Siesta Key, FL Homes

/47
$1,099,000
- 2 Beds
- 2 Baths
- 1,337 Sq Ft
5770 Midnight Pass Rd Unit 301, Sarasota, FL 34242

Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium association. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi

Anthony DeLuca

DELUCA REALTY INC

(941) 368-4048

5770 Midnight Pass Rd Unit 301, 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
$650,000 Sold Sep 12, 2025

6415 Midnight Pass Rd Unit 502, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,287 Sq Ft
- Built 1975
Last Sold Summary
- 6% Below List Price
- $505/SF
- 11 Days On Market
Current Estimated Value $630,066

Last Listing Agent Mina Johnson MICHAEL SAUNDERS & COMPANY

6415 Midnight Pass Rd Unit 502, Sarasota, FL 34242

/39
Est $1,884,975 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

/64
$595,800
- 2 Beds
- 2 Baths
- 1,287 Sq Ft
6415 Midnight Pass Rd Unit 306, Sarasota, FL 34242

Welcome to one of the best locations on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Location is fantastic! Wait until you see the grounds! You have the best of both worlds. Your new condominium is a 2 bedroom 2 bathroom split plan with brand-new hurricane sliding doors. Inside you have abundant

Anthony DeLuca

DELUCA REALTY INC

(941) 919-5593

6415 Midnight Pass Rd Unit 306, 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
$2,650,000 Sold Oct 14, 2025

512 Treasure Boat Way, Sarasota, FL 34242
- 4 Beds
- 4.5 Baths
- 5,078 Sq Ft
- Built 1979
Last Sold Summary
- 11% Below List Price
- $522/SF
- 88 Days On Market
Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

512 Treasure Boat Way, Sarasota, FL 34242

/46
Est $650,416 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

/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
$600,000 Sold Jan 30, 2025

671 Avenida Del Norte, Sarasota, FL 34242
- 1 Bed
- 2 Baths
- 1,314 Sq Ft
- Built 1951
Last Sold Summary
- 33% Below List Price
- $457/SF
- 59 Days On Market
Current Estimated Value $612,736

Last Listing Agent Melissa Caldwell PREMIER SOTHEBYS INTL REALTY

671 Avenida Del Norte, Sarasota, FL 34242

/47
Est $2,114,553 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

/67
$679,000
- 2 Beds
- 2 Baths
- 1,165 Sq Ft
5855 Midnight Pass Rd Unit 311, Sarasota, FL 34242

This stunning condo at Harbor Towers Yacht & Racquet Club offers an unparalleled investment opportunity, combining luxurious living with a resort-style ambiance. Thoughtfully updated with meticulous attention to detail, the condo now features NEW HVAC (Nov. 2025), ELECTRICAL PANEL (Nov. 2025), luxury vinyl flooring, a beautifully remodeled kitchen with solid wood cabinets and granite countertops,

Jennifer Thompson

WILLIAM RAVEIS REAL ESTATE

(941) 207-5546

5855 Midnight Pass Rd Unit 311, 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
$1,100,000 Sold Jun 27, 2025

4857 Primrose Path, Sarasota, FL 34242
- 3 Beds
- 3 Baths
- 2,519 Sq Ft
- Built 1957
Last Sold Summary
- 37% Below List Price
- $437/SF
- 83 Days On Market
Current Estimated Value $1,160,472

Last Listing Agent Nadiya Marisol-Pote MICHAEL SAUNDERS & COMPANY

4857 Primrose Path, Sarasota, FL 34242

/68
Est $646,615 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

/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
/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
$1,890,000 Sold Feb 07, 2025

5125 Oxford Dr, Sarasota, FL 34242
- 4 Beds
- 4 Baths
- 2,704 Sq Ft
- Built 1992
Last Sold Summary
- 10% Below List Price
- $699/SF
- 16 Days On Market
Current Estimated Value $1,691,349

Last Listing Agent Joel Schemmel DOUGLAS ELLIMAN

5125 Oxford Dr, Sarasota, FL 34242

/2
Est $1,305,368 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

/85
$1,800,000
- 4 Beds
- 2 Baths
- 2,185 Sq Ft
746 Plymouth St, Sarasota, FL 34242

Nestled in the heart of Siesta Key, this home offers the perfect blend of relaxation and opportunity. Whether you're seeking a serene beach getaway, a lucrative vacation rental, or a full-time residence, this property checks all the boxes. The home’s unique floor plan is flooded with natural light, creating a bright, inviting atmosphere throughout. A rare find, both the home and the garage are

Carla Rayman Kidd

COLDWELL BANKER REALTY

(941) 239-2641

746 Plymouth St, 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
$650,000 Sold Jul 30, 2025

813 Plymouth St, Sarasota, FL 34242
- 3 Beds
- 2.5 Baths
- 2,919 Sq Ft
- Built 1953
Last Sold Summary
- 43% Below List Price
- $223/SF
- 130 Days On Market
Current Estimated Value $915,438

Last Listing Agent Georgia Salaverri COMPASS FLORIDA LLC

813 Plymouth St, Sarasota, FL 34242

/27
Est $714,471 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

/54
$80,000
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
915 Seaside Dr Unit 312, Weeks 8-9, Sarasota, FL 34242

Fractional Ownership. Introducing the Winter Fractional Package, offering 1/16th ownership in a stunning luxury residence on Siesta Key Beach. Now, your dream of owning a beachfront home on America's most celebrated shore can become a reality. Enjoy the benefits of owning a slice of paradise, complete with world-class amenities and services. This exclusive opportunity offers the ultimate in

Kelly Mooney

DOUGLAS ELLIMAN

(941) 389-0934

915 Seaside Dr Unit 312, Weeks 8-9, 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
$3,000,000 Sold Oct 15, 2025

137 Big Pass Ln, Sarasota, FL 34242
- 5 Beds
- 4.5 Baths
- 4,486 Sq Ft
- Built 2006
Last Sold Summary
- 30% Below List Price
- $669/SF
- 148 Days On Market
Last Listing Agent Dion Souza SARABAY REAL ESTATE INC

137 Big Pass Ln, Sarasota, FL 34242

/53
Est $505,811 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
/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
$452,000 Sold Dec 18, 2025

73 Avenida Messina Unit 15, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 408 Sq Ft
- Built 1969
Last Sold Summary
- 5% Below List Price
- $1,108/SF
Last Listing Agent Maxwell Mann MICHAEL SAUNDERS & COMPANY

73 Avenida Messina Unit 15, Sarasota, FL 34242

/77
Est $651,432 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

/69
$2,695,000
- 5 Beds
- 3.5 Baths
- 3,205 Sq Ft
430 Island Cir, Sarasota, FL 34242

Welcome to 430 Island Circle, where island living feels both luxurious and refreshingly relaxed. Set on Palm Island, the “heart of Siesta Key”, just moments from the sugar-white sands of Siesta Key Beach, this home offers the perfect balance of modern comfort and coastal charm. Completely reimagined from top to bottom, this five bedroom, three and a half bathroom residence opens with sun-filled

Jesse Bauer KELLER WILLIAMS ON THE WATER S

430 Island Cir, 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
$990,000 Sold Jun 25, 2025

20 Whispering Sands Dr Unit 306, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 1,464 Sq Ft
- Built 1973
Last Sold Summary
- 38% Below List Price
- $676/SF
- 117 Days On Market
Current Estimated Value $1,014,937

Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

20 Whispering Sands Dr Unit 306, Sarasota, FL 34242

/66
Est $529,839 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

/71
$1,250,000
- 4 Beds
- 3.5 Baths
- 2,659 Sq Ft
5354 Calle Florida, Sarasota, FL 34242

Tucked away on Palm Island, one of Siesta Key’s most exclusive neighborhoods, this stunning Spanish-inspired home is more than a place to live, it’s a way of life. Just a short stroll from the sugar-white sands of Siesta Key Beach and the boutiques and cafés of the Village, every day feels like a vacation. Step inside and you’re instantly transported. Arched windows frame the open courtyard,

Angelica Ridley KELLER WILLIAMS ON THE WATER S

5354 Calle Florida, 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
$400,000 Sold Aug 20, 2025

6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
- Built 1974
Last Sold Summary
- 26% Below List Price
- $300/SF
- 86 Days On Market
Current Estimated Value $441,722

Last Listing Agent Julia Montei COLDWELL BANKER REALTY

6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

/41
Est $666,149 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

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