Siesta Key, FL Homes

/53
$75,000
- 3 Beds
- 3 Baths
- 2,255 Sq Ft
915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242

Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the

Kelly Mooney

DOUGLAS ELLIMAN

(941) 352-4595

915 Seaside Dr Unit 607, Weeks 14-15, Sarasota, FL 34242
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/20
$6,500 per month
- 2 Beds
- 2 Baths
- 1,264 Sq Ft
- House for Rent
143 Whispering Sands Dr, Sarasota, FL 34242

Available for season 2026! This 2 bedroom 2 bath villa with easy ground floor entry features tile flooring in the main living areas and plush new carpeting in the bedrooms. The stylish galley kitchen has been fully updated with custom white cabinetry, granite countertops and backsplash, recessed lighting, and brand-new GE appliances, perfect for preparing meals after a day at the beach.Enjoy

Maureen Plichta STRINGER MANAGEMENT INC

143 Whispering Sands Dr, Sarasota, FL 34242
/2
$729,000 Sold Oct 17, 2025
- 1,280 Sq Ft
- $570/SF
- 96 Days On Market
- 2 Beds
- 2 Baths
- Built 1988
1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242

Casual Elegance defines this Refined Residence. Whether a year-round retreat, vacation or investment property, this luxuriously appointed turnkey-furnished 2B/2B in Gulf & Bay Club Bayside will leave you feeling refreshed! Immaculately clean and featuring: a lovely water view, easy single level living, Private Beach access and Deeded Driveway w GARAGE makes coming home to this unit a breeze ~

Gina LaRouche COLDWELL BANKER REALTY

1240 Siesta Bayside Dr Unit 1240C, Sarasota, FL 34242

/47
Est $827,714 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,307 Sq Ft
1321 Dockside Place, Sarasota, FL 34242

1321 Dockside Place, Sarasota, FL 34242

/52
$75,000
- 3 Beds
- 3 Baths
- 1,780 Sq Ft
915 Seaside Dr Unit 606, Weeks 12-13, Sarasota, FL 34242

Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the

Kelly Mooney

DOUGLAS ELLIMAN

(941) 271-5462

915 Seaside Dr Unit 606, Weeks 12-13, Sarasota, FL 34242
/36
$7,500 per month
- 1 Bed
- 1 Bath
- 728 Sq Ft
- Condo for Rent
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

Robert Bevington SHOWTIME REALTY

5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
/2
$4,300,000 Sold Oct 17, 2025
- 3,721 Sq Ft
- $1,156/SF
- 108 Days On Market
- 4 Beds
- 4 Baths
- Built 2000
244 Cedar Park Cir, Sarasota, FL 34242

Located in an exclusive enclave of multi-million-dollar homes, this custom residence offers a special combination of privacy, prestige, and move-in-ready waterfront living. Ideal for boating and car enthusiasts, this residence was completely updated in 2018 and is set on a beautifully landscaped 0.6-acre lot. Cedar Park owners can enjoy private beach access to a pristine beach overlooking Big

Bev Murray BERKSHIRE HATHAWAY HOMESERVICE

244 Cedar Park Cir, Sarasota, FL 34242

/2
Est $6,582,490 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 7,506 Sq Ft
1250 Hidden Harbor Way, Sarasota, FL 34242

1250 Hidden Harbor Way, Sarasota, FL 34242

/28
$695,000
- 2 Beds
- 2 Baths
- 1,025 Sq Ft
145 Avenida Messina Unit 3, Sarasota, FL 34242

Welcome to this wonderful condominium complex directly on the edge of the Siesta Key Village! This UPSTAIRS unit has been completely remodeled from top to bottom and is absolutely stunning! The opened kitchen features stainless steel appliances, handsome quartz counters, and a tan tiger-look cabinetry. There is all new lighting, fans, receptacles and switches, and a neutral plank-like ceramic

Joe Cleary

RE/MAX ALLIANCE GROUP

(941) 941-9881

145 Avenida Messina Unit 3, Sarasota, FL 34242
/70
$7,500 per month
- 2 Beds
- 2 Baths
- 896 Sq Ft
- Condo for Rent
1137 N Moonmist Ct Unit L7, Sarasota, FL 34242

This is a short term rental. Listing reflects peak season rate. Available peak season months: January 2026, February 2026, April 2026. Welcome to The Blue Luna, a serene stand-alone villa nestled in the tropical paradise of Polynesian Gardens on Siesta Key. This two-bedroom, two-bathroom home has been thoughtfully decorated with a calming, coastal blue palette that reflects the soft light of the

Beth Dilley ASCENDIA REAL ESTATE

1137 N Moonmist Ct Unit L7, Sarasota, FL 34242
/2
$1,000,000 Sold Oct 17, 2025
- 2,753 Sq Ft
- $363/SF
- 263 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1959
5072 Higel Ave, Sarasota, FL 34242

SIGNIFICANT PRICE IMPROVEMENT! Discover the rare opportunity to build or renovate on an exceptional .36-acre canal-front property located in the sought-after Sara Sands neighborhood on Siesta Key. Tucked away in a serene, upscale enclave just moments from the vibrant Siesta Key Village and the world-renowned Siesta Key Beach, this property offers the perfect blend of tranquility and convenience.

Susie Gillum COLDWELL BANKER REALTY

5072 Higel Ave, Sarasota, FL 34242

/72
Est $1,371,651 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,876 Sq Ft
22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

/53
$695,000
- 2 Beds
- 2 Baths
- 1,035 Sq Ft
141 Avenida Messina Unit 4, Sarasota, FL 34242

The absolute best of both worlds! About a 2/3 mile walk to the gulf beach access and about 100 feet to the Siesta Key Village! This second-floor condo was completely renovated in 2020. The owners created a stunning home away from home that features a relaxing front sliding glass-enclosed patio that can be opened to enjoy the gentle gulf breezes. The opened kitchen has lightly veined white quartz

Joe Cleary

RE/MAX ALLIANCE GROUP

(941) 336-4378

141 Avenida Messina Unit 4, Sarasota, FL 34242
/17
$2,000 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Apartment for Rent
6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242

What a deal!! Included is water, electric, wi-fi and cable. Tenant has access to all amenities located within Midnight Cove II such as tennis courts, swimming pool and grilling/picnic area.

Michelle Lentini EXCEPTIONS REALTY

6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242
/2
$3,000,000 Sold Oct 15, 2025
- 4,486 Sq Ft
- $669/SF
- 148 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2006
137 Big Pass Ln, Sarasota, FL 34242

**BELOW APPRAISED VALUE**This exquisite Key West-inspired residence, perfectly positioned along Siesta Key's pristine Gulf waters, embodies the epitome of sophisticated coastal living. Spanning an impressive 4,486 square feet, this custom-built haven seamlessly blends casual elegance with luxurious comfort.The home's grand entrance welcomes you through a covered porch into a spectacular

Dion Souza SARABAY REAL ESTATE INC

137 Big Pass Ln, Sarasota, FL 34242

/46
Est $1,318,589 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,898 Sq Ft
22 Sandy Cove Rd Unit 501, Sarasota, FL 34242

22 Sandy Cove Rd Unit 501, Sarasota, FL 34242

/7
$750,000
- Land
- 0.31 Acre
- $2,419,355 per Acre
4637 Ocean Blvd, Sarasota, FL 34242

Being Sold For Lot Value - Motivated Seller - Bring All Offers - Build Your Dream Home! .3 Acres with 96' of frontage on Lake Norma, Awesome Location, Location, Location!!! 1 Mile to Siesta Key Beach, 25 Homes to The Village, 6 Homes to Out of Door Academy, 5 Homes to Siesta Key Chapel. ~ Make your offer today!!! (Storm Damaged Home on site is a tear down)

Albert Wooster

ALBERT WOOSTER & COMPANY

(941) 231-7499

4637 Ocean Blvd, Sarasota, FL 34242
/77
$6,000 per month
- 3 Beds
- 2.5 Baths
- 2,012 Sq Ft
- Townhouse for Rent
357 Tierra Mar Ln Unit 5, Sarasota, FL 34242

Siesta Key Furnished Annual or Seasonal Rental (4 month minimum). You will love living in this quiet enclave of 6 homes, tucked away from all of the hustle and bustle but walkable to all of the many dining, shopping and entertainment venues the vibrant Siesta Key Village offers! This amazing Townhome lives like a private residence and offers 3 bedrooms, and 2 and one half baths. This gorgeous

Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

357 Tierra Mar Ln Unit 5, Sarasota, FL 34242
/83
$580,000 Sold Oct 14, 2025
- 1,791 Sq Ft
- $324/SF
- 77 Days On Market
- 4 Beds
- 2 Baths
- Built 1958
4959 Commonwealth Dr, Sarasota, FL 34242

Incredible Investment Opportunity on Siesta Key! Welcome to 4959 Commonwealth Drive, an exceptional property offering endless possibilities in one of Florida's most desirable coastal communities. This hurricane-damaged home has already undergone professional mold remediation and is ready for your vision - whether you're dreaming of a full renovation or starting fresh with new construction.

Geri Scheckner Bright Realty

4959 Commonwealth Dr, Sarasota, FL 34242

/40
Est $1,212,621 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,564 Sq Ft
19 Whispering Sands Dr Unit 1202, Sarasota, FL 34242

19 Whispering Sands Dr Unit 1202, Sarasota, FL 34242

/86
$628,999
- 2 Beds
- 2 Baths
- 1,259 Sq Ft
5600 Beach Way Dr Unit 201, Sarasota, FL 34242

JUST REDUCED OVER $20K and recently re-landscaped! Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom condo is ideally

Dawn Bear

WILLIAM RAVEIS REAL ESTATE

(941) 304-5005

5600 Beach Way Dr Unit 201, 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 comfort and

Robert Bevington SHOWTIME REALTY

4660 Ocean Blvd Unit N1, Sarasota, FL 34242
/2
$2,650,000 Sold Oct 14, 2025
- 5,078 Sq Ft
- $522/SF
- 88 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1979
512 Treasure Boat Way, Sarasota, FL 34242

Elevated Living. Expanded Luxury. Move-In Ready.More space. More land. More peace of mind — and better value than new construction.This rare Siesta Key estate offers twice the living space and double the lot size of typical new construction homes on the Key, while sitting high and dry on an above-flood-level lot. No construction delays. No compromises.Designer Waterfront

Derek Edwards KELLER WILLIAMS ON THE WATER S

512 Treasure Boat Way, Sarasota, FL 34242

/39
Est $1,880,199 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,234 Sq Ft
340 Canal Rd Unit B, Sarasota, FL 34242

340 Canal Rd Unit B, Sarasota, FL 34242

/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
/34
$6,000 per month
- 2 Beds
- 2 Baths
- 1,210 Sq Ft
- House for Rent
6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242

Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Beach, just steps away, where sun and surf await. Relax by Siesta Key’s largest heated pool or unwind in the lush, park-like setting with peaceful bay views. Explore the nearby vibrant Village on Siesta Key, filled with diverse dining, unique shops, and lively events. With

Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242
/2
$913,500 Sold Oct 10, 2025
- 2,956 Sq Ft
- $309/SF
- 96 Days On Market
- 3 Beds
- 2 Baths
- Built 1981
5385 Avenida Del Mare, Sarasota, FL 34242

Beachside Oasis with Income Potential – Just 2 Blocks from Siesta Key Beach!Welcome to your slice of paradise! This spacious 2,956 sq ft single-family home is perfectly positioned just two blocks from the world-famous Siesta Key Beach. With 3 bedrooms and 2 bathrooms on the upper level, plus a fully equipped 1-bedroom 1-bath apartment/in-law suite with private entrance on the lower level,

Tracey Bodmer THE BREEZE REALTY GROUP INC

5385 Avenida Del Mare, Sarasota, FL 34242

/46
Est $650,744 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
1166 W Peppertree Dr Unit 112, Sarasota, FL 34242

1166 W Peppertree Dr Unit 112, 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
/23
$3,600 per month
- 3 Beds
- 2 Baths
- 1,737 Sq Ft
- Condo for Rent
1255 Dockside Place Unit 211, Sarasota, FL 34242

Welcome to your ideal Siesta Key retreat! This charming 2-bedroom, 2-bath condo comfortably sleeps up to 6 guests and is just a short walk from the world-famous Siesta Key Beach. Whether you’re looking to relax or stay active, this inviting property offers everything you need for an unforgettable vacation.The Space:Step inside this peaceful condo featuring a spacious main bedroom with

Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

1255 Dockside Place Unit 211, Sarasota, FL 34242
/2
$578,000 Sold Oct 08, 2025
- 1,287 Sq Ft
- $449/SF
- 185 Days On Market
- 2 Beds
- 2 Baths
- Built 1975
6415 Midnight Pass Rd Unit 607, Sarasota, FL 34242

Discover this beautifully renovated and fully furnished 1,287 square foot condominium on Siesta Key, featuring 2 spacious bedrooms and 2 modern bathrooms. Nestled in the prestigious Anchorage Yacht and Tennis Club, this southern-exposure gem offers breathtaking views of both the Gulf and the Intercoastal Waterway. Ideal for both personal use and investment, the HOA permits weekly rentals

James Hirschman SARASOTA LAND AND HOMES LLC

6415 Midnight Pass Rd Unit 607, Sarasota, FL 34242

/47
Est $2,045,651 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,358 Sq Ft
6906 Bochi Cir, Sarasota, FL 34242

6906 Bochi Cir, 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
/20
$3,150 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 302, Sarasota, FL 34242

55+ Harbor View Haven on Siesta Key w/beach access!Discover relaxation and adventure at our Siesta Harbor condo on Siesta Key. This bright 2 bedroom unit offers modern comfort and stunning harbor views from the screened porch. Enjoy deeded beach access and watch breathtaking sunsets. You'll have access to amenities like a fishing pier, boat slips, a pool, and clubhouse activities. Whether

Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

1250 N Portofino Dr Unit 302, Sarasota, FL 34242
/2
$640,000 Sold Oct 06, 2025
- 1,348 Sq Ft
- $475/SF
- 78 Days On Market
- 2 Beds
- 2 Baths
- Built 1961
5369 Shadow Lawn Dr, Sarasota, FL 34242

Discover a rare opportunity to own a piece of Siesta Key history with this early Ruth Richmond designed single family home, ideally situated on a spacious high and dry 12,000 sq ft lot surrounded by sea grape and mature oaks. The two bedroom two bath fixer upper includes a studio with full bath and separate entrance - perfect for guests or rental income. Inside, enjoy a wood burning

Nancy Drake ACCARDI & ASSOCIATES REAL ESTA

5369 Shadow Lawn Dr, Sarasota, FL 34242

/68
Est $643,581 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

101 Whispering Sands Dr Unit 204TRO, Sarasota, FL 34242

/48
$960,000
- 3 Beds
- 2 Baths
- 1,730 Sq Ft
711 Birdsong Ln, Sarasota, FL 34242

Located in the heart of Siesta Key, this three-bedroom, two-bath home with a two-car garage offers a rare opportunity to experience island living just one mile from Siesta Key Beach—consistently ranked the #1 beach in the United States for its white quartz sand, turquoise waters, and year-round appeal.This property is perched on an elevated lot that has never experienced flooding. Recent

Julianna Burns

BERKSHIRE HATHAWAY HOMESERVICE

(941) 390-4919

711 Birdsong Ln, Sarasota, FL 34242
/27
$2,800 per month
- 1 Bed
- 1 Bath
- 748 Sq Ft
- House for Rent
6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242

Welcome to Sunrise Porch Lookout — your peaceful intercoastal retreat in the heart of Siesta Key. This bright and tropical second-floor condo is perfectly situated in the highly sought-after Provincial Gardens community, where Old Florida charm meets serene waterfront beauty. Overlooking the intercoastal waterway and lush park-like lawn, the screened-in wraparound porch is your front-row seat to

Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
/2
$692,000 Sold Oct 06, 2025
- 1,387 Sq Ft
- $499/SF
- 165 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242

Welcome to this beautifully updated 2-bedroom, 2-bath condo in the highly desirable Excelsior Beach to Bay Resort. Nestled in a serene, park- like setting with private beach access to the world-famous Crescent Beach, this Bayside end-unit offers the perfect blend ofrelaxation and resort-style living. From the moment you step inside, you’ll be captivated by the lushly landscaped grounds,

Marci McFarland MICHAEL SAUNDERS & COMPANY

6285 Midnight Pass Rd Unit 201, Sarasota, FL 34242

/84
Est $614,243 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
5600 Beach Way Dr Unit 113, Sarasota, FL 34242

5600 Beach Way Dr Unit 113, Sarasota, FL 34242

Showing Results 41 - 80, Page 2 of 18

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