Siesta Key 55+ Community Homes for Sale

16 homes in 55+ communities for sale in Siesta Key, median asking price $468,000, mostly $405,000 – $620,000. Homes in communities the MLS marks as senior (55+) communities. All of Siesta Key (ZIP 34242). As of Oct 9, 2026.

1250 PORTOFINO DRIVE #304, SARASOTA
Active

$394,000

1250 PORTOFINO DRIVE #304

SARASOTA, FL 34242

1 bed
2 bath
780 sqft

MLS# A4708535 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1300 PORTOFINO DRIVE #105, SARASOTA
Active

$399,900

1300 PORTOFINO DRIVE #105

SARASOTA, FL 34242

1 bed
2 bath
865 sqft

MLS# A4708269 · Listing courtesy of JUDITH GUZZI & ASSOCIATES LLC

1300 PORTOFINO DRIVE #103, SARASOTA
Active

$449,500

1300 PORTOFINO DRIVE #103

SARASOTA, FL 34242

2 bed
2 bath
929 sqft

MLS# A4704416 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1300 PORTOFINO DRIVE #305, SARASOTA
Active

$467,000

1300 PORTOFINO DRIVE #305

SARASOTA, FL 34242

1 bed
2 bath
780 sqft

MLS# A4703610 · Listing courtesy of JUDITH GUZZI & ASSOCIATES LLC

20 WHISPERING SANDS DRIVE #501, SARASOTA
Active

$1,199,000

20 WHISPERING SANDS DRIVE #501

SARASOTA, FL 34242

2 bed
2 bath
1,282 sqft

MLS# A4697523 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

1250 PORTOFINO DRIVE #202, SARASOTA
Active

$469,900

1250 PORTOFINO DRIVE #202

SARASOTA, FL 34242

2 bed
2 bath
929 sqft

MLS# A4695140 · Listing courtesy of BECKMANN REAL ESTATE

1257 PORTOFINO DRIVE #104, SARASOTA
Active

$429,900

1257 PORTOFINO DRIVE #104

SARASOTA, FL 34242

1 bed
2 bath
780 sqft

MLS# A4692335 · Listing courtesy of KELLER WILLIAMS ON THE WATER S

1215 PORTOFINO DRIVE #406, SARASOTA
Active

$410,000

1215 PORTOFINO DRIVE #406

SARASOTA, FL 34242

2 bed
2 bath
929 sqft

MLS# A4691798 · Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICE

239 HOURGLASS WAY #V7, SARASOTA
Pending

$640,000

239 HOURGLASS WAY #V7

SARASOTA, FL 34242

3 bed
2 bath
1,327 sqft

MLS# A4691064 · Listing courtesy of COLDWELL BANKER REALTY

206 HOURGLASS WAY #V10, SARASOTA
Active

$600,000

206 HOURGLASS WAY #V10

SARASOTA, FL 34242

2 bed
2 bath
1,462 sqft

MLS# A4690141 · Listing courtesy of COLDWELL BANKER REALTY

1300 PORTOFINO DRIVE #406, SARASOTA
Active

$487,500

1300 PORTOFINO DRIVE #406

SARASOTA, FL 34242

2 bed
2 bath
929 sqft

MLS# A4692022 · Listing courtesy of JUDITH GUZZI & ASSOCIATES LLC

225 HOURGLASS WAY #106, SARASOTA
Active

$500,000

225 HOURGLASS WAY #106

SARASOTA, FL 34242

2 bed
2 bath
1,271 sqft

MLS# A4683200 · Listing courtesy of COLDWELL BANKER REALTY

1257 PORTOFINO DRIVE #307, SARASOTA
Active

$419,900

1257 PORTOFINO DRIVE #307

SARASOTA, FL 34242

2 bed
2 bath
929 sqft

MLS# A4679704 · Listing courtesy of JUDITH GUZZI & ASSOCIATES LLC

915 BEACH ROAD #216, SARASOTA
Active

$575,000

915 BEACH ROAD #216

SARASOTA, FL 34242

2 bed
1 bath
753 sqft

MLS# A4677981 · Listing courtesy of COLDWELL BANKER REALTY

101 WHISPERING SANDS DRIVE #107, SARASOTA
Active

$450,000

101 WHISPERING SANDS DRIVE #107

SARASOTA, FL 34242

2 bed
2 bath
1,271 sqft

MLS# A4674069 · Listing courtesy of COLDWELL BANKER REALTY

225 HOURGLASS WAY #103, SARASOTA
Active

$550,000

225 HOURGLASS WAY #103

SARASOTA, FL 34242

2 bed
2 bath
1,271 sqft

MLS# A4664460 · Listing courtesy of COLDWELL BANKER REALTY

More in Siesta Key

55+ Community Homes for Sale nearby

Questions about Siesta Key 55+ Community Homes for Sale

How many homes in 55+ communities are for sale in Siesta Key?

16 homes in 55+ communities are listed on this site as of Oct 9, 2026, from Stellar MLS. The list updates every hour.

What is the median asking price of homes in 55+ communities in Siesta Key?

The median asking price is $468,000; most are listed between $405,000 and $620,000. These are asking prices, not sale prices.

Can George help me buy in Siesta Key?

Yes. George Predescu, REALTOR® with Horizon Realty International, can set up showings for any listing here, including ones listed by other brokers. Call or text (941) 899-3045.

Want to see one of these homes in 55+ communities?

George Predescu, REALTOR® with Horizon Realty International, can answer questions and set up showings.

Listings courtesy of Stellar MLS as distributed by MLS GRID

Based on information submitted to the MLS GRID as of Oct 9, 2026, 3:15 PM EDT. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some IDX listings have been excluded from this website. Full IDX / DMCA disclaimer