25

Siesta Key, FL Homes for Sale in a Senior Community

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  • /55

    $374,900

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft

    1350 N Portofino Dr Unit 107, Sarasota, FL 34242

    SIESTA HARBOR...55+...BEAUTIFUL CANAL & Intercoastal Water Way VISTAS with boats slowly IDILYING By and YOU HAVE BEACH ACCESS. BRING YOUR BOAT up to 30' because it only costs $1,000 ANNUALLY to berth your boat at your home! BUT WAIT till you see this TOTALLY RENOVATED BEAUTIFUL 1 bedroom 2 full bathroom condo! NEW, NEW, NEW...everything is new...Ceramic tile flooring, baseboards, interior doors &

    Agent Photo

    Scotty Ledford

    VUE REALTY, LLC

    (941) 207-7524

    1350 N Portofino Dr Unit 107, Sarasota, FL 34242
  • /71

    $699,000

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

    101 Whispering Sands Dr Unit 105, Sarasota, FL 34242

    INCREDIBLE VIEWS!.....INCREDIBLE LOCATION!.....INCREDIBLE COMMUNITY!....You will be Impressed by this Special & Rare Opportunity for TURNKEY FURNISHED Residence with FULL WATER VIEWS throughout all Living Areas!..... Located in the Whispering Sands Community you will be able to WALK to the adjacent Village as well as ENJOY over 800' of PRIVATE deeded "white baby powder quartz sands" Beach Access;

    Michael A Martino KELLER WILLIAMS ON THE WATER S

    101 Whispering Sands Dr Unit 105, Sarasota, FL 34242
  • /30

    $575,000

    • 2 Beds
    • 1 Bath
    • 753 Sq Ft

    915 Beach Rd Unit 216, Sarasota, FL 34242

    An exceptional investment opportunity on Siesta Key, located directly across the street from the highly rated Siesta Key Beach. This updated second-floor condominium features two bedrooms and one bathroom, offering a highly desirable layout for both personal use and income production in one of Florida’s most sought-after vacation destinations. The residence includes a private balcony overlooking

    Sheryl Vanduren COLDWELL BANKER REALTY

    915 Beach Rd Unit 216, Sarasota, FL 34242
  • /64

    $609,000

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

    199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

    Welcome to effortless coastal living in this beautifully UPDATED second floor midrise residence in the premier GULF FRONT property of Whispering Sands! Designed with an OPEN CONCEPT floor plan, this light-filled condo showcases a bright, sophisticated 2023/2024 REMODELED kitchen featuring quartz countertops, stainless Samsung appliances, an impressive 8' breakfast bar with seating for 3, soft

    Harriet Stopher COLDWELL BANKER REALTY

    199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242
  • /20

    $589,000

    • 2 Beds
    • 2 Baths
    • 1,091 Sq Ft

    1250 N Portofino Dr Unit 408, Sarasota, FL 34242

    Welcome to Siesta Harbor, one of Siesta Key’s most desirable waterfront condominium communities. This beautifully updated 2-bedroom, 2-bath residence in the Marlin House building offers a light-filled open floor plan with serene water views and direct access to the community’s private marina and boat docks. The spacious living area flows seamlessly into the dining room and remodeled kitchen,

    Sonya Kis HARBOUR SHORES REALTY

    1250 N Portofino Dr Unit 408, Sarasota, FL 34242
  • /71

    $640,000

    • 2 Beds
    • 2 Baths
    • 1,462 Sq Ft

    206 Hourglass Way Unit V10, Sarasota, FL 34242

    Welcome to your coastal retreat in the form of this secluded, 2 bed/2 bath freestanding villa with one car garage in the premiere GULF FRONT property of Whispering Sands. OFFERED FURNISHED. This surprisingly large, 1,462 square foot property has been UPDATED in 2025 with fresh paint, NEW crown molding & baseboards, NEW kitchen and updated baths. The exceptionally large living room allows for

    Harriet Stopher COLDWELL BANKER REALTY

    206 Hourglass Way Unit V10, Sarasota, FL 34242
  • /93

    $500,000

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

    225 Hourglass Way Unit 103, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. GREAT PRICE IMPROVEMENT! Welcome to this RARE, 2 bed/2 bath, double lanai corner residence with peaceful lagoon views in the premiere Gulf front property of Whispering Sands! Nestled in the desirable Sunset House building, this freshly painted, updated unit offers a quiet, private setting, with serene views of lush landscaping and the shimmering

    Harriet Stopher COLDWELL BANKER REALTY

    225 Hourglass Way Unit 103, Sarasota, FL 34242
  • /65

    $399,000

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft

    1300 N Portofino Dr Unit 103, Sarasota, FL 34242

    Welcome to your slice of paradise on world-renowned Siesta Key! Located just steps from the powdery white sands of the #1 beach in the U.S., this beautifully updated 2-bedroom, 2-bathroom condo in the highly desirable Siesta Harbor 55+ community is the ultimate coastal retreat. Bright, spacious, and thoughtfully designed, this residence features stylish luxury vinyl flooring, a beautifully

    Rachelle Golden MICHAEL SAUNDERS & COMPANY

    1300 N Portofino Dr Unit 103, Sarasota, FL 34242
  • /93

    $499,000

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

    225 Hourglass Way Unit 303, Sarasota, FL 34242

    3RD FLOOR FLOODPROOF CORNER UNIT TOP FLOOR PENTHOUSE PRIVATE BEACH RESORT APPROX.1,665 sf. The Treehouse at Beautiful Whispering Sands Siesta Key the World's Finest White Sand Beach. This is a unique opportunity to own a rare corner unit on the green belt Not a Parking Lot View, double Lanai flood proof no damage from Hurricanes. The breeze you get going through this condo is incredible, also

    Jonathan Minerick HOMECOIN.COM

    225 Hourglass Way Unit 303, Sarasota, FL 34242
  • /68

    $510,000

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

    225 Hourglass Way Unit 202, Sarasota, FL 34242

    Discover elevated, light-filled coastal living in this beautifully updated 2nd floor residence in the premiere Gulf front property of Whispering Sands! Offered completely TURNKEY FURNISHED. The wonderful OPEN CONCEPT layout flows seamlessly from the kitchen, living and dining spaces into your own private, 34’ south facing lanai—perfect for enjoying sunny mornings, gentle breezes, and relaxed

    Harriet Stopher COLDWELL BANKER REALTY

    225 Hourglass Way Unit 202, Sarasota, FL 34242
  • /61

    $1,395,000

    • 2 Beds
    • 2 Baths
    • 1,464 Sq Ft

    20 Whispering Sands Dr Unit 1102, Sarasota, FL 34242

    GET READY to experience breathtaking GULF-FRONT views unlike any other at this price! Completely remodeled with meticulous attention to detail, this exceptional two-bed, two-bath condo offers refined coastal living in one of Siesta Key’s most desirable areas...the heart of world-famous Siesta Key Village. From the moment you enter, panoramic Gulf views immediately capture your attention.

    Christa Spalding COLDWELL BANKER REALTY

    20 Whispering Sands Dr Unit 1102, Sarasota, FL 34242
  • /72

    $615,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    113 Whispering Sands Dr Unit V47, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. NEW PRICE! Discover the ease of island living in this newly REMODELED 3BR/2BA villa with garage in the premier GULF FRONT property of Whispering Sands! As a rare freestanding villa, this residence offers the privacy of no shared walls and lives like a single family residence. Every detail has been thoughtfully curated, from the reimagined open

    Harriet Stopher COLDWELL BANKER REALTY

    113 Whispering Sands Dr Unit V47, Sarasota, FL 34242
  • /60

    $629,900

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft

    111 Whispering Sands Cir Unit V38, Sarasota, FL 34242

    Set within one of the few 55+ private Gulf-front communities on Siesta Key, this beautifully updated two-bedroom, two-bath villa blends refined comfort with a relaxed coastal lifestyle. COMES FULLY FURNISHED. Every corner of this residence has been carefully renewed to create a light-filled, contemporary retreat just moments from the famous white powder sand and Siesta Village. Inside, the

    Domanic Calamese KW COASTAL LIVING III

    111 Whispering Sands Cir Unit V38, Sarasota, FL 34242
  • /78

    $419,900

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft

    1257 S Portofino Dr Unit 307, Sarasota, FL 34242

    PRICED TO SELL! LOWEST PRICE RENOVATED 2 bedroom 2 bath condo is Siesta Harbor! So many upgrades, granite counters, stainless appliances, ceramic tile, impact sliders, turnkey Furnished! Water views from the living room, main bedroom and lanai, screened in lanai, great active clubhouse, heated pool, outdoor spa, out door shower, shuffleboard, barbecue area and outdoor shower. Private Beach access

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1257 S Portofino Dr Unit 307, Sarasota, FL 34242
  • /90

    $467,000

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft

    1300 N Portofino Dr Unit 305, Sarasota, FL 34242

    SPACIOUS ONE BEDROOM 2 FULL BATHS, OPEN FLOOR PLAN! Stunning turn key unit at Siesta Harbor! Fabulous Lanai overlooking the canal with a view of the Intracoastal Waterway! Beautiful heated pool, outdoor spa, shower, shuffleboard, barbecue area, clubhouse, full kitchen with fitness room, sauna, library and Boat Slips available for rent through the Harbor Master.The complex and the fishing pier

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1300 N Portofino Dr Unit 305, Sarasota, FL 34242
  • /69

    $995,000

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

    19 Whispering Sands Dr Unit 204, Sarasota, FL 34242

    Embrace the rare opportunity to own a GULF FRONT residence in the coveted Siesta Key community of Whispering Sands – where breathtaking FULL GULF views, an unbeatable location, and endless potential come together. This 2 bed/2 bath 2nd floor tower unit showcases panoramic vistas of the shimmering Gulf, on 800’ of your own PRIVATE quartz sand beach, and the nightly spectacle of vibrant symphonies

    Harriet Stopher COLDWELL BANKER REALTY

    19 Whispering Sands Dr Unit 204, Sarasota, FL 34242
  • /58

    $435,000

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft

    1215 S Portofino Dr Unit 406, Sarasota, FL 34242

    Escape the winter chill and step into your endless summer at this meticulously maintained, fully turn-key furnished 2-bedroom, 2-bathroom condo in the desirable Siesta Harbor community on Siesta Key. This 4th-floor gem has been lovingly cared for by the owners and offers charming peek-a-boo ocean views along with direct canal frontage — perfect for morning coffee with a waterfront breeze or

    Miao Whiteside BERKSHIRE HATHAWAY HOMESERVICE

    1215 S Portofino Dr Unit 406, Sarasota, FL 34242
  • /45

    $428,000

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft

    1250 N Portofino Dr Unit 304, Sarasota, FL 34242

    Looking for a home for your boat, a beach lifestyle, or an investment? Enjoy sunrises over the marina, afternoons on Siesta Key Beach, and evenings on your enclosed balcony overlooking the boats and colorful skies. This furnished 1BR/2BA condo in Siesta Harbor is beautifully updated with an open floor plan, luxury vinyl flooring, remodeled kitchen (2022) with white shaker cabinetry, granite

    Marci McFarland MICHAEL SAUNDERS & COMPANY

    1250 N Portofino Dr Unit 304, Sarasota, FL 34242
  • /69

    $525,000

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft

    119 Whispering Sands Cir Unit V36, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. BEST PRICED VILLA IN WHISPERING SANDS! Don't miss this opportunity to own this lovely REMODELED VILLA just steps from the sand! This 2 bed/2 bath villa in the premiere GULF FRONT property of Whispering Sands is the perfect island getaway. A 3rd bedroom could also be added. Remodeled in 2025, this villa features all NEW luxury vinyl plank flooring,

    Harriet Stopher COLDWELL BANKER REALTY

    119 Whispering Sands Cir Unit V36, Sarasota, FL 34242
  • /66

    $525,000

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft

    1300 N Portofino Dr Unit 406, Sarasota, FL 34242

    BEAUTIFUL RENOVQTION ON THE CANAL! WATERVIEWS! Live the Florida dream in this recently remodeled CANAL-FRONT home, designer 2 bedroom, 2 bathroom condo nestled within the coveted Siesta Harbor community, offering private beach access to world-famous Siesta Key Beach just across the street. Situated on the fourth floor with picturesque water views, this beautifully updated unit features gorgeous

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1300 N Portofino Dr Unit 406, Sarasota, FL 34242
  • /73

    $1,195,000

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

    20 Whispering Sands Dr Unit 1201, Sarasota, FL 34242

    A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every

    Harriet Stopher COLDWELL BANKER REALTY

    20 Whispering Sands Dr Unit 1201, Sarasota, FL 34242
  • /78

    $640,000

    • 3 Beds
    • 2 Baths
    • 1,327 Sq Ft

    239 Hourglass Way Unit V7, Sarasota, FL 34242

    Tucked away in a peaceful, private setting overlooking the tranquil, shimmering lagoon - with its abundant fish, birds, and aquatic life - this beautifully updated 3 Bed/2 Bath villa in the premier GULF FRONT property of Whispering Sands offers the perfect blend of comfort, style and serenity. Step inside to discover a bright NEW kitchen featuring new granite countertops, stainless appliances,

    Harriet Stopher COLDWELL BANKER REALTY

    239 Hourglass Way Unit V7, Sarasota, FL 34242
  • /57

    $950,000

    • 2 Beds
    • 2 Baths
    • 1,464 Sq Ft

    19 Whispering Sands Dr Unit 201, Sarasota, FL 34242

    Front row FULL Gulf views—just one floor above the sand! Priced below market, this lovely 2 bed/2 bath GULF FRONT tower residence in the premiere Siesta Key property of Whispering Sands represents an opportunity to move right in, and if desired, ultimately take your time to create your own vision and make it your own - and enjoy a lifetime of memories. Don’t hesitate - this is currently the best

    Harriet Stopher COLDWELL BANKER REALTY

    19 Whispering Sands Dr Unit 201, Sarasota, FL 34242
  • /68

    $475,000

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

    101 Whispering Sands Dr Unit 107, Sarasota, FL 34242

    One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! Welcome to affordable GULF FRONT living! This is the BEST PRICED CONDO in Whispering Sands. The sellers are also willing to offer a $60,000 SELLER CREDIT with an acceptable offer, to offset any future improvements or assessments. This recently updated, 2 bed/2 bath, DOUBLE LANAI CORNER unit is nestled in the southwest corner of

    Harriet Stopher COLDWELL BANKER REALTY

    101 Whispering Sands Dr Unit 107, Sarasota, FL 34242
  • /72

    $500,000

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

    225 Hourglass Way Unit 106, Sarasota, FL 34242

    Step into your own island retreat with this rare ground floor END unit in the highly sought after GULF FRONT property of Whispering Sands! Perfectly positioned with a full length screened & glassed lanai overlooking the picturesque lagoon and lush tropical landscaping, this residence captures a peaceful, serene setting with a touch of everyday luxury. Thoughtfully updated and designed for

    Harriet Stopher COLDWELL BANKER REALTY

    225 Hourglass Way Unit 106, Sarasota, FL 34242

Home Trends in Siesta Key, FL

Housing Trends

Median Sale Price
$1,985,000
Median Single Family Sale Price
$3,250,000
Median 1 Bedroom Sale Price
$575,000
Average Price Per Sq Ft
$862
Number of Homes for Sale
7
Last 12 months Home Sales
4
Months of Supply
21.00
Median List Price
$3,250,000
Median Change From 1st List Price
33%
Median Home Sale Price YoY Change
-25%
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