Siesta Key, FL Homes

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  $1,795,000

  • Land
  • 0.25 Acre
  • $7,180,000 per Acre

  9238 Midnight Pass Rd, Sarasota, FL 34242

  Building Permit Has been issed for this property. INCREDIBLE WATERFRONT OPPORTUNITY ON WORLD RENOWNED SIESTA KEY !!! This 10,857 square foot vacant lot is shovel ready with permits and plans approved and in hand, This lot lies within RMF zoning which allows for short-term rentals. This is the perfect location for your new home or your next income property: close to the restaurants

  Robert Louloudes STARZ REAL ESTATE, LLC

  9238 Midnight Pass Rd, Sarasota, FL 34242
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  /96

  $4,500 per month

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

  1257 S Portofino Dr Unit 38, Sarasota, FL 34242

  Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice decor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the

  Kay Esposito SIGNATURE REALTY ASSOCIATES

  1257 S Portofino Dr Unit 38, Sarasota, FL 34242
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  $357,000 Sold Sep 19, 2025

  1300 N Portofino Dr Unit 208, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft
  • Built 1969

  Last Sold Summary

  • 29% Below List Price
  • $360/SF
  • 403 Days On Market

  Current Estimated Value $378,741

  Last Listing Agent Jill Thomas BERKSHIRE HATHAWAY HOMESERVICE

  1300 N Portofino Dr Unit 208, Sarasota, FL 34242
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  /33

  Est $810,218 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 35, Sarasota, FL 34242
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  /12

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 1,831 Sq Ft

  4894 Oxford Dr, Sarasota, FL 34242

  POOL HOME!! Priced To Sell!! Nestled on the peaceful tranquil island of Siesta Key, renowned for its world-class beach and romantic sunsets. JUST MINUTES FROM Siesta Beach & Village. This is the most wonderful place to embrace island-style living. This north island location on a quiet canopy street is walkable to the village, beach, and renowned Out-of-Door Academy. This 3 Bedroom and 2 & 1/2

  Marc Overfelt FLORIDA BAY REALTY INC

  4894 Oxford Dr, Sarasota, FL 34242
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  /57

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Condo for Rent

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

  Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot

  Beth Dilley ASCENDIA REAL ESTATE

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
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  /2

  $840,000 Sold Feb 25, 2025

  5420 Cape Leyte Dr, Sarasota, FL 34242

  • Land
  • 0.35 Acre
  • $2,400,000 per Acre

  Last Sold Summary

  • 1% Above List Price
  • 2 Days On Market

  Current Estimated Value $823,859

  Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

  5420 Cape Leyte Dr, Sarasota, FL 34242
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  /59

  Est $692,059 Not Listed For Sale

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

  6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 18, Sarasota, FL 34242
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  $499,000

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft

  1257 S Portofino Dr Unit 208, Sarasota, FL 34242

  This appealing corner residence located on the second level in the Albacore Building inside SIESTA HARBOR offers the convenience of a walk-up or elevator access. This home boasts a large covered balcony showcasing stunning canal views and beautiful landscaping. Community docks are available on a first come first serve basis; accommodating boats up to 30 ft. Deep water canal with direct access

  Ingrid Caruso COLDWELL BANKER REALTY

  1257 S Portofino Dr Unit 208, Sarasota, FL 34242
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  /42

  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft
  • Condo for Rent

  6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

  Variable rent based on season

  Terry Dorrity INTEGRITY INVESTMENTS REALTY

  6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
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  /2

  $700,000 Sold Aug 27, 2025

  1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1988

  Last Sold Summary

  • 18% Below List Price
  • $547/SF
  • 155 Days On Market

  Current Estimated Value $691,864

  Last Listing Agent Fred Sieger Jr COMPASS FLORIDA LLC

  1228 Siesta Bayside Dr Unit 1228C, Sarasota, FL 34242
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  /39

  Est $724,063 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 939 Sq Ft

  6150 Midnight Pass Rd Unit 17, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 17, Sarasota, FL 34242
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  /76

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft

  1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242

  Price Reduction! An amazing year-round residence, vacation or investment property! Don't miss this rare opportunity to own a beautifully furnished 3-bedroom, 2-bath + loft unit just steps from world-renowned Siesta Beach with dedicated beach access. Recently renovated, this turnkey residence features a bright open floor plan with wood-look tile, shiplap accents, and raised ceilings in the

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
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  $6,500 per month

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

  1250 N Portofino Dr Unit 102, Sarasota, FL 34242

  Available January to April 1, 2026! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 102, Sarasota, FL 34242
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  /2

  $1,350,000 Sold Dec 08, 2025

  5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $901/SF
  • 38 Days On Market

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242
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  /57

  Est $717,987 Not Listed For Sale

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

  6150 Midnight Pass Rd Unit 7, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 7, Sarasota, FL 34242
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  /19

  $349,000

  • 1 Bed
  • 1 Bath
  • 857 Sq Ft

  5683 Midnight Pass Rd Unit 110, Sarasota, FL 34242

  5683 Midnight Pass Rd #110 — Siesta Key Beach Condo 1 Bed | 1 Bath | ~857 Sq Ft | Turnkey | White Sands Village Discover your slice of paradise at White Sands Village, perfectly located just across the street from world-famous Siesta Key Beach. This beautifully maintained 1-bedroom, 1-bath condo at 5683 Midnight Pass Rd #110 combines the ultimate beach lifestyle with outstanding rental income

  Bradley Kayser COLDWELL BANKER REALTY

  5683 Midnight Pass Rd Unit 110, Sarasota, FL 34242
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  $3,800 per month

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Condo for Rent

  4660 Ocean Blvd Unit B2, Sarasota, FL 34242

  SIESTA KEY WATERFRONT UNIT AVAILABLE starting April 1, 2026. Close proximity to beach. Sea Village offers million dollar views and is situated on 5 acres overlooking the Gulf. It provides a peaceful retreat with opportunities to witness breathtaking sunsets, the full moon reflecting on the water, and serene walks to the beach and Siesta Village. Additionally, its location on the north end of the

  Margaret Young JENNETTE PROPERTIES, INC.

  4660 Ocean Blvd Unit B2, Sarasota, FL 34242
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  /2

  $900,000 Sold Dec 26, 2024

  337 Avenida Madera, Sarasota, FL 34242

  • Land
  • 0.19 Acre
  • $4,736,842 per Acre

  Last Sold Summary

  • 21 Days On Market

  Current Estimated Value $839,267

  Last Listing Agent Bob Stahlschmidt II BRIGHT REALTY

  337 Avenida Madera, Sarasota, FL 34242
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  /61

  Est $746,690 Not Listed For Sale

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

  6150 Midnight Pass Rd Unit 5, Sarasota, FL 34242

  6150 Midnight Pass Rd Unit 5, Sarasota, FL 34242
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  /54

  $995,000 Open Sun 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 928 Sq Ft

  5400 Ocean Blvd Unit 9-4, Sarasota, FL 34242

  Discover coastal luxury at Beach Terrace, one of Siesta Key's most coveted addresses. Perfectly positioned at the end of the village with direct Gulf of Mexico frontage, this exceptional 1 bedroom, 1 bathroom corner residence offers an unparalleled beachfront lifestyle with breathtaking panoramic views that truly set it apart. This thoughtfully designed condominium showcases sweeping vistas that

  Mickey Kiernan MICHAEL SAUNDERS & COMPANY

  5400 Ocean Blvd Unit 9-4, Sarasota, FL 34242
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  /14

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 3,395 Sq Ft
  • House for Rent

  95 Sandy Hook Rd S, Sarasota, FL 34242

  6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!TROPICAL PARADISE. SIESTA KEY'S "OUTDOOR ACADEMY"!!! ONLY 1/2 MILE AWAY! One-of-a-kind enclave of Sandy Hook at USA's No 1 BEACH. A private road takes you to Elevated living area with entry

  Joseph Russo COURTYARD MODERN

  95 Sandy Hook Rd S, Sarasota, FL 34242
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  /2

  $4,325,000 Sold Jan 30, 2025

  5300 Avenida Del Mare, Sarasota, FL 34242

  • 4 Beds
  • 7 Baths
  • 3,234 Sq Ft
  • Built 2023

  Last Sold Summary

  • 4% Below List Price
  • $1,337/SF
  • 33 Days On Market

  Current Estimated Value $4,068,363

  Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5300 Avenida Del Mare, Sarasota, FL 34242
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  /57

  Est $764,834 Not Listed For Sale

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

  6140 Midnight Pass Rd Unit B1, Sarasota, FL 34242

  6140 Midnight Pass Rd Unit B1, Sarasota, FL 34242
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  /53

  $674,900

  • 2 Beds
  • 1 Bath
  • 753 Sq Ft

  925 Beach Rd Unit 311, Sarasota, FL 34242

  This third-floor unit in La Siesta offers the updated features that make this a sought-after rental unit. La Siesta is directly across from the main entrance to the world-renowned Siesta Key Public Beach with white sands and turquoise waters. Take your morning coffee on the lanai where you’ll enjoy delightful breezes and gulf views. This two-bedroom one bath unit” a blue heaven” has been totally

  June Howell MICHAEL SAUNDERS & COMPANY

  925 Beach Rd Unit 311, Sarasota, FL 34242
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  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft
  • Condo for Rent

  5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

  ** BOOKED JANUARY THROUGH MARCH 2025 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor 2 Bedroom/ 2 Bath luxury condo. Full Gulf views from living room/dining room combo and master bedroom! Gulf & Bay Club is located on Siesta Key Beach, voted #1 Beach in the USA! The spacious unit

  Kayla Lamb NEXTHOME EXCELLENCE

  5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
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  $780,000 Sold Mar 11, 2025

  5133 Sandy Beach Ave, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1969

  Last Sold Summary

  • 8% Below List Price
  • $523/SF
  • 99 Days On Market

  Current Estimated Value $731,630

  Last Listing Agent Joanna Benante MICHAEL SAUNDERS & COMPANY

  5133 Sandy Beach Ave, Sarasota, FL 34242
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  /21

  Est $531,760 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 766 Sq Ft

  5128 Calle Minorga Unit 5128, Sarasota, FL 34242

  5128 Calle Minorga Unit 5128, Sarasota, FL 34242
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  /57

  $2,675,000 New Construction

  • 4 Beds
  • 4 Baths
  • 2,729 Sq Ft

  6913 Bochi Cir, Sarasota, FL 34242

  Under Construction. Under Construction. **Short term promotional pricing, take advantage now while it's available!** Discover La Linda, an exclusive collection ofeight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought-after Siesta Key, theseelevated residences are crafted to the highest standards, featuring solid block

  Jeremy Hartmark LPT REALTY, LLC

  6913 Bochi Cir, Sarasota, FL 34242
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  /15

  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 1,363 Sq Ft
  • Condo for Rent

  460 Beach Rd Unit A1, Sarasota, FL 34242

  Available May 2026. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take a walk along the

  Brenda Cozy COLDWELL BANKER REALTY

  460 Beach Rd Unit A1, Sarasota, FL 34242
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  /2

  $650,000 Sold Nov 25, 2025

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1974

  Last Sold Summary

  • 21% Below List Price
  • $650/SF
  • 199 Days On Market

  Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242
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  /64

  Est $627,161 Not Listed For Sale

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

  225 Hourglass Way Unit 307, Sarasota, FL 34242

  225 Hourglass Way Unit 307, Sarasota, FL 34242
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  /56

  $2,750,000

  • 4 Beds
  • 3.5 Baths
  • 3,232 Sq Ft

  4757 Higel Ave, Sarasota, FL 34242

  Welcome to Villa del Roble on Siesta Key’s Grand Canal—a true boater’s dream and an elevated waterfront residence that remained free of flooding during recent hurricanes. Timeless elegance and refined sophistication define this thoughtfully remodeled home, offering over 3,200 sq. ft. across two floors with four bedrooms, an office, and three full and one-half baths.Light-filled living spaces

  Victoria Turner MICHAEL SAUNDERS & COMPANY

  4757 Higel Ave, Sarasota, FL 34242
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,123 Sq Ft
  • Condo for Rent

  1250 N Portofino Dr Unit 301, Sarasota, FL 34242

  Immaculate End Unit in the Marlin building, Ready for you to Enjoy through January 2026 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers a

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 301, Sarasota, FL 34242
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  /2

  $1,266,700 Sold Dec 19, 2025

  307 Avenida de Paradisio, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,511 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $838/SF
  • 28 Days On Market

  Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC

  307 Avenida de Paradisio, Sarasota, FL 34242
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  /34

  Est $617,131 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  4660 Ocean Blvd Unit F1, Sarasota, FL 34242

  4660 Ocean Blvd Unit F1, Sarasota, FL 34242
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  $2,800,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,970 Sq Ft

  6924 Bochi Cir, Sarasota, FL 34242

  Under Construction. **Short term promotional pricing, take advantage now while it's available!**Discover La Linda, an exclusive collection of eight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought-after Siesta Key, these elevated residences are crafted to the highest standards, featuring solid block construction on all levels,

  Jeremy Hartmark LPT REALTY, LLC

  6924 Bochi Cir, Sarasota, FL 34242
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  $5,000 per month

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

  1257 S Portofino Dr Unit 36, Sarasota, FL 34242

  Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a new coffee table, an electric fireplace, new shower heads, a portable electric grill, bikes, beach

  Margaret Young JENNETTE PROPERTIES, INC.

  1257 S Portofino Dr Unit 36, Sarasota, FL 34242
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  /2

  $1,259,000 Sold Jul 16, 2025

  20 Whispering Sands Dr Unit 406, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1973

  Last Sold Summary

  • 10% Below List Price
  • $982/SF
  • 61 Days On Market

  Current Estimated Value $1,190,516

  Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 406, Sarasota, FL 34242
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  /47

  Est $695,738 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,469 Sq Ft

  6267 Midnight Pass Rd Unit 107, Sarasota, FL 34242

  6267 Midnight Pass Rd Unit 107, Sarasota, FL 34242

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