Siesta Key, FL Homes

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  $2,554,250 New Construction

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

  5019 Commonwealth Dr, Sarasota, FL 34242

  Pre-Construction. To be built. An exceptional pre-construction opportunity awaits on Commonwealth Drive, one of Siesta Key’s most coveted and picturesque streets. This .26-acre lot, surrounded by multi-million-dollar homes and lush, mature landscaping, is being offered with thoughtfully crafted custom home plans by Yoder Construction—giving buyers a rare chance to build new in a prime island

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 326-4411

  5019 Commonwealth Dr, Sarasota, FL 34242
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  /47

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • Condo for Rent

  4822 Ocean Blvd Unit 8B, Sarasota, FL 34242

  Annual turnkey furnished Live on the GULF OF MEXICO, ON SIESTA KEY!!! Siesta Towers is a luxury 11 story, 65 unit condominium that is oceanfront Siesta Key with panoramic views of the Gulf of Mexico. This condo is a comfortably and stylishly furnished 2/2 with open floor plan and is flooded with natural light from double sliding glass doors that lead to your massive balcony. The balcony

  Henry Rossi RENT SARASOTA

  4822 Ocean Blvd Unit 8B, 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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  /27

  Est $502,840 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft

  1257 S Portofino Dr Unit 107, Sarasota, FL 34242

  1257 S Portofino Dr Unit 107, Sarasota, FL 34242
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  /76

  $18,900,000

  • 4 Beds
  • 6 Baths
  • 8,138 Sq Ft

  3799 Flamingo Ave, Sarasota, FL 34242

  Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished down to dishes, silverware and a Buddha living wall. The coexistence of indoor and outdoor space blends over 8,000 square feet of indoor space with

  Joel Schemmel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3799 Flamingo Ave, Sarasota, FL 34242
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  /36

  $5,250 per month

  • 2 Beds
  • 2 Baths
  • 1,254 Sq Ft
  • Townhouse for Rent

  9 Sandy Cove Rd Unit 8A, Sarasota, FL 34242

  Newly renovated one story 2bed/2 bath condo with its own private beach and fishing pier. Just a 5 minute walk to Siesta village! Unit also comes with 1 car garage. Rarest of Rare! Welcome to the ultimate beachfront escape! This one-story gem perfectly blends luxury, convenience, and breathtaking natural beauty. Private Beachfront Oasis without the hassle of finding parking at the main beach or

  Sandra LaFlamme EXP REALTY LLC

  9 Sandy Cove Rd Unit 8A, 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
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  /47

  Est $896,257 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,307 Sq Ft

  1321 Dockside Place, Sarasota, FL 34242

  1321 Dockside Place, Sarasota, FL 34242
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  /73

  $6,900,000

  • 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 PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5132 Jungle Plum Rd, Sarasota, FL 34242
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  /57

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Condo for Rent

  5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242

  BEAUTIFULLY UPDATED 4th Floor Condo is quietly peaceful The 2-bedroom, 2-bathroom condo with coastal decour is turn-key furnished split- floor plan. Includes a washer and dryer. The gated community offers large pool and resident and guest parking. within the Harbor Towers Yacht & Racquet Club on Siesta Key, home to #1 beach in USA. Condo has spacious 1,056 sq ft layout with luxury vinyl plank

  Anna Williams SHOWTIME REALTY

  5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242
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  /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
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  /72

  Est $1,555,692 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,876 Sq Ft

  22 Sandy Cove Rd Unit 502, Sarasota, FL 34242

  22 Sandy Cove Rd Unit 502, Sarasota, FL 34242
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  /42

  $410,000

  • 1 Bed
  • 1 Bath
  • 656 Sq Ft

  105 Pass Key Rd Unit 105, Sarasota, FL 34242

  ATTENTION: ALL BEACH LOVERS!! Want to own a piece of paradise? Here is your chance!! This FIRST FLOOR 1+ bdrm is located in a private gulf front community. (That is PET FRIENDLY too!) This secluded enclave offers oceanfront panoramic views and just two blocks to Siesta Key VILLAGE! NO hurricane damage and NO upcoming assessments! New AC, hot water tank and hurricane sliders! Your condo boasts

  Laura Rodriguez COLDWELL BANKER REALTY

  105 Pass Key Rd Unit 105, Sarasota, FL 34242
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  /18

  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit B, Sarasota, FL 34242

  Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit B, Sarasota, FL 34242
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  /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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  /46

  Est $1,406,406 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,898 Sq Ft

  22 Sandy Cove Rd Unit 501, Sarasota, FL 34242

  22 Sandy Cove Rd Unit 501, Sarasota, FL 34242
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  /40

  $739,000

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft

  1001 Beach Rd Unit A203, Sarasota, FL 34242

  Reduced 20K and Seller Pays Upcoming Assessment! This totally updated 2 bed and 2 bath unit is on the 2nd floor of the West Tower at super well maintained and managed “Our House at The Beach”. The Living room and dining room have an L shape with forty-six feet of sliders that look around nearly 270 degrees. Across the street from what Trip Advisor called the number one beach in the US for 2024

  Mike Winger RE/MAX PLATINUM

  1001 Beach Rd Unit A203, Sarasota, FL 34242
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  /34

  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit A, Sarasota, FL 34242

  Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated, this home

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit A, 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
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  /40

  Est $1,245,141 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,564 Sq Ft

  19 Whispering Sands Dr Unit 1202, Sarasota, FL 34242

  19 Whispering Sands Dr Unit 1202, Sarasota, FL 34242
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  /100

  $699,000

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft

  6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242

  Stunning Intracoastal and Gulf views from this rare 9th-floor corner unit on Siesta Key.Welcome to Unit #909 at The Anchorage—a beautifully updated condo offering breathtaking panoramic views of the Intracoastal Waterway and Gulf glimpses from three private balconies. This light-filled corner unit is perched on the 9th floor and designed to capture peaceful coastal living from every

  Crystal Saly RE/MAX PLATINUM

  6415 Midnight Pass Rd Unit 909, Sarasota, FL 34242
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  /79

  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,439 Sq Ft
  • House for Rent

  4852 Featherbed Ln, Sarasota, FL 34242

  SIESTA KEY, Sarasota, Single Family Pool Home….Well-positioned for convenience and natural attractions . . . and dinners are breezy on your patio! The advantages of this appealing home in the Siesta area of Siesta Key become apparent while you are still walking the perimeter. The clear blue pool and the patio are a perfect pairing of amenities, supporting a variety of social activities and

  Jane Hunter JENNETTE PROPERTIES INC

  4852 Featherbed Ln, Sarasota, FL 34242
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  /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
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  /39

  Est $1,905,159 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
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  /46

  $1,349,000

  • 3 Beds
  • 3 Baths
  • 1,963 Sq Ft

  710 Treasure Boat Way, Sarasota, FL 34242

  PRICE IMPROVEMENT !! THIS GEM STANDS UNTOUCHED BY THE RECENT HURRICANSES. ABSOLUTELY NO DAMAGE !! NEW VINYL FENCE WILL BE INSTALLED FOR CLOSING. Your own resort awaits you in the most sought-after Siesta Key. This Paradise has everything that you could possibly think of for a vacation home or a beach style living. Situated on a MORE THAN ONE-THIRD ACRE parcel surrounded by palm trees, home feels

  Parvathi Ganduri 1ST CLASS REAL ESTATE GULF TO BAY

  710 Treasure Boat Way, Sarasota, FL 34242
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  /51

  $8,900 per month

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

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

  Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
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  /2

  $670,000 Sold May 28, 2025

  • 1,352 Sq Ft
  • $496/SF
  • 23 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  1113 Lake House Cir Unit C110, Sarasota, FL 34242

  Rarely available, this recently fully-renovated lake-front townhome is steps away from the crystal sands of Siesta Key Beach! Beautifully updated with a Coastal Chic interior, this end unit townhouse lives large. Light & bright with high ceilings, an open floor plan & four sets of glass sliders inviting the Gulf breezes inside makes each new day a delight. This 2-bedroom, 2-full bathroom home

  Jennifer Putnam COLDWELL BANKER SARASOTA CENT.

  1113 Lake House Cir Unit C110, Sarasota, FL 34242
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  /46

  Est $717,319 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
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  /44

  $1,295,000

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

  5107 Saint Albans Ave, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. **Seller Financing and Seller-Paid Rate Buy Down Available** Welcome to 5107 Saint Albans Avenue, Sarasota, Florida 34242 – a beautifully reimagined home on one of Siesta Key's most sought-after streets. This exceptional 3-bedroom, 2.5-bathroom ranch home, plus den, has been meticulously updated and nearly rebuilt with every modern convenience in

  Brian Partie ENGEL + VOELKERS SARASOTA

  5107 Saint Albans Ave, Sarasota, FL 34242
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  /36

  $2,500 per month

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

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242

  Available now through Dec 2025 for $2,500 per month. Available Jan-Mar 2026 for $6,000 per month. Welcome to your dream coastal escape in beautiful Siesta Harbor on Siesta Key! This turnkey furnished; spacious one-bedroom, two-bath condo is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short

  Jonathan OSteen O'STEEN GROUP INC

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242
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  /2

  $550,000 Sold May 27, 2025

  • 748 Sq Ft
  • $735/SF
  • 1 Day On Market

  • 1 Bed
  • 1 Bath
  • Built 1967

  6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242

  SIESTA KEY INTERCOASTAL WATERFRONT, WATERVIEW...Welcome to Paradise in PROVINCIAL GARDENS, a small 26 unit enclave. You will love the MILLION DOLLAR VIEW from this quaint, Mid-Century Modern one bedroom, one bath first floor condo with Florida room addition overlooking the community park, NEW fishing pier with new sea wall and the Intercoastal channel. Deeded beach access and Olympic pool use

  Scotty Ledford VUE REALTY, LLC

  6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242
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  /92

  Est $523,718 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft

  25 Sandy Cove Rd Unit 1-H, Sarasota, FL 34242

  25 Sandy Cove Rd Unit 1-H, Sarasota, FL 34242
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  /59

  $750,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242

  Wow, WHAT A VIEW! Gulf and sunset views from both bedrooms and the living room of this 5th-floor condo. Beautifully turnkey furnished, this large 2 bedroom, 2 bath condo boasts a double master layout, an extended living room/sunroom, and a gorgeously updated kitchen with stainless steel appliances and granite counter tops. Both bathrooms have also been exquisitely updated to maximize space and

  Shana Hamel NEXTHOME EXCELLENCE

  5855 Midnight Pass Rd Unit 520, Sarasota, FL 34242
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  /18

  $4,500 per month

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • House for Rent

  733 Tropical Cir, Sarasota, FL 34242

  Availability June 1st for Annual Lease. Welcome to your tropical escape on Siesta Key! This serene 3-bedroom, 2-bath annual rental offers a wide open floor plan with vaulted ceilings, split bedrooms, and a spacious 2-car garage. The stone-accented great room flows effortlessly into the kitchen with a unique breakfast bar, all overlooking the screened-in pool and lush tropical landscaping. Recent

  Anthony Dalesandro BRIGHT REALTY

  733 Tropical Cir, Sarasota, FL 34242
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  /2

  $525,000 Sold May 27, 2025

  • 748 Sq Ft
  • $702/SF
  • 2 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1967

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242

  SIESTA KEY INTERCOASTAL WATERFRONT, WATERVIEW...Welcome to Paradise in PROVINCIAL GARDEN, a small enclave of only 26 units. You will love the MILLION DOLLAR VIEW from this quaint, Mid-Century Modern one bedroom, one bath condo with SCREENED Florida room overlooking the community park, its own washer & dryer. There is a NEW fishing pier with new seawall and vistas of the Intercoastal channel.

  Scotty Ledford VUE REALTY, LLC

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
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  /47

  Est $2,163,187 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
• 

  

  /80

  $4,445,000

  • 4 Beds
  • 4 Baths
  • 5,988 Sq Ft

  815 Tropical Cir, Sarasota, FL 34242

  Step into your coastal waterfront dream home at 815 Tropical Circle on Siesta Key, unscathed by the two storms that impacted Sarasota. This exquisite four-bedroom, four-bath residence spans 5,988 square feet of meticulously updated living space, offering an unparalleled island lifestyle all while remaining unscathed by the two major hurricanes that impacted Sarasota and the Barrier Islands. A

  Joel Schemmel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  815 Tropical Cir, Sarasota, FL 34242
• 

  

  /40

  $8,500 per month

  • 3 Beds
  • 4 Baths
  • 2,168 Sq Ft
  • House for Rent

  1256 Riegels Landing Dr, Sarasota, FL 34242

  This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full

  Christopher Davenport STARLINK REALTY INC

  1256 Riegels Landing Dr, Sarasota, FL 34242
• 

  /2

  $1,185,000 Sold May 23, 2025

  • 1,288 Sq Ft
  • $920/SF
  • 90 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1962

  615 Avenida Del Norte, Sarasota, FL 34242

  WOW!...Move in NOW!***Updated & VERY DESIRABLE VILLAGE Area Location w/ Private Boat Dock on the Grand Canal*** Modern Beach Cottage with Extensive Indoor/Outdoor Living Spaces---Providing the ULTIMATE in Island Lifestyle Living: Over-sized Screened Lanai with Salt Water Pool & Spa; Outdoor Kitchen & MULTIPLE Entertaining and Lounge Areas. BRIGHT OPEN SPACIOUS Interior Living that Seamlessly

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  615 Avenida Del Norte, Sarasota, FL 34242
• 

  

  /17

  Est $1,483,552 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,292 Sq Ft

  6912 Bochi Cir, Sarasota, FL 34242

  6912 Bochi Cir, Sarasota, FL 34242

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