Siesta Key, FL Homes for Sale with Pool

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  $500,000

  $75K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft

  225 Hourglass Way Unit 106, Sarasota, FL 34242

  Step into your own island retreat with this rare END unit in the highly sought after GULF FRONT property of Whispering Sands! Perfectly positioned with a full length screened & glassed lanai overlooking the picturesque lagoon and lush tropical landscaping, this residence captures a peaceful, serene setting with a touch of everyday luxury. Thoughtfully updated and designed for effortless living,

  Harriet Stopher COLDWELL BANKER REALTY

  225 Hourglass Way Unit 106, Sarasota, FL 34242
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  /15

  $4,795,000

  New Construction $800K PRICE INCREASE

  • 4 Beds
  • 4.5 Baths
  • 3,995 Sq Ft

  601 Tremont St, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Under Construction. Set in a hammock of old growth oak trees and mature landscaping, this masterpiece of a home sits on over 1/3 of an acre and is located on one of the most treasured streets on Siesta Key. It is just a short walk from The Out-of-Door Academy, minutes from the world-famous Siesta Key Village and another few blocks to our cherished

  Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

  601 Tremont St, Sarasota, FL 34242
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  /48

  $5,750,000

  New Construction

  • 5 Beds
  • 8 Baths
  • 4,191 Sq Ft

  5547 Avenida Del Mare, Sarasota, FL 34242

  Experience elevated coastal living in this exceptional 5-bedroom, 5.3-bath contemporary retreat, ideally located just steps from world-famous Siesta Public Beach and a short stroll to Siesta Village, where boutique shopping, dining, lively nightlife, and island charm await. Thoughtfully designed for effortless resort-style living, this four-level residence offers breathtaking Gulf views,

  Thomas Cail RE/MAX ALLIANCE GROUP

  5547 Avenida Del Mare, Sarasota, FL 34242
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  /57

  $2,900,000

  $300K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,854 Sq Ft

  238 Island Cir, Sarasota, FL 34242

  Welcome to your dream island retreat, perfectly nestled in the heart of Siesta Key’s Palm Island, just minutes away from the world-famous Siesta Beach and vibrant Siesta Village. This beautifully renovated 4-bedroom, 4-bathroom home is the epitome of coastal luxury, offering the ultimate island lifestyle where you can enjoy sun, sand, and all the amenities of this exclusive locale. Meticulously

  Thomas Cail RE/MAX ALLIANCE GROUP

  238 Island Cir, Sarasota, FL 34242
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  /57

  $1,295,000

  $55K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 928 Sq Ft

  5400 Ocean Blvd Unit 5-3, Sarasota, FL 34242

  New price! Experience the ultimate in Siesta Key beachfront living. Directly on world-renowned Siesta Beach, rated #1 in the U.S. and #4 worldwide by TripAdvisor, this stunning fifth-floor corner residence captures the essence of luxury coastal living. Recently renovated to perfection, this one-bedroom, 1.5-bath condominium offers a rare combination of modern sophistication, coastal elegance and

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5400 Ocean Blvd Unit 5-3, Sarasota, FL 34242
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  /59

  $1,350,000

  $50K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 4 Baths
  • 2,927 Sq Ft

  4646 Gleason Ave, Sarasota, FL 34242

  Experience the epitome of luxury with this stunning home that defines coastal elegance. Nestled on a quiet island street, this Florida Coastal masterpiece is set on a large 12,805 square foot lot with 75 ft of private lakefront overlooking the serene waters of Lake Norma, on our famed Siesta Key. Renovated with meticulous attention to detail, this newly updated home features an expansive,

  Victor Maravi Passara KELLER WILLIAMS ON THE WATER S

  4646 Gleason Ave, Sarasota, FL 34242
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  /53

  $2,299,000

  $90K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,396 Sq Ft

  5966 Midnight Pass Rd Unit G-67, Sarasota, FL 34242

  Fully insured, fully compliant building with clean structural inspections, funded reserves, new elevators and roof, and the rare and lucrative 3-day rental flexibility. The unit is stocked and move-in as well as rental-ready. Just bring your suitcase. Own a piece of paradise at the Palm Bay Club tower, where Siesta Key sunsets and Gulf views become a part of daily life. Positioned in the

  Ryan Skrzypkowski COLDWELL BANKER REALTY

  5966 Midnight Pass Rd Unit G-67, Sarasota, FL 34242
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  /18

  $575,000

  $55K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 753 Sq Ft

  925 Beach Rd Unit 310, Sarasota, FL 34242

  Siesta Key 2BR/1BA condo updated in 2021 with sweeping Gulf views from a private balcony. Bright, open living area flows to the outdoors. Prime island location close to dining and shops. A standout coastal retreat or investment. Come enjoy the Siesta Key lifestyle!

  Colin Mooney BRICK STREET REALTY

  925 Beach Rd Unit 310, Sarasota, FL 34242
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  /20

  $435,000

  • 2 Beds
  • 1 Bath
  • 754 Sq Ft

  5955 Midnight Pass Rd Unit 20E, Sarasota, FL 34242

  Community Beach access to Siesta Key's Beach. Community Dock and Fishing Pier. Community Marina. Large Community Heated Pool. Community BBQs. Poolside Tiki Cabana, Bathrooms and showers, Community laundry machines on first floor. Gated and community building at entrance. 1–7-day rentals grandfather in so great rental income or come enjoy it as your family beach/bay condo!Great option for

  David Butler Jr RE/MAX ALLIANCE GROUP

  5955 Midnight Pass Rd Unit 20E, Sarasota, FL 34242
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  $1,224,000

  $71K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,241 Sq Ft

  5107 Saint Albans Ave, Sarasota, FL 34242

  Virtually Staged. Welcome to this beautifully renovated ranch-style home, ideally located within minutes to the #1 beach in the United States—Siesta Key Beach! Set on an oversized lot, this property offers a private outdoor oasis with a relaxing pool surrounded by lush, mature landscaping, perfect for entertaining or unwinding after a day at the beach. Designed for effortless single-level living,

  Austin Solari FINE PROPERTIES

  5107 Saint Albans Ave, Sarasota, FL 34242
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  /20

  $2,999,000

  New Construction $2M PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,735 Sq Ft

  7401-B Midnight Pass Rd, Sarasota, FL 34242

  Pre-Construction. To be built. Seller Will Consider All Offers. Pre-construction new construction land and home package offered with Yoder Homes as the builder, ideally located for Siesta Key–area waterfront living with direct Sarasota Bay access. This all–concrete block home is thoughtfully designed with high-end luxury finishes, including a Thermador appliance package, designer lighting, solid

  Michelle Shiver KELLER WILLIAMS ON THE WATER S

  7401-B Midnight Pass Rd, Sarasota, FL 34242
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  /58

  $1,124,000

  $101K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  6140 Midnight Pass Rd Unit 603, Sarasota, FL 34242

  Perched on the 6th floor with sweeping, unobstructed western views of the Gulf and world famous Crescent Beach, this spectacular Siesta Key condo delivers front row sunsets and frequent dolphin sightings, stretching from Point of Rocks to north Siesta Key. Ideally positioned above the gulf front pool and spa, this partially furnished island retreat is move in ready and features a full length

  Suki Scollo COLDWELL BANKER REALTY

  6140 Midnight Pass Rd Unit 603, Sarasota, FL 34242
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  /64

  $1,000,000

  • 2 Beds
  • 2 Baths
  • 1,559 Sq Ft

  226 Ogden St, Sarasota, FL 34242

  Tucked away on the quiet, residential north side of Siesta Key, this once-charming 2-bedroom pool home is ready for its next chapter. The property was impacted by last summer’s hurricanes, but the good news is: the metal roof held strong and didn’t leak. With solid bones, a private pool, and a cute backyard that still hints at the home’s former charm, this is a golden opportunity for someone with

  Beth Helvey MICHAEL SAUNDERS & COMPANY

  226 Ogden St, Sarasota, FL 34242
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  /99

  $12,900,000

  • 5 Beds
  • 6.5 Baths
  • 5,273 Sq Ft

  3750 Bayou Louise Ln, Sarasota, FL 34242

  Tucked on the coveted north end of Siesta Key, this extraordinary double-lot point estate is positioned at the tip of a protected peninsula, offering panoramic water views and unforgettable sunsets. Surrounded by water and set directly across from protected parkland, the setting feels like your own private island. The property features three separate structures: a main residence, a guest house,

  Nora Johnson MICHAEL SAUNDERS & COMPANY

  3750 Bayou Louise Ln, Sarasota, FL 34242
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  /28

  $2,590,000

  Open House 9/15 $660K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,256 Sq Ft

  300 Garden Ln, Sarasota, FL 34242

  A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront!Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on

  Holly Parry WILLIAM RAVEIS - FLORIDA LLC

  300 Garden Ln, Sarasota, FL 34242
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  /53

  $3,500,000

  $1M PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,471 Sq Ft

  1444 Ridgewood Ln, Sarasota, FL 34231

  Substantial bayfront property with sweeping views , this rare waterfront location offers an unparalleled opportunity for builders and investors alike. Boasting an impressive 255 feet of water frontage, this 4-bedroom, 3-bath home is perfectly positioned to capture breathtaking sunsets and panoramic bay views. Whether you choose to renovate the existing residence or create a custom luxury estate

  Barbara Dumbaugh MICHAEL SAUNDERS & COMPANY

  1444 Ridgewood Ln, Sarasota, FL 34231
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  /91

  $6,000,000

  • 4 Beds
  • 4.5 Baths
  • 4,964 Sq Ft

  1516 Ridgewood Ln, Sarasota, FL 34231

  Some homes are built. Others are envisioned. 1516 Ridgewood is the result of an uncompromising pursuit of excellence—a California Pacific Palisades-inspired waterfront estate where timeless architecture, extraordinary craftsmanship, and Sarasota's coveted boating lifestyle converge into one remarkable residence. Completely reimagined with virtually every surface, system, and space thoughtfully

  Natalie Gutwein MICHAEL SAUNDERS & COMPANY

  1516 Ridgewood Ln, Sarasota, FL 34231
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  /8

  $4,250,000

  New Construction $3M PRICE INCREASE

  • 5 Beds
  • 4.5 Baths
  • 4,086 Sq Ft

  160 Garden Ln, Sarasota, FL 34242

  Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key’s coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet

  Chad Fonder COLDWELL BANKER REALTY

  160 Garden Ln, Sarasota, FL 34242
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  $1,149,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft

  6480 Midnight Pass Rd Unit 503, Sarasota, FL 34242

  Turnkey-furnished and move-in ready, experience the ultimate coastal lifestyle in this beautifully maintained beachfront condo located on the beautiful, world-famous Siesta Key. Enjoy the soft, white sand of Crescent beach, with a Beach Attendant managing a 200 ft section of private beach. Whether you’re searching for a full-time residence, seasonal getaway, or income-producing investment

  Heather Lakeman EXIT KING REALTY

  6480 Midnight Pass Rd Unit 503, Sarasota, FL 34242

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