Sarasota, FL Homes

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  /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
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  /26

  $6,900 per month

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft
  • Condo for Rent

  1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242

  This lovely well-maintained and upgraded condo in a gated community, is located on the ground floor and offers one bedroom plus an additional den furnished as a small guest bedroom. The condo is turnkey furnished including washer /dryer and private garage, an approximate 5-minute walk, via deeded, walking access across the street, to the #1 beach in the U.S.A., Siesta Key! Choose to enjoy two

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
• 

  

  /2

  $1,910,000 Sold Apr 21, 2025

  • 1,919 Sq Ft
  • $995/SF
  • 9 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  5780 Midnight Pass Rd Unit 501, Sarasota, FL 34242

  Your dream home awaits — this rarely available, turnkey furnished, 3 bedrooms, with 2 ½ baths, offers 1919 sq ft of luxurious living space. This stunning end unit at the prestigious Gulf & Bay Club boasts expansive windows filling the condo with natural light and providing breathtaking views of the freshwater lakes and fountains. The open kitchen is the heart of the condo featuring Corian

  Tina Johns COLDWELL BANKER REALTY

  5780 Midnight Pass Rd Unit 501, Sarasota, FL 34242
• 

  

  

  /52

  Est $530,437 Not Listed For Sale

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

  6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit E02, Sarasota, FL 34242
• 

  

  

  /72

  $3,500,000

  • 6 Beds
  • 4.5 Baths
  • 4,699 Sq Ft

  1240 Solitude Ln, Sarasota, FL 34242

  Discover Unrivaled Coastal Elegance Steps from Siesta Key Beach!This rare gem features two meticulously remodeled canal-front homes with stunning partial views of the bay, perfectly situated in a prestigious neighborhood. The main residence boasts a contemporary design with open and spacious layouts, highlighted by soaring 24 ft ceilings adorned with stylish gray wooden accent beams.Culinary

  Karl Helbig SUNREAL ESTATE INC

  1240 Solitude Ln, Sarasota, FL 34242
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  /36

  $9,300 per month

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

  1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242

  Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute walk. Tile floors throughout and completely re-decorated and furnished with many amenities for your family’s enjoyment. King bed in the master and two doubles in the guest room.*Taxes and fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
• 

  /2

  $1,960,000 Sold Apr 21, 2025

  • 1,316 Sq Ft
  • $1489/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  420 Beach Rd Unit 407, Sarasota, FL 34242

  Step into the realm of unparalleled luxury at this one-of-a-kind organic modern beachfront condo, a meticulously designed and professionally finished residence that has been transformed down to the framing by the designer and builder as their personal home. Offered fully furnished, this 3-bedroom, 2-bathroom masterpiece boasts a coveted Gulf-front location with expansive water views and private

  Anthony Dalesandro BRIGHT REALTY

  420 Beach Rd Unit 407, Sarasota, FL 34242
• 

  

  /23

  Est $545,376 Not Listed For Sale

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

  6157 Midnight Pass Rd Unit E01, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit E01, Sarasota, FL 34242
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  /26

  $749,900

  • 2 Beds
  • 2 Baths
  • 1,348 Sq Ft

  5369 Shadow Lawn Dr, Sarasota, FL 34242

  Discover a rare opportunity to own a piece of Siesta Key history with this early Ruth Richmond designed single family home, ideally situated on a spacious high and dry 12,000 sq ft lot surrounded by sea grape and mature oaks. The two bedroom two bath fixer upper includes a studio with full bath and separate entrance - perfect for guests or rental income. Inside, enjoy a wood burning

  Nancy Drake ACCARDI & ASSOCIATES REAL ESTA

  5369 Shadow Lawn Dr, Sarasota, FL 34242
• 

  

  /31

  $9,300 per month

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

  1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242

  Relax in this spacious two bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private, walking 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

  1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
• 

  /2

  $3,100,000 Sold Apr 18, 2025

  • 2,533 Sq Ft
  • $1224/SF
  • 76 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2017

  601 Lotus Ln, Sarasota, FL 34242

  Indulge in the epitome of waterfront luxury living at this exceptional custom-built residence on Siesta’s grand canal, a five-minute boat ride to open water. Crafted by NC Ferguson with meticulous attention to detail and completed in 2017, this three-bedroom plus office home blends sleek contemporary finishes with comforting style, offering peace of mind with recent hurricane specifications,

  Roger Pettingell COLDWELL BANKER REALTY

  601 Lotus Ln, Sarasota, FL 34242
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  /71

  Est $403,392 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit D21, Sarasota, FL 34242
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  /49

  $5,985,000

  • 8 Beds
  • 6.5 Baths
  • 4,094 Sq Ft

  538 Canal Rd, Sarasota, FL 34242

  Welcome to Sea Spray, a beach and boaters paradise with a private dock across the street and just a block from the famous Siesta Key beach! This eight-bedroom and six-and-a-half-bathroom home boasts a spectacular backyard built like a private waterpark with a Private Resort Style Heated Pool featuring a Rock Water Slide, Waterfall, Grotto, Swim-up bar, Sun Shelf, and Spa. Pack your bags for the

  Constantine Stratos COLDWELL BANKER REALTY

  538 Canal Rd, Sarasota, FL 34242
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  /30

  $7,000 per month

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft
  • Condo for Rent

  1360 Siesta Bayside Dr, Sarasota, FL 34242

  This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The 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

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1360 Siesta Bayside Dr, Sarasota, FL 34242
• 

  /2

  $1,600,000 Sold Apr 16, 2025

  • 2,200 Sq Ft
  • $727/SF
  • 49 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1981

  6283 Midnight Pass Rd Unit 6283, Sarasota, FL 34242

  Discover this RARE and exquisite waterfront condominium home with deeded beach access on Siesta Key! Offering over 36 feet of unparalleled intracoastal water views, this masterpiece is located at Excelsior Beach to Bay. This furnished 3-bedroom, 3-bathroom end-unit residence is situated above your private 2-CAR GARAGE and is located directly on the intracoastal waterway. With hurricane impact

  Angela Lista MICHAEL SAUNDERS & COMPANY

  6283 Midnight Pass Rd Unit 6283, Sarasota, FL 34242
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  /82

  Est $561,040 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft

  6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit C32, Sarasota, FL 34242
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  /33

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft

  5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242

  Gulf & Bay is one of the finest properties on the island with 32 acres of manicured grounds and 800 feet of private white quartz powder beach. Lush tropical courtyard featuring 3 swimming pools, commercial grade fitness center, racquetball courts, tennis courts, freshwater lake with a unique island barbeque area, two clubhouses, dry saunas and hot tub, and electric charging stations. This is

  Brian Livesey WATERSIDE REALTY LLC

  5750 Midnight Pass Rd Unit 203, Sarasota, FL 34242
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  /31

  $9,300 per month

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

  1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242

  Deeded Walking Access Directly to the Beach!New on the rental program - Beautifully updated 2-bedroom near the pool, tennis courts and path to the beach! Please be one of our first Guests!The moment you arrive at Gulf & Bay Club Bayside, you’ll appreciate the beauty, serenity, and charm of this "Key West” style village. Located on the bay across the street from world-famous Siesta

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
• 

  /2

  $615,000 Sold Apr 16, 2025

  • 1,352 Sq Ft
  • $455/SF
  • 222 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  1125 Lake House Cir Unit C112, Sarasota, FL 34242

  ** THIS HOME WAS NOT AFFECTED BY THE PAST STORMS AND IS MOVE IN READY! ** BREATHTAKING WATERFRONT CONDO WITH PANORAMIC LAKE VIEWS LOCATED ACROSS THE STREET FROM SIESTA KEY BEACH! This stunning condo is everything you have been looking for. The high ceilings, large sliding glass doors and bi-level floor plan gives this home a light, bright and open feeling. When you walk in you will be pleasantly

  Kayla Lamb NEXTHOME EXCELLENCE

  1125 Lake House Cir Unit C112, Sarasota, FL 34242
• 

  

  /54

  Est $483,382 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit B31, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit B31, Sarasota, FL 34242
• 

  

  /78

  $2,600,000

  • 4 Beds
  • 3.5 Baths
  • 2,757 Sq Ft

  3959 Somerset Dr, Sarasota, FL 34242

  BOATERS: this one is rare! On deep, protected water in Cocoanut Bayou with no fixed bridges. This fully remodeled home on Siesta Key’s north end includes a deeded dock with water, electric, and a 20,000-pound lift—holds up to a 38' boat—with fast access to Sarasota Bay and the Gulf in under 10 minutes. Inside and out, this free-standing four-bedroom, 3.5-bath home has been thoughtfully upgraded.

  Peter Mason PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3959 Somerset Dr, Sarasota, FL 34242
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  /38

  $9,350 per month

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

  Unlisted Address

  Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Club Bayside. The Key West style cluster buildings afford you a quiet residential feel while you are just a short walk to the powdery white quartz sand of the world famous Siesta Key/Crescent Beach.New to the rental program, our condo has previously been owner occupied and

  Andy Moore GULF COAST REALTY & MANAGEMENT

  Unlisted Address
• 

  /2

  $470,000 Sold Apr 15, 2025

  • 1,101 Sq Ft
  • $427/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242

  Condo being sold Turn-Key! Welcome to Paradise on Siesta Key!This charming 2-bedroom, 2-bathroom condo offers 1,101 square feet of coastal living at its finest. Nestled in the heart of Siesta Key, this home is perfect for those seeking a relaxing island retreat or an ideal investment opportunity.Step inside to discover an open kitchen with granite countertops, a convenient

  Frank Harris COAST 2 COAST HOME REALTY, PLLC

  6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242
• 

  

  /26

  Est $635,668 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft

  6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit A52, Sarasota, FL 34242
• 

  

  /49

  $997,000

  • 2 Beds
  • 2 Baths
  • 1,094 Sq Ft

  385 Avenida Madera, Sarasota, FL 34242

  Beaches, Boating & Bistros!!! Excellent Investment, 2nd Home or Build new. Island Style Canal Front Home on Siesta Key, steps to World Famous Siesta Village & the cool quartz sands of Siesta Beach. This Island Style 2 bed, 2 bath home in close proximity to all the food & exciting nightlife that Siesta Key has to offer. 1 car garage. This home on a Cul de sac is light & bright with Terrazzo floors

  Dan Miller PREFERRED SHORE LLC

  385 Avenida Madera, Sarasota, FL 34242
• 

  

  /27

  $6,900 per month

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

  1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

  Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key just offshore of Sarasota, Florida. Private access to Crescent Beach on the Gulf of Mexico - just steps to the beach. Free high-speed Internet connection. Please note the garage for this unit is the middle garage in the building to the right.*Taxes and Fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
• 

  /2

  $2,100,000 Sold Apr 14, 2025

  • 2,758 Sq Ft
  • $761/SF
  • 64 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1990

  3927 Somerset Dr, Sarasota, FL 34242

  This gorgoeus home is being sold FULLY furnished, has a dedicated boat dock/lift, pool, private elevator, in a gated community! Somerset Cove is located on the coveted north end of the world-famous Siesta Key, in Sarasota, FL just a short distance to Shell Beach. This premier community, with only eleven (11) homes on property, is island living at its finest! As you pass through the electronic

  Patrick Dipinto, III COLDWELL BANKER REALTY

  3927 Somerset Dr, Sarasota, FL 34242
• 

  

  /35

  Est $440,111 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  6157 Midnight Pass Rd Unit A41, Sarasota, FL 34242

  6157 Midnight Pass Rd Unit A41, Sarasota, FL 34242
• 

  

  /48

  $578,000

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft

  1116 S Moonmist Ct Unit M12, Sarasota, FL 34242

  Welcome to your tropical retreat on Siesta Key! This beautifully maintained turnkey furnished 2-bedroom, 2-bathroom villa in the desirable Polynesian Gardens community offers the perfect blend of island charm and effortless comfort. Perched on an elevated lot, it features a freshly repainted interior, breezy coastal decor, and all-tile flooring for easy, care-free living. Offering 1,120 total

  Christina Gaskill COLDWELL BANKER REALTY

  1116 S Moonmist Ct Unit M12, Sarasota, FL 34242
• 

  

  /60

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 2,259 Sq Ft
  • House for Rent

  5516 Avenida Del Mare, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kiddos

  Beth Dilley ASCENDIA REAL ESTATE

  5516 Avenida Del Mare, Sarasota, FL 34242
• 

  /2

  $870,000 Sold Apr 14, 2025

  • 1,361 Sq Ft
  • $639/SF
  • 79 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  5780 Midnight Pass Rd Unit 408, Sarasota, FL 34242

  RESORT STYLE LIVING IN THIS EXQUISITELY RENOVATED 2-BEDROOM/2-BATH CONDO. THE LANAI FRAMES THE VIEW OF THE SPARKLING WATERS OF GULF OF MEXICO & AMAZING SUNSETS. OPEN FLOOR PLAN WITH SPACIOUS LIVING ROOM/DINING ROOM WITH SLIDERS TO THE LANAI. KITCHEN FEATURES QUARTZ COUNTERS, ALL STAINLESS STEEL APPLIANCES, DECORATIVE TILE BACKSPLASH & WOOD PAINTED CABINETRY WITH ADJACENT BREAKFAST ROOM. LARGE

  Betsy Campbell MICHAEL SAUNDERS & COMPANY

  5780 Midnight Pass Rd Unit 408, Sarasota, FL 34242
• 

  

  /65

  Est $796,620 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  1100 Cove II Place Unit 933, Sarasota, FL 34242

  1100 Cove II Place Unit 933, Sarasota, FL 34242
• 

  

  /65

  $509,900

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft

  1300 N Portofino Dr Unit 103, Sarasota, FL 34242

  Welcome to your slice of paradise on world-renowned Siesta Key! Located just steps from the powdery white sands of the #1 beach in the U.S., this beautifully updated 2-bedroom, 2-bathroom condo in the highly desirable Siesta Harbor 55+ community is the ultimate coastal retreat. Bright, spacious, and thoughtfully designed, this residence features stylish luxury vinyl flooring, a beautifully

  Rachelle Golden MICHAEL SAUNDERS & COMPANY

  1300 N Portofino Dr Unit 103, Sarasota, FL 34242
• 

  

  /65

  $8,700 per month

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Condo for Rent

  5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, April 2026. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot,

  Beth Dilley ASCENDIA REAL ESTATE

  5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
• 

  /2

  $3,300,000 Sold Apr 10, 2025

  • 3,362 Sq Ft
  • $982/SF
  • 14 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2009

  317 Beach Rd, Sarasota, FL 34242

  ONE-OF-A-KIND IN THE HEART OF SIESTA KEY! With more than 3,300 square feet of beautifully designed living space, this meticulously maintained 4-bed, 3.5-bath single-family home is move-in ready and available for a quick close, as it sustained NO storm damage. From the moment you arrive, the classic architecture, tile roof and detailed craftsmanship are bound to leave a lasting impression. The

  Christa Spalding COLDWELL BANKER REALTY

  317 Beach Rd, Sarasota, FL 34242
• 

  

  /34

  Est $580,381 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1500 Cove II Place Unit 533, Sarasota, FL 34242

  1500 Cove II Place Unit 533, Sarasota, FL 34242
• 

  

  /100

  $6,499,500

  • 10 Beds
  • 10 Baths
  • 7,052 Sq Ft

  1204 Derby Ln, Sarasota, FL 34242

  Welcome to an unparalleled luxury coastal retreat in the heart of SIESTA KEY, home to Tripadvisor’s #1 Beach in America! This turn-key luxury vacation rental boasts a potential $966,192 in first-year cash flow ($575,000+ from rental income and up to $391,192 from 100 percent bonus depreciation, reinstated by the Big Beautiful Bill), making it an extraordinary investment opportunity. Built in 2017

  Jeffrey Stuben CHARLES RUTENBERG REALTY INC

  1204 Derby Ln, Sarasota, FL 34242
• 

  

  /98

  $18,000 per month

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft
  • House for Rent

  345 Avenida Leona, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a

  Beth Dilley ASCENDIA REAL ESTATE

  345 Avenida Leona, Sarasota, FL 34242
• 

  /2

  $2,300,000 Sold Apr 10, 2025

  • 4,071 Sq Ft
  • $565/SF
  • 299 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1979

  5422 Siesta Cove Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Home has sustained significant water damage on the first floor. Rehab or build your dream home on 90 feet of water frontage in Siesta Cove, a highly sought after neighborhood on the North end of Siesta Key. Unobstructed views of the Intracoastal, Phillippi creek and downtown. 10 minute walk to the public beach, biking distance to the village.

  Tori Harless COLDWELL BANKER REALTY

  5422 Siesta Cove Dr, Sarasota, FL 34242
• 

  

  /61

  Est $743,166 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  6145 Midnight Pass Rd Unit F7, Sarasota, FL 34242

  6145 Midnight Pass Rd Unit F7, Sarasota, FL 34242

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