Siesta Key, FL Homes

/48
$1,175,000 Pending
- 2 Beds
- 2 Baths
- 1,173 Sq Ft
5916 Midnight Pass Rd Unit 102, Sarasota, FL 34242

Under contract-accepting backup offers. If tennis and pickleball courts, beachfront living, and exceptional rental potential are at the top of your list, welcome to Surf & Racquet Club on Siesta Key—where resort-style amenities and timeless island appeal come together seamlessly. This sought-after ground-floor residence in Building W (5916) offers effortless access, direct proximity to the beach,

Rudy Dudon MICHAEL SAUNDERS & COMPANY

5916 Midnight Pass Rd Unit 102, Sarasota, FL 34242
/19
$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 March and April 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

Maureen Plichta STRINGER MANAGEMENT INC

143 Whispering Sands Dr, Sarasota, FL 34242
/2
$465,000 Sold Dec 18, 2025

1125 N Moonmist Ct Unit L5, Sarasota, FL 34242
- 2 Beds
- 1.5 Baths
- 1,120 Sq Ft
- Built 1968
Last Sold Summary
- 32% Below List Price
- $415/SF
- 321 Days On Market
Last Listing Agent Kari Klein KW COASTAL LIVING III

1125 N Moonmist Ct Unit L5, Sarasota, FL 34242

/75
Est $3,616,940 Not Listed For Sale
- 4 Beds
- 5.5 Baths
- 5,098 Sq Ft
5315 Hidden Harbor Rd, Sarasota, FL 34242

5315 Hidden Harbor Rd, Sarasota, FL 34242

/12
$5,400,000 New Construction
- 3 Beds
- 4 Baths
- 4,154 Sq Ft
70 Avenida Veneccia Unit 204, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Under Construction. One or more photos have been virtually staged. Currently under construction with an estimated completion in the first half of 2026, Sunset Beach embodies the pinnacle of luxurious beachfront living on Siesta Key. Nestled within a neighborhood-inspired enclave surrounded by newly built homes, it offers a prime location just steps

David Lehrman THE SARASOTA REAL ESTATE COMP.

70 Avenida Veneccia Unit 204, 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
$1,300,000 Sold Jun 30, 2025

5402 Shadow Lawn Dr, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,886 Sq Ft
- Built 1962
Last Sold Summary
- 12% Below List Price
- $689/SF
- 98 Days On Market
Current Estimated Value $1,225,775

Last Listing Agent Jimmy Raybon BERKSHIRE HATHAWAY HOMESERVICE

5402 Shadow Lawn Dr, Sarasota, FL 34242

/64
Est $808,775 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,340 Sq Ft
5740 Midnight Pass Rd Unit 207, Sarasota, FL 34242

5740 Midnight Pass Rd Unit 207, Sarasota, FL 34242

/69
$1,295,000
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
625 Beach Rd Unit 602, Sarasota, FL 34242

DIRECT GULF VIEWS accompany this FULLY REMODELED two-bedroom, two-bath PENTHOUSE offering WEEKLY RENTALS AT TIVOLI BY THE SEA on SIESTA KEY. The residence is presented TURNKEY FURNISHED and ready for immediate occupancy or rental. Comparable units in Tivoli generate APPROXIMATELY $100,000 IN ANNUAL BOOKINGS providing an excellent opportunity to own a piece of Siesta Key while enjoying personal

Susanne Losso COLDWELL BANKER REALTY

625 Beach Rd Unit 602, 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
$13,000 Sold Feb 12, 2025

915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242
- 2 Beds
- 3 Baths
- 1,750 Sq Ft
- Built 2009
Last Sold Summary
- 68% Below List Price
- $7/SF
- 159 Days On Market
Last Listing Agent Kelly Mooney DOUGLAS ELLIMAN

915 Seaside Dr Unit 402, Weeks 28-29, Sarasota, FL 34242

/64
Est $1,387,743 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,187 Sq Ft
5400 Ocean Blvd Unit 5-4, Sarasota, FL 34242

5400 Ocean Blvd Unit 5-4, Sarasota, FL 34242

/34
$685,000
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5961 Midnight Pass Rd Unit 319, Sarasota, FL 34242

Looking for the perfect balance of location, lifestyle and income potential? This one delivers all three. Welcome to your slice of paradise on world-renowned Siesta Key! This spacious 2-bedroom, 2-bath condo is located in the highly sought-after Palm Bay Club, offering the perfect blend of coastal living and resort-style amenities. Located on the second floor, step inside to an open-concept

Rudy Dudon MICHAEL SAUNDERS & COMPANY

5961 Midnight Pass Rd Unit 319, 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
/2
$303,500 Sold Apr 28, 2025

5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 797 Sq Ft
- Built 1975
Last Sold Summary
- 13% Below List Price
- $381/SF
- 45 Days On Market
Current Estimated Value $312,428

Last Listing Agent Mary Jo Violett MICHAEL SAUNDERS & COMPANY

5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242

/47
Est $1,727,537 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,616 Sq Ft
615 Calle Del Otono, Sarasota, FL 34242

615 Calle Del Otono, Sarasota, FL 34242

/25
$1,550,000
- 3 Beds
- 2 Baths
- 2,037 Sq Ft
5880 Midnight Pass Rd Unit 207, Sarasota, FL 34242

See this beautifully decorated three-bedroom home, at the top rated condominium, Casarina. Escape winter's gloom and embrace the sun-kissed shores of Siesta Key, America's number one beach. Go from your door onto the sugar white sands for sunset visits, invigorating swims, or lively tennis and pickleball matches. This rare three-bedroom condominium, ideal for year-round living or as a seasonal

Maureen Morris PREMIER SOTHEBY'S INTERNATIONAL REALTY

5880 Midnight Pass Rd Unit 207, 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
$650,000 Sold Jan 16, 2026

5830 Midnight Pass Rd Unit 89, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 921 Sq Ft
- Built 1970
Last Sold Summary
- 7% Below List Price
- $706/SF
- 117 Days On Market
Last Listing Agent Steve Cavanaugh TIDELINE REAL ESTATE BROKERS

5830 Midnight Pass Rd Unit 89, Sarasota, FL 34242

/68
Est $2,632,119 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,950 Sq Ft
5132 Sandy Shore Ave, Sarasota, FL 34242

5132 Sandy Shore Ave, Sarasota, FL 34242

/79
$2,200,000 Open Sun 1PM - 4PM
- 3 Beds
- 2 Baths
- 1,798 Sq Ft
6140 Midnight Pass Rd Unit 401, Sarasota, FL 34242

Full west-facing gulf and beach views from this exquisitely designed 3-bedroom condo on Siesta Key’s famed Crescent Beach. This highly desirable end-unit has views from Point of Rocks to the north end of Siesta Key Beach. Never miss a sunset from this turnkey-furnished, move in ready home. No expense was spared in creating this seaside oasis. The original space was reconfigured to add a 3rd

Suki Scollo COLDWELL BANKER REALTY

6140 Midnight Pass Rd Unit 401, 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
$840,000 Sold May 16, 2025

1273 Dockside Place Unit 116, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,343 Sq Ft
- Built 1982
Last Sold Summary
- 7% Below List Price
- $625/SF
- 41 Days On Market
Current Estimated Value $807,068

Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

1273 Dockside Place Unit 116, Sarasota, FL 34242

/47
Est $801,917 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,224 Sq Ft
4532 Ocean Blvd Unit 209, Sarasota, FL 34242

4532 Ocean Blvd Unit 209, Sarasota, FL 34242

/41
$598,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 61, Sarasota, FL 34242

Welcome to a place where mornings begin with the sound of gentle waves and evenings settle into sunsets that linger long after the sky fades. This ground-level villa places you within steps of the Gulf in one of Siesta Key’s most cherished beachfront communities. The interior of this home has been completely transformed with a full remodel, bringing a fresh, modern feel to every room. This

Domanic Calamese KW COASTAL LIVING III

5830 Midnight Pass Rd Unit 61, 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
$2,550,000 Sold Jul 07, 2025

601 Avenida de Mayo, Sarasota, FL 34242
- 4 Beds
- 3 Baths
- 3,496 Sq Ft
- Built 2005
Last Sold Summary
- 11% Below List Price
- $729/SF
- 26 Days On Market
Current Estimated Value $2,397,576

Last Listing Agent Camilla Hildebrand Norberg FINE PROPERTIES

601 Avenida de Mayo, Sarasota, FL 34242

/52
Est $952,494 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
1334 Siesta Bayside Dr Unit 1334B, Sarasota, FL 34242

1334 Siesta Bayside Dr Unit 1334B, Sarasota, FL 34242

/43
$1,100,000
- 3 Beds
- 2 Baths
- 1,582 Sq Ft
310 Avenida Milano, Sarasota, FL 34242

Discover the potential of this canal-front property, perfectly positioned just steps from Siesta Key Village and minutes from the island’s world-famous beach. This rare offering presents the perfect opportunity for visionaries, builders, or investors to renovate the existing home or build your custom luxury retreat in one of Sarasota’s most desirable coastal communities. With 75 linear feet of

Domanic Calamese KW COASTAL LIVING III

310 Avenida Milano, 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
$1,110,000 Sold Jun 12, 2025

4818 Givens Ct, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,138 Sq Ft
- Built 1989
Last Sold Summary
- 23% Below List Price
- $519/SF
- 37 Days On Market
Current Estimated Value $1,135,357

Last Listing Agent Lisa Bouck, PA RE/MAX ALLIANCE GROUP

4818 Givens Ct, Sarasota, FL 34242

/50
Est $470,835 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
5667 Midnight Pass Rd Unit 304, Sarasota, FL 34242

5667 Midnight Pass Rd Unit 304, Sarasota, FL 34242

/79
$1,335,000 Open Sun 12PM - 3PM
- 3 Beds
- 2 Baths
- 1,642 Sq Ft
5880 Midnight Pass Rd Unit 206, Sarasota, FL 34242

Find your beach get-away in this remodeled three-bedroom Casarina condo located on Siesta Key’s famous Crescent Beach. This stunning TURNKEY FURNISHED and updated unit includes an open concept kitchen with high-end custom soft-close cabinetry, designer hardware and granite countertops. The great room was extended to incorporate the balcony into the living space creating an open and airy feeling

Suki Scollo COLDWELL BANKER REALTY

5880 Midnight Pass Rd Unit 206, 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
$900,000 Sold Sep 24, 2025

5572 Shadow Lawn Dr, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,039 Sq Ft
- Built 1963
Last Sold Summary
- 25% Below List Price
- $441/SF
- 77 Days On Market
Current Estimated Value $933,396

Last Listing Agent Chris Kernan RE/MAX ALLIANCE GROUP

5572 Shadow Lawn Dr, Sarasota, FL 34242

/2
Est $724,331 Not Listed For Sale
- 2 Beds
- 2 Baths
- 925 Sq Ft
5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242

5900 Midnight Pass Rd Unit 201, Sarasota, FL 34242

/69
$1,300,000
- 3 Beds
- 3.5 Baths
- 2,798 Sq Ft
3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242

A unique opportunity to renovate and create your dream coastal retreat in one of Siesta Key’s sought-after gated enclaves Hamilton Club, an exclusive boating community on North Siesta Key. Rarely available, this spacious, elevated townhome is one of only 18 residences in a private, pet-friendly, deep-water boating community offering a deeded dock with sailboat-water access—no fixed bridges to

Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

3954 Hamilton Club Cir Unit 14, Siesta Key, 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
$9,250,000 Sold Dec 12, 2025

4214 Higel Ave, Sarasota, FL 34242
- Land
- 1.54 Acres
- $6,006,494 per Acre
Last Sold Summary
- 6% Below List Price
- 168 Days On Market
Last Listing Agent Hailey Kendall WILLIAM RAVEIS REAL ESTATE

4214 Higel Ave, Sarasota, FL 34242

/36
Est $620,953 Not Listed For Sale
- 2 Beds
- 2 Baths
- 921 Sq Ft
5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242

5830 Midnight Pass Rd Unit 86, Sarasota, FL 34242

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