Siesta Key, FL Homes

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  $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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  $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 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 $424,221

  Last Listing Agent Cheryl Santelli PEPPERTREE BAY REALTY INC

  6029 E Peppertree Way Unit 116, Sarasota, FL 34242
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  /73

  Est $543,882 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1500 Cove II Place Unit 532, Sarasota, FL 34242

  1500 Cove II Place Unit 532, Sarasota, FL 34242
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  $2,950,000

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

  5236 Siesta Cove Dr, Sarasota, FL 34242

  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 panoramic patio terraces provide endless

  Bradley Kayser COLDWELL BANKER REALTY

  5236 Siesta Cove Dr, Sarasota, FL 34242
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  $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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  $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 $965,719

  Last Listing Agent Frederick Insogna COLDWELL BANKER REALTY

  Unlisted Address
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  /79

  Est $668,799 Not Listed For Sale

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

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

  1325 S Portofino Dr Unit 505 PH-D, Sarasota, FL 34242
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  $2,249,000

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  5361 Siesta Ct, Sarasota, FL 34242

  Experience tranquility and peace of mind in Siesta Key! Located in the highly sought-after neighborhood of Siesta Cove, this 4-bedroom, 2.5-bath home has been meticulously maintained and generously updated. The current owners completed extensive renovations including a newly remodeled primary bathroom, a custom locally handcrafted iron front door, and stunning iron interior doors with switchable

  David James CHARLES RUTENBERG REALTY INC

  5361 Siesta Ct, Sarasota, FL 34242
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  $2,000 per month

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

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242

  Available Nov through Dec 2025 for $2,000 per month. 55+ community. Available Jan-Mar 2026 for $4,000 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.

  Jonathan OSteen O'STEEN GROUP INC

  1300 N Portofino Dr Unit 205, 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 $695,327

  Last Listing Agent Michelle Shiver KELLER WILLIAMS ON THE WATER S

  4522 Banan Place, Sarasota, FL 34242
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  /79

  Est $783,445 Not Listed For Sale

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

  1600 Cove II Place Unit 424, Sarasota, FL 34242

  1600 Cove II Place Unit 424, Sarasota, FL 34242
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  $599,000

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft

  5950 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  Gulf-side living at its best! This cute-as-a-button 2-bedroom, 2-bath ground-floor unit has been completely remodeled from top to bottom, featuring new electrical and plumbing, impact windows and doors, stylish new flooring, beautifully updated baths, and a stunning new kitchen with quartz countertops, tile backsplash, countertop breakfast bar, and stainless-steel appliances. The primary bedroom

  Christine Green COLDWELL BANKER REALTY

  5950 Midnight Pass Rd Unit 201, Sarasota, FL 34242
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  $6,500 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
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  $650,000 Sold Jan 16, 2025

  675 Avenida Del Norte, Sarasota, FL 34242

  • Land
  • 0.14 Acre
  • $4,642,857 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 22 Days On Market

  Current Estimated Value $645,230

  Last Listing Agent Kevin Henry BAY VISION REALTY INC

  675 Avenida Del Norte, Sarasota, FL 34242
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  /17

  Est $486,245 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242

  6334 Midnight Pass Rd Unit 45, Sarasota, FL 34242
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  $440,000

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft

  1250 N Portofino Dr Unit 305, Sarasota, FL 34242

  Relax in Paradise for under $500,000! MOTIVATED SELLER!!! Stunning, Oversized One Bedroom Waterfront condo with 2 full Bathrooms in the highly sought after Siesta Harbor community on Siesta Key! Whether you enjoy the sunrise over your morning coffee or work from your glass-enclosed lanai, enjoy beautiful views of the canal and Intracoastal Waterway, where you watch for dolphin while the Mullet

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 305, Sarasota, FL 34242
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  $7,500 per month

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

  6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242

  No roads to cross to get to the beach! Just listed- This clean, updated, cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
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  $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 $706,418

  Last Listing Agent Brian Cirillo BALDWIN PARK REALTY LLC

  5239 Winding Way, Sarasota, FL 34242
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  Est $571,320 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  5600 Beach Way Dr Unit 209, Sarasota, FL 34242

  5600 Beach Way Dr Unit 209, Sarasota, FL 34242
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  $1,350,000

  • 2 Beds
  • 2 Baths
  • 1,552 Sq Ft

  6140 Midnight Pass Rd Unit 601, Sarasota, FL 34242

  Rare Opportunity to acquire an upper floor end unit with full western Gulf and Crescent Beach views extending from Point of Rocks to northern Siesta Key. This 6th floor condo has beach views from all rooms – even the bathrooms. Make this the perfect owner-occupied or second home retreat as the possibilities are endless: Remove the NON-load bearing wall between the living room and 30-foot balcony

  Suki Scollo COLDWELL BANKER REALTY

  6140 Midnight Pass Rd Unit 601, Sarasota, FL 34242
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  $4,995 per month

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

  5770 Midnight Pass Rd Unit 405, Sarasota, FL 34242

  Immaculate well maintained 2 beds 2 bath condo situated in the desirable Gulf & Bay Club on Siesta Key. This 4th floor unit is meticulously maintained and tastefully decorated. Amenities include three pools, saunas, fitness center, tennis, basketball, racquetball, & 24hr security. A must see! Wake up to views of the Gulf and enjoy living your Siesta Key dream. AVAILABLE SEPTEMBER-DECEMBER 2025

  Pamala Casey CASEY REALTY CORPORATION

  5770 Midnight Pass Rd Unit 405, 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

  Last Listing Agent Jonathan Minerick HOMECOIN.COM

  5430 Avenida Del Mare, Sarasota, FL 34242
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  Est $993,339 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,827 Sq Ft

  1319 Dockside Place Unit 221, Sarasota, FL 34242

  1319 Dockside Place Unit 221, Sarasota, FL 34242
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  /29

  $549,000

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242

  Step into luxury with this fully renovated 1 bed, 1 bath condo featuring high-end finishes and thoughtful upgrades throughout. The kitchen features a stunning coastal-inspired backsplash, quartz countertops, soft-close cabinetry, and brand-new stainless steel appliances, all centered around a spacious island. Luxury waterproof vinyl plank (LVP) flooring flows throughout the living area, where

  Noelle Vihrachoff KELLER WILLIAMS ON THE WATER S

  5830 Midnight Pass Rd Unit 25, Sarasota, FL 34242
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  /23

  $2,500 per month

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

  111 Pass Key Rd Unit 111, Sarasota, FL 34242

  Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private beach access, and a fishing pier for those who love to cast a line. Enjoy the convenience of in-unit laundry and make use of the outdoor BBQ for al fresco dining. The clubhouse is perfect for social

  Ray Shope ROSEBAY INTERNATIONAL REALTY, INC

  111 Pass Key Rd Unit 111, Sarasota, FL 34242
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  $1,595,000 Sold Sep 02, 2025

  5121 Oxford Dr, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,270 Sq Ft
  • Built 1983

  Last Sold Summary

  • $703/SF
  • 1 Day On Market

  Current Estimated Value $1,568,993

  Last Listing Agent Mark Coppens EXP REALTY LLC

  5121 Oxford Dr, Sarasota, FL 34242
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  Est $569,166 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1400 Cove Place Unit 631, Sarasota, FL 34242

  1400 Cove Place Unit 631, Sarasota, FL 34242
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  $1,499,000

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

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242

  Beachfront Penthouse Condo on Siesta Key! Have you been waiting for an opportunity that’s just too good to pass up? This spacious two bedroom, two bathroom home offers a versatile layout perfect for personal use or entertaining family and friends. Recently renovated, this top-floor condo places you directly above Siesta Key's powdery quartz sands and offers unobstructed, breathtaking views of the

  Christa Spalding COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 1205, Sarasota, FL 34242
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  $17,000 per month

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Condo for Rent

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242

  Beachfront Bliss at Casa Mar – Siesta KeyDiscover this beautifully updated two-bedroom, two-bathroom beachfront condo in Casa Mar, offering direct access to Crescent Beach, a serene and less crowded alternative to Siesta Key’s main beach.Why You’ll Love This Condo:Prime Beachfront Location – Step right onto the powdery white sands of Crescent BeachClassic Coastal Charm –

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
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  $1,000,000 Sold Mar 24, 2025

  6300 Midnight Pass Rd Unit 810, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1970

  Last Sold Summary

  • 13% Below List Price
  • $787/SF
  • 46 Days On Market

  Current Estimated Value $1,004,980

  Last Listing Agent Rudy Dudon MICHAEL SAUNDERS & COMPANY

  6300 Midnight Pass Rd Unit 810, Sarasota, FL 34242
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  Est $720,486 Not Listed For Sale

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

  5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242

  5963 Midnight Pass Rd Unit 331, Sarasota, FL 34242
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  /27

  $1,200,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft

  4920 Higel Ave, Sarasota, FL 34242

  Under contract-accepting backup offers. Opportunity Awaits on this .37 of an acre (approximate dimensions 100' x 158') on Siesta Key with Western Exposure. The existing structure is ready to be removed and a new home would be best suited for this great lot. Current structure features 3BR/3BA with a pool ~ but the home did suffer severe water damage and is now being "sold as is" for lot value

  Tony Andrews ANDREWS & ASSOCIATES REALTY

  4920 Higel Ave, Sarasota, FL 34242
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  $16,000 per month

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • House for Rent

  327 Avenida Milano, Sarasota, FL 34242

  Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street, this home has so much to offer. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with

  Chrissie Cummings JENNETTE PROPERTIES INC

  327 Avenida Milano, Sarasota, FL 34242
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  $690,000 Sold Nov 24, 2025

  114 Whispering Sands Dr Unit V21, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,387 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $497/SF
  • 0 Days On Market

  Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

  114 Whispering Sands Dr Unit V21, Sarasota, FL 34242
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  /30

  Est $523,873 Not Listed For Sale

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

  5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242

  5855 Midnight Pass Rd Unit 127, Sarasota, FL 34242
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  $659,000 Open Sun 12PM - 2PM

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

  4660 Ocean Blvd Unit E2, Sarasota, FL 34242

  FULL GULF & SUNSET VIEWS---You will be WOWED by this TURNKEY FURNISHED Siesta Key residence, just moments to the "baby powder" quartz white sands of TOP RATED Siesta Key Beach....This Well-Appointed, Spacious & Pet Friendly Two Bedroom/2 Bath condo has many desired UPDATES: Impact Windows/Sliders; Vinyl Plank Flooring Throughout; Custom Millwork& Plantation Shutters; HVAC & Hot Water Tank

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  4660 Ocean Blvd Unit E2, Sarasota, FL 34242
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  $9,000 per month

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

  4822 Ocean Blvd Unit 2F, Sarasota, FL 34242

  Gulf Views!!Siesta Key! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key and is close to restaurants and outdoor recreation. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The large

  Jane Hunter JENNETTE PROPERTIES INC

  4822 Ocean Blvd Unit 2F, 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 $522,606

  Last Listing Agent Scotty Ledford VUE REALTY, LLC

  6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242
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  Est $606,485 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  141 Avenida Messina Unit 1, Sarasota, FL 34242

  141 Avenida Messina Unit 1, Sarasota, FL 34242

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