Siesta Key, FL Homes

/58
$1,700,000
- 4 Beds
- 4 Baths
- 2,397 Sq Ft
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 SOTHEBYS INTL REALTY

1014 Contento St, Sarasota, FL 34242
/58
$8,000 per month
- 3 Beds
- 2 Baths
- 2,002 Sq Ft
- House for Rent
5640 Cape Leyte Dr, Sarasota, FL 34242

It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

Beth Dilley ASCENDIA REAL ESTATE

5640 Cape Leyte Dr, Sarasota, FL 34242
/2
$300,000 Sold Mar 25, 2025
- 975 Sq Ft
- $308/SF
- 4 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
6063 E Peppertree Way Unit 111, Sarasota, FL 34242

Opportunity knocks in the highly sought-after Peppertree community on Siesta Key! This 2-bedroom, 2-bathroom condo boasts stunning views of the Intercoastal Waterway and is just a short walk to the world-famous Siesta Key Beach. Located minutes from the South Bridge, you’ll enjoy easy access to shopping, dining, and all the best island amenities. While the unit was affected by flooding during the

Terri West MICHAEL SAUNDERS & COMPANY

6063 E Peppertree Way Unit 111, Sarasota, FL 34242

/46
Est $634,174 Not Listed For Sale
- 2 Beds
- 2 Baths
- 900 Sq Ft
141 Avenida Messina Unit 1, Sarasota, FL 34242

141 Avenida Messina Unit 1, Sarasota, FL 34242

/37
$599,000
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1200 Cove II Place Unit 832, Sarasota, FL 34242

Turnkey 2BR/1.5BA Condo with Stunning Water Views – Steps from Crescent & Siesta Beaches!Welcome to your slice of paradise! This beautifully maintained 2-bedroom, 1.5-bath condo sits on the 3rd floor, directly across from the sugar sands of Crescent Beach and just a short stroll to world-famous Siesta Beach.Enjoy breathtaking views overlooking the marina and Intracoastal Waterway from your

Peter Lev EXCEPTIONS REALTY

1200 Cove II Place Unit 832, Sarasota, FL 34242
/65
$15,000 per month
- 3 Beds
- 3 Baths
- 2,823 Sq Ft
- House for Rent
5129 Sandy Cove Ave, Sarasota, FL 34242

An ultimate water lover's dream home on Siesta Key (Sleeps 8) this property truly has it all. Kayak or paddle board right from your backyard. Fish from your private dock, and grill your fresh catch poolside while your family splashes in the crystal clear waters of the oversized pool. Watch colorful sunsets while sipping your favorite beverage in the bubbling outdoor spa. This expansive

Beth Dilley ASCENDIA REAL ESTATE

5129 Sandy Cove Ave, Sarasota, FL 34242
/2
$2,750,000 Sold Mar 25, 2025
- 3,198 Sq Ft
- $860/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 1979
5412 Siesta Cove Dr, Sarasota, FL 34242

Set on 110+ feet of waterfront with an impressive 11’ elevation, this exceptional 4BR/3BA, 2-story home is in beautiful condition and is perfectly located in the highly sought-after Siesta Cove neighborhood. Offering peace of mind and luxury living directly on the Intracoastal Waterway in a quiet no-wake zone, the setting is idyllic, with abundant wildlife and frequent dolphin sightings

Ryan Ackerman COLDWELL BANKER REALTY

5412 Siesta Cove Dr, Sarasota, FL 34242

/33
Est $591,470 Not Listed For Sale
- 2 Beds
- 2 Baths
- 900 Sq Ft
137 Avenida Messina Unit 2, Sarasota, FL 34242

137 Avenida Messina Unit 2, Sarasota, FL 34242

/50
$360,000
- 1 Bed
- 1 Bath
- 857 Sq Ft
5631 Midnight Pass Rd Unit 1007, Sarasota, FL 34242

Experience the ultimate paradise at Sands Village in Siesta Key! Whether you're seeking an investment opportunity or a personal oasis, this property has it all. Turn-key furnished, open concept living, full tile flooring, abundance of natural light and plenty of living space are just the beginning of what this property offers. Enjoy access to a beautiful pool, community clubhouse, dedicated

Emily Williams KW COASTAL LIVING III

5631 Midnight Pass Rd Unit 1007, Sarasota, FL 34242
/59
$10,500 per month
- 3 Beds
- 3 Baths
- 1,999 Sq Ft
- House for Rent
5024 Higel Ave, Sarasota, FL 34242

Spectacular is an understatement when describing this updated Siesta Key CANAL FRONT POOL HOME. Once you step inside you'll notice an open-airy floor plan, beautifully decorated to reflect a modern beach-style home! Enjoy the master bedroom with BEAUTIFUL VIEWS of the canal and your very own access to the refreshing POOL and SPACIOUS PATIO! The additional two bedrooms are roomy and private with

Beth Dilley ASCENDIA REAL ESTATE

5024 Higel Ave, Sarasota, FL 34242
/2
$1,295,000 Sold Mar 24, 2025
- 1,009 Sq Ft
- $1283/SF
- 11 Days On Market
- 2 Beds
- 2 Baths
- Built 1968
6312 Midnight Pass Rd Unit 301S, Sarasota, FL 34242

Don’t miss this one. Crescent Arms direct gulf front unit. This unit has a 180 degree view of beautiful Crescent Beach. This unit has been updated completely and the rental numbers reflect it. Two bedrooms Two bath split plan offers complete privacy to all guests. Large family room with fabulous views of the gulf. This unit comes equipped with Hurricane protective doors and was untouched by the

Tom Ward WATERSIDE REALTY LLC

6312 Midnight Pass Rd Unit 301S, Sarasota, FL 34242

/62
Est $763,971 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,212 Sq Ft
6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242

6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242

/50
$1,295,000
- 3 Beds
- 2 Baths
- 1,659 Sq Ft
5432 Cape Leyte Dr, Sarasota, FL 34242

Grab your sunglasses and flip-flops, because this charming Siesta Key retreat is just minutes from world-famous Siesta Beach, the #1 beach in the USA! With powdery white sands and crystal-clear, turquoise waters right around the corner, your beach getaway is within easy reach. Whether you're basking in the sun by day or catching the mesmerizing Gulf sunsets every evening, this is island living at

Judie Berger PREMIER SOTHEBYS INTL REALTY

5432 Cape Leyte Dr, Sarasota, FL 34242
/41
$5,000 per month
- 2 Beds
- 2 Baths
- 1,424 Sq Ft
- House for Rent
5577 Contento Dr, Sarasota, FL 34242

Check out this COMPLETELY REMODELED canal-front pool home on Siesta Key! Picture this: you roll out of bed and grab your coffee, take two steps out of the sliding glass doors, and enjoy it by the saltwater pool. After your coffee, take your morning swim. Then take another 10 steps, or so, and catch some significant fish in the canal which happens to be in your backyard. Chances are that an

Beth Dilley ASCENDIA REAL ESTATE

5577 Contento Dr, Sarasota, FL 34242
/2
$1,000,000 Sold Mar 24, 2025
- 1,271 Sq Ft
- $787/SF
- 46 Days On Market
- 2 Beds
- 2 Baths
- Built 1970
6300 Midnight Pass Rd Unit 810, Sarasota, FL 34242

Ten stack of Crystal Sands on the 8th floor overlooking Crescent Beach on Siesta Key! Original owner, this unit was never rented as an income property. Partially updated over the years, this unit is a blank canvas ready for your vision and beach-inspired design. Onsite management available with a two week minimum. Crystal Sands offers private beach access, two heated swimming pool, and

Rudy Dudon MICHAEL SAUNDERS & COMPANY

6300 Midnight Pass Rd Unit 810, Sarasota, FL 34242

/83
Est $655,675 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
101 Whispering Sands Dr Unit 203, Sarasota, FL 34242

101 Whispering Sands Dr Unit 203, Sarasota, FL 34242

/30
$1,399,000
- 3 Beds
- 4 Baths
- 2,337 Sq Ft
5502 Shadow Lawn Dr, Sarasota, FL 34242

Build your Dream Home or renovate the existing home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Siesta Key. This 14,200 square foot lot boasts approximately 80 feet on a deep canal with a boat dock. New homes and extensive renovations are occurring in this highly sought after neighborhood with its excellent boating water and close proximity to the

Dan Miller PREFERRED SHORE LLC

5502 Shadow Lawn Dr, Sarasota, FL 34242
/52
$6,500 per month
- 2 Beds
- 1 Bath
- 680 Sq Ft
- Condo for Rent
446 Canal Rd Unit 5, Sarasota, FL 34242

You will be charmed by how vibrant and quaint this midcentury ground floor condo is... from the lime green exterior, to the pink hibiscus bushes blooming around the turquoise pool, which is nestled behind the privacy of a fence and garden surrounding the property! THE BEST PART ABOUT THIS UNIT... the Keylime Retreat is a 5 minute walk to the pure white sands of Siesta Beach, and an 8 minute walk

Beth Dilley ASCENDIA REAL ESTATE

446 Canal Rd Unit 5, Sarasota, FL 34242
/2
$1,350,000 Sold Mar 18, 2025
- 1,258 Sq Ft
- $1073/SF
- 1 Day On Market
- 3 Beds
- 2 Baths
- Built 1949
5448 Avenida Del Mare, Sarasota, FL 34242

- Canal front, mangrove lined 100 ft. on the Grand Canal.- 2 buildable lots of record according to Sarasota County- Opportunity to build beautiful waterfront home or develop 2 waterfront homes on separate lots.- Short stroll to the Crystal sands of Siesta Key Beach and Siesta Key Village- Cottage has water damage from recent storms- Property being sold for Land Value

Constantine Stratos COLDWELL BANKER REALTY

5448 Avenida Del Mare, Sarasota, FL 34242

/37
Est $632,122 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1300 Cove II Place Unit 731, Sarasota, FL 34242

1300 Cove II Place Unit 731, Sarasota, FL 34242

/18
$799,900
- Land
- 0.18 Acre
- $4,443,889 per Acre
0 Avenida Leona, Siesta Key, FL 34242

Design Your Legacy on Siesta Key – Premier Waterfront Lot in Siesta ManorWelcome to Lot 17 on Avenida Leona—an extraordinary opportunity to create your own masterpiece in one of Florida’s most coveted coastal enclaves. Nestled along a private, tree-lined lane in Siesta Manor, this canal-front parcel offers the rare combination of deep water access, walkability to Siesta Key Village, and the

Ron Pepka KELLER WILLIAMS ON THE WATER

0 Avenida Leona, Siesta Key, FL 34242
/25
$6,500 per month
- 1 Bed
- 1 Bath
- 959 Sq Ft
- Condo for Rent
1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242

Heaven on Siesta Key, in perfect condition, up to date, and simply beautiful. This spacious, first floor one bedroom with a bay/harbor water view from your lanai is immaculate, beautifully decorated and offers every comfort for your favorite vacation stay. The modern kitchen shines with new cabinets, lighting, paint, and kitchen work desk. Elegant bathroom with new walk in shower featuring

Andy Moore GULF COAST REALTY & MANAGEMENT

1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
/2
$2,210,000 Sold Mar 17, 2025
- 3,889 Sq Ft
- $568/SF
- 18 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1979
5235 Siesta Cove Dr, Sarasota, FL 34242

You will absolutely fall in love with this carefully curated masterpiece on Siesta Key! Nestled in the coveted Siesta Cove neighborhood, this stunning, fully renovated home offers a rare blend of old Florida charm and modern luxury. Situated just half a mile from Siesta Beach, this exceptional residence rests on nearly half an acre, adorned with majestic live oak trees, creating a serene and

Jen Topjun COLDWELL BANKER REALTY

5235 Siesta Cove Dr, Sarasota, FL 34242

/27
Est $630,048 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1600 Cove II Place Unit 414, Sarasota, FL 34242

1600 Cove II Place Unit 414, Sarasota, FL 34242

/22
$1,399,000
- Land
- 0.33 Acre
- $4,239,394 per Acre
5502 Shadow Lawn Dr, Sarasota, FL 34242

Build your Dream Home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Siesta Key. This 14,200 square foot lot is located boasts approximately 80 feet on a deep canal with a boat dock. New homes and extensive renovations are occurring in this fabulous neighborhood with its excellent boating water and close proximity to the beach. The current home

Dan Miller PREFERRED SHORE LLC

5502 Shadow Lawn Dr, Sarasota, FL 34242
/16
$2,750 per month
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
- Condo for Rent
5681 Midnight Pass Rd Unit 104, Sarasota, FL 34242

AVAILABLE FOR 2025 SEASON. Explore the charm of WHITE SANDS VILLAGE, conveniently located just opposite Siesta Key Beach Access. Revel in the updated 2-bedroom, 2-bathroom 2nd floor condo, tucked away serenely at the rear of the picturesque 7-acre community surrounded by lush tropical foliage and gardens. Indulge in the community amenities, including a heated pool, an active clubhouse, and

Michael Sorensen STRINGER MANAGEMENT INC

5681 Midnight Pass Rd Unit 104, Sarasota, FL 34242
/2
$1,575,000 Sold Mar 17, 2025
- 2,156 Sq Ft
- $731/SF
- 272 Days On Market
- 4 Beds
- 3 Baths
- Built 1997
5566 Siesta Estates Ct, Sarasota, FL 34242

PARADISE FOUND! An extremely rare opportunity in a peaceful gated community just ONE block to Siesta Key Beach! Featuring an open floor plan with high ceilings and a plethora of sliding glass doors to access and enjoy the beautiful pool, lanai and private yard beyond, this stunning 4 bed/3 bath home exudes the attention to detail that legendary John Cannon built homes are known for. Details which

George Miller COLDWELL BANKER REALTY

5566 Siesta Estates Ct, Sarasota, FL 34242

/30
Est $580,642 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 872 Sq Ft
5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242

5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242

/56
$685,000
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
225 Hourglass Way Unit 101, Sarasota, FL 34242

Completely renovated from top to bottom, this stunning 2-bedroom, 2-bath condo is located in the highly desirable Whispering Sands community on Siesta Key. Designed with a modern coastal aesthetic, the open-concept layout features luxury vinyl plank flooring, 5-inch baseboards, and all-new 2-panel and louvered doors throughout. The air conditioning ducts in the living areas have been rerouted

Cooper Daves WILLIAM RAVEIS REAL ESTATE

225 Hourglass Way Unit 101, Sarasota, FL 34242
/15
$3,000 per month
- 2 Beds
- 2 Baths
- 1,102 Sq Ft
- House for Rent
5242 Winding Way, Sarasota, FL 34242

Adorable home for rent on Siesta Key. Less than one mile walk to the beach! Open floorplan with tasteful modern furnishings and huge back porch with no rear neighbors all on a quiet little circle neighborhood with a pond in the middle of the circle. Rent starting at $3000 per month. Rate depends on what time of year the rental is for.

Allan Nemore KELLER WILLIAMS ON THE WATER S

5242 Winding Way, Sarasota, FL 34242
/54
$732,000 Sold Mar 14, 2025
- 1,469 Sq Ft
- $498/SF
- 4 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
6285 Midnight Pass Rd Unit 101, Sarasota, FL 34242

Welcome to the Picturesque, Excelsior Beach to Bay condo community on Siesta Key! This 2 bedroom 2 bath home is absolutely delightful from the moment you walk in! With this rarely available end unit...loads of natural light pour in through the abundant windows and glass doors. This desirable open floor plan is ideal for entertaining. The kitchen is immaculate with SS appliances, recessed

Julie Froeschle BERKSHIRE HATHAWAY HOMESERVICE

6285 Midnight Pass Rd Unit 101, Sarasota, FL 34242

/53
Est $704,778 Not Listed For Sale
- 2 Beds
- 2 Baths
- 975 Sq Ft
1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242

1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242

/56
$510,000
- 1 Bed
- 1 Bath
- 751 Sq Ft
5855 Midnight Pass Rd Unit 512, Sarasota, FL 34242

Experience the epitome of coastal living in this beautifully renovated, turn-key furnished 1 bedroom, 1 bath condo, perfectly situated on the 5th floor with breathtaking views of the Intracoastal Waterway. This condo boasts an updated kitchen and bathroom, featuring modern finishes and appliances. Enjoy peace of mind with new hurricane windows and sliding glass doors complete with plantation

Julie Kell COLDWELL BANKER REALTY

5855 Midnight Pass Rd Unit 512, Sarasota, FL 34242
/58
$8,000 per month
- 3 Beds
- 3 Baths
- 1,835 Sq Ft
- Condo for Rent
1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242

Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural

Andy Moore GULF COAST REALTY & MANAGEMENT

1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
/50
$850,000 Sold Mar 14, 2025
- 1,282 Sq Ft
- $663/SF
- 44 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
19 Whispering Sands Dr Unit 103, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Fantastic price reduction on this miracle condo! No storm damage! What a wonderful opportunity for someone to own a ground floor condo steps to a private beach only for Whispering Sands owners and their guests, and the beautiful sparkling blue Gulf waters. This 2 bedroom/2 bath condo has been lovingly cared for by the same family for 27 years. They

Stacy Liljeberg MICHAEL SAUNDERS & COMPANY

19 Whispering Sands Dr Unit 103, Sarasota, FL 34242

/37
Est $655,733 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,259 Sq Ft
5600 Beach Way Dr Unit 315, Sarasota, FL 34242

5600 Beach Way Dr Unit 315, Sarasota, FL 34242

/31
$450,000
- 2 Beds
- 1 Bath
- 690 Sq Ft
6157 Midnight Pass Rd Unit B51, Sarasota, FL 34242

SIESTA KEY BEACH! This is the #1 beach in the US and # 4 in the world! relax in your chaise lounge, on the beach, Listening to Jimmy Buffet and sipping a cold margarita? sounds perfect. Well, It’s here, and just a short walk to the crystal powdery white sandy beach and turquoise waters at your footsteps. The dream of owning Siesta Key is still possible, good rental income. This 1st floor condo

Robin Jones EXIT KING REALTY

6157 Midnight Pass Rd Unit B51, Sarasota, FL 34242
/33
$8,500 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242

Embrace coastal living in this inviting 2-bedroom, 2-bathroom first-level condo nestled within the prestigious Gulf & Bay Club Bayside in Siesta Key, Florida. Step inside to discover a thoughtfully designed space adorned with coastal-inspired décor and an abundance of natural light. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating an ideal space for

Andy Moore GULF COAST REALTY & MANAGEMENT

1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
/2
$1,275,000 Sold Mar 14, 2025
- 1,173 Sq Ft
- $1087/SF
- 27 Days On Market
- 2 Beds
- 2 Baths
- Built 1971
5924 Midnight Pass Rd Unit 209, Sarasota, FL 34242

Just in time for the lucrative winter and spring season on Siesta Key, this stunning two bed, two bath beach condo presents an enticing opportunity to own at the incomparable Sarasota Surf & Racquet while earning income. Located in the highly sought after building Y, this spacious retreat blends coastal living and modern comfort. Located just steps from the sandy shore, life is (literally) a

Rudy Dudon MICHAEL SAUNDERS & COMPANY

5924 Midnight Pass Rd Unit 209, Sarasota, FL 34242

/33
Est $677,416 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5963 Midnight Pass Rd Unit 339, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 339, Sarasota, FL 34242

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