Siesta Key, FL Homes

/46
$1,795,000
- 3 Beds
- 3 Baths
- 2,200 Sq Ft
1260 Dolphin Bay Way Unit 301, Sarasota, FL 34242

Discover this truly exceptional 3-bedroom, 3-bathroom condominium offering mesmerizing views of the Intracoastal Waterway. Redesigned with modern elegance, this home features a spacious chef's kitchen equipped with Sub Zero, Monogram, and Viking appliances, along with an impressive six-foot-tall built-in double-door wine cellar. This stunning residence boasts 9-foot ceilings, copious custom

Mina Johnson MICHAEL SAUNDERS & COMPANY

1260 Dolphin Bay Way Unit 301, Sarasota, FL 34242
/35
$8,200 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242

Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are

Andy Moore GULF COAST REALTY & MANAGEMENT

1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
/2
$455,000 Sold Aug 08, 2025
- 991 Sq Ft
- $459/SF
- 125 Days On Market
- 2 Beds
- 2 Baths
- Built 1969
1250 N Portofino Dr Unit 201, Sarasota, FL 34242

Experience breathtaking views from this stunning, fully remodeled 2-bedroom, 2-bath waterfront condo with Deeded Beach Access! Natural light pours into this corner unit through hurricane impact windows and doors, highlighting the gorgeous canal and Bay vistas. Thoughtfully renovated throughout, this home is move-in ready, offering the perfect space to enjoy the best of Florida living. The open,

Jessica Bow RE/MAX PALM

1250 N Portofino Dr Unit 201, Sarasota, FL 34242

/100
Est $8,793,647 Not Listed For Sale
- 6 Beds
- 9 Baths
- 8,615 Sq Ft
4300 Higel Ave, Sarasota, FL 34242

4300 Higel Ave, Sarasota, FL 34242

/31
$490,000
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242

If you're searching for deeded beach access and resort-style living on beautiful Siesta Key, this 2-bedroom, 1.5-bath condo could be your perfect match. Enjoy peaceful canal views and lush, mature landscaping in a community that remained untouched by flooding during recent hurricanes. The condo is in original condition and ready for your personal touch to transform it into your coastal retreat.

Nancie Kalin MICHAEL SAUNDERS & COMPANY

6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242
/27
$6,300 per month
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Condo for Rent
1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242

Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area,

Andy Moore GULF COAST REALTY & MANAGEMENT

1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
/2
$1,100,000 Sold Aug 05, 2025
- 1,085 Sq Ft
- $1,014/SF
- 119 Days On Market
- 2 Beds
- 1 Bath
- Built 1945
554 Canal Rd, Sarasota, FL 34242

RMF Lot Zoned for WEEKLY RENTALS. Deeded Canal Access Across the street. Investment Opportunity!!!

Curtis Ware KW COASTAL LIVING III

554 Canal Rd, Sarasota, FL 34242

/81
Est $6,879,910 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 7,003 Sq Ft
4205 Higel Ave, Sarasota, FL 34242

4205 Higel Ave, Sarasota, FL 34242

/53
$674,900
- 2 Beds
- 1 Bath
- 753 Sq Ft
925 Beach Rd Unit 311, Sarasota, FL 34242

This third-floor unit in La Siesta offers the updated features that make this a sought-after rental unit. La Siesta is directly across from the main entrance to the world-renowned Siesta Key Public Beach with white sands and turquoise waters. Take your morning coffee on the lanai where you’ll enjoy delightful breezes and gulf views. This two-bedroom one bath unit” a blue heaven” has been totally

June Howell MICHAEL SAUNDERS & COMPANY

925 Beach Rd Unit 311, Sarasota, FL 34242
/54
$9,500 per month
- 3 Beds
- 2 Baths
- 1,835 Sq Ft
- Condo for Rent
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

Andy Moore GULF COAST REALTY & MANAGEMENT

1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
/2
$725,000 Sold Aug 05, 2025
- 980 Sq Ft
- $740/SF
- 152 Days On Market
- 2 Beds
- 2 Baths
- Built 1970
524 Beach Rd Unit A, Sarasota, FL 34242

Welcome to your Oceanfront Oasis! SIESTA KEY is truly in your BACKYARD, so no need to drive or cross the street to get to the soft white sands of this highly acclaimed beach on Florida's Gulf Coast. This downstairs condo unit has been completely renovated in 2024 and is now fully equipped with new appliances, new cabinetry, new bathrooms, new HVAC, new water heater, new flooring, new bathrooms,

Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

524 Beach Rd Unit A, Sarasota, FL 34242

/68
Est $535,310 Not Listed For Sale
- 2 Beds
- 2 Baths
- 900 Sq Ft
1113 N Moonmist Ct Unit L3, Sarasota, FL 34242

1113 N Moonmist Ct Unit L3, Sarasota, FL 34242

/69
$1,000,000
- 4 Beds
- 2 Baths
- 1,859 Sq Ft
630 Venice Ln, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Nestled near the gentle waters of Roberts Bay, this enchanting Siesta Key home rests on a quiet cul de sac street where the only sounds are the whisper of palms and the laughter of neighbors walking by. Though not waterfront, the location captures the essence of island life — peaceful, private, and just moments from where the sun dips into the Gulf.

Rudy Dudon MICHAEL SAUNDERS & COMPANY

630 Venice Ln, Sarasota, FL 34242
/35
$7,400 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242

Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle

Andy Moore GULF COAST REALTY & MANAGEMENT

1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
/2
$570,000 Sold Aug 01, 2025
- 1,152 Sq Ft
- $495/SF
- 59 Days On Market
- 2 Beds
- 2 Baths
- Built 1976
5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242

LOCATION, LOCATION, LOCATION. Welcome to Harbor Towers Yacht & Racquet Club, which recently underwent a full building renovation, including new impact windows and sliders resulting in no damage from the 2024 storms! This fabulous resort-style community allows easy access to the world-famous Siesta Key beach with its quartz sand and stunning sunsets, as well as the Siesta Key Village, offering an

Christine Green COLDWELL BANKER REALTY

5855 Midnight Pass Rd Unit 303, Sarasota, FL 34242

/26
Est $524,800 Not Listed For Sale
- 1 Bed
- 1 Bath
- 728 Sq Ft
6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

/53
$690,000
- 2 Beds
- 2 Baths
- 1,352 Sq Ft
1093 Lake House Cir Unit C205, Sarasota, FL 34242

Discover this wonderful beach retreat and investment opportunity! Perfectly located in one of the most desirable locations in the community and just across the street from the soft, powdery sands of Siesta Key Public Beach ranked # 1 in the USA. This true split plan 2 -bedroom, 2-bath condo at Our House at the Beach offers the ideal setup for coastal living and rental potential. As you step

Pamela Wall MICHAEL SAUNDERS & COMPANY

1093 Lake House Cir Unit C205, Sarasota, FL 34242
/36
$9,500 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242

Welcome to your elevated sanctuary in paradise – a second-floor two-bedroom condo at Gulf & Bay Bayside on the enchanting Siesta Key, Florida. Upon entering, you're immediately greeted by an open-concept living space that seamlessly integrates the interior with the scenic beauty beyond. The living area, adorned with coastal-inspired décor, invites you to relax in comfort while large

Andy Moore GULF COAST REALTY & MANAGEMENT

1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
/2
$2,950,000 Sold Aug 01, 2025
- 3,928 Sq Ft
- $751/SF
- 129 Days On Market
- 4 Beds
- 5 Baths
- Built 2019
4940 Peaceable Way, Sarasota, FL 34242

New price! Experience the epitome of Siesta Key living in this exquisitely crafted residence near Siesta Village and renowned pristine beaches, with every conceivable amenity nearby. On a generous one-third-acre lot, this 2019 custom masterpiece by award-winning John Cannon Homes epitomizes luxury and sophistication. Boasting four spacious bedrooms, an office, and five baths, this home is an

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

4940 Peaceable Way, Sarasota, FL 34242

/2
Est $486,601 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

/12
$1,150,000
- 3 Beds
- 3 Baths
- 1,510 Sq Ft
5453 Avenida Del Mare, Sarasota, FL 34242

Exceptional opportunity on TWO buildable lots just 15 houses from Siesta Key Beach and a leisurely stroll from the village. The existing midcentury durable concrete block 3br/2ba home features pecky cypress siding and beamed ceilings. There is an additional free standing guest cottage. The home was impacted by last years storms, but has been stripped to the studs and is waiting for someone to put

Sue Ann Levin COLDWELL BANKER REALTY

5453 Avenida Del Mare, Sarasota, FL 34242
/41
$7,600 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your

Andy Moore GULF COAST REALTY & MANAGEMENT

1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
/2
$1,300,000 Sold Jul 31, 2025
- 1,902 Sq Ft
- $683/SF
- 43 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
572 Commonwealth Ln, Sarasota, FL 34242

INCREDIBLE VIEWS!.....INCREDIBLE ISLAND LOCATION!....INCREDIBLE INDOOR/OUTDOOR LIVING!....Turnkey Furnished & Located on a Quiet Cul-de-Sac street along the GRAND CANAL with Long Water Views ..... YOU will be "Wowed" by this 3 Bedroom/ 2 Bath Bright and Spacious Open Floor Plan that Seamlessly Flows to Over-Sized Screened Lanai with Heated Salt Water Pool--- Excellent for Entertaining as well as

Michael A Martino KELLER WILLIAMS ON THE WATER S

572 Commonwealth Ln, Sarasota, FL 34242

/52
Est $497,348 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,101 Sq Ft
6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242

6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242

/27
$950,000
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
315 Avenida de Paradisio, Sarasota, FL 34242

Bring your hammer! If you want a house on the water with rock solid bones and a great floorplan this is probably it. 1/4 acre lot, nice covered lanai, walking distance to the Village and beach just beyond that. House has brand new plumbing, windows and roof only a couple years old, ready to be put back together. Can be purchased in tandem with 307 Avenida if you want to start fresh and combined

Jason Skowronski COMPASS FLORIDA LLC

315 Avenida de Paradisio, Sarasota, FL 34242
/30
$7,700 per month
- 2 Beds
- 2 Baths
- 1,130 Sq Ft
- Condo for Rent
1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242

A spacious two bedroom/two bath ground floor home with attached garage. Relax on the private south-facing lanai overlooking a lake featuring a fountain and frequent visits by numerous water birds. After a long day enjoy HDTV and high-speed internet ready to stream your favorite programs. Wireless internet is also available throughout Bayside and at the pools. The living area is tiled, and the

Andy Moore GULF COAST REALTY & MANAGEMENT

1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
/2
$2,900,000 Sold Jul 31, 2025
- 5,423 Sq Ft
- $535/SF
- 117 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1990
875 Siesta Key Cir, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Stunning Waterfront Home on Siesta Key with Spectacular Bayou and Bay Views. Welcome to this exceptional waterfront property located on the serene and sought-after Siesta Key. Situated on a quiet dead-end street, this gorgeous home offers breathtaking views of the bayou and open bay, along with direct access to protected sailboat waters, just 100

Thomas Cail RE/MAX ALLIANCE GROUP

875 Siesta Key Cir, Sarasota, FL 34242

/71
Est $383,267 Not Listed For Sale
- 2 Beds
- 1 Bath
- 690 Sq Ft
6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

/41
$1,300,000
- 3 Beds
- 2 Baths
- 1,511 Sq Ft
307 Avenida de Paradisio, Sarasota, FL 34242

It looks new, because it is new! Nearly every surface touched in this fresh remodel, you'll be the first to spend a night in it since completion. The roof, the AC, the plumbing lines, pool surface and pool equipment, all new. Owned by the same family for decades, and taken care of extremely well. Pocket sliders, a good-sized pool with covered area, and pavered patio. Windows newish as well, only

Jason Skowronski COMPASS FLORIDA LLC

307 Avenida de Paradisio, Sarasota, FL 34242
/24
$4,500 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242

Enjoy our beautiful holiday retreat on Siesta Key Island, with private access to the stunning whites sands of Crescent Beach – Previously voted No. 1 beach in USA! Our 2 bed/2 bath condo located in this uniquely designed low rise ‘Key West’ style complex has ground floor access with sheltered South facing Garden – free WIFI throughout the condo. While away your lazy days on our fishing dock when

Andy Moore GULF COAST REALTY & MANAGEMENT

1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
/2
$650,000 Sold Jul 30, 2025
- 2,919 Sq Ft
- $223/SF
- 130 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1953
813 Plymouth St, Sarasota, FL 34242

Home did have water intrusion and significant damage during the storms. The value is in the land as it Can Be Divided into 2 Parcels. Great opportunity to build 1 or 2 homes in quiet neighborhood near Siesta Key Beach. Short bike ride away to the beach. Located within one mile of Siesta Village! Easy access to the mainland via the North Siesta Bridge to enjoy Southside Village, Downtown,

Georgia Salaverri COMPASS FLORIDA LLC

813 Plymouth St, Sarasota, FL 34242

/82
Est $539,025 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

/53
$1,250,000
- 4 Beds
- 4 Baths
- 2,100 Sq Ft
5244 Winding Way, Sarasota, FL 34242

Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire

Justin Shirley SHIRLEY INTERNATIONAL REALTY

5244 Winding Way, Sarasota, FL 34242
/24
$7,200 per month
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Condo for Rent
1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242

Indulge in the ultimate relaxation experience at our exquisite vacation rental in Gulf and Bay - Bayside on Siesta Key. This meticulously appointed condo offers an abundance of space and comfort, allowing you to unwind in style. From savoring a glass of fine wine on the expansive lanai to reveling in the convenience of a fully equipped, turnkey furnished unit complete with a washer/dryer and a

Andy Moore GULF COAST REALTY & MANAGEMENT

1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242
/2
$1,625,000 Sold Jul 29, 2025
- 2,927 Sq Ft
- $555/SF
- 51 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1978
5181 Sandy Shore Ave, Sarasota, FL 34242

Tucked away at the end of a quiet cul-de-sac on Siesta Key, this well-kept four-bedroom, three-and-a-half-bathroom pool home offers an easygoing waterfront lifestyle with access to the Gulf of Mexico. Set on a corner canal lot with water on two sides and 286 feet of frontage, the property feels private and peaceful, surrounded by the calm beauty of the water. With 2,927 square feet of living

Shasta DeGraw REALTY ONE GROUP MVP

5181 Sandy Shore Ave, Sarasota, FL 34242

/54
Est $464,617 Not Listed For Sale
- 2 Beds
- 1 Bath
- 690 Sq Ft
6157 Midnight Pass Rd Unit B31, Sarasota, FL 34242

6157 Midnight Pass Rd Unit B31, Sarasota, FL 34242

/80
$6,000,000
- 4 Beds
- 3.5 Baths
- 3,446 Sq Ft
251 Cedar Park Cir, Sarasota, FL 34242

This award-winning Modernist home was designed to provide privacy while maintaining direct tranquil water views framed by mature tropical landscaping. In the desired and private lot enclave of Cedar Park, one approaches the residence via a canopied private lane before entering the ideal spot for boaters, car enthusiasts, or those who just enjoy the serenity of the .6-acre grounds with plus/minus

Steve Wexler PREMIER SOTHEBY'S INTERNATIONAL REALTY

251 Cedar Park Cir, Sarasota, FL 34242
/23
$6,900 per month
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Condo for Rent
1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242

This fabulous, updated, one-bedroom PLUS separate sleeping den easily sleeps four guests. The den has a queen size bed for additional sleeping space - Complete with a closet and door for privacy.Relax in the spacious living area or enjoy a glass of wine on the lanai where you can enjoy watching the multitude of birds who visit each day.The condo is turnkey furnished including a

Andy Moore GULF COAST REALTY & MANAGEMENT

1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242
/2
$1,250,000 Sold Jul 28, 2025
- 2,397 Sq Ft
- $521/SF
- 54 Days On Market
- 4 Beds
- 4 Baths
- Built 1969
1014 Contento St, Sarasota, FL 34242

Here's the opportunity you have been waiting for. Incredible floor plan with this concrete block home. Large bedrooms with three on one side and the owner's suite on the other. Large in-home laundry, oversized garage and a corner lot. Wonderful private waterfront living with a pool, dock and easy access to Siesta Beach. The existing floor plan makes it easy to update and if you love terrazzo

Brian Snyder PREMIER SOTHEBY'S INTERNATIONAL REALTY

1014 Contento St, Sarasota, FL 34242

/26
Est $600,870 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

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