Siesta Key, FL Homes

/55
$1,975,000
- 3 Beds
- 3 Baths
- 2,210 Sq Ft
868 Siesta Key Cir, Sarasota, FL 34242

PRICE IMPROVEMENT... This island-style, ranch waterfront home offers an incredible opportunity to renovate and make it your own. While it did take on water during Hurricanes Helene and Milton, it boasts several key updates including a newer roof, fresh exterior paint, impact windows and doors, vaulted ceilings, and charming plantation shutters—just a few of the features that make this Siesta Key

Jennifer Thompson

WILLIAM RAVEIS REAL ESTATE

(941) 326-5697

868 Siesta Key Cir, Sarasota, FL 34242
/73
$10,000 per month
- 2 Beds
- 2 Baths
- 1,361 Sq Ft
- Condo for Rent
5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242

Welcome to Gulf Horizon, your luxurious coastal escape at the Gulf & Bay Club in beautiful Siesta Key. Professionally managed by Gulf Coast Vacations, this stunning 2-bedroom, 2-bathroom sixth-floor gulf-view condo offers the ultimate blend of elegance, comfort, and breathtaking scenery in one of the island’s most exclusive beachfront communities.From the moment you step into the elegant

Andy Moore GULF COAST REALTY & MANAGEMENT

5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
/2
$962,500 Sold Oct 03, 2025
- 1,335 Sq Ft
- $721/SF
- 86 Days On Market
- 2 Beds
- 2 Baths
- Built 1984
5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242

Gulf & Bay is one of the finest properties on the island with 32 acres of manicured grounds and 800 feet of private white quartz powder beach. Lush tropical courtyard featuring 3 swimming pools, commercial grade fitness center, racquetball courts, tennis courts, freshwater lake with a unique island barbeque area, two clubhouses, dry saunas and hot tub, and electric charging stations. This is

Brian Livesey WATERSIDE REALTY LLC

5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242

/2
Est $1,258,939 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,520 Sq Ft
312 Calle Miramar Unit S1, Sarasota, FL 34242

312 Calle Miramar Unit S1, Sarasota, FL 34242

/99
$875,000
- Land
- 0.26 Acre
- $3,365,385 per Acre
5019 Commonwealth Dr, Sarasota, FL 34242

A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision—whether you’re seeking a full-time

Dawn Bear

WILLIAM RAVEIS REAL ESTATE

(941) 394-0942

5019 Commonwealth Dr, Sarasota, FL 34242
/45
$5,000 per month
- 3 Beds
- 2 Baths
- 1,840 Sq Ft
- House for Rent
735 Birdsong Ln, Sarasota, FL 34242

Looking for the ultimate Siesta Key getaway? This stunning 3-bedroom, 2-bath home offers everything you need for a dream vacation, just 1 mile from the famous Siesta Key Beach and a quick bike ride to the lively Siesta Key Village! Available Nov 1-Dec 21, 2025, and May 1-Nov 21, 2026. 30 day minimum stay, NOT available annually. Fully turnkey furnished, this home is ready to welcome you the

Scott Nold TNG PROPERTY MANAGEMENT

735 Birdsong Ln, Sarasota, FL 34242
/2
$860,000 Sold Oct 03, 2025
- 1,204 Sq Ft
- $714/SF
- 262 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
1055 Beach Rd Unit B302, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Beautiful sunsets of Siesta Key from one of your private terraces and a complete renovation! This condo offers weekly rentals, 2 spacious balconies, and over $200K in updates. Situated just steps away from the renowned Siesta Beach, famous for its soft, powdery sand. This stunning end unit on the third floor boasts breathtaking views of the Gulf of

Michele Tanner PREFERRED SHORE LLC

1055 Beach Rd Unit B302, Sarasota, FL 34242

/27
Est $730,835 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,043 Sq Ft
5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

5964 Midnight Pass Rd Unit 141, Sarasota, FL 34242

/77
$1,900,000
- 3 Beds
- 3.5 Baths
- 2,480 Sq Ft
548 Beach Rd Unit 540A, Sarasota, FL 34242

Rarely available, this stunning Tiffany Sands townhome on Siesta Key offers an open floor plan with 3 spacious bedrooms featuring walk-in closets, 3.5 baths, and a versatile first-floor bonus room with a full bath and private entrance.Beautifully renovated, this exquisite residence boasts a one-car garage and storage space, multiple large decks, and a patio—perfect for soaking in breathtaking

Jennifer Thompson

WILLIAM RAVEIS REAL ESTATE

(941) 206-4108

548 Beach Rd Unit 540A, Sarasota, FL 34242
/42
$8,500 per month
- 2 Beds
- 2 Baths
- 1,130 Sq Ft
- Condo for Rent
1221 Siesta Bayside Dr Unit 1221A, Sarasota, FL 34242

Beautifully turnkey furnished 2-bedroom, 2-bathroom, ground-floor condo available for monthly rent in a gated, resort-style community on Siesta Key. Just a short 5-minute walk to private access at world-famous Siesta Key Beach, known for its fine quartz sand and turquoise waters. This tropical retreat features a spacious open-concept layout, a fully equipped kitchen, in-unit laundry, private

Sinan Turkomer BROKER & BAKER INTERNATIONAL REALTY

1221 Siesta Bayside Dr Unit 1221A, Sarasota, FL 34242
/2
$715,000 Sold Oct 02, 2025
- 1,652 Sq Ft
- $433/SF
- 87 Days On Market
- 3 Beds
- 2 Baths
- Built 1968
755 Edgemere Ln, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Nestled in a tropical setting, this charming newly updated 3-bedroom 2-bath "beach retreat" located one mile from Siesta Key ‘s #1 ranked beach internationally ...checks all the boxes! New roof, new doors & hurricane impact windows – check! Upon entering a fresh, airy feeling is welcoming. From the ceramic-tiled living room your eye travels beyond

Ryan Ackerman COLDWELL BANKER REALTY

755 Edgemere Ln, Sarasota, FL 34242

/53
Est $508,697 Not Listed For Sale
- 1 Bed
- 1 Bath
- 561 Sq Ft
44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

44 Sandy Cove Rd Unit A4, Sarasota, FL 34242

/42
$5,392,000 New Construction
- 4 Beds
- 6 Baths
- 4,220 Sq Ft
4819 Higel Ave, Sarasota, FL 34242

New Construction. Come see this coastal Siesta Key home located on the Grand Canal. The home is located on prime waterfront property with the best views of the Grand Canal, which provides easy access to the bay. A boater's dream! This three-level waterfront property offers the best in luxurious living, with four spacious bedrooms and four full baths and two half baths. Step inside the impressive

Cassandra Meyer

BRIGHT REALTY

(941) 231-6297

4819 Higel Ave, Sarasota, FL 34242
/49
$10,500 per month
- 2 Beds
- 2 Baths
- 1,270 Sq Ft
- Condo for Rent
5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242

Welcome to your perfect Siesta Key getaway! This beautifully updated 2-bedroom, 2-bath end-unit condo in the Palm Bay Club offers stunning bay views, a bright, open interior, and resort-style amenities—just steps from the Bayfront pool.At 1,270 sq. ft., this is one of the largest condos in Palm Bay. You'll love the driftwood-style cabinetry, quartz countertops, and stainless steel appliances

Robert Bevington SHOWTIME REALTY

5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
/2
$710,000 Sold Oct 01, 2025
- 1,469 Sq Ft
- $483/SF
- 83 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
6265 Midnight Pass Rd Unit 205, Sarasota, FL 34242

Experience the ultimate beachside lifestyle with this beautifully renovated 2-bedroom, 2-bath condo in the sought-after Excelsior community on world-renowned Siesta Key Beach. Designed with a bright, open layout and coastal-inspired finishes, this spacious residence features an updated kitchen and baths, in-unit laundry, and a private screened lanai perfect for relaxing after a day at the

Jake Wittmer THE SUNSHINE STATE COMPANY

6265 Midnight Pass Rd Unit 205, Sarasota, FL 34242

/77
Est $663,225 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

6145 Midnight Pass Rd Unit F-1, Sarasota, FL 34242

/26
$2,554,250 New Construction
- 4 Beds
- 4.5 Baths
- 2,735 Sq Ft
5019 Commonwealth Dr, Sarasota, FL 34242

Pre-Construction. To be built. An exceptional pre-construction opportunity awaits on Commonwealth Drive, one of Siesta Key’s most coveted and picturesque streets. This .26-acre lot, surrounded by multi-million-dollar homes and lush, mature landscaping, is being offered with thoughtfully crafted custom home plans by Yoder Construction—giving buyers a rare chance to build new in a prime island

Dawn Bear

WILLIAM RAVEIS REAL ESTATE

(941) 326-4411

5019 Commonwealth Dr, Sarasota, FL 34242
/53
$5,000 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Condo for Rent
6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

Beachfront Bliss at Casa Mar – Siesta KeyDreaming of a Siesta Key getaway? Welcome to Unit 15 at Casa Mar, a charming 1BR/1BA beachfront condo that offers the perfect mix of relaxation and resort-style fun.Step outside and enjoy exclusive access to Casa Mar’s private stretch of quartz-white sand, complete with lounge chairs for sunbathing and unforgettable Gulf views. Cool off with a swim

Robert Bevington SHOWTIME REALTY

6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
/2
$625,000 Sold Sep 30, 2025
- 1,130 Sq Ft
- $553/SF
- 115 Days On Market
- 2 Beds
- 2 Baths
- Built 1988
1311 Siesta Bayside Dr Unit 1311A, Sarasota, FL 34242

Perfect home for full-time Florida living or a great investment property in highly sought-after Siesta Key! Centrally located at an unbeatable price, this 2-bedroom, 2-bath ground-level condo offers incomparable value. Can be furnished (with the exception of a few personal items) or unfurnished. Neither the unit nor the complex sustained flooding or material damage from the 2024 hurricanes -

Marni Hayden CHROME REALTY LLC

1311 Siesta Bayside Dr Unit 1311A, Sarasota, FL 34242

/66
Est $539,942 Not Listed For Sale
- 1 Bed
- 1 Bath
- 561 Sq Ft
23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

23 Sandy Cove Rd Unit B1-G, Sarasota, FL 34242

/100
$2,659,999
- 4 Beds
- 3 Baths
- 3,541 Sq Ft
5012 Higel Ave, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Discover this FULLY RENOVATED four-bedroom, three-bathroom sanctuary spanning 3,541 square feet, where luxury living meets WATERFRONT tranquility. Situated on almost a half acre lot, with rear views facing west for colorful sunsets, this meticulously crafted residence boasts a heated pool, a floating dock and long seawall inviting water enthusiasts

Rachelle Tirey PREFERRED SHORE LLC

5012 Higel Ave, Sarasota, FL 34242
/37
$6,500 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1215 S Portofino Dr Unit 202, Sarasota, FL 34242

BEAUTIFUL WATERFRONT CONDO ON SIESTA KEY AVAILABLE NOW AND the month of January! CANAL VIEW • BEACH ACCESS • BOAT SLIPS UPON AVAILABILITY - REASONABLY PRICED. Now available In Season and as an annual Rental! Private, beautifully furnished condo with a gorgeous view of the Harbor and Sailboat Water Canal in Siesta Harbor. Enjoy water views of the canal from your enclosed balcony and just a

Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

1215 S Portofino Dr Unit 202, Sarasota, FL 34242
/2
$775,000 Sold Sep 29, 2025
- 1,238 Sq Ft
- $626/SF
- 175 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
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

/41
Est $697,366 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,016 Sq Ft
141 Avenida Messina Unit 3, Sarasota, FL 34242

141 Avenida Messina Unit 3, Sarasota, FL 34242

/76
$18,500,000
- 4 Beds
- 6 Baths
- 8,138 Sq Ft
3799 Flamingo Ave, Sarasota, FL 34242

Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished down to dishes, silverware and a Buddha living wall. The coexistence of indoor and outdoor space blends over 8,000 square feet of indoor space with

Joel Schemmel DOUGLAS ELLIMAN

3799 Flamingo Ave, Sarasota, FL 34242
/38
$15,000 per month
- 3 Beds
- 3 Baths
- 1,898 Sq Ft
- Condo for Rent
22 Sandy Cove Rd Unit 10-5, Sarasota, FL 34242

RATES AND AVAILABILITY VARY. AVAILABLE SEASON 2026! Welcome to a completely renovated, light-filled penthouse in the exclusive Sandy Cove community — where coastal design meets breathtaking Gulf views in every direction. This professionally managed 3-bedroom, 3-bath residence is fully turnkey furnished and thoughtfully designed for relaxed, upscale living.Every inch of the home has been

Cole Collins COLDWELL BANKER REALTY

22 Sandy Cove Rd Unit 10-5, Sarasota, FL 34242
/2
$1,527,000 Sold Sep 26, 2025
- 2,496 Sq Ft
- $612/SF
- 124 Days On Market
- 3 Beds
- 3 Baths
- Built 1960
5033 Oxford Dr, Sarasota, FL 34242

TWO BUILDABLE LOTS! Motivated Seller! Incredible opportunity to build your dream home—or two—on Siesta Key’s iconic Grand Canal. This exceptional waterfront property is located on picturesque Oxford Street, a charming canopy road with direct boating access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Features include an updated seawall cap, a rare covered boat slip and

Jackie Eberley COLDWELL BANKER REALTY

5033 Oxford Dr, Sarasota, FL 34242

/2
Est $756,316 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,660 Sq Ft
1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

1315 Siesta Bayside Dr Unit B, Sarasota, FL 34242

/73
$6,900,000
- 5 Beds
- 7 Baths
- 6,928 Sq Ft
5132 Jungle Plum Rd, Sarasota, FL 34242

Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm

Joel Schemmel DOUGLAS ELLIMAN

5132 Jungle Plum Rd, Sarasota, FL 34242
/36
$14,000 per month
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
- House for Rent
211 Island Cir, Sarasota, FL 34242

AVAILABLE for 2026... Jan., Feb and April Fantastic pool home located .4 mile from Siesta Beach access! Enjoy this completely renovated 3 bedroom / 2bath pool home in Palm Island on Siesta Key. With comfort in mind, vacation memories are waiting to be made here! All furnishings, appliances and flooring are new and decorated in coastal colors. Enjoy a morning walk to the powdery sand beach less

Brenda Cozy COLDWELL BANKER REALTY

211 Island Cir, Sarasota, FL 34242
/2
$375,000 Sold Sep 25, 2025
- 656 Sq Ft
- $572/SF
- 138 Days On Market
- 1 Bed
- 1 Bath
- Built 1973
105 Pass Key Rd Unit 105, Sarasota, FL 34242

ATTENTION: ALL BEACH LOVERS!! Want to own a piece of paradise? Here is your chance!! This FIRST FLOOR 1+ bdrm is located in a private gulf front community. (That is PET FRIENDLY too!) This secluded enclave offers oceanfront panoramic views and just two blocks to Siesta Key VILLAGE! NO hurricane damage and NO upcoming assessments! New AC, hot water tank and hurricane sliders! Your condo boasts

Laura Rodriguez COLDWELL BANKER REALTY

105 Pass Key Rd Unit 105, Sarasota, FL 34242

/68
Est $536,386 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1600 Cove II Place Unit 421, Sarasota, FL 34242

1600 Cove II Place Unit 421, Sarasota, FL 34242

/59
$730,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242

Wow, WHAT A VIEW! Gulf and sunset views from both bedrooms and the living room of this 5th-floor condo. Beautifully turnkey furnished, this large 2 bedroom, 2 bath condo boasts a double master layout, an extended living room/sunroom, and a gorgeously updated kitchen with stainless steel appliances and granite counter tops. Both bathrooms have also been exquisitely updated to maximize space and

Shana Hamel NEXTHOME EXCELLENCE

5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242
/76
$3,500 per month
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
- Condo for Rent
1700 Cove II Place Unit 310, Sarasota, FL 34242

Available 3500.00 Monthly - September 17th 2026 through December 31st 2026... Available January 2026 - 5,000.00 May be rented weekly. l – Stunning Water Views & Deeded Beach Access | Siesta Keyplus taxes and fees. Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the spacious patio, along with

Robert Bevington SHOWTIME REALTY

1700 Cove II Place Unit 310, Sarasota, FL 34242
/2
$875,000 Sold Sep 25, 2025
- 1,361 Sq Ft
- $643/SF
- 493 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
5780 Midnight Pass Rd Unit 710, Sarasota, FL 34242

Gulf & Bay is undeniably one of the top tropical resorts on Siesta Key. Eight Hundred feet of beautiful white sand that makes up famous Siesta Key Beach is just steps outside of your building. Amenity-rich Gulf & Bay boasts Basketball, Tennis, Pickleball, Shuffleboard, Fitness center with Spa and Sauna, grills with picnic areas, three swimming pools, two club houses, electric car charging

Carol Thomas MICHAEL SAUNDERS & COMPANY

5780 Midnight Pass Rd Unit 710, Sarasota, FL 34242

/42
Est $807,587 Not Listed For Sale
- 1 Bed
- 1 Bath
- 816 Sq Ft
5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

5966 Midnight Pass Rd Unit G-62, Sarasota, FL 34242

/32
$539,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 42, Sarasota, FL 34242

Discover the charm of island living in this beautifully remodeled 1-bedroom, 1-bath condo on the Gulf side of Siesta Key. Designed with a laid-back coastal vibe, this home perfectly blends style, comfort, and functionality.The open-concept floor plan showcases luxury vinyl plank flooring throughout, creating a seamless flow from the spacious kitchen to the dining area and inviting living

Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

5830 Midnight Pass Rd Unit 42, Sarasota, FL 34242
/55
$5,000 per month
- 3 Beds
- 2.5 Baths
- 2,080 Sq Ft
- House for Rent
4946 Commonwealth Dr, Sarasota, FL 34242

Short Term Rental-Not available January-April of 2026Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the

Beth Dilley ASCENDIA REAL ESTATE

4946 Commonwealth Dr, Sarasota, FL 34242
/2
$900,000 Sold Sep 24, 2025
- 2,039 Sq Ft
- $441/SF
- 77 Days On Market
- 3 Beds
- 2 Baths
- Built 1963
5572 Shadow Lawn Dr, Sarasota, FL 34242

OWNER IS MOTIVATED! PLEASE BRING A REASONABLE OFFER. WATERFRONT HOME HALF A MILE TO SIESTA BEACH. Welcome to 5572 Shadow Lawn Drive on Siesta Key. This 3 Bedroom, 2 Bath home sits on a 14,300 SQ. FT. LOT, has a private dock and features 102 FEET OF FRONTAGE ON THE GRAND CANAL. Only one fixed bridge at Midnight Pass Rd means GREAT BOATING ACCESS to Sarasota Bay and the Gulf. Or take a short bike

Chris Kernan RE/MAX ALLIANCE GROUP

5572 Shadow Lawn Dr, Sarasota, FL 34242

/43
Est $703,431 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,270 Sq Ft
5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

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