Siesta Key, FL Homes

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  $2,795,000

  • 3 Beds
  • 2 Baths
  • 3,201 Sq Ft

  5303 Hidden Harbor Rd, Sarasota, FL 34242

  Now is your opportunity to own this waterfront tropical oasis on Siesta Key in the highly sought after exclusive community of Hidden Harbor. Comprised of just 36 homes, Hidden Harbor located on the North end of Siesta Key, is one of the most unique developments in Sarasota with its tropical landscaping reminiscent of old Florida. Most known for its waterfront lots and brick paver streets shaded

  Walter Shepherd COLDWELL BANKER REALTY

  5303 Hidden Harbor Rd, Sarasota, FL 34242
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  $7,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Apartment for Rent

  6154 Midnight Pass Rd Unit 104, Sarasota, FL 34242

  Watch the magnificent sunsets over blue gulf waters from the lanai of a newly, up-dated, completely renovated, and re-decorated ground floor apartment on the white sands of Crescent Beach on Siesta Key. The 2 bedroom, 2 bathroom, apartment sleeps 4. The beds can be arranged as 1 King and 2 twin beds pushed together to form 1 Large Queen with advance notice to the office. The kitchen is granite

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 104, Sarasota, FL 34242
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  $550,000 Sold May 27, 2025

  6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft
  • Built 1967

  Last Sold Summary

  • $735/SF
  • 1 Day On Market

  Current Estimated Value $533,353

  Last Listing Agent Scotty Ledford VUE REALTY, LLC

  6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242
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  Est $669,494 Not Listed For Sale

  1400 Cove Place Unit 631, Sarasota, FL 34242

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Built 1979

  1400 Cove Place Unit 631, Sarasota, FL 34242

  Last Sold Summary

  • 5% Above List Price
  • $744/SF
  • 11 Days On Market

  • Last Sold Price $640,000
  • Jun 02, 2023

  Last Listing Agent Grace Bergeron MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC
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  $975,000

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242

  Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities.Spanning nearly

  Roger Pettingell COLDWELL BANKER REALTY

  1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
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  $6,900 Per Month

  • 2 Beds
  • 1 Bath
  • 941 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit 16, Sarasota, FL 34242

  Enjoy the beach life in this recently upgraded villa just a few steps from beautiful Siesta Key Beach. The entire villa has been newly painted and contains all new windows, window treatments and flooring. The master bedroom features a queen bed with new coastal furniture, and the guest bedroom has 2 twin beds. Both bedrooms also have new pillow top mattresses and bed coverings. The living room

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 16, Sarasota, FL 34242
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  $1,175,000 Sold Feb 10, 2026

  19 Whispering Sands Dr Unit 1204, Sarasota, FL 34242

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

  Last Sold Summary

  • 9% Below List Price
  • $917/SF
  • 9 Days On Market

  Current Estimated Value $1,183,422

  Last Listing Agent Chelsa Vahtomin COLDWELL BANKER REALTY

  19 Whispering Sands Dr Unit 1204, Sarasota, FL 34242
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  Est $720,840 Not Listed For Sale

  5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Built 1974

  5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

  Last Sold Summary

  • 13% Below List Price
  • $650/SF
  • 66 Days On Market

  • Last Sold Price $825,000
  • Aug 04, 2023

  Last Listing Agent Linda Stowe Michael Saunders
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  $2,300,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,468 Sq Ft

  5024 Commonwealth Dr, Sarasota, FL 34242

  Under contract-accepting backup offers. Nestled in the quaint neighborhood along the Grand Canal on Siesta Key, this Key West style home offers the perfect blend of old-world charm and modern living. This well-appointed custom-built home has a spectacular open floor plan. The home's grand entrance welcomes you through a covered porch that leads to an oversized foyer. An abundance of natural

  Gabi Charity CHARITY & WEISS INTERNATIONAL LLC

  5024 Commonwealth 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
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  $1,120,000 Sold Apr 23, 2026

  5790 Midnight Pass Rd Unit 406, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $782/SF
  • 3 Days On Market

  Current Estimated Value $1,185,686

  Last Listing Agent linda duquette ENGEL & VOELKERS VENICE DOWNTOWN

  5790 Midnight Pass Rd Unit 406, Sarasota, FL 34242
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  /30

  Est $552,422 Not Listed For Sale

  5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1976

  5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242

  Last Sold Summary

  • $521/SF
  • 368 Days On Market

  • Last Sold Price $550,000
  • May 07, 2024

  Last Listing Agent Ethel Lovelace Michael Saunders
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  $2,865,000 Pending

  • 4 Beds
  • 4 Baths
  • 2,819 Sq Ft

  4881 Oxford Dr, Siesta Key, FL 34242

  Why wait to build an elevated home? Here is your chance to have a modern coastal retreat on Siesta Key’s Grand Canal — beautifully designed, impeccably finished, and perfectly positioned for the ultimate waterfront lifestyle. This exceptional 2020 built three-story residence combines luxury, comfort, and an effortless indoor–outdoor flow, all just moments from Siesta Key Village. From the moment

  Darlene Gamble FINE PROPERTIES

  4881 Oxford Dr, Siesta Key, FL 34242
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  $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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  $4,000,000 Sold Apr 08, 2026

  7707 Midnight Pass Rd, Sarasota, FL 34242

  • Land
  • 2 Acres
  • $2,000,000 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 462 Days On Market

  Current Estimated Value $3,782,635

  Last Listing Agent Lisa Maria 1ST VISION REALTY OF FLORIDA I

  7707 Midnight Pass Rd, Sarasota, FL 34242
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  Est $609,664 Not Listed For Sale

  141 Avenida Messina Unit 1, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • Built 1966

  141 Avenida Messina Unit 1, Sarasota, FL 34242

  Last Sold Summary

  • 5% Below List Price
  • $711/SF
  • 119 Days On Market

  • Last Sold Price $640,000
  • Sep 06, 2023

  Last Listing Agent Susan Christy BANZHAF & ASSOCIATES INC
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  $1,000,000 Pending

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

  19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242

  Under contract-accepting backup offers. PRICE IMPROVEMENT!! Welcome to this beautifully remodeled 11th floor GULF FRONT Whispering Sands tower residence – just one floor below the penthouse level – where sweeping, unobstructed FULL Gulf views meet breathtaking, colorful sunsets that paint the sky each evening. This light filled 2BR/2BA condo is the perfect combination of refined coastal style

  Harriet Stopher COLDWELL BANKER REALTY

  19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242
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  $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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  $2,875,000 Sold Oct 24, 2025

  5169 Sandy Shore Ave, Sarasota, FL 34242

  • 3 Beds
  • 3.5 Baths
  • 2,885 Sq Ft
  • Built 2015

  Last Sold Summary

  • 18% Below List Price
  • $997/SF
  • 219 Days On Market

  Current Estimated Value $2,828,511

  Last Listing Agent Andy Barnhardt WATERSIDE REALTY LLC

  5169 Sandy Shore Ave, Sarasota, FL 34242
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  Est $791,019 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,212 Sq Ft
  • Built 1968

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

  Last Sold Summary

  • 5% Above List Price
  • $619/SF
  • 115 Days On Market

  • Last Sold Price $750,000
  • Jul 19, 2023

  Last Listing Agent Suki Scollo COLDWELL BANKER REALTY
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  $2,600,000

  • 3 Beds
  • 3.5 Baths
  • 3,795 Sq Ft

  5331 Siesta Cove Dr, Sarasota, FL 34242

  Immerse yourself in the tranquility of 5331 Siesta Cove Drive, a stunning jewel situated on a corner lot in the premier Siesta Key neighborhood. With a Mediterranean architectural aesthetic that radiates finesse, this residence features a stunningly crafted exterior adorned with European copper domes perfectly poised on an impressive 11’ elevation. Upon entry, one is greeted by an expansive, open

  Mary Tardi LOKATION

  5331 Siesta Cove Dr, Sarasota, FL 34242
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  $8,970 Per Month

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 59, Sarasota, FL 34242

  Villa 59 at Aloha Kai invites you to kick back and escape the traffic and long lines—no need to leave the property! Enjoy the pristine beach, the refreshing pool, and your fully equipped kitchen, all designed to make your stay effortless and relaxing. The comfortable furnishings and soothing neutral colors create a welcoming atmosphere where you can truly feel at home. Savor your morning coffee

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 59, Sarasota, FL 34242
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  $1,400,000 Sold Jul 28, 2025

  309 Avenida Milano, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • Built 1974

  Last Sold Summary

  • $973/SF
  • 64 Days On Market

  Current Estimated Value $1,343,852

  Last Listing Agent Tim Yocum, Sr COLDWELL BANKER REALTY

  309 Avenida Milano, Sarasota, FL 34242
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  Est $4,058,723 Not Listed For Sale

  5310 Avenida Del Mare, Siesta Key, FL 34242

  • 5 Beds
  • 8 Baths
  • 3,759 Sq Ft
  • Built 2023

  5310 Avenida Del Mare, Siesta Key, FL 34242

  Last Sold Summary

  • 8% Below List Price
  • $1,171/SF
  • 132 Days On Market

  • Last Sold Price $4,400,000
  • Aug 02, 2024

  Last Listing Agent Rudy Dudon Michael Saunders
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  $750,000

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

  4900 Ocean Blvd Unit 304, Sarasota, FL 34242

  TURNKEY FURNISHED: Perched among the treetops in the beloved Sandy Cove community on Siesta Key, this beautifully renovated 2BR/2BA residence offers a rare blend of privacy, charm and authentic island living. With 1,200+/- sq. ft. of thoughtfully designed space and three private balconies, life here feels like a peaceful retreat surrounded by nature, where sunlight filters through the trees and

  Tracey Stetler COLDWELL BANKER REALTY

  4900 Ocean Blvd Unit 304, Sarasota, FL 34242
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  $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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  $975,000 Sold Dec 09, 2025

  568 Venice Ln, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 1,818 Sq Ft
  • Built 1975

  Last Sold Summary

  • 13% Below List Price
  • $536/SF
  • 141 Days On Market

  Current Estimated Value $1,010,698

  Last Listing Agent Wade Stafford ALL FLORIDA PROPERTY GROUP,INC

  568 Venice Ln, Sarasota, FL 34242
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  Est $709,448 Not Listed For Sale

  5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Built 1974

  5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  Last Sold Summary

  • 12% Below List Price
  • $634/SF
  • 0 Days On Market

  • Last Sold Price $805,000
  • May 17, 2024

  Last Listing Agent Rudy Dudon Michael Saunders
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  $850,000

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft

  1055 W Peppertree Dr Unit 102AA, Sarasota, FL 34242

  Rare opportunity to own one of the most resilient and desirable residences on Siesta Key! This 2-bedroom, 2-bath condominium offers 1,163 square feet of living space (1,462 gross square feet) and is ideally positioned on the west side of the building on an elevated first floor, approximately 15 feet above sea level. It is also the closest high-rise condominium to the beach, offering exceptional

  Tanya Stutzman REALTY HUB

  1055 W Peppertree Dr Unit 102AA, Sarasota, FL 34242
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  /17

  $7,470 Per Month

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 48, Sarasota, FL 34242

  New photos coming soon! Villa 48 at Aloha Kai offers the perfect setting for your next beach escape. Located on Siesta Key—a popular barrier island on Florida’s West Coast—this family-friendly, gated resort community is nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its powdery white quartz sand and emerald-green waters, Siesta Key

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 48, Sarasota, FL 34242
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  $869,000 Sold Mar 12, 2026

  795 Plymouth St, Sarasota, FL 34242

  • 4 Beds
  • 2.5 Baths
  • 1,967 Sq Ft
  • Built 1986

  Last Sold Summary

  • 24% Below List Price
  • $442/SF
  • 181 Days On Market

  Current Estimated Value $905,052

  Last Listing Agent Stephanie Church COLDWELL BANKER REALTY

  795 Plymouth St, Sarasota, FL 34242
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  Est $705,700 Not Listed For Sale

  1101 Lake House Cir Unit C-206, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1981

  1101 Lake House Cir Unit C-206, Sarasota, FL 34242

  Last Sold Summary

  • 9% Below List Price
  • $573/SF
  • 154 Days On Market

  • Last Sold Price $775,000
  • Jun 27, 2024

  Last Listing Agent Kenneth Ipox DOUGLAS ELLIMAN
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  $775,000

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

  6204 Midnight Pass Rd Unit 205, Sarasota, FL 34242

  Welcome to your slice of paradise at Siesta Dunes Beach Community. This beautifully maintained 2-bedroom, 2-bath end-unit is located on the second floor and is offered turnkey furnished, making it ideal as a vacation getaway, investment property, or full-time residence. Being an end unit, the condo is filled with extra natural light and offers a charming peek-a-boo ocean view to remind you just

  Christine Green COLDWELL BANKER REALTY

  6204 Midnight Pass Rd Unit 205, Sarasota, FL 34242
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  $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
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  $1,300,000 Sold Jun 11, 2025

  329 Avenida Leona, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1972

  Last Sold Summary

  • 20% Below List Price
  • $781/SF
  • 81 Days On Market

  Current Estimated Value $1,259,741

  Last Listing Agent Randy Owens COLDWELL BANKER REALTY

  329 Avenida Leona, Sarasota, FL 34242
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  Est $1,032,180 Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft
  • Built 1970

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

  Last Sold Summary

  • $1,261/SF
  • 214 Days On Market

  • Last Sold Price $1,029,000
  • Apr 22, 2025

  Last Listing Agent Robert Anderson Jr RE/MAX
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  $825,000

  • 2 Beds
  • 2 Baths
  • 1,115 Sq Ft

  6063 E Peppertree Way Unit 111, Sarasota, FL 34242

  First-Floor Bayfront | No Stairs | Full Bay Views | Outdoor Patio.Enjoy effortless coastal living in this like-new, fully rebuilt residence (from the studs in), featuring all-new electrical, plumbing, HVAC, insulation, interior wall soundproofing, hurricane-impact windows, and five-year warranties on major appliances. HOA includes building and structural insurance, and internet/cable. Home

  Eliza Miller PEPPERTREE BAY REALTY INC

  6063 E Peppertree Way Unit 111, Sarasota, FL 34242
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  $7,500 Per Month

  • 2 Beds
  • 1 Bath
  • 941 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit C05, Sarasota, FL 34242

  Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually owned. The minimum stay is 5 or 7 nights, depending on the owner. Every Unit at Casa Blanca is individually decorated and fully furnished including all cookware and linens including beach towels. They have individually controlled AC/Heating and color cable TVs, WIFI, telephones

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit C05, Sarasota, FL 34242
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  $640,000 Sold Dec 08, 2025

  141 Avenida Messina Unit 4, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft
  • Built 1966

  Last Sold Summary

  • 8% Below List Price
  • $618/SF
  • 60 Days On Market

  Current Estimated Value $641,800

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

  141 Avenida Messina Unit 4, Sarasota, FL 34242
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  Est $648,786 Not Listed For Sale

  5600 Beach Way Dr Unit 213, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1970

  5600 Beach Way Dr Unit 213, Sarasota, FL 34242

  Last Sold Summary

  • 5% Below List Price
  • $534/SF
  • 141 Days On Market

  • Last Sold Price $685,000
  • Nov 01, 2023

  Last Listing Agent Lori Carey PREMIER SOTHEBY'S INTERNATIONAL REALTY

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