Siesta Key, FL Homes

/40
$820,000
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242

Don't miss out on this opportunity for a turn-key bayside residence in one of Siesta Key's most sought-after resorts. The Palm Bay Club is a beach to bay resort condominium community with an abundance of fine amenities sure to please you and your guests. This residence located on the 2nd floor provides easy access to the day docks, fishing pier, heated pool and large custom hot tub overlooking

Mary Beth Hudson COLDWELL BANKER REALTY

5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242
/57
$7,900 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Property for Rent
4660 Ocean Blvd Unit N1, Sarasota, FL 34242

Escape to Paradise on Siesta Key! Your dream seasonal getaway awaits at 4660 Ocean Blvd Unit N1, Sarasota, FL 34242. Immerse yourself in the tranquil beauty of the Gulf coast, where pristine sands meet crystal-clear waters. This exquisite 2-bedroom, 2-bathroom condo is your ticket to an unforgettable retreat. Step into your sun-drenched sanctuary, tastefully furnished to embody

Robert Bevington SHOWTIME REALTY

4660 Ocean Blvd Unit N1, Sarasota, FL 34242
/2
$375,000 Sold Apr 01, 2025
- 780 Sq Ft
- $481/SF
- 118 Days On Market
- 1 Bed
- 2 Baths
- Built 1968
1215 S Portofino Dr Unit 404, Sarasota, FL 34242

Unbelievable $50K price reduction on this move-in ready Canal front condo. Escape the winter chill and embrace endless summer in this meticulously remodeled 1 bedroom, 2 bathroom Siesta Key condo at Siesta Harbor, priced at only $450,000 with a peek-a-boo ocean view from the 4th floor. The owners have invested over $100K in premium upgrades, including a glassed-in lanai with hurricane impact

Miao Whiteside BERKSHIRE HATHAWAY HOMESERVICE

1215 S Portofino Dr Unit 404, Sarasota, FL 34242

/27
Est $723,959 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

/52
$1,925,000 Open Sun 1PM - 4PM
- 4 Beds
- 5 Baths
- 3,680 Sq Ft
5512 Avenida Del Mare, Sarasota, FL 34242

Siesta Key paradise just steps from the world-famous beach. Embrace the ultimate island lifestyle just moments from the powdery white sands of Siesta Key Beach. Thoughtfully designed for seamless indoor-outdoor living, this expansive coastal haven is perfect as a vacation getaway, lucrative rental, or full-time dream home. Some of the important features included a new roof, Ipe hardwood decks,

Mette Milland MICHAEL SAUNDERS & COMPANY

5512 Avenida Del Mare, Sarasota, FL 34242
/35
$5,000 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Condo for Rent
6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

Welcome to Siesta Dreams at Casa Mar! This 1br/1ba fully equipped condo is perfect for your next beach vacation! Enjoy the resort's private beach in the provided lounge chairs while you dig your toes into the quartz sand. Need a break from the salt water? Take a swim in one of two pools on the property instead. Shuffleboard, tennis, or pickleball interest you? We've got it! The serene

Robert Bevington SHOWTIME REALTY

6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
/2
$890,000 Sold Apr 01, 2025
- 1,361 Sq Ft
- $654/SF
- 124 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242

Rare opportunity to own a turnkey-furnished two-bedroom, two-bath beach oasis on the seventh floor in the highly sought-after D Building with beach access just steps away. Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club offering an incredibly beautiful lifestyle right on the Gulf of Mexico. Enjoy breathtaking sunsets from your personal enclosed veranda. With

Robert Sherman PREMIER SOTHEBYS INTL REALTY

5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242

/73
Est $599,768 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1500 Cove II Place Unit 532, Sarasota, FL 34242

1500 Cove II Place Unit 532, Sarasota, FL 34242

/22
$2,070,000
- 3 Beds
- 2 Baths
- 1,358 Sq Ft
5179 Hidden Harbor Rd, Sarasota, FL 34242

SUBSTANTIAL PRICE DECREASE! Welcome to Hidden Harbor, the premier yachting community located on Siesta Key. The canopy lined, brick paver streets are as lush and tropical as it gets, offering an unparalleled old Florida look and feel. Location, Location, Location... Just minutes away from award winning Siesta Key Beach, Siesta Key Village, and world class shopping, dinning and entertainment in

Todd Nahrwold PREFERRED SHORE LLC

5179 Hidden Harbor Rd, Sarasota, FL 34242
/44
$10,500 per month
- 2 Beds
- 2 Baths
- 1,270 Sq Ft
- Condo for Rent
5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242

SHORT TERM RENTAL This 2 bedroom condo offers bay views, is an end unit, has a light and bright interior and is just steps from the Bayfront pool! There is a sleeper sofa in the living room to accommodate 2 as well. This condo has been beautifully updated and is one of the larger Palm Bay condos boasting 1270 square feet! Spacious open kitchen with driftwood cabinets, stunning quartz

Robert Bevington SHOWTIME REALTY

5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
/2
$1,650,000 Sold Apr 01, 2025
- 3,924 Sq Ft
- $420/SF
- 353 Days On Market
- 6 Beds
- 5.5 Baths
- Built 2000
5598 Siesta Estates Ct, Sarasota, FL 34242

This luxurious John Cannon built home is in a small gated community that is just a short walk to the world famous Siesta Key beach. Enjoy privacy and security at the end of a Cul-de-sac in this well maintained 6 bedroom, 5 ½ bath home, and is being offered Turn-Key furnished. It's the perfect home for Vacationing with Family and Friends. Features include a beautiful Kitchen with granite counter

Darren Duffy RE/MAX PALM REALTY

5598 Siesta Estates Ct, Sarasota, FL 34242

/79
Est $694,947 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,139 Sq Ft
1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

/40
$875,000
- 2 Beds
- 2 Baths
- 1,238 Sq Ft
1900 Cove II Place Unit 133, Sarasota, FL 34242

Welcome to this stunning top-floor condo on Siesta Key, offering breathtaking, panoramic views of the Intracoastal Waterway, a playground to wildlife and impressive boat traffic year-round. This meticulously maintained property combines luxury, comfort, and serene waterfront living, all within steps of the world-renowned Siesta Key Beach. Upon entering, you’re greeted with an expansive open

Rudy Dudon MICHAEL SAUNDERS & COMPANY

1900 Cove II Place Unit 133, Sarasota, FL 34242
/36
$2,300 per month
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1350 N Portofino Dr Unit 207, Sarasota, FL 34242

This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1350 N Portofino Dr Unit 207, Sarasota, FL 34242
/2
$950,000 Sold Mar 31, 2025
- 1,510 Sq Ft
- $629/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 1957
431 Avenida de Mayo, Sarasota, FL 34242

Siesta Key waterfront home, prime location and endless potential! Location, location, location. This exceptional Siesta Key beach home is just near world-famous Siesta Beach and vibrant Siesta Village, offering easy access to top-rated dining, shopping and entertainment. On a large, beautifully landscaped lot along the coveted Grand Canal, this property is a rare find with direct waterfront

Mike Warm PREMIER SOTHEBYS INTL REALTY

431 Avenida de Mayo, Sarasota, FL 34242

/79
Est $802,466 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
1600 Cove II Place Unit 424, Sarasota, FL 34242

1600 Cove II Place Unit 424, Sarasota, FL 34242

/43
$2,095,000
- 4 Beds
- 4 Baths
- 2,767 Sq Ft
4922 Commonwealth Dr, Sarasota, FL 34242

Welcome your Siesta Key dream home Commonwealth Drive, a stunning custom residence located directly on the Grand Canal. This four bedroom, four bathroom home exudes island style and warmth from the moment you see it. The Key West style build has a concrete base level, hardy plank cement siding, and a standing seam metal roof. The main living areas all give way to sunny and palm-lined views of

Drew Russell MICHAEL SAUNDERS & COMPANY

4922 Commonwealth Dr, Sarasota, FL 34242
/59
$6,000 per month
- 2 Beds
- 2 Baths
- 1,840 Sq Ft
- Condo for Rent
1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242

Enjoy one of the best views on Siesta Key ~ unobstructed WATER VIEWS of the Bay/Intercoastal from your private large covered lanai with all new impact glass doors, and have coffee on your own private brick patio with water views that leads right out to the dock. This seasonal rental is available MAY 1, 2025, but this unit does have a 3 month minimum stay. This spacious unit is one of Siesta Key's

Tony Andrews ANDREWS & ASSOCIATES REALTY

1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242
/2
$660,000 Sold Mar 28, 2025
- 1,130 Sq Ft
- $584/SF
- 108 Days On Market
- 2 Beds
- 2 Baths
- Built 1988
1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

Deeded Beach access on Siesta Key! This immaculate corner unit condo is the perfect blend of serenity and modern living, boasting breathtaking views and top-notch amenities. Tucked away amidst lush tropical landscaping, this single-level ground floor condo offers a peaceful pond and fountain view right from your private lanai. It’s an ideal retreat for those seeking tranquility and a connection

Kaitlin Kuhn MICHAEL SAUNDERS & COMPANY

1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

/17
Est $541,625 Not Listed For Sale
- 1 Bed
- 1 Bath
- 612 Sq Ft
6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

/12
$2,200,000 New Construction
- 5 Beds
- 4 Baths
- 3,723 Sq Ft
5174 Sandy Cove Ave, Sarasota, FL 34242

Pre-Construction. To be built. PLEASE READ Pre-Construction. This is your opportunity to take over this project in it's current condition. Welcome to 5174 Sandy Cove Ave, a pinnacle of contemporary elegance nestled in the heart of Sarasota, Florida. Crafted by architect Mark Sultana. This 3900 sq foot new construction home epitomizes the fusion of exquisite design and impeccable craftsmanship,

Troy Jenkins REALTY EXECUTIVES GALLERY

5174 Sandy Cove Ave, Sarasota, FL 34242
/28
$34,995 per month
- 3 Beds
- 4 Baths
- 2,454 Sq Ft
- House for Rent
216 Tenacity Ln, Sarasota, FL 34242

There is nothing like this on Siesta Key available for rental on short term basis. This is truly a beach house, immaculate and beautiful! While there are many gulf front condos, and single family homes are available for rent- there are no private homes directly on the beach, where you can walk right off of the yard on a short path to the powdery Siesta Key beach sands! Direct Gulf of Mexico views

Robin Turner WATERSIDE REALTY LLC

216 Tenacity Ln, Sarasota, FL 34242
/2
$1,800,000 Sold Mar 28, 2025
- 3,653 Sq Ft
- $493/SF
- 212 Days On Market
- 5 Beds
- 4 Baths
- Built 1966
5531 Contento Dr, Sarasota, FL 34242

One or more photo(s) has been virtually staged. This property is priced to sell! Situated on one of the most beautiful boat basins on the island providing exceptional open serene views. Ideally poised on a generous 16,000+ sq ft lot close to the world-renowned Siesta Key Beach, this home offers easy access to powdery white sands and breathtaking sunsets. Enjoy the convenience of Siesta Village

Kim Ogilvie MICHAEL SAUNDERS & COMPANY

5531 Contento Dr, Sarasota, FL 34242

/69
Est $541,362 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,182 Sq Ft
5600 Beach Way Dr Unit 209, Sarasota, FL 34242

5600 Beach Way Dr Unit 209, Sarasota, FL 34242

/29
$525,000
- 1 Bed
- 1 Bath
- 956 Sq Ft
1223 Siesta Bayside Dr Unit 1223D, Sarasota, FL 34242

Welcome to paradise on Siesta Key! This delightful elevated first-floor one-bedroom, one-bath unit in the highly sought-after Gulf and Bay Club Bayside combines comfort, style, and unbeatable convenience—with no flood or storm damage.Enjoy direct deeded beach access just across the street to world-famous Siesta Key Beach, and embrace true resort-style living with incredible amenities at your

Gigi Kuster COLDWELL BANKER REALTY

1223 Siesta Bayside Dr Unit 1223D, Sarasota, FL 34242
/40
$11,000 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242

Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach

Andy Moore GULF COAST REALTY & MANAGEMENT

1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
/2
$3,995,000 Sold Mar 27, 2025
- 4,974 Sq Ft
- $803/SF
- 4 Beds
- 5.5 Baths
- Built 1981
5306 Siesta Cove Dr, Sarasota, FL 34242

This elegant 5,000-square-foot waterfront home offers an exceptional blend of timeless style and modern functionality, with 4 en-suite bedrooms, 6 bathrooms, 2 home offices, 2 laundry rooms, and unmatched storage. A conforming home elevated to 10’ and recently remodeled (2023) with no detail overlooked, it exudes sophistication from the authentic copper lanterns outside to the finest-quality

Nick Gard COLDWELL BANKER REALTY

5306 Siesta Cove Dr, Sarasota, FL 34242

/46
Est $1,831,801 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,088 Sq Ft
5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242

5966 Midnight Pass Rd Unit G-51 & G-58, Sarasota, FL 34242

/33
$1,000,000
- Land
- 0.28 Acre
- $3,571,429 per Acre
734 Canal Rd, Sarasota, FL 34242

Endless Possibilities Just Two Blocks from Siesta Beach! Whether you're looking to build a brand-new island retreat or remodel the existing structure, opportunity awaits—a prime 12,229-square-foot property in the highly sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create

Judie Berger PREMIER SOTHEBYS INTL REALTY

734 Canal Rd, Sarasota, FL 34242
/99
$6,000 per month
- 2 Beds
- 2 Baths
- 1,840 Sq Ft
- Condo for Rent
1280 Dolphin Bay Way Unit 504, Sarasota, FL 34242

LUXURY SIESTA KEY CONDO LIVING ..A beautiful Turnkey 2 bedroom/2 bathroom Penthouse Condominium Plus Den/Office overlooking Sarasota Bay and the Intracoastal Waterway. A king size bed is in the master bedroom with a large walk in closet with built ins and a en suite bathroom. Second bedroom offers a queen size bed along with a walk in closet and en suite bathroom. There is a fabulous enclosed

Jane Hunter JENNETTE PROPERTIES INC

1280 Dolphin Bay Way Unit 504, Sarasota, FL 34242
/2
$2,260,000 Sold Mar 26, 2025
- 3,677 Sq Ft
- $615/SF
- 9 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1961
815 Paradise Way, Sarasota, FL 34242

Luxury Waterfront Home on Siesta Key - Boater's and Entertainer's Paradise! Welcome to your dream waterfront retreat on Siesta Key! This stunning 4 bedroom, 3.5-bathroom home plus bonus room comes FULLY turnkey furnished ready to live in or make it an income earning vacation rental (monthly rentals allowed -some wall art is not included). There are 3 bedrooms on the main floor each with walk-in

Doug Addeo COMMUNITY REALTY ASSOCIATES

815 Paradise Way, Sarasota, FL 34242

/36
Est $615,326 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1400 Cove Place Unit 631, Sarasota, FL 34242

1400 Cove Place Unit 631, Sarasota, FL 34242

/52
$1,000,000
- 3 Beds
- 2 Baths
- 1,412 Sq Ft
734 Canal Rd, Sarasota, FL 34242

Endless Possibilities Just Two Blocks from Siesta Beach! Whether you're looking to remodel the existing structure or build a brand-new island retreat, opportunity awaits—a prime 12,229-square-foot property in the highly sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create

Judie Berger PREMIER SOTHEBYS INTL REALTY

734 Canal Rd, Sarasota, FL 34242
/35
$4,500 per month
- 3 Beds
- 2 Baths
- 1,290 Sq Ft
- House for Rent
5216 Calle de Costa Rica, Sarasota, FL 34242

This cheerful 3 bedroom, 2 bathroom island home begs you to relax, unwind, and take in the warm sunshine. From the moment you walk in the front door its tasteful decor and a cozy comfortable atmosphere will make you feel right at home. Perfect location near the #1 beach in the USA, Siesta Village, and an abundance of shopping, restaurants, bars, coffee shops, and entertainment. The tastefully

Beth Dilley ASCENDIA REAL ESTATE

5216 Calle de Costa Rica, Sarasota, FL 34242
/2
$1,200,000 Sold Mar 26, 2025
- 3,017 Sq Ft
- $398/SF
- 24 Days On Market
- 4 Beds
- 3 Baths
- Built 1977
1225 S View Dr, Sarasota, FL 34242

Welcome to Siesta Cove, a hidden tropical paradise with around 80 homes, just a breezy bike ride away from the world-famous Siesta Key Beach. Larger lots and no-cookie cutter feel here. For a buyer's convenience, this charming residence is offered furnished. Its tucked away from the road, enveloped by mature trees and lush landscaping, offering a serene retreat with its spacious rooms, soaring

Pam Charron COMPASS FLORIDA LLC

1225 S View Dr, Sarasota, FL 34242

/34
Est $691,669 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
199 Whispering Sands Dr Unit 105, Sarasota, FL 34242

199 Whispering Sands Dr Unit 105, Sarasota, FL 34242

/60
$585,000
- 2 Beds
- 2 Baths
- 1,291 Sq Ft
6415 Midnight Pass Rd Unit 204, Sarasota, FL 34242

THE ANCHORAGE - PARADISE AWAITS: A UNIQUE CORNER CONDO WITH DEEDED ACCESS TO SIESTA KEY BEACH ....Experience coastal paradise at this stunning 2-bedroom, 2-bathroom corner condo offering three private balconies and coveted deeded access to TripAdvisor's #1 Rated Beach in the USA. This fully furnished retreat captures Florida's natural beauty through its unique double-aspect design,

Steven McNally ENGEL + VOELKERS SARASOTA

6415 Midnight Pass Rd Unit 204, Sarasota, FL 34242
/48
$13,200 per month
- 3 Beds
- 2.5 Baths
- 2,041 Sq Ft
- Condo for Rent
306 Beach Rd Unit 306, Sarasota, FL 34242

Take some time to get away from it all.. we have the perfect place for you and your family to stay! This Spanish style tri-level home is in one of the greatest locations on Siesta Key Beach, Florida. Walk up the windowed staircase to the second floor where you’ll enjoy cooking and hanging out with the family! Enjoy your morning coffee or dinner on the balcony. Time for some fun in the sun! Walk,

Beth Dilley ASCENDIA REAL ESTATE

306 Beach Rd Unit 306, Sarasota, FL 34242
/2
$520,000 Sold Mar 26, 2025
- 975 Sq Ft
- $533/SF
- 36 Days On Market
- 2 Beds
- 2 Baths
- Built 1974
1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242

Prime second floor walkup, ready for you to enjoy the laid back Siesta Key lifestyle. Meticulously maintained by the current owners for the last 15 years. Warm neutral coastal decor, with an emphasis on preserving the mid-century modern Siesta Key beach vibe. Features include new fridge, range, microwave and dryer (2024). Hurricane grade window installed in 2019. Flatscreen TV's in living area

Marc Rasmussen CORCORAN DWELLINGS REALTY

1048 W Peppertree Ln Unit 118B, Sarasota, FL 34242

/30
Est $769,250 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,270 Sq Ft
5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

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