Sarasota, FL Homes

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  /39

  $625,000

  • 2 Beds
  • 2 Baths
  • 940 Sq Ft

  915 Beach Rd Unit 321, Sarasota, FL 34242

  INVESTOR ALERT!! THIS IS THE LEAST EXPENSIVE 2 bed / 2 bath condo on Siesta Key that allows weekly rentals and one pet!! Being the only 2/2 on the market in LA SIESTA makes this the best value in the development! Offered turnkey furnished, this spacious condo is located DIRECTLY ACROSS from the main entrance of world-renowned Siesta Key Public Beach, providing effortless access to the powdery

  Lori Madden MANGROVE REALTY ASSOCIATES

  915 Beach Rd Unit 321, Sarasota, FL 34242
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  /41

  $7,600 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

  Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
• 

  

  /2

  $630,000 Sold Apr 30, 2025

  • 1,512 Sq Ft
  • $417/SF
  • 69 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  5239 Winding Way, Sarasota, FL 34242

  ***PRICE IMPROVMENT*** ***PRICE IMPROVEMET*** Discover your own private oasis at 5239 Winding Way, just minutes from Siesta Beach. Come and see for yourself this lovely and charming home that is an absolute MUST SEE! Nestled in a canopy-protected neighborhood, this property features a spacious open floor plan that connects the kitchen and living areas, creating a perfect space for entertaining

  Brian Cirillo BALDWIN PARK REALTY LLC

  5239 Winding Way, Sarasota, FL 34242
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  /72

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  1640 Summerhouse Ln Unit 502B, Sarasota, FL 34242

  1640 Summerhouse Ln Unit 502B, Sarasota, FL 34242
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  /9

  $799,000

  • Land
  • 0.29 Acre
  • $2,755,172 per Acre

  5587 Shadow Lawn Dr, Sarasota, FL 34242

  Nestled on picturesque Shadow Lawn Drive, this 12,800-square-foot lot offers an exceptional canvas for your custom home. Framed by mature live oaks on the front left and back right corners, the property blends natural beauty with an enviable location.Enjoy the best of Siesta Key living—just an 8-minute stroll to the powdery sands of world-famous Siesta Beach and just over a mile to the

  Nick Gard COLDWELL BANKER REALTY

  5587 Shadow Lawn Dr, Sarasota, FL 34242
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  /30

  $7,700 per month

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Condo for Rent

  1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242

  A spacious two bedroom/two bath ground floor home with attached garage. Relax on the private south-facing lanai overlooking a lake featuring a fountain and frequent visits by numerous water birds. After a long day enjoy HDTV and high-speed internet ready to stream your favorite programs. Wireless internet is also available throughout Bayside and at the pools. The living area is tiled, and the

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
• 

  /2

  $1,175,000 Sold Apr 30, 2025

  • 2,147 Sq Ft
  • $547/SF
  • 76 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  1211 N View Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. This home had no water intrusion nor structural damage through hurricanes. Welcome to this beautifully updated home in the highly sought-after Siesta Cove neighborhood on Siesta Key, just a short distance from the world-renowned Siesta Beach and the vibrant Siesta Key Village, offering an array of shopping, dining, and entertainment options. This

  Thomas Cail RE/MAX ALLIANCE GROUP

  1211 N View Dr, Sarasota, FL 34242
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  /48

  Est $684,018 Not Listed For Sale

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

  199 Whispering Sands Dr Unit 202, Sarasota, FL 34242

  199 Whispering Sands Dr Unit 202, Sarasota, FL 34242
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  /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
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  /24

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242

  Enjoy our beautiful holiday retreat on Siesta Key Island, with private access to the stunning whites sands of Crescent Beach – Previously voted No. 1 beach in USA! Our 2 bed/2 bath condo located in this uniquely designed low rise ‘Key West’ style complex has ground floor access with sheltered South facing Garden – free WIFI throughout the condo. While away your lazy days on our fishing dock when

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
• 

  /2

  $303,500 Sold Apr 28, 2025

  • 797 Sq Ft
  • $381/SF
  • 45 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1975

  5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242

  Lowest price condo on Siesta Key. Rarely available first-floor 1/1 condo located right across the street from Siesta Key public beach in beautiful White Sands Village. This affordable and well-maintained community with pavers throughout the roadways and carport areas is a hidden gem. Onsite management, heated pool, community boat docks that are available on a first-come basis for a small fee, and

  Mary Jo Violett MICHAEL SAUNDERS & COMPANY

  5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242
• 

  

  /41

  Est $1,297,266 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft

  19 Whispering Sands Dr Unit 1005, Sarasota, FL 34242

  19 Whispering Sands Dr Unit 1005, Sarasota, FL 34242
• 

  

  /19

  $785,000

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft

  753 Tropical Cir, Sarasota, FL 34242

  Siesta Key house! This three bedroom, two bath, two car garage home with a swimming pool sits high and dry in the most elevated neighborhood on Siesta Key. This house is built on a concrete block 5ft stem wall and did NOT flood in 2024. Behind the lot line there is a natural retention swale to control potential water. Minutes to beautiful Siesta Key beach, and the Village. Invest in this land

  Patrick Ritchey RE/MAX ALLIANCE GROUP

  753 Tropical Cir, Sarasota, FL 34242
• 

  

  /24

  $7,200 per month

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Condo for Rent

  1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242

  Indulge in the ultimate relaxation experience at our exquisite vacation rental in Gulf and Bay - Bayside on Siesta Key. This meticulously appointed condo offers an abundance of space and comfort, allowing you to unwind in style. From savoring a glass of fine wine on the expansive lanai to reveling in the convenience of a fully equipped, turnkey furnished unit complete with a washer/dryer and a

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242
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  /2

  $1,630,000 Sold Apr 28, 2025

  • 1,782 Sq Ft
  • $915/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1964

  320 Avenida Leona, Sarasota, FL 34242

  CANAL FRONT home only a 2 minute walk to Siesta Key Village loaded with upgrades and a BRIGHT, OPEN layout that's ideal for entertaining. Features include custom kitchen with quartz countertops, tile backsplash and stainless appliances, tile flooring throughout, impact sliders and windows, 6-panel doors, custom closets with motion-sensor lighting. Three bedrooms plus an office with a HUGE

  Ryan Vlasic COLDWELL BANKER REALTY

  320 Avenida Leona, Sarasota, FL 34242
• 

  /2

  Est $508,881 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  5600 Beach Way Dr Unit 107, Sarasota, FL 34242

  5600 Beach Way Dr Unit 107, Sarasota, FL 34242
• 

  

  /62

  $535,000

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft

  1250 N Portofino Dr Unit 208, Sarasota, FL 34242

  Second Floor CORNER END UNIT ON THE CANAL! This is the One You've Been Waiting For on Siesta Key, 2 bedroom 2 bathroom condo next to the Heated Pool and an easy walk across the street to our Private Beach Access through Crescent Arms! Welcome to this delightful, ready to move in 2-bedroom, 2-bath canal front condominium, ideally situated near the Stickney Point Bridge on Siesta Key. Easy on and

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 208, Sarasota, FL 34242
• 

  

  /23

  $6,900 per month

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Condo for Rent

  1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242

  This fabulous, updated, one-bedroom PLUS separate sleeping den easily sleeps four guests. The den has a queen size bed for additional sleeping space - Complete with a closet and door for privacy.Relax in the spacious living area or enjoy a glass of wine on the lanai where you can enjoy watching the multitude of birds who visit each day.The condo is turnkey furnished including a

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242
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  /2

  $650,000 Sold Apr 28, 2025

  • 1,453 Sq Ft
  • $447/SF
  • 209 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  631 Venice Ln, Sarasota, FL 34242

  Welcome to great potential and endless possibilities on Siesta Key. This three bedroom, 2 bath pool home on one third of an acre in the Waterside East neighborhood is conveniently located for easy access on and off the island via the north bridge, and just a short bike ride to the vibrant Siesta Key Village and the world-famous Siesta Key beach. Enjoyed as a permanent residence by the current

  Kelly Rosenberg COLDWELL BANKER REALTY

  631 Venice Ln, Sarasota, FL 34242
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  /72

  Est $4,936,217 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,131 Sq Ft

  5119 Jungle Plum Rd, Sarasota, FL 34242

  5119 Jungle Plum Rd, Sarasota, FL 34242
• 

  

  /33

  $795,000

  • Land
  • 0.15 Acre
  • $5,300,000 per Acre

  5531 Calle Del Verano, Sarasota, FL 34242

  LOCATION, LOCATION, LOCATION!!! THIS LOT IS ONLY 2 BLOCKS TO SIESTA KEY BEACH, WITH NO HOA'S!Come see the possibilities of this lot to build your dream home. This location gives you a short walk, or use of the Frog Hop to the village, or a Sunset walk on the beach. This home DID take on water, and is UNINHABITABLE to live in. Both buildings on the property will be locked, and unavailable

  Mary Kassen PREFERRED SHORE LLC

  5531 Calle Del Verano, Sarasota, FL 34242
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  /27

  $9,900 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242

  Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park your car and store all the beach equipment you will need for the beach. It's only a short 10 min. walk down the private deeded beach access to the beautiful white sands of Siesta Key beach. We share

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
• 

  /2

  $590,000 Sold Apr 25, 2025

  • 1,287 Sq Ft
  • $458/SF
  • 17 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  6415 Midnight Pass Rd Unit 508, Sarasota, FL 34242

  Real estate is always about location, and your new condominium has it. No need for a car when you live here! Leave your condo, down the elevator and walk out the front door of The Anchorage to the Daiquiri Deck, Captain Curt’s Crab & Oyster Bar, plus a variety of other restaurants and shops along with the Siesta Key Marina and private access to Siesta Key Beach! If you are looking for

  Anthony DeLuca DELUCA REALTY INC

  6415 Midnight Pass Rd Unit 508, Sarasota, FL 34242
• 

  

  /45

  Est $1,553,273 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  313 Beach Rd Unit 313S1, Sarasota, FL 34242

  313 Beach Rd Unit 313S1, Sarasota, FL 34242
• 

  

  /51

  $750,000

  • 2 Beds
  • 1.5 Baths
  • 834 Sq Ft

  6020 Midnight Pass Rd Unit 49, Sarasota, FL 34242

  Welcome to your coastal retreat on world-renowned Siesta Key! Located in the highly sought-after Aloha Kai beachfront community, this updated 2-bedroom, 1.5-bath villa is offered turnkey furnished and ready to enjoy. This property allows for short-term rentals, offering exceptional potential as both a personal getaway and income-producing investment. The villa has been thoughtfully updated with a

  Connor Meckley PREFERRED SHORE LLC

  6020 Midnight Pass Rd Unit 49, Sarasota, FL 34242
• 

  

  /22

  $7,200 per month

  • 1 Bed
  • 1 Bath
  • 959 Sq Ft
  • Condo for Rent

  1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242

  Relax in the spacious living area or enjoy a glass of wine on the lanai.This condo is turnkey furnished including washer /dryer and private garage. Guests are walking distance away from private beach access to Siesta Key's world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key!**Taxes and fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242
• 

  /2

  $1,200,000 Sold Apr 25, 2025

  • 2,111 Sq Ft
  • $568/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  5602 Cape Leyte Dr, Sarasota, FL 34242

  Nestled in the highly sought-after Siesta Isle neighborhood, this exceptional 14,000+ sq. ft. corner lot presents an unparalleled opportunity to create your dream home just steps from the main entrance of world-renowned Siesta Key Beach. Whether you choose to remodel the existing two-bedroom, two-bath single-family home to your specifications or build an exquisite custom estate, this prime

  Ben Angerami PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5602 Cape Leyte Dr, Sarasota, FL 34242
• 

  

  /100

  Est $9,025,006 Not Listed For Sale

  • 6 Beds
  • 9 Baths
  • 8,615 Sq Ft

  4300 Higel Ave, Sarasota, FL 34242

  4300 Higel Ave, Sarasota, FL 34242
• 

  

  /72

  $2,990,000

  • 4 Beds
  • 4.5 Baths
  • 5,078 Sq Ft

  512 Treasure Boat Way, Sarasota, FL 34242

  Designer Waterfront Living on Treasure Boat Way – Rare Value Meets Lasting StyleModern Waterfront Estate on Siesta Key | 512 Treasure Boat WayPerfectly situated on a spacious .44-acre corner lot in one of Siesta Key’s most sought-after boating communities, this fully renovated modern estate offers over 5,000 square feet of sophisticated living. With 4 bedrooms, 4.5 bathrooms, and a

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  512 Treasure Boat Way, Sarasota, FL 34242
• 

  

  /24

  $9,300 per month

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Condo for Rent

  1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242

  This fabulous two bedroom features the primary bedroom with a King bed and the guest with a queen bed. The spacious living area opens onto a tiled lanai surrounded with sliding windows/doors that can be opened or closed as desired. Enjoy your breakfast there in the morning sun or relax with a glass of wine as the sun sets.The condo is turnkey furnished including washer / dryer and private

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242
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  /2

  $20,000 Sold Apr 25, 2025

  • 1,900 Sq Ft
  • $11/SF
  • 175 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2009

  915 Seaside Dr Unit 410, Weeks 14-15, 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

  915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242
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  /68

  Est $565,687 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  1113 N Moonmist Ct Unit L3, Sarasota, FL 34242

  1113 N Moonmist Ct Unit L3, Sarasota, FL 34242
• 

  

  /50

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 2,039 Sq Ft

  5572 Shadow Lawn Dr, Sarasota, FL 34242

  WATERFRONT HOME HALF A MILE TO SIESTA BEACH. Welcome to 5572 Shadow Lawn Drive on Siesta Key. This 3 Bedroom, 2 Bath home sits on a 14,300 SQ. FT. LOT, has a private dock and features 102 FEET OF FRONTAGE ON THE GRAND CANAL. Only one fixed bridge at Midnight Pass Rd means GREAT BOATING ACCESS to Sarasota Bay and the Gulf. Or take a short bike ride or walk to SIESTA BEACH, the #1 beach in the US.

  Chris Kernan RE/MAX ALLIANCE GROUP

  5572 Shadow Lawn Dr, Sarasota, FL 34242
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  /21

  $9,300 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242

  This spacious, private and light-colored 2-bedroom/2-bathroom end unit has a lanai that overlooks a lake with frequent bird sightings. Walk right out to an inland waterway and fishing dock. A large, heated pool is just across from the unit. Beach accessories as well as fishing gear and bicycles are available in the private garage.THIS CONDO REQUIRES A TWO WEEK MINIMUM

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
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  /2

  $1,029,000 Sold Apr 22, 2025

  • 816 Sq Ft
  • $1261/SF
  • 214 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1970

  5966 Midnight Pass Rd Unit G-92, Sarasota, FL 34242

  Siesta Key ~ Palm Bay Club ~ 9th Floor ~ Breathtaking "Direct" Siesta Key Beach & Gulf of Mexico Views ~ Direct Siesta Beach Access ~ Rental Income $90K +/- ~ this property is updated throughout (including windows) ~ 1 bedroom / 1 bath / open or closed balcony ~ sold turnkey furnished ~ managed on-site ~ offering an excellent investment with its rare three day minimum rental policy and on-site

  Robert Anderson Jr RE/MAX ALLIANCE GROUP

  5966 Midnight Pass Rd Unit G-92, Sarasota, FL 34242
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  /26

  Est $523,906 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

  6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242
• 

  

  /69

  $4,895,000

  • 3 Beds
  • 4 Baths
  • 3,654 Sq Ft

  5569 Cape Leyte Dr, Sarasota, FL 34242

  LOCATION, LOCATION, LOCATION !!!Live like a Lottery Winner on the Crystal Sands & Aqua Waters of Siesta Key. Literally, You can walk one block to be with the playful dolphins at the #1 Beach in the USA, or out your back door, to spend the day on the Intercoastal Waterway or the Gulf of America with two boats on lifts, and/or fish off the dock and watch Manatees in the Grand Canal. This is not

  Steve Hagan MICHAEL SAUNDERS & COMPANY

  5569 Cape Leyte Dr, Sarasota, FL 34242
• 

  

  /27

  $12,000 per month

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft
  • Condo for Rent

  1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242

  Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
• 

  /2

  $910,000 Sold Apr 22, 2025

  • 1,375 Sq Ft
  • $662/SF
  • 267 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  5300 Ocean Blvd Unit 803, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. ICONIC BEACH, ICONIC BUILDING, INCREDIBLE PRICE! NEW A/C, NEW PAINT! Are you ready for breathtaking views of the Gulf of Mexico from your luxury condominium? Discover a rare chance to own a condominium in the vibrant heart of Siesta Key Village with easy access to the beautiful quartz beach of Siesta Key. The island lifestyle is here for you.

  Diane Goodwin EXP REALTY LLC

  5300 Ocean Blvd Unit 803, Sarasota, FL 34242
• 

  /2

  Est $469,877 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,101 Sq Ft

  6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit E93, Sarasota, FL 34242

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