenida Messina Unit 2, Sarasota, FL 34242
/54
$861,360 Sold May 15, 2025

19 Whispering Sands Dr Unit 303, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
- Built 1973
Last Sold Summary
- 9% Below List Price
- $672/SF
- 1 Day On Market
Current Estimated Value $831,676

Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

19 Whispering Sands Dr Unit 303, Sarasota, FL 34242

/54
Est $1,745,903 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,758 Sq Ft
3902 Somerset Dr Unit 10, Sarasota, FL 34242

3902 Somerset Dr Unit 10, Sarasota, FL 34242

/31
$550,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
1140 S Moonmist Ct Unit M5, Sarasota, FL 34242

FULLY renovated and appointed, in 2025, villa. Offered turnkey furnished, ready to use or rent for the season! The Polynesian Gardens community is well located on Siesta Key's south end; Walking distance to shopping, dining, nightlife of Captain Curt's corner, coffee and ice cream shops, grocery store, public beach access, boat rentals, and all things Siesta Key! Grab a golf cart or Free Trolly

Heide Crino BLUESRQ REAL ESTATE INC

1140 S Moonmist Ct Unit M5, Sarasota, FL 34242
/21
$8,500 per month
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
- Apartment for Rent
5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242

Newly remodeled and furnished “Bougie beach bungalow” on Siesta Key Island. This Condo will “wow” you from the first moment you enter. Just say Alexa turn lights on and your command will be answered. This condo is on the first floor and it’s just a few minutes walk from the siesta key public beach access. The community is very welcoming to all guest and has a heated pool year-round and also many

Stephanie Fox EXP REALTY LLC

5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242
/2
$2,200,000 Sold Feb 06, 2025

452 Canal Rd, Sarasota, FL 34242
- 5 Beds
- 3.5 Baths
- 3,384 Sq Ft
- Built 2008
Last Sold Summary
- 10% Below List Price
- $650/SF
- 29 Days On Market
Current Estimated Value $2,026,433

Last Listing Agent Joseph Kesslak COLDWELL BANKER REALTY

452 Canal Rd, Sarasota, FL 34242

/75
Est $1,673,840 Not Listed For Sale
- 2 Beds
- 3 Baths
- 1,437 Sq Ft
5400 Ocean Blvd Unit 9-3, Sarasota, FL 34242

5400 Ocean Blvd Unit 9-3, Sarasota, FL 34242

/76
$1,299,900
- 2 Beds
- 2 Baths
- 1,915 Sq Ft
1260 Dolphin Bay Way Unit 403, Sarasota, FL 34242

Experience coastal luxury in this beautifully updated 2BR/2BA condo in the gated, waterfront community of Dolphin Bay on Siesta Key. This exceptional 4th floor residence blends modern sophistication with breathtaking Intracoastal Waterway views, creating a serene yet elevated island lifestyle. A charming front porch welcomes you—perfect for relaxing with a favorite beverage while grilling and

Stacey Andrews ANDREWS & ASSOCIATES REALTY

1260 Dolphin Bay Way Unit 403, Sarasota, FL 34242
/70
$6,000 per month
- 2 Beds
- 2 Baths
- 1,182 Sq Ft
- Condo for Rent
5600 Beach Way Dr Unit 113, Sarasota, FL 34242

**FULLY REMODELED, GROUND FLOOR CONDO, ACROSS FROM SIESTA KEY BEACH ** Seasonal Rental only, $6,900/mo plus fees, Minimum Stay required Sandy Feet Retreat is a fully remodeled ground-floor condo located directly across the street from Siesta Key’s main beach access. Recently updated throughout, the residence features a brand-new kitchen with modern appliances, beautifully renovated bathrooms, and

Dave Holt PMI SOUTHWEST FLORIDA

5600 Beach Way Dr Unit 113, Sarasota, FL 34242
/2
$630,000 Sold Jan 07, 2026

753 Tropical Cir, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,695 Sq Ft
- Built 1979
Last Sold Summary
- 21% Below List Price
- $372/SF
- 82 Days On Market
Last Listing Agent Patrick Ritchey RE/MAX ALLIANCE GROUP

753 Tropical Cir, Sarasota, FL 34242

/27
Est $1,011,884 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,650 Sq Ft
717 Edgemere Ln, Sarasota, FL 34242

717 Edgemere Ln, Sarasota, FL 34242

/40
$1,390,000
- 4 Beds
- 3 Baths
- 2,165 Sq Ft
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’s most sought-after neighborhoods. This versatile two-story property is ready for you to move in, renovate, or rebuild into your dream retreat. Designed with entertaining in mind, the home offers multiple outdoor decks and living spaces, plus a relaxing hot tub overlooking the

Kelley Callaway MICHAEL SAUNDERS & COMPANY

4114 Roberts Point Cir, Sarasota, FL 34242
/49
$1,875 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Apartment for Rent
6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242

**DON’T MISS THIS OPPORTUNITY TO LIVE ON WORLD-FAMOUS SIESTA KEY!**ALL UTILITIES & WIFI INCLUDED**Welcome to Midnight Cove II—an impeccably maintained community on Siesta Key, just moments from the powdery white sands of Crescent Beach and minutes from iconic Siesta Beach. A quick ride brings you to Siesta Key Village, where you can enjoy boutique shopping, great dining, cocktails, live music,

Cody Smith RENT SARASOTA

6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242
/2
$660,000 Sold Sep 17, 2025

6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
- Built 1975
Last Sold Summary
- 12% Below List Price
- $512/SF
- 187 Days On Market
Current Estimated Value $652,672

Last Listing Agent Crystal Saly RE/MAX PALM

6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242

/63
Est $3,310,894 Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,457 Sq Ft
5349 Hidden Harbor Rd, Sarasota, FL 34242

5349 Hidden Harbor Rd, Sarasota, FL 34242

/88
$2,199,000
- 5 Beds
- 3.5 Baths
- 3,009 Sq Ft
513 Venice Ln, Sarasota, FL 34242

Welcome to coastal living on Siesta Key. Set along a peaceful canal, 513 Venice Lane blends relaxed comfort, making it ideal as a full-time home, vacation property, or income-producing retreat. With 5 bedrooms, 3.5 baths, multiple indoor/outdoor living spaces, a heated pool with spa, and private dockage, this home captures the best of waterfront living.The main level features two bedrooms,

Curtis Ware KW COASTAL LIVING III

513 Venice Ln, Sarasota, FL 34242
/16
$4,500 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
4660 Ocean Blvd Unit P1, Sarasota, FL 34242

Long term rental turnkey furnished waterfront condo in the desirable Sea Village community. Enjoy stunning views of Big Pass and the Gulf, plus easy access to the community pool. The home features travertine flooring, crown molding, hurricane-rated sliders, plantation shutters, and an open living/dining layout. The kitchen includes wood cabinetry, granite countertops, a breakfast bar, and quality

Nelson Reyes SHOWTIME REALTY

4660 Ocean Blvd Unit P1, Sarasota, FL 34242
/2
$3,995,000 Sold Mar 27, 2025

5306 Siesta Cove Dr, Sarasota, FL 34242
- 4 Beds
- 5.5 Baths
- 4,974 Sq Ft
- Built 1981
Last Sold Summary
- $803/SF
Current Estimated Value $3,549,677

Last Listing Agent Nick Gard COLDWELL BANKER REALTY

5306 Siesta Cove Dr, Sarasota, FL 34242

/32
Est $1,819,386 Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,097 Sq Ft
525 Treasure Boat Way, Sarasota, FL 34242

525 Treasure Boat Way, Sarasota, FL 34242

/49
$1,500,000
- 2 Beds
- 2 Baths
- 1,996 Sq Ft
1374 Moonmist Dr Unit B1, Sarasota, FL 34242

A rare bayfront opportunity to create your dream retreat in Polynesian Gardens on Siesta Key. Experience the allure of waterfront living in this rarely available detached bayfront villa, poised for a fresh vision in the desirable Polynesian Gardens community on Siesta Key. One of only 11 exclusive bayfront residences, this end-unit villa offers sweeping, unobstructed views of the Intracoastal

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

1374 Moonmist Dr Unit B1, Sarasota, FL 34242
/63
$6,400 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 303, Sarasota, FL 34242

Available for season 2026! Welcome to Coastal Living at its finest, perfectly nestled on the sought after barrier island of Siesta Key. Updated unit offers serene water views, abundant natural light and the relaxed elegance that defines Florida living. Located in a meticulously maintained waterfront community, this spacious unit features an open and inviting layout ideal for seasonal

Angela Bailey MONARCH PROPERTY GROUP LLC

1250 N Portofino Dr Unit 303, Sarasota, FL 34242
/2
$1,450,000 Sold Jun 23, 2025

420 Beach Rd Unit 502, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1980
Last Sold Summary
- 18% Below List Price
- $1,102/SF
- 56 Days On Market
Current Estimated Value $1,382,075

Last Listing Agent Anthony Dalesandro BRIGHT REALTY

420 Beach Rd Unit 502, Sarasota, FL 34242

/40
Est $3,296,701 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,416 Sq Ft
250 Island Cir, Sarasota, FL 34242

250 Island Cir, Sarasota, FL 34242

/45
$3,100,000 New Construction
- 4 Beds
- 3 Baths
- 2,292 Sq Ft
276 Island Cir, Sarasota, FL 34242

Under Construction. Flooring is in! Interior and exterior just painted! On schedule to be completed March 2026. Photos are of previous model, finishings may vary. Located just half a mile from the world-famous Siesta Key Beach, this brand-new coastal retreat is nestled on Palm Island, one of the Key’s most coveted waterfront enclaves. Sophisticated yet welcoming, this four bedroom, three bathroom

Michael Cella CELLA'S REAL ESTATE INC

276 Island Cir, Sarasota, FL 34242
/45
$4,500 per month
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- Condo for Rent
5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242

AVAILABLE again starting April 1, 2026! Experience the best of Siesta Key living in this beautifully updated 2-bedroom, 2-bathroom condo at the sought-after Harbor Towers Yacht & Racquet Club. Fully furnished and thoughtfully renovated, this 1,056 sq ft residence offers a perfect blend of comfort and luxury. The primary suite has a king-sized bed and en-suite bath, while the guest bedroom

Anna Williams SHOWTIME REALTY

5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242
/2
$1,400,000 Sold Feb 07, 2025

44 Rockwell Ln, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 1,986 Sq Ft
- Built 1957
Last Sold Summary
- 22% Below List Price
- $705/SF
- 15 Days On Market
Current Estimated Value $2,162,431

Last Listing Agent Erika B EXP REALTY LLC

44 Rockwell Ln, Sarasota, FL 34242

/80
Est $2,814,155 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,571 Sq Ft
5322 Siesta Cove Dr, Sarasota, FL 34242

5322 Siesta Cove Dr, Sarasota, FL 34242

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