Siesta Key, FL Homes

• 

  

  

  /60

  $3,850,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,122 Sq Ft

  5263 Avenida de Cortez, Sarasota, FL 34242

  Welcome to a residence where inspired design meets the effortless elegance of Island living. Tucked away on the tranquil side of the Siesta Key Village, this extraordinary home places you at the heart of it all while having it all. With World-renowned beaches and the charming village just steps away... you truly can not beat the location. This 4 bedroom, 3100 sq.ft. home boasts a private boat

  Jessica Hoffman COLDWELL BANKER REALTY

  5263 Avenida de Cortez, Sarasota, FL 34242
• 

  

  

  /10

  $9,420 per month

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

  6154 Midnight Pass Rd Unit 101, Sarasota, FL 34242

  Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach, from the 1st floor of this beautifully appointed two- bedroom, two-bathroom apartment with fully-equipped kitchen. Relax in the living room that overlooks the gulf. Enjoy your morning coffee sitting out on the screened in lanai just steps from the sand.This unit features Private wireless internet, Double

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 101, Sarasota, FL 34242
• 

  

  /2

  $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 $391,893

  Last Listing Agent Jill Thomas BERKSHIRE HATHAWAY HOMESERVICE

  1300 N Portofino Dr Unit 208, Sarasota, FL 34242
• 

  

  /2

  Est $487,803 Not Listed For Sale

  6415 Midnight Pass Rd Unit 206, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft
  • Built 1975

  6415 Midnight Pass Rd Unit 206, Sarasota, FL 34242

  Last Sold Summary

  • 7% Above List Price
  • $356/SF
  • 4 Days On Market

  Last Sold Price $458,000

  Last Listing Agent Deborah Miller RE/MAX PALM
• 

  

  

  /61

  $2,590,000

  • 4 Beds
  • 3.5 Baths
  • 3,228 Sq Ft

  467 Canal Rd Unit 467, Sarasota, FL 34242

  Possible Seller Finance. High & Dry!! BEACH, BOATING & BISTROS!!!! SIESTA KEY`CANAL FRONT featuring WEEKLY RENTALS!! DOCK & LIFT!! GULF VIEWS!! BEACH ACCESS STEPS AWAY!!! Great location with Gulf Views steps to Public Beach Access #8 offering the ultimate waterfront lifestyle of this rare, furnished 3 bedroom/3.5 Bath plus office (or 4th bedroom), RMF-zoned opportunity on Siesta Key. Built in

  Dan Miller PREFERRED SHORE LLC

  467 Canal Rd Unit 467, Sarasota, FL 34242
• 

  

  /11

  $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
• 

  /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 $688,236

  Last Listing Agent Fred Sieger Jr COMPASS FLORIDA LLC

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

  

  /32

  Est $1,410,856 Not Listed For Sale

  4708 Ocean Blvd Unit E1, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 2,277 Sq Ft
  • Built 1981

  4708 Ocean Blvd Unit E1, Sarasota, FL 34242

  Last Sold Summary

  • 10% Below List Price
  • $692/SF
  • 4 Days On Market

  Last Sold Price $1,575,000

  Last Listing Agent Doug Parks Michael Saunders
• 

  

  /99

  $690,000

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft

  797 Beach Rd Unit 509, Sarasota, FL 34242

  PENTHOUSE" OPPORTUNITY on the 5th Floor of Building 797 in Sought After & Gated CRESCENT ROYALE! As you walk through the door you will be astounded with the beautiful views of the Gulf of Mexico & Siesta Beach! Own your own piece of Siesta Key and enjoy the gorgeous nightly sunsets on the top floor. This updated unit has been well maintained and tastefully furnished, updated with a functional

  Sandy Gamble Hulvat WATERSIDE REALTY LLC

  797 Beach Rd Unit 509, Sarasota, FL 34242
• 

  

  /9

  $10,770 per month

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

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242

  We welcome you to stay in our updated oceanfront condo on Siesta Key Crescent Beach - the best beach in Florida! Our spacious 2 bed/2 bath oceanfront home is 1080 square feet with an ocean view that cannot be beat! Unit #206 is part of the Casa Blanca Vacation Beach Resort, and the crystal white sand is steps away! Remodeled in 2023, fully equipped kitchen with quiet dishwasher, spacious living

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242
• 

  /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

  Current Estimated Value $1,324,977

  Last Listing Agent Christa Spalding COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 403, Sarasota, FL 34242
• 

  

  /67

  Est $1,769,253 Not Listed For Sale

  4960 Commonwealth Dr, Sarasota, FL 34242

  • 3 Beds
  • 3.5 Baths
  • 3,063 Sq Ft
  • Built 2004

  4960 Commonwealth Dr, Sarasota, FL 34242

  Last Sold Summary

  • 6% Below List Price
  • $612/SF
  • 241 Days On Market

  Last Sold Price $1,875,000

  Last Listing Agent Glenn Brown RE/MAX
• 

  

  /75

  $1,125,000

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

  19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242

  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 with effortless, comfortable living. The

  Harriet Stopher COLDWELL BANKER REALTY

  19 Whispering Sands Dr Unit 1104, Sarasota, FL 34242
• 

  

  /11

  $10,230 per month

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

  6154 Midnight Pass Rd Unit 102, Sarasota, FL 34242

  Wake up to views of the beautiful gulf and beach from every room. Walk out to the best beach in the world. End your day with a breathtaking sunset dinner on the lanai. 102 is a ground floor, beach front apartment with 2 bedrooms and 2 baths. It is an open floor plan with porcelain tile throughout, comfortable seating in the living area, a full kitchen with all cookware and service items, and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 102, Sarasota, FL 34242
• 

  /2

  $420,000 Sold Jan 05, 2026

  6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242

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

  Last Sold Summary

  • 14% Below List Price
  • $488/SF
  • 30 Days On Market

  Current Estimated Value $425,839

  Last Listing Agent Nancie Kalin MICHAEL SAUNDERS & COMPANY

  6350 Midnight Cove Rd Unit 710, Sarasota, FL 34242
• 

  

  /36

  Est $1,314,169 Not Listed For Sale

  5790 Midnight Pass Rd Unit 608, Sarasota, FL 34242

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

  5790 Midnight Pass Rd Unit 608, Sarasota, FL 34242

  Last Sold Summary

  • 15% Below List Price
  • $1,082/SF
  • 19 Days On Market

  Last Sold Price $1,550,000

  Last Listing Agent Rudy Dudon Michael Saunders
• 

  /2

  $6,750,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 5,400 Sq Ft

  44 Rockwell Ln, Sarasota, FL 34242

  Pre-Construction. To be built. Call for all details and plans.All info coming soon!

  Joseph Russo JOSEPH RUSSO, LICENSED R.E. BROKER

  44 Rockwell Ln, Sarasota, FL 34242
• 

  

  /11

  $8,070 per month

  • 1 Bed
  • 1 Bath
  • 757 Sq Ft
  • Apartment for Rent

  6154 Midnight Pass Rd Unit 103, Sarasota, FL 34242

  Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach from the 1st floor of this tastefully decorated one bedroom, one bath apartment with tile throughout. Enjoy morning coffee and stunning sunsets on the lanai every day! Newly updated fully equipped kitchen. The property offers one of the largest pools on Siesta Key. Come in, unpack and relax! Siesta Key Beach has

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 103, Sarasota, FL 34242
• 

  /2

  $852,500 Sold Jan 07, 2026

  5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $626/SF
  • 20 Days On Market

  Current Estimated Value $856,375

  Last Listing Agent Curtis Ware KW COASTAL LIVING III

  5780 Midnight Pass Rd Unit 303, Sarasota, FL 34242
• 

  

  /35

  Est $602,072 Not Listed For Sale

  915 Beach Rd Unit 114, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 940 Sq Ft
  • Built 1972

  915 Beach Rd Unit 114, Sarasota, FL 34242

  Last Sold Summary

  • 13% Below List Price
  • $734/SF
  • 23 Days On Market

  Last Sold Price $690,000

  Last Listing Agent Colleen Finnegan RE/MAX
• 

  

  /39

  $1,675,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  5966 Midnight Pass Rd Unit G113, Sarasota, FL 34242

  Discover the rare opportunity to own a penthouse-level residence in the iconic Tower at the Palm Bay Club on Siesta Key—where panoramic Gulf views and effortless island living come together in one exceptional offering. This spacious 2-bedroom, 2-bath condominium sits high above the shoreline, capturing sweeping vistas of the turquoise waters and legendary Siesta Key sunsets from its exclusive

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  5966 Midnight Pass Rd Unit G113, Sarasota, FL 34242
• 

  

  /22

  $9,000 per month

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

  1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242

  Indulge in coastal luxury with this beautifully decorated Gulfside unit nestled on the 1st floor of a stunning high-rise. With hardwood floors throughout and thoughtfully curated decor, this retreat offers the perfect blend of elegance and comfort. Step into the spacious living area, where natural light floods through large windows, illuminating the stylish furnishings and inviting ambiance. The

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 106AA, Sarasota, FL 34242
• 

  /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

  Current Estimated Value $651,560

  Last Listing Agent Mary Beth Hudson COLDWELL BANKER REALTY

  5963 Midnight Pass Rd Unit 355, Sarasota, FL 34242
• 

  /2

  Est $616,808 Not Listed For Sale

  1137 Lake House Cir Unit C215, Sarasota, FL 34242

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

  1137 Lake House Cir Unit C215, Sarasota, FL 34242

  Last Sold Summary

  • 1% Below List Price
  • $461/SF
  • 37 Days On Market

  Last Sold Price $623,000

  Last Listing Agent Mike Winger TIDELINE REAL ESTATE BROKERS
• 

  

  /21

  $4,850,000 Pending

  • Land
  • 2 Acres
  • $2,425,000 per Acre

  7707 Midnight Pass Rd, Sarasota, FL 34242

  Two-acre+/- lot on Little Sarasota Bay with exceptional privacy, views, boating access and development potential. This listing includes twocontiguous buildable parcels (ID#s 0127030017 & 0127030018) which are only offered together. This unique lot with mature trees and lushlandscaping includes a secluded bay offering protection of your lot and future dock from the elements as well as

  Lisa Maria 1ST VISION REALTY OF FLORIDA I

  7707 Midnight Pass Rd, Sarasota, FL 34242
• 

  

  /31

  $8,500 per month

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

  1055 W Peppertree Dr Unit 206AA, Sarasota, FL 34242

  2 BR - 2 BA - 6 person Max - Highrise - Pond View - Approx. 75 yards from beach This property is a 30 night minimum. Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The unit is in a gulf side high rise building on the 2nd floor. Assigned covered parking located in the parking garage under the building. A luxurious dining area greets you

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 206AA, Sarasota, FL 34242
• 

  /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

  Current Estimated Value $1,227,143

  Last Listing Agent Jason Skowronski COMPASS FLORIDA LLC

  307 Avenida de Paradisio, Sarasota, FL 34242
• 

  

  /76

  Est $585,270 Not Listed For Sale

  5855 Midnight Pass Rd Unit 505, Sarasota, FL 34242

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

  5855 Midnight Pass Rd Unit 505, Sarasota, FL 34242

  Last Sold Summary

  • 10% Below List Price
  • $616/SF
  • 33 Days On Market

  Last Sold Price $650,000

  Last Listing Agent John Masters COLDWELL BANKER REALTY
• 

  

  /31

  $8,750,000

  • 3 Beds
  • 4 Baths
  • 4,750 Sq Ft

  648 Beach Rd, Sarasota, FL 34242

  Welcome back to 648 Beach Road, you’ve seen it before, but it’s better than ever. Reconstructed, reimagined, and elevated in every detail, this extraordinary residence delivers the same breathtaking, front-row views you remember... with an entirely new feel that’s fresh, refined, and built for the way you live now. This expansive three-bedroom retreat lives like a private resort, with the space

  Inbal August DOUGLAS ELLIMAN

  648 Beach Rd, Sarasota, FL 34242
• 

  

  /27

  $5,700 per month

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

  1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242

  Steps from beautiful Crescent Beach, this fully renovated 2 bedroom 2 full bathroom unit is located in Gulf-side High-rise on the 8th floor. Step into the extended living lanai area to experience wrap around views of the gulf. Enjoy a window bench, choice of comfy loveseats, or dine with a view of the blue waters and white sand.An updated kitchen with stainless steel appliances peeks through

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242
• 

  /2

  $325,000 Sold Dec 31, 2025

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $256/SF
  • 25 Days On Market

  Current Estimated Value $443,220

  Last Listing Agent Julie Froeschle BERKSHIRE HATHAWAY HOMESERVICE

  101 Whispering Sands Dr Unit 205, Sarasota, FL 34242
• 

  

  /49

  Est $610,358 Not Listed For Sale

  5855 Midnight Pass Rd Unit 209, Sarasota, FL 34242

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

  5855 Midnight Pass Rd Unit 209, Sarasota, FL 34242

  Last Sold Summary

  • 6% Below List Price
  • $616/SF
  • 92 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Mina Johnson Michael Saunders
• 

  

  /44

  $474,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  6157 Midnight Pass Rd Unit E24, Sarasota, FL 34242

  Elevated Living on the 4th Floor! Discover this well appointed 1-bedroom, 1-bath condo just minutes from the world-renowned Siesta Key Beach. This TURN KEY residence offers the ideal blend of relaxed Florida living and exceptional value. Step into a bright and airy space where natural light pours into the east-facing screened balcony, overlooking lush tropical landscaping. The interior features

  Ingrid Caruso COLDWELL BANKER REALTY

  6157 Midnight Pass Rd Unit E24, Sarasota, FL 34242
• 

  

  /32

  $11,100 per month

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

  1055 W Peppertree Dr Unit 805AA, Sarasota, FL 34242

  2 BR - 2 BA - 4 Person Max - High-rise - Pond View - Approximately 75 yards away from Crescent BeachThis property is a 30 night minimum.This luxurious 2 bedroom, 2 full bathroom unit is only steps from Crescent Beach. Located on the 8th floor in a Gulf-side High-rise, you will experience the many beautiful views of Siesta Key.The kitchen has stainless steel appliances, updated floors,

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 805AA, Sarasota, FL 34242
• 

  /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 $1,178,198

  Last Listing Agent Harriet Stopher COLDWELL BANKER REALTY

  20 Whispering Sands Dr Unit 406, Sarasota, FL 34242
• 

  

  /34

  Est $1,095,232 Not Listed For Sale

  5579 Cape Aqua Dr, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft
  • Built 1973

  5579 Cape Aqua Dr, Sarasota, FL 34242

  Last Sold Summary

  • 16% Below List Price
  • $835/SF
  • 8 Days On Market

  Last Sold Price $1,300,000

  Last Listing Agent Moe Mossa SAVVY AVENUE, LLC
• 

  

  /58

  $1,750,000

  • 3 Beds
  • 3 Baths
  • 2,724 Sq Ft

  1260 Dolphin Bay Way Unit 401, Sarasota, FL 34242

  Stunning 3-bedroom, 3-bath residence on the 4th floor of Dolphin Bay, offering spectacular wide-water views of the Intracoastal. This end-unit condo lives like a single-family home with its open, spacious layout, light and bright floor plan, and beautifully curated coastal design—a true retreat that blends comfort, style, and everyday livability. The heart of the home is the impressive gourmet

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  1260 Dolphin Bay Way Unit 401, Sarasota, FL 34242
• 

  

  /22

  $9,550 per month

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

  1125 W Peppertree Dr Unit 407, Sarasota, FL 34242

  Discover modern comfort in this stylishly updated 2BR/2BA vacation rental condo. Perfect for relaxation and rejuvenation, this well-appointed space offers everything you need for a memorable getaway. Enjoy garden views from the lanai. Modern amenities include new coastal-inspired furniture and stainless steel appliances. Enjoy community pool access for refreshing dips after beach days. Bask in

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 407, Sarasota, FL 34242
• 

  /2

  $990,000 Sold Apr 03, 2025

  5159 Oakmont Place, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,953 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Below List Price
  • $507/SF
  • 47 Days On Market

  Current Estimated Value $966,337

  Last Listing Agent Jenni Burnette COLDWELL BANKER REALTY

  5159 Oakmont Place, Sarasota, FL 34242
• 

  

  /55

  Est $829,781 Not Listed For Sale

  777 Beach Rd Unit 5A, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft
  • Built 1970

  777 Beach Rd Unit 5A, Sarasota, FL 34242

  Last Sold Summary

  • 10% Below List Price
  • $789/SF
  • 42 Days On Market

  Last Sold Price $920,000

  Last Listing Agent Bill McCue BRIGHT REALTY

Showing Results 441 - 480, Page 12 of 18