Siesta Key, FL Homes

• 

  

  

  /79

  $1,566,000

  • 3 Beds
  • 2.5 Baths
  • 2,041 Sq Ft

  221 Tenacity Ln, Sarasota, FL 34242

  This stunning three-bedroom, two-bathroom Spanish-style villa stands as a testament to resilience and quality. Experience peace of mind knowing this beautiful home endured no storm damage, standing high and dry with top-notch construction that allowed for zero impact from recent storms. Purchase with confidence, as this beachside sanctuary continues to shine. Nestled on a serene, private lane

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 842-0063

  221 Tenacity Ln, Sarasota, FL 34242
• 

  

  

  /68

  $2,900 per month

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

  1215 S Portofino Dr, Siesta Key, FL 34242

  AVAILABLE NOW! Enjoy the island living in this cute and cozy 2 bedroom, 2 bathroom condo with canal views! Nestled in the heart of Siesta Key, this 55+ Community has it all! The unit is newly painted and adorned with coastal flair, a king size bed in the master bedroom and a queen size in the guest bedroom, vinyl flooring and a screened in lanai. One of the best features of this unit is the water

  1215 S Portofino Dr, Siesta Key, FL 34242
• 

  

  /2

  $850,000 Sold May 01, 2025

  • 1,550 Sq Ft
  • $548/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  6267 Midnight Pass Rd Unit 105, Sarasota, FL 34242

  Experience the ultimate beachfront lifestyle in this charming 2-bedroom, 2-bathroom condo, perfectly located in the heart of Siesta Key. Nestled in a sought-after community, this ground-floor unit offers easy access to the world-renowned quartz sand beaches and the crystal-clear waters of the Gulf of Mexico.Step inside to find a bright, open-concept living space with large windows that invite in

  Jeff Bray LPT REALTY, LLC

  6267 Midnight Pass Rd Unit 105, Sarasota, FL 34242
• 

  

  

  /42

  Est $906,013 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  5966 Midnight Pass Rd Unit G-42, Sarasota, FL 34242

  5966 Midnight Pass Rd Unit G-42, Sarasota, FL 34242
• 

  

  

  /64

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,902 Sq Ft

  5341 Siesta Ct, Sarasota, FL 34242

  ***ALL NEW IMPACT WINDOWS and DOORS ordered and scheduled for installation*** Step into effortless island elegance at 5341 Siesta Cove—a rare blend of coastal modern design and timeless mid-century flair in one of Siesta Key’s most desirable neighborhoods. Pet friendly, golf cart friendly…just plain friendly! AND, no water or wind damage. This move-in-ready home is storm-tested, sun-kissed, and

  

  Christa Spalding

  COLDWELL BANKER REALTY

  (941) 239-2198

  5341 Siesta Ct, Sarasota, FL 34242
• 

  

  /30

  $2,499 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  4439 Ocean Blvd Unit 2A, Sarasota, FL 34242

  Take a look at this beautifully decorated well priced 3 bed 2 bath home for rent in a prime location! This home is within walking distance to the beach, and several other restaurants and amenities. Call today for a showing, this won't last long! Can come furnished or unfurnished.

  Dalton Hope REALTY ONE GROUP MVP

  4439 Ocean Blvd Unit 2A, Sarasota, FL 34242
• 

  /2

  $630,000 Sold Apr 30, 2025

  • 1,512 Sq Ft
  • $417/SF
  • 69 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  5239 Winding Way, Sarasota, FL 34242

  ***PRICE IMPROVMENT*** ***PRICE IMPROVEMET*** Discover your own private oasis at 5239 Winding Way, just minutes from Siesta Beach. Come and see for yourself this lovely and charming home that is an absolute MUST SEE! Nestled in a canopy-protected neighborhood, this property features a spacious open floor plan that connects the kitchen and living areas, creating a perfect space for entertaining

  Brian Cirillo BALDWIN PARK REALTY LLC

  5239 Winding Way, Sarasota, FL 34242
• 

  

  /60

  Est $757,254 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft

  5970 Midnight Pass Rd Unit 166, Sarasota, FL 34242

  5970 Midnight Pass Rd Unit 166, Sarasota, FL 34242
• 

  

  /85

  $1,800,000

  • 4 Beds
  • 2 Baths
  • 2,185 Sq Ft

  746 Plymouth St, Sarasota, FL 34242

  Nestled in the heart of Siesta Key, this home offers the perfect blend of relaxation and opportunity. Whether you're seeking a serene beach getaway, a lucrative vacation rental, or a full-time residence, this property checks all the boxes. The home’s unique floor plan is flooded with natural light, creating a bright, inviting atmosphere throughout. A rare find, both the home and the garage are

  

  Carla Rayman Kidd

  COLDWELL BANKER REALTY

  (941) 239-2641

  746 Plymouth St, Sarasota, FL 34242
• 

  

  /32

  $5,800 per month

  • 4 Beds
  • 3 Baths
  • 1,798 Sq Ft
  • House for Rent

  5585 Contento Dr, Sarasota, FL 34242

  Experience Siesta Key living at 5585 Contento Dr; a furnished 4 bedroom 3 bath pool home that is available immediately for rent. This home sits at the end of a quiet cult de sac in the front and offers beautiful canal views, a wooden boat dock, and heated pool in the back. This split floor plan home boasts 1,921 square feet under air and a two car garage that includes a full sized washer and

  Joe Failla PREMIER SOTHEBYS INTL REALTY

  5585 Contento Dr, Sarasota, FL 34242
• 

  /2

  $1,175,000 Sold Apr 30, 2025

  • 2,147 Sq Ft
  • $547/SF
  • 76 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  1211 N View Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. This home had no water intrusion nor structural damage through hurricanes. Welcome to this beautifully updated home in the highly sought-after Siesta Cove neighborhood on Siesta Key, just a short distance from the world-renowned Siesta Beach and the vibrant Siesta Key Village, offering an array of shopping, dining, and entertainment options. This

  Thomas Cail RE/MAX ALLIANCE GROUP

  1211 N View Dr, Sarasota, FL 34242
• 

  

  /50

  Est $4,983,802 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,214 Sq Ft

  3954 Roberts Point Rd, Sarasota, FL 34242

  3954 Roberts Point Rd, Sarasota, FL 34242
• 

  

  /37

  $724,900

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  145 Avenida Messina Unit 3, Sarasota, FL 34242

  Welcome to this wonderful condominium complex directly on the edge of the Siesta Key Village! This UPSTAIRS unit has been completely remodeled from top to bottom and is absolutely stunning! The opened kitchen features stainless steel appliances, handsome quartz counters, and a tan tiger-look cabinetry. There is all new lighting, fans, receptacles and switches, and a neutral plank-like ceramic

  

  Joe Cleary

  RE/MAX ALLIANCE GROUP

  (941) 219-0452

  145 Avenida Messina Unit 3, Sarasota, FL 34242
• 

  

  /18

  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit B, Sarasota, FL 34242

  Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit B, Sarasota, FL 34242
• 

  /2

  $303,500 Sold Apr 28, 2025

  • 797 Sq Ft
  • $381/SF
  • 45 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1975

  5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242

  Lowest price condo on Siesta Key. Rarely available first-floor 1/1 condo located right across the street from Siesta Key public beach in beautiful White Sands Village. This affordable and well-maintained community with pavers throughout the roadways and carport areas is a hidden gem. Onsite management, heated pool, community boat docks that are available on a first-come basis for a small fee, and

  Mary Jo Violett MICHAEL SAUNDERS & COMPANY

  5641 Midnight Pass Rd Unit 903, Sarasota, FL 34242
• 

  

  /60

  Est $7,860,701 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 6,369 Sq Ft

  5131 Jungle Plum Rd, Sarasota, FL 34242

  5131 Jungle Plum Rd, Sarasota, FL 34242
• 

  

  /44

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242

  Welcome to Harbor Towers Yacht & Racquet Club, where luxury meets the laid-back charm of Florida’s beautiful Gulf Coast! This beautifully furnished 2-bedroom, 2-bath condo is your gateway to paradise, with an incredible view of the Intracoastal Waterway and resort-style amenities right at your doorstep. Perfectly positioned in a gated waterfront community, this home invites you to experience

  

  Christa Spalding

  COLDWELL BANKER REALTY

  (941) 352-8069

  5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242
• 

  

  /34

  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit A, Sarasota, FL 34242

  Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated, this home

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit A, Sarasota, FL 34242
• 

  /2

  $1,630,000 Sold Apr 28, 2025

  • 1,782 Sq Ft
  • $915/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1964

  320 Avenida Leona, Sarasota, FL 34242

  CANAL FRONT home only a 2 minute walk to Siesta Key Village loaded with upgrades and a BRIGHT, OPEN layout that's ideal for entertaining. Features include custom kitchen with quartz countertops, tile backsplash and stainless appliances, tile flooring throughout, impact sliders and windows, 6-panel doors, custom closets with motion-sensor lighting. Three bedrooms plus an office with a HUGE

  Ryan Vlasic COLDWELL BANKER REALTY

  320 Avenida Leona, Sarasota, FL 34242
• 

  

  /62

  Est $659,275 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,359 Sq Ft

  5600 Beach Way Dr Unit 101, Sarasota, FL 34242

  5600 Beach Way Dr Unit 101, Sarasota, FL 34242
• 

  

  /52

  $550,000 Pending

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242

  SIESTA KEY INTERCOASTAL WATERFRONT, WATERVIEW...Welcome to Paradise in PROVINCIAL GARDENS, a small 26 unit enclave. You will love the MILLION DOLLAR VIEW from this quaint, Mid-Century Modern one bedroom, one bath first floor condo with Florida room addition overlooking the community park, NEW fishing pier with new sea wall and the Intercoastal channel. Deeded beach access and Olympic pool use

  

  Scotty Ledford

  VUE REALTY, LLC

  (941) 367-2633

  6005 Midnight Pass Rd Unit N11, Sarasota, FL 34242
• 

  

  /79

  $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
• 

  /2

  $650,000 Sold Apr 28, 2025

  • 1,453 Sq Ft
  • $447/SF
  • 209 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  631 Venice Ln, Sarasota, FL 34242

  Welcome to great potential and endless possibilities on Siesta Key. This three bedroom, 2 bath pool home on one third of an acre in the Waterside East neighborhood is conveniently located for easy access on and off the island via the north bridge, and just a short bike ride to the vibrant Siesta Key Village and the world-famous Siesta Key beach. Enjoyed as a permanent residence by the current

  Kelly Rosenberg COLDWELL BANKER REALTY

  631 Venice Ln, Sarasota, FL 34242
• 

  

  /72

  Est $687,583 Not Listed For Sale

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

  101 Whispering Sands Dr Unit 206, Sarasota, FL 34242

  101 Whispering Sands Dr Unit 206, Sarasota, FL 34242
• 

  

  /59

  $550,000 Pending

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242

  SIESTA KEY INTERCOASTAL WATERFRONT, WATERVIEW...Welcome to Paradise in PROVINCIAL GARDEN, a small enclave of only 26 units. You will love the MILLION DOLLAR VIEW from this quaint, Mid-Century Modern one bedroom, one bath condo with SCREENED Florida room overlooking the community park, its own washer & dryer. There is a NEW fishing pier with new seawall and vistas of the Intercoastal channel.

  

  Scotty Ledford

  VUE REALTY, LLC

  (941) 297-5381

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
• 

  

  /14

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Condo for Rent

  5600 Beach Way Dr Unit 310, Sarasota, FL 34242

  ONE MONTH MINIMUM - Siesta Key! Voted number 1 by Mr. Beach. 3 rd floor condo in an elevator building, directly across form the public beach, no obstructions to toes in the sand. Spacious 2 bedrooms, 2 baths. King bed, queen bed and a full bed. Granite counters counters with stainless steal appliances and a lanai over looking the heated pool. There are also 2 grill areas for cooking out. Island

  Robin De Busk STRINGER MANAGEMENT INC

  5600 Beach Way Dr Unit 310, Sarasota, FL 34242
• 

  /2

  $590,000 Sold Apr 25, 2025

  • 1,287 Sq Ft
  • $458/SF
  • 17 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  6415 Midnight Pass Rd Unit 508, Sarasota, FL 34242

  Real estate is always about location, and your new condominium has it. No need for a car when you live here! Leave your condo, down the elevator and walk out the front door of The Anchorage to the Daiquiri Deck, Captain Curt’s Crab & Oyster Bar, plus a variety of other restaurants and shops along with the Siesta Key Marina and private access to Siesta Key Beach! If you are looking for

  Anthony DeLuca DELUCA REALTY INC

  6415 Midnight Pass Rd Unit 508, Sarasota, FL 34242
• 

  

  /62

  Est $615,851 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 872 Sq Ft

  5962 Midnight Pass Rd Unit 132, Sarasota, FL 34242

  5962 Midnight Pass Rd Unit 132, Sarasota, FL 34242
• 

  

  /77

  $537,500

  • 2 Beds
  • 2.5 Baths
  • 1,332 Sq Ft

  6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242

  VIEWS, VALUE, & VACATION INCOME! Lowest price per sq. foot in Bay Oaks on the market with the best views! Siesta Key Waterfront for a Great Price! TWO-STORY, 2 BEDROOMS, 3 BATHROOMS, & 1-WEEK RENTALS PERMITTED gem in the popular Bay Oaks community. This spacious condo features two oversized ensuite bedrooms, a guest half bath, and three private lanais—two of them covered, and two with stunning

  

  Julia Montei

  COLDWELL BANKER REALTY

  (941) 909-3685

  6157 Midnight Pass Rd Unit B42, Sarasota, FL 34242
• 

  

  /51

  $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
• 

  /2

  $1,200,000 Sold Apr 25, 2025

  • 2,111 Sq Ft
  • $568/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  5602 Cape Leyte Dr, Sarasota, FL 34242

  Nestled in the highly sought-after Siesta Isle neighborhood, this exceptional 14,000+ sq. ft. corner lot presents an unparalleled opportunity to create your dream home just steps from the main entrance of world-renowned Siesta Key Beach. Whether you choose to remodel the existing two-bedroom, two-bath single-family home to your specifications or build an exquisite custom estate, this prime

  Ben Angerami PREMIER SOTHEBYS INTL REALTY

  5602 Cape Leyte Dr, Sarasota, FL 34242
• 

  

  /53

  Est $2,028,466 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,796 Sq Ft

  6925 Bochi Cir, Sarasota, FL 34242

  6925 Bochi Cir, Sarasota, FL 34242
• 

  

  /66

  $1,375,000

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft

  4818 Givens Ct, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Charming Key West Style Home on World-Renowned Siesta Key Step into coastal elegance with this beautifully maintained 3-bedroom, 2-bath elevated home with a versatile second-story loft, located on a private street with only 8 homes—just short drive down Ocean Blvd to the public beach access.As you ascend the newly updated stairs, you’re welcomed

  

  Lisa Bouck, PA

  RE/MAX ALLIANCE GROUP

  (941) 352-2835

  4818 Givens Ct, Sarasota, FL 34242
• 

  

  /36

  $3,000 per month

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

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242

  Welcome to your newly renovated dream coastal escape in beautiful Siesta Harbor on Siesta Key! This turnkey furnished; spacious one-bedroom, two-bath condo featuring brand new furniture is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short 5 minute stroll, you’ll enjoy deeded access to Siesta

  Jonathan OSteen O'STEEN GROUP INC

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242
• 

  /2

  $20,000 Sold Apr 25, 2025

  • 1,900 Sq Ft
  • $11/SF
  • 175 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2009

  915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242

  Fractional Ownership. Introducing the Winter Fractional Package, offering 1/16th ownership in a stunning luxury residence on Siesta Key Beach. Now, your dream of owning a beachfront home on America's most celebrated shore can become a reality. Enjoy the benefits of owning a slice of paradise, complete with world-class amenities and services.This exclusive opportunity offers the ultimate in

  Kelly Mooney THE SARASOTA REAL ESTATE COMP.

  915 Seaside Dr Unit 410, Weeks 14-15, Sarasota, FL 34242
• 

  

  /35

  Est $2,143,278 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,774 Sq Ft

  6900 Bochi Cir, Sarasota, FL 34242

  6900 Bochi Cir, Sarasota, FL 34242
• 

  

  /99

  $875,000

  • Land
  • 0.26 Acre
  • $3,365,385 per Acre

  5019 Commonwealth Dr, Sarasota, FL 34242

  A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision—whether you’re seeking a full-time

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 394-0942

  5019 Commonwealth Dr, Sarasota, FL 34242
• 

  

  /18

  $4,500 per month

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • House for Rent

  733 Tropical Cir, Sarasota, FL 34242

  Availability June 1st for Annual Lease. Welcome to your tropical escape on Siesta Key! This serene 3-bedroom, 2-bath annual rental offers a wide open floor plan with vaulted ceilings, split bedrooms, and a spacious 2-car garage. The stone-accented great room flows effortlessly into the kitchen with a unique breakfast bar, all overlooking the screened-in pool and lush tropical landscaping. Recent

  Anthony Dalesandro BRIGHT REALTY

  733 Tropical Cir, Sarasota, FL 34242
• 

  /2

  $1,029,000 Sold Apr 22, 2025

  • 816 Sq Ft
  • $1261/SF
  • 214 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1970

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

  Siesta Key ~ Palm Bay Club ~ 9th Floor ~ Breathtaking "Direct" Siesta Key Beach & Gulf of Mexico Views ~ Direct Siesta Beach Access ~ Rental Income $90K +/- ~ this property is updated throughout (including windows) ~ 1 bedroom / 1 bath / open or closed balcony ~ sold turnkey furnished ~ managed on-site ~ offering an excellent investment with its rare three day minimum rental policy and on-site

  Robert Anderson Jr RE/MAX ALLIANCE GROUP

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

  

  /27

  Est $532,318 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft

  1257 S Portofino Dr Unit 107, Sarasota, FL 34242

  1257 S Portofino Dr Unit 107, Sarasota, FL 34242

Showing Results 1 - 40, Page 1 of 18