Sarasota, FL Homes

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  /52

  $875,000

  • 2 Beds
  • 2 Baths
  • 1,253 Sq Ft

  6300 Midnight Pass Rd Unit 5, Sarasota, FL 34242

  Rarely available beach villa on Siesta Key in Crystal Sands. Experience the ultimate in island living with this beautifully renovated, free-standing villa in Crystal Sands — a sought-after beachfront community ideally positioned on the powdery white sands of world-renowned Siesta Beach. Offering the privacy and comfort of a single-family home with ease of condominium ownership, this rare

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6300 Midnight Pass Rd Unit 5, Sarasota, FL 34242
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  /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 piece of paradise at Jamaica Royale, your unit is 5 steps from the refreshing waters of heated pool #1, while a mere twominute stroll takes you to the pristine Siesta Key beach. Jamaica Royale's prime location on these dazzling sands provides easy access to all. Enjoy assigned covered parking space just steps from your front door. This updated, tastefully decorated

  Robert Bevington SHOWTIME REALTY

  5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
• 

  

  /2

  $1,221,750 Sold Jun 10, 2025

  • Land
  • 0.28 Acre
  • $4,363,393 per Acre

  • 8 Days On Market

  609 Lotus Ln, Sarasota, FL 34242

  Presenting an extraordinary opportunity to build your dream estate on one of Siesta Key’s desirable addresses—609 Lotus Lane, an exceptional canal-front vacant lot just off the prestigious Grand Canal. This quiet, private canal offers deep, navigable waters with direct access to the bay, only one tall (15-foot clearance) bridge away, ideal for the discerning boating enthusiast. Tucked away on a

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  609 Lotus Ln, Sarasota, FL 34242
• 

  

  

  /17

  Est $571,649 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242
• 

  

  

  /53

  $800,000

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft

  1255 E Peppertree Dr Unit 507, Sarasota, FL 34242

  Magnificent water views! It is like watching a boat parade every day! Welcome to Peppertree Bay, a sought-after beach to bay community on Siesta Key. This pristine 2-bedroom 2-bath condo has been beautifully updated to appeal to the modern discerning buyer, with clean contemporary finishes showcasing its coastal charm. Step inside to find a spacious open floor plan incorporating gorgeous

  Ethel Lovelace MICHAEL SAUNDERS & COMPANY

  1255 E Peppertree Dr Unit 507, Sarasota, FL 34242
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  /26

  $7,400 per month

  • 4 Beds
  • 3 Baths
  • 2,248 Sq Ft
  • House for Rent

  5153 Sandy Cove Ave, Sarasota, FL 34242

  You will Never Want to Leave this 4-bedroom house on Siesta Key! Mid-Century Modern, 4 bedroom home with saltwater, heated Pool with canal views. Located within a 6 minute bike ride to Siesta Key's Beach Access #5 and walking distance to everything that Siesta Key Village has to offer. This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, "Sarasota School of Architecture style"

  Kelly Anderson RE/MAX ALLIANCE GROUP

  5153 Sandy Cove Ave, Sarasota, FL 34242
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  /2

  $440,000 Sold Jun 10, 2025

  • 751 Sq Ft
  • $586/SF
  • 22 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1976

  5855 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  Say Hello to a Good Buy! Best value -1BD/1BA condo with Open Balcony plus private Florida Room offers fabulous views of the pool area and Intercoastal. Enjoy peace of mind, HVAC, and a new dishwasher in 2024, a new water heater, and a new main electrical panel in 2023. The remodeled condo offers stunning travertine stone floors, granite countertops, stainless steel appliances, and a

  Lynn Brock BROCK REALTY INC.

  5855 Midnight Pass Rd Unit 201, Sarasota, FL 34242
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  /69

  Est $567,699 Not Listed For Sale

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

  5600 Beach Way Dr Unit 209, Sarasota, FL 34242

  5600 Beach Way Dr Unit 209, Sarasota, FL 34242
• 

  

  /41

  $730,000

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242

  Paradise awaits at Gulf & Bay Club Bayside on Siesta Key. FIRST-FLOOR, TURNKEY FURNISHED, 2-bedroom, 2-bathroom residence includes a deep one-car GARAGE. Flexibility of weekly rentals, perfect for personal enjoyment or as a lucrative income-producing property. Located in a popular gated community just steps from DEEDED BEACH ACCESS to world-famous Siesta Key and Crescent Beach. This home invites

  Dana Cook Westmark MICHAEL SAUNDERS & COMPANY

  1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
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  /30

  $3,500 per month

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

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242

  BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available Fall 2025 — and May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242
• 

  /2

  $1,568,000 Sold Jun 09, 2025

  • 2,736 Sq Ft
  • $573/SF
  • 49 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1952

  288 Island Cir, Sarasota, FL 34242

  Auction Property. AUCTION - Renovated waterfront home in the heart of Siesta Key on Palm Island

  Derek Billib BILLIB & BILLIB P A

  288 Island Cir, Sarasota, FL 34242
• 

  

  /61

  Est $1,030,757 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,827 Sq Ft

  1319 Dockside Place Unit 221, Sarasota, FL 34242

  1319 Dockside Place Unit 221, Sarasota, FL 34242
• 

  

  /26

  $875,000

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  5855 Midnight Pass Rd Unit 621, Sarasota, FL 34242

  Breathtaking Gulf Views and Spectacular Sunsets Await!Perched on the 6th floor, this beautifully updated condo offers sweeping views of the Gulf and stunning nightly sunsets. The building has recently completed a $12 million structural renovation, featuring all-new hurricane-impact windows and sliding glass doors, along with fresh exterior stucco and paint—making it one of the most modern and

  Heidi Scholten MEDWAY REALTY

  5855 Midnight Pass Rd Unit 621, Sarasota, FL 34242
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  /17

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • House for Rent

  339 Avenida de Paradisio, Sarasota, FL 34242

  scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort.??? Just a 3-Min Drive to Siesta Beach??? 10 Minutes to Crescent Beach????? 13-Min Walk to a Local BeachDiscover the best of Sarasota with us!

  Valerie McInerney LPT REALTY, LLC

  339 Avenida de Paradisio, Sarasota, FL 34242
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  /2

  $482,500 Sold Jun 06, 2025

  • 1,012 Sq Ft
  • $477/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242

  Your coastal oasis awaits! This charming 1st floor condo is a short walk away from the award-winning Siesta Key Beach, known for its quartz-filled, cool sand and turquoise waters. This tastefully furnished, spacious 2-bedroom, 2-bath condo is being offered turnkey furnished and features additional storage as well as an in-unit laundry, a thoughtful improvement by the current owners. Whether

  Linda Williams GULF SHORES REALTY

  5643 Midnight Pass Rd Unit 909, Sarasota, FL 34242
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  /36

  Est $594,206 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1400 Cove Place Unit 631, Sarasota, FL 34242

  1400 Cove Place Unit 631, Sarasota, FL 34242
• 

  

  /55

  $1,975,000

  • 3 Beds
  • 3 Baths
  • 2,210 Sq Ft

  868 Siesta Key Cir, Sarasota, FL 34242

  PRICE IMPROVEMENT... This island-style, ranch waterfront home offers an incredible opportunity to renovate and make it your own. While it did take on water during Hurricanes Helene and Milton, it boasts several key updates including a newer roof, fresh exterior paint, impact windows and doors, vaulted ceilings, and charming plantation shutters—just a few of the features that make this Siesta Key

  Jennifer Thompson WILLIAM RAVEIS REAL ESTATE

  868 Siesta Key Cir, Sarasota, FL 34242
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  /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

  Robert Bevington SHOWTIME REALTY

  4660 Ocean Blvd Unit N1, Sarasota, FL 34242
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  /2

  $4,400,000 Sold Jun 05, 2025

  • 2,838 Sq Ft
  • $1550/SF
  • 112 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1979

  600 Beach Rd Unit 1 & 2, Sarasota, FL 34242

  NEW PRICE!! RARE SIESTA KEY BEACHFRONT OPPORTUNITY! This direct Gulf-front property offers private beach access, unobstructed sunset views, and is just a short stroll from the vibrant and eclectic Siesta Village. The property includes two individual, recently renovated 3-bedroom, 2.5-bath homes styled in a charming beach cottage aesthetic. Refinished kitchens and bathrooms include stainless

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  600 Beach Rd Unit 1 & 2, Sarasota, FL 34242
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  /30

  Est $744,776 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft

  5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

  5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242
• 

  

  /40

  $1,999,900

  • 3 Beds
  • 3 Baths
  • 3,324 Sq Ft

  681 Avenida de Mayo, Sarasota, FL 34242

  Price REDUCED so you can BUY your boat and bring it with you to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations.Step inside to find over-sized rooms that can be utilized for

  Colette Jay HORIZON REALTY INTERNATIONAL

  681 Avenida de Mayo, Sarasota, FL 34242
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  /36

  $2,300 per month

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft
  • Condo for Rent

  1350 N Portofino Dr Unit 207, Sarasota, FL 34242

  This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1350 N Portofino Dr Unit 207, Sarasota, FL 34242
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  /2

  $850,000 Sold Jun 05, 2025

  • 1,471 Sq Ft
  • $578/SF
  • 165 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  5750 Midnight Pass Rd Unit 105, Sarasota, FL 34242

  Rarely available first-floor condo. Take your groceries, golf clubs & luggage directly into your convenient located ground floor unit no waiting for the elevator. Or, walk right outside your condo to the Gulf front pool and barbeque grill….then a few more steps to the crystal white sands of world-famous Siesta Key beach. This nicely maintained and easy-to-care-for unit is light and bright. The

  Peg Davant PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5750 Midnight Pass Rd Unit 105, Sarasota, FL 34242
• 

  

  /30

  Est $527,774 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242

  5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242
• 

  

  /45

  $795,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  6204 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  Virtually staged to showcase the full potential of this beautiful Siesta Key condo! Just steps from the powdery sands of Siesta Key Beach, this turnkey 2-bedroom, 2-bath unit offers the perfect blend of comfort, style, and value. New hurricane-impact windows and doors are scheduled for installation, adding peace of mind for future owners. This unit has had no flood damage during current ownership

  Nili Blaha VUE REALTY, LLC

  6204 Midnight Pass Rd Unit 201, Sarasota, FL 34242
• 

  

  /40

  $11,000 per month

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

  1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242

  Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
• 

  /2

  $2,250,000 Sold Jun 03, 2025

  • 1,848 Sq Ft
  • $1218/SF
  • 49 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  1241 Big Oak Ln, Sarasota, FL 34242

  Welcome to 1241 Big Oak Lane, a stunning waterfront property on one of Siesta Key’s most private and desirable streets. Boasting nearly 200 feet of frontage directly on the bay-front of Sarasota and a Deep water Canal, this home is a boater’s dream, offering breathtaking water views and endless possibilities. Located in a rare RMF-zoned area, the property allows for completely legal short-term

  Anthony Dalesandro BRIGHT REALTY

  1241 Big Oak Ln, Sarasota, FL 34242
• 

  

  /46

  Est $662,922 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  141 Avenida Messina Unit 1, Sarasota, FL 34242

  141 Avenida Messina Unit 1, Sarasota, FL 34242
• 

  

  /97

  $1,725,000

  • 3 Beds
  • 2 Baths
  • 2,217 Sq Ft

  1038 Contento St, Sarasota, FL 34242

  Siesta Key Canal Front Home with 175’ of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world-famous Siesta Key Beach rated #1 in USA. This beautifully well-kept 3 bedroom, 2 bath Rutenberg built home is located on a quiet cul-de-sac that is a perennial favorite with lush tropical landscaping and great privacy. The

  Sara Leicht SARASELLSSARASOTA.COM

  1038 Contento St, Sarasota, FL 34242
• 

  

  /80

  $8,500 per month

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • House for Rent

  5216 Calle de Costa Rica, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely

  Beth Dilley ASCENDIA REAL ESTATE

  5216 Calle de Costa Rica, Sarasota, FL 34242
• 

  /2

  $875,000 Sold Jun 02, 2025

  • 1,472 Sq Ft
  • $594/SF
  • 65 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1966

  6005 Midnight Pass Rd Unit N8, Sarasota, FL 34242

  Experience a perfect blend of condo convenience and the comfort of a home with old Florida charm in this free-standing villa located in the sought-after Provincial Gardens on Siesta Key. Turnkey furnished and ready for rental, this villa boasts 2 bedrooms, 2 baths, and 1,472 square feet of living space. Additional special features include the bright and airy "Florida room" and stunning terrazzo

  Cathy Loeppke CORCORAN DWELLINGS REALTY

  6005 Midnight Pass Rd Unit N8, Sarasota, FL 34242
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  /33

  Est $557,765 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  137 Avenida Messina Unit 2, Sarasota, FL 34242

  137 Avenida Messina Unit 2, Sarasota, FL 34242
• 

  

  /54

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 3,451 Sq Ft

  940 Siesta Key Place, Sarasota, FL 34242

  Exceptional New Price for Siesta Key Canal-Front Living.Discover an unparalleled waterfront retreat on the highly coveted North Siesta Key, where luxury and tranquility converge. This extraordinary property boasts over 300 feet of pristine water frontage, offering breathtaking panoramic views and seamless access to Sarasota’s renowned waterways.Spanning over 3,450 sq. ft. of

  Frederick Insogna COLDWELL BANKER REALTY

  940 Siesta Key Place, Sarasota, FL 34242
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  /48

  $13,200 per month

  • 3 Beds
  • 2.5 Baths
  • 2,041 Sq Ft
  • Condo for Rent

  306 Beach Rd Unit 306, Sarasota, FL 34242

  Take some time to get away from it all.. we have the perfect place for you and your family to stay! This Spanish style tri-level home is in one of the greatest locations on Siesta Key Beach, Florida. Walk up the windowed staircase to the second floor where you’ll enjoy cooking and hanging out with the family! Enjoy your morning coffee or dinner on the balcony. Time for some fun in the sun! Walk,

  Beth Dilley ASCENDIA REAL ESTATE

  306 Beach Rd Unit 306, Sarasota, FL 34242
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  /2

  $1,550,000 Sold May 30, 2025

  • 1,358 Sq Ft
  • $1141/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  5179 Hidden Harbor Rd, Sarasota, FL 34242

  SUBSTANTIAL PRICE DECREASE! Welcome to Hidden Harbor, the premier yachting community located on Siesta Key. The canopy lined, brick paver streets are as lush and tropical as it gets, offering an unparalleled old Florida look and feel. Location, Location, Location... Just minutes away from award winning Siesta Key Beach, Siesta Key Village, and world class shopping, dinning and entertainment in

  Todd Nahrwold PREFERRED SHORE LLC

  5179 Hidden Harbor Rd, Sarasota, FL 34242
• 

  

  /62

  Est $716,987 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,212 Sq Ft

  6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242

  6145 Midnight Pass Rd Unit Villa F-8, Sarasota, FL 34242
• 

  

  /61

  $449,000

  • 1 Bed
  • 1 Bath
  • 522 Sq Ft

  5955 Midnight Pass Rd Unit 4E, Sarasota, FL 34242

  ***Seller Financing Available*** Discover a rare investment opportunity at Sea Club II, one of the few Siesta Key communities that allows nightly rentals—making it a standout choice for short-term vacation income. This turnkey furnished, ground-floor one-bedroom, one-bath unit sustained no flood damage and boasts a strong rental history. Fully equipped for a seamless guest experience, it’s ready

  Taylor Thompson WILLIAM RAVEIS REAL ESTATE

  5955 Midnight Pass Rd Unit 4E, Sarasota, FL 34242
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  /58

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 2,002 Sq Ft
  • House for Rent

  5640 Cape Leyte Dr, Sarasota, FL 34242

  It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

  Beth Dilley ASCENDIA REAL ESTATE

  5640 Cape Leyte Dr, Sarasota, FL 34242
• 

  /2

  $425,000 Sold May 30, 2025

  • 1,163 Sq Ft
  • $365/SF
  • 88 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  1255 E Peppertree Dr Unit 402, Sarasota, FL 34242

  Your Slice of Paradise Awaits at Siesta Key!Live the dream on the #1 beach in the USA with this adorable 4th-floor condo. This 2-bedroom, 2-bath gem offers a serene pool view and direct beach access, making it the perfect place to unwind. Move right in – it’s fully furnished and features luxurious vinyl flooring, new carpet, and fresh paint throughout.Relax on your enclosed lanai, where you can

  Cheryl Santelli PEPPERTREE BAY REALTY INC

  1255 E Peppertree Dr Unit 402, Sarasota, FL 34242
• 

  /2

  Est $4,158,515 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 3,759 Sq Ft

  5310 Avenida Del Mare, Siesta Key, FL 34242

  5310 Avenida Del Mare, Siesta Key, FL 34242

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