Homes in ZIP Code 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
/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
$1,200,000 Sold Apr 25, 2025

5602 Cape Leyte Dr, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,111 Sq Ft
- Built 1960
Last Sold Summary
- 9% Below List Price
- $568/SF
- 50 Days On Market
Current Estimated Value $1,119,751

Last Listing Agent Ben Angerami PREMIER SOTHEBY'S INTERNATIONAL REALTY

5602 Cape Leyte Dr, 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

/90
$2,690,000 Open Sun 1PM - 3PM
- 3 Beds
- 2 Baths
- 2,238 Sq Ft
4508 Woodside Rd, Sarasota, FL 34242

Luxury Exclusive Living – Boaters’ Paradise Welcome to 4508 Woodside Rd., a true waterfront retreat on Siesta Key offering privacy, boating convenience, and refined coastal living. Positioned on one of the deepest canals on the island, this home delivers three-minute access to the Intracoastal and Sarasota Bay. With 97 feet of water frontage and a 75-foot new dock, this is a legitimate boater’s

Derek Edwards KELLER WILLIAMS ON THE WATER S

4508 Woodside Rd, 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
$1,500,000 Sold Dec 01, 2025

1038 Contento St, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 2,217 Sq Ft
- Built 1972
Last Sold Summary
- 13% Below List Price
- $677/SF
- 169 Days On Market
Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

1038 Contento St, Sarasota, FL 34242

/2
Est $706,717 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,357 Sq Ft
8735 Midnight Pass Rd Unit 606B, Sarasota, FL 34242

8735 Midnight Pass Rd Unit 606B, Sarasota, FL 34242

/67
$2,447,000
- 3 Beds
- 3.5 Baths
- 2,766 Sq Ft
7665 Sanderling Rd, Sarasota, FL 34242

Photos 1–3 showcase preliminary renderings of a proposed architectural concept for this exceptional property. Envisioned as a modern coastal retreat, the design celebrates the relaxed luxury of mid-century architecture while maximizing the natural beauty of its surroundings. This residence is a modern coastal retreat set on over an acre and blends luxury with the charm of mid-century design.

Joel Schemmel DOUGLAS ELLIMAN

7665 Sanderling Rd, 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
$925,000 Sold Jan 28, 2025

4439 Ocean Blvd, Sarasota, FL 34242
- 1 Bed
- 1 Bath
- 3,042 Sq Ft
- Built 1951
Last Sold Summary
- 16% Below List Price
- $304/SF
- 67 Days On Market
Current Estimated Value $853,620

Last Listing Agent Jay Hogue DALTON WADE INC

4439 Ocean Blvd, 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

/72
$550,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
4660 Ocean Blvd Unit Q1, Sarasota, FL 34242

Experience million-dollar, direct Gulf views from this ground floor condominium in the sought after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private screened-in lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring

Halie Monde KELLER WILLIAMS ON THE WATER S

4660 Ocean Blvd Unit Q1, 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
$3,300,000 Sold Apr 10, 2025

317 Beach Rd, Sarasota, FL 34242
- 4 Beds
- 3.5 Baths
- 3,362 Sq Ft
- Built 2009
Last Sold Summary
- 6% Below List Price
- $982/SF
- 14 Days On Market
Current Estimated Value $3,277,405

Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

317 Beach Rd, Sarasota, FL 34242

/2
Est $462,554 Not Listed For Sale
- 2 Beds
- 2 Baths
- 980 Sq Ft
110 Vista Hermosa Cir Unit 304, Sarasota, FL 34242

110 Vista Hermosa Cir Unit 304, 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
/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
$425,000 Sold Sep 11, 2025

6029 E Peppertree Way Unit 116, Sarasota, FL 34242
- 2 Beds
- 1.5 Baths
- 975 Sq Ft
- Built 1973
Last Sold Summary
- 27% Below List Price
- $436/SF
- 234 Days On Market
Current Estimated Value $424,221

Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

6029 E Peppertree Way Unit 116, Sarasota, FL 34242

/2
Est $856,608 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,886 Sq Ft
8770 Midnight Pass Rd Unit B304, Sarasota, FL 34242

8770 Midnight Pass Rd Unit B304, Sarasota, FL 34242

/100
$2,550,000
- 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
/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
$1,000,000 Sold May 12, 2025

Unlisted Address
- 3 Beds
- 2 Baths
- 2,049 Sq Ft
- Built 1952
Last Sold Summary
- 13% Below List Price
- $488/SF
- 6 Days On Market
Current Estimated Value $965,719

Last Listing Agent Frederick Insogna COLDWELL BANKER REALTY

Unlisted Address

/2
Est $389,671 Not Listed For Sale
- 1 Bed
- 1 Bath
- 946 Sq Ft
9397 Midnight Pass Rd Unit PH3, Sarasota, FL 34242

9397 Midnight Pass Rd Unit PH3, Sarasota, FL 34242

/32
$595,000
- 1 Bed
- 1 Bath
- 728 Sq Ft
5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242

An investor’s dream! Discover unbeatable income potential with this fully renovated 1 bed, 1 bath condo at Jamaica Royale—a proven high-performing rental generating up to $58,000 annually and already secured with over $25,000 in bookings for 2026. Whether you're seeking a profitable income property, a personal beach retreat, or both, this turnkey unit is positioned to deliver.The spacious

Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

5830 Midnight Pass Rd Unit 52, 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
$414,000 Sold Jun 16, 2025

6727 Midnight Pass Rd Unit 202, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Built 1971
Last Sold Summary
- 3% Below List Price
- $460/SF
- 29 Days On Market
Current Estimated Value $497,365

Last Listing Agent Patti O Grady WATERSIDE REALTY LLC

6727 Midnight Pass Rd Unit 202, Sarasota, FL 34242

/2
Est $661,382 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,421 Sq Ft
8779 Midnight Pass Rd Unit 404H, Sarasota, FL 34242

8779 Midnight Pass Rd Unit 404H, Sarasota, FL 34242

/27
$639,000
- 1 Bed
- 1.5 Baths
- 728 Sq Ft
5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242

Experience the best of Gulf-side living in this beautifully renovated 1-bed, 1.5-bath condo on Siesta Key — just steps from the world-famous quartz-sand beaches of Siesta Key. Completely updated from top to bottom, this turnkey coastal retreat features brand-new designer furniture and appliances, making it move-in or rental-ready from the moment you arrive. The spacious layout includes a highly

Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

5830 Midnight Pass Rd Unit 63, 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
$600,000 Sold Aug 29, 2025

4522 Banan Place, Sarasota, FL 34242
- 2 Beds
- 2 Baths
- 978 Sq Ft
- Built 1962
Last Sold Summary
- 17% Below List Price
- $613/SF
- 191 Days On Market
Current Estimated Value $695,327

Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

4522 Banan Place, 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

/73
$6,400,000
- 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
/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
$650,000 Sold Jan 16, 2025

675 Avenida Del Norte, Sarasota, FL 34242
- Land
- 0.14 Acre
- $4,642,857 per Acre
Last Sold Summary
- 17% Below List Price
- 22 Days On Market
Current Estimated Value $645,230

Last Listing Agent Kevin Henry BAY VISION REALTY INC

675 Avenida Del Norte, 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

/51
$2,295,000
- 3 Beds
- 3 Baths
- 2,676 Sq Ft
518 Venice Ln, Sarasota, FL 34242

ELEGANT SIESTA KEY WATERFRONT RETREAT - Welcome to a truly distinguished canal-front residence, where timeless design meets the effortless beauty of waterfront living. Set beneath majestic oaks and tropical landscaping, the canopied circular paver driveway greets you. This exquisite pool home offers privacy, sophistication and an extraordinary outdoor lifestyle. An avid boater's dream with 110

Pamela Pileggi PREFERRED SHORE LLC

518 Venice Ln, 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
$630,000 Sold Apr 30, 2025

5239 Winding Way, Sarasota, FL 34242
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
- Built 1958
Last Sold Summary
- 33% Below List Price
- $417/SF
- 69 Days On Market
Current Estimated Value $706,418

Last Listing Agent Brian Cirillo BALDWIN PARK REALTY LLC

5239 Winding Way, Sarasota, FL 34242

/2
Est $734,455 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,875 Sq Ft
8773 Midnight Pass Rd Unit 206G, Sarasota, FL 34242

8773 Midnight Pass Rd Unit 206G, Sarasota, FL 34242

Showing Results 161 - 200, Page 5 of 18

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