Siesta Key, FL Homes

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  $1,200,000 Pending

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

  5790 Midnight Pass Rd Unit 406, Sarasota, FL 34242

  Under contract-accepting backup offers. Experience quintessential Siesta Key living at 5790 Midnight Pass Rd, Unit 406, a beautifully updated 2-bedroom, 2-bath residence with sweeping Gulf views and an unbeatable location just minutes from the sugar-white sands and the energy of Siesta Village. Inside, a thoughtfully designed layout offers a spacious living and dining area that flows to the

  linda duquette ENGEL & VOELKERS VENICE DOWNTOWN

  5790 Midnight Pass Rd Unit 406, Sarasota, FL 34242
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  /17

  $8,010 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Condo for Rent

  1200 E Peppertree Ln Unit 406, Sarasota, FL 34242

  This property is a 30 night minimum. Central property, High-rise style unit with 2 Bedrooms and 2 Bathrooms. All rental properties are turn-key furnished and include washer & dryer. Fully equipped kitchens, Internet access, beach access, tennis courts and exercise facilities available, access to two swimming pools. No pets are permitted on the property.

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1200 E Peppertree Ln Unit 406, Sarasota, FL 34242
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  $1,500,000 Sold Dec 01, 2025

  1038 Contento St, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,217 Sq Ft
  • Built 1972

  Last Sold Summary

  • 13% Below List Price
  • $677/SF
  • 169 Days On Market

  Current Estimated Value $1,480,445

  Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

  1038 Contento St, Sarasota, FL 34242
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  /43

  Est $683,788 Not Listed For Sale

  5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

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

  5963 Midnight Pass Rd Unit 362, Sarasota, FL 34242

  Last Sold Summary

  • 15% Below List Price
  • $630/SF
  • 29 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY
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  $595,000

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242

  An investor’s dream! Discover unbeatable income potential with this fully renovated 1 bed, 1 bath condo at Jamaica Royale—a proven high-performing rental generating up to $58,000 annually and already secured with over $30,000 in bookings for 2026. Whether you're seeking a profitable income property, a personal beach retreat, or both, this turnkey unit is positioned to deliver.The spacious

  Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 52, Sarasota, FL 34242
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  /17

  $8,400 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Condo for Rent

  1200 E Peppertree Ln Unit 206, Sarasota, FL 34242

  his property is a 30-night minimum.This 2-bedroom, 2 bath has benefits of both sides being located on the bay side with beach access and on the second floor.The master bedroom has a king bed with a 50 inch flat screen TV, a ceiling fan, and access to the lanai. The master bathroom is a walk-in shower with a glass door and a grab bar.The guest bedroom has a king size bed with a 32 inch

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1200 E Peppertree Ln Unit 206, Sarasota, FL 34242
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  $3,300,000 Sold Apr 10, 2025

  317 Beach Rd, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 3,362 Sq Ft
  • Built 2009

  Last Sold Summary

  • 6% Below List Price
  • $982/SF
  • 14 Days On Market

  Current Estimated Value $3,258,539

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  317 Beach Rd, Sarasota, FL 34242
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  /73

  Est $628,412 Not Listed For Sale

  5600 Beach Way Dr Unit 215, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,259 Sq Ft
  • Built 1970

  5600 Beach Way Dr Unit 215, Sarasota, FL 34242

  Last Sold Summary

  • 2% Below List Price
  • $508/SF
  • 142 Days On Market

  Last Sold Price $640,000

  Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.
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  /27

  $639,000

  • 1 Bed
  • 1.5 Baths
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242

  Experience the best of Gulf-side living in this beautifully renovated 1-bed, 1.5-bath condo on Siesta Key — just steps from the world-famous quartz-sand beaches of Siesta Key. Completely updated from top to bottom, this turnkey coastal retreat features brand-new designer furniture and appliances, making it move-in or rental-ready from the moment you arrive. The spacious layout includes a highly

  Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 63, Sarasota, FL 34242
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  /21

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • House for Rent

  6026 E Peppertree Way Unit 221A, Sarasota, FL 34242

  This property is a 30 night minimum.6026 EPW is a Large garden unit, located on the Bay-side of Midnight Pass.Open porch lanai. This specific unit has a garage.Located about 35 yards away from the Bay.Approx. 1250 Sq. Ft. (1350 including the lanai). Condo Summary:Bedding: Master bedroom: King - Guest Bedroom: 2 TwinsElectronics: Living room: 70 inch Flat Screen - Master

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6026 E Peppertree Way Unit 221A, Sarasota, FL 34242
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  $425,000 Sold Sep 11, 2025

  6029 E Peppertree Way Unit 116, Sarasota, FL 34242

  • 2 Beds
  • 1.5 Baths
  • 975 Sq Ft
  • Built 1973

  Last Sold Summary

  • 27% Below List Price
  • $436/SF
  • 234 Days On Market

  Current Estimated Value $429,748

  Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

  6029 E Peppertree Way Unit 116, Sarasota, FL 34242
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  /45

  Est $607,661 Not Listed For Sale

  5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1974

  5963 Midnight Pass Rd Unit 359, Sarasota, FL 34242

  Last Sold Summary

  • 11% Below List Price
  • $618/SF
  • 172 Days On Market

  Last Sold Price $680,000

  Last Listing Agent Kara Wootson COLDWELL BANKER REALTY
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  /73

  $6,400,000

  • 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 DOUGLAS ELLIMAN

  5132 Jungle Plum Rd, Sarasota, FL 34242
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  /16

  $8,800 per month

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  6030 E Peppertree Way Unit 222A, Sarasota, FL 34242

  This property is a 30 night minimum. 6030 is a small garden unit, located on the Bayside of Midnight Pass Ground Floor unit. 2 bedroom, 2 bath unit . Approx. 1250 Sq. Ft. (1350 including the lanai). Bedding:Master bedroom: KingGuest Bedroom: Queen Electronics:Living room: 32 inch Flat PanelMaster Bedroom: 20 inchGuest Bedroom: 12 inch Bathrooms:Master: ShowerGuest:

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6030 E Peppertree Way Unit 222A, Sarasota, FL 34242
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  $1,000,000 Sold May 12, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 2,049 Sq Ft
  • Built 1952

  Last Sold Summary

  • 13% Below List Price
  • $488/SF
  • 6 Days On Market

  Current Estimated Value $962,296

  Last Listing Agent Frederick Insogna COLDWELL BANKER REALTY

  Unlisted Address
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  /45

  Est $640,376 Not Listed For Sale

  5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

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

  5963 Midnight Pass Rd Unit 328, Sarasota, FL 34242

  Last Sold Summary

  • 15% Below List Price
  • $750/SF
  • 18 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY
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  /66

  $650,000

  • 2 Beds
  • 1.5 Baths
  • 840 Sq Ft

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

  Welcome to your Siesta Key Beach escape at 6006 Midnight Pass Rd, Unit 44! This charming, fully furnished 2-bedroom condo places you steps from the world-famous powdery white sands and turquoise waters of Siesta Key Beach. Enjoy direct private beach access, breathtaking Gulf views, and endless sunsets right from this coveted coastal community. Inside, an open and inviting layout features vaulted

  Michael Mitchell MITCHELL REAL ESTATE

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
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  /15

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 306, Sarasota, FL 34242

  2 BR - 2 BA - 6 Person Max - High-rise - Greenbelt View This property is a 30 night minimum.1255 - 306 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.Hardwood floors on the lanai. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master Bedroom: King - Guest Bedroom:

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 306, Sarasota, FL 34242
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  $600,000 Sold Aug 29, 2025

  4522 Banan Place, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft
  • Built 1962

  Last Sold Summary

  • 17% Below List Price
  • $613/SF
  • 191 Days On Market

  Current Estimated Value $630,910

  Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

  4522 Banan Place, Sarasota, FL 34242
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  /47

  Est $1,460,941 Not Listed For Sale

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

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

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

  Last Sold Summary

  • 46% Above List Price
  • $780/SF
  • 15 Days On Market

  Last Sold Price $1,000,000

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY
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  /51

  $2,295,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,676 Sq Ft

  518 Venice Ln, Sarasota, FL 34242

  Under contract-accepting backup offers. ELEGANT SIESTA KEY WATERFRONT RETREAT - Welcome to a truly distinguished canal-front residence, where timeless design meets the effortless beauty of waterfront living. Set beneath majestic oaks and tropical landscaping, the canopied circular paver driveway greets you. This exquisite pool home offers privacy, sophistication and an extraordinary outdoor

  Pamela Pileggi PREFERRED SHORE LLC

  518 Venice Ln, Sarasota, FL 34242
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  /30

  $6,100 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 601, Sarasota, FL 34242

  255-601 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.This unit does not have a bed in the guest bedroom, it will have a sleeper sofa. Open kitchen floor plan with stainless steel appliances. Open porch lanai. Guest bedroom TV is mounted on the wall. Dual sink vanity in the master bathroom, seat in the master bathroom shower. Assigned covered parking located in

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 601, Sarasota, FL 34242
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  $5,600,000 Sold Jan 22, 2026

  251 Cedar Park Cir, Sarasota, FL 34242

  • 4 Beds
  • 3.5 Baths
  • 3,446 Sq Ft
  • Built 2013

  Last Sold Summary

  • 7% Below List Price
  • $1,625/SF
  • 20 Days On Market

  Current Estimated Value $5,844,799

  Last Listing Agent Steve Wexler PREMIER SOTHEBY'S INTERNATIONAL REALTY

  251 Cedar Park Cir, Sarasota, FL 34242
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  /27

  Est $629,365 Not Listed For Sale

  6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1967

  6140 Midnight Pass Rd Unit VILLA D3, Sarasota, FL 34242

  Last Sold Summary

  • 13% Below List Price
  • $676/SF
  • 0 Days On Market

  Last Sold Price $722,500

  Last Listing Agent Barrett Webber BEACHY PROPERTIES
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  /56

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 2,233 Sq Ft

  5155 Hidden Harbor Rd, Sarasota, FL 34242

  Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded.Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating

  Matt Buttner LIST NOW REALTY, LLC

  5155 Hidden Harbor Rd, Sarasota, FL 34242
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  /19

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 501, Sarasota, FL 34242

  Welcome to this beautifully remodeled Bayside Mid-rise unit. This spacious 2-bedroom, 2-bathroom condo is situated on the 5th floor, As you step inside, you'll be greeted by a tastefully decorated living area with modern furnishings and a serene coastal color palette. The open-concept design seamlessly connects the living, dining, and kitchen areas, creating a perfect space for relaxation and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 501, Sarasota, FL 34242
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  /2

  $630,000 Sold Apr 30, 2025

  5239 Winding Way, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1958

  Last Sold Summary

  • 33% Below List Price
  • $417/SF
  • 69 Days On Market

  Current Estimated Value $665,617

  Last Listing Agent Brian Cirillo BALDWIN PARK REALTY LLC

  5239 Winding Way, Sarasota, FL 34242
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  /73

  Est $543,755 Not Listed For Sale

  1500 Cove II Place Unit 532, Sarasota, FL 34242

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

  1500 Cove II Place Unit 532, Sarasota, FL 34242

  Last Sold Summary

  • 14% Below List Price
  • $733/SF
  • 41 Days On Market

  Last Sold Price $630,000

  Last Listing Agent Jason Wood CORCORAN DWELLINGS REALTY
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  /59

  $730,000

  • 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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  /15

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 101, Sarasota, FL 34242

  This property is a 30 night minimum.This 2 bedroom, 2 bath is located on the first floor in a bay-side mid-rise and is approximately 75 yards from the Bay.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and access to the extended living lanai. The updated master bathroom has new finishes and a walk-in glass door shower with a removable shower head.The guest bedroom has

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 101, Sarasota, FL 34242
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  $1,950,000 Sold Dec 18, 2025

  5430 Avenida Del Mare, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,010 Sq Ft
  • Built 1951

  Last Sold Summary

  • 22% Below List Price
  • $970/SF
  • 225 Days On Market

  Current Estimated Value $1,841,031

  Last Listing Agent Jonathan Minerick HOMECOIN.COM

  5430 Avenida Del Mare, Sarasota, FL 34242
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  /79

  Est $704,368 Not Listed For Sale

  1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft
  • Built 1975

  1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242

  Last Sold Summary

  • 4% Below List Price
  • $641/SF
  • 48 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Ian McPherson COLDWELL BANKER REALTY
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  /60

  $2,735,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,254 Sq Ft

  5236 Siesta Cove Dr, Sarasota, FL 34242

  Under contract-accepting backup offers. No Hurricane or Flood Damage. A coastal modern oasis in Siesta Cove, Siesta Key’s premier neighborhood, highlights 80 feet of waterfront with convenient boat access to Gulf and Bay, with newer seawall, boat dockage, and an extraordinary pool that invites you to enjoy Siesta Key’s relaxed lifestyle. Breathtaking Sarasota Bay vistas along the many peaceful

  Bradley Kayser COLDWELL BANKER REALTY

  5236 Siesta Cove Dr, Sarasota, FL 34242
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  /22

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 403, Sarasota, FL 34242

  This property is a 30 night minimum.This stunning, updated 2 bedroom, 2 bath is located in a bay-side mid-rise unit and is approximately 75 yards from the bay.The master bedroom has a king bed, a TV, and pocket sliding glass doors that gives access to the extended lanai living. The master bathroom has a walk-in glass door shower with grab bars and a beautiful granite vanity.The guest

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 403, Sarasota, FL 34242
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  $4,095,000 Sold Jan 26, 2026

  5078 Sandy Beach Ave, Sarasota, FL 34242

  • 4 Beds
  • 4 Baths
  • 3,164 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Below List Price
  • $1,294/SF
  • 2 Days On Market

  Current Estimated Value $3,290,187

  Last Listing Agent Darlene Gamble FINE PROPERTIES

  5078 Sandy Beach Ave, Sarasota, FL 34242
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  /79

  Est $813,858 Not Listed For Sale

  1600 Cove II Place Unit 424, Sarasota, FL 34242

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft
  • Built 1979

  1600 Cove II Place Unit 424, Sarasota, FL 34242

  Last Sold Summary

  • $474/SF
  • 28 Days On Market

  Last Sold Price $815,000

  Last Listing Agent Peter Lev EXCEPTIONS REALTY
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  /61

  $3,657,625 New Construction

  • 3 Beds
  • 4.5 Baths
  • 3,034 Sq Ft

  5103 Windward Ave, Sarasota, FL 34242

  Completed new construction! Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white

  Karen Greco GRECO REAL ESTATE

  5103 Windward Ave, Sarasota, FL 34242
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  /26

  $7,000 per month

  • 2 Beds
  • 11 Baths
  • 1,163 Sq Ft
  • Condo for Rent

  1200 E Peppertree Ln Unit 602, Sarasota, FL 34242

  This property is a 30 night minimum.1200-602 is a Penthouse unit in a Bay-side Mid-rise, located approximately 150 yards away from the Bay with a view of the waterway and downtown Sarasota in the distance. Approx. 1200 Sq. Ft. (1462 including the lanai)Lanai has a twin daybed with a trundle, eating area, and desk setup for remote work. Assigned covered parking located in parking garage

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1200 E Peppertree Ln Unit 602, Sarasota, FL 34242
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  /2

  $700,000 Sold Dec 22, 2025

  5223 Shadow Lawn Dr, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1967

  Last Sold Summary

  • 30% Below List Price
  • $480/SF
  • 161 Days On Market

  Current Estimated Value $725,098

  Last Listing Agent Justin Harris REAL BROKER, LLC

  5223 Shadow Lawn Dr, Sarasota, FL 34242
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  /17

  Est $479,648 Not Listed For Sale

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft
  • Built 1962

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

  Last Sold Summary

  • 13% Below List Price
  • $899/SF
  • 0 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Melissa Cheetham LPT REALTY, LLC

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