Siesta Key Homes Under $500K

39 homes under $500K for sale in Siesta Key, median asking price $399,000, mostly $59,000 – $476,000. Homes with an asking price under $500,000. All of Siesta Key (ZIP 34242). As of Oct 9, 2026.

Active

$385,000

8911 MIDNIGHT PASS ROAD #511

SARASOTA, FL 34242

1 bed

1 bath

726 sqft

MLS# A4708929 · Listing courtesy of COLDWELL BANKER REALTY

Active

$429,000

5830 MIDNIGHT PASS ROAD #8

SARASOTA, FL 34242

0 bed

1 bath

392 sqft

MLS# A4708909 · Listing courtesy of KELLER WILLIAMS ON THE WATER S

Active

$394,000

1250 PORTOFINO DRIVE #304

SARASOTA, FL 34242

1 bed

2 bath

780 sqft

MLS# A4708535 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

Active Under Contract

$475,000

5661 MIDNIGHT PASS ROAD #401

SARASOTA, FL 34242

2 bed

2 bath

1,012 sqft

MLS# A4708540 · Listing courtesy of COLDWELL BANKER REALTY

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

Active

$479,999

5673 MIDNIGHT PASS ROAD #202

SARASOTA, FL 34242

2 bed

2 bath

1,012 sqft

MLS# A4707278 · Listing courtesy of GULF SHORES REALTY & RENTALS

116 VISTA HERMOSA CIRCLE #108C, SARASOTA

Active

$400,000

116 VISTA HERMOSA CIRCLE #108C

SARASOTA, FL 34242

2 bed

2 bath

900 sqft

MLS# N6145721 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

Active

$399,000

6157 MIDNIGHT PASS ROAD #G11

SARASOTA, FL 34242

2 bed

1 bath

690 sqft

MLS# A4704655 · Listing courtesy of COLDWELL BANKER REALTY

Active

$449,500

1300 PORTOFINO DRIVE #103

SARASOTA, FL 34242

2 bed

2 bath

929 sqft

MLS# A4704416 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

Active

$399,000

9034 MIDNIGHT PASS ROAD #6

SARASOTA, FL 34242

2 bed

2 bath

1,124 sqft

MLS# A4704019 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

915 SEASIDE DR #405, WEEKS 22-23, SARASOTA

Active

$45,000

915 SEASIDE DR #405, WEEKS 22-23

SARASOTA, FL 34242

4 bed

3 bath

2,460 sqft

MLS# A4703483 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

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

Active

$450,000

1020 SUN N SEA DRIVE #102

SARASOTA, FL 34242

1 bed

1 bath

524 sqft

MLS# A4702764 · Listing courtesy of KW COASTAL LIVING III

Active

$479,000

6006 MIDNIGHT PASS ROAD #60

SARASOTA, FL 34242

1 bed

1 bath

708 sqft

MLS# A4702254 · Listing courtesy of LACEY REALTY INC

Active

$299,000

5641 MIDNIGHT PASS ROAD #902

SARASOTA, FL 34242

1 bed

1 bath

797 sqft

MLS# A4702107 · Listing courtesy of WILLIAM RAVEIS - FLORIDA LLC

915 SEASIDE DRIVE #613, Weeks 32-33, SARASOTA

Active Under Contract

$5,000

915 SEASIDE DRIVE #613, Weeks 32-33

SARASOTA, FL 34242

4 bed

3 bath

2,460 sqft

MLS# A4700052 · Listing courtesy of DOUGLAS ELLIMAN

Pending

$369,000

159 VISTA HERMOSA CIRCLE #27B

SARASOTA, FL 34242

2 bed

2 bath

1,036 sqft

MLS# A4698551 · Listing courtesy of CP REALTY INTERNATIONAL

Active

$349,000

5683 MIDNIGHT PASS ROAD #105

SARASOTA, FL 34242

1 bed

1 bath

797 sqft

MLS# A4699427 · Listing courtesy of COMPASS FLORIDA LLC

Active

$499,000

6157 MIDNIGHT PASS ROAD #E12

SARASOTA, FL 34242

2 bed

2 bath

1,101 sqft

MLS# A4698724 · Listing courtesy of CORCORAN DWELLINGS REALTY

Active

$364,000

9397 MIDNIGHT PASS ROAD #903

SARASOTA, FL 34242

1 bed

1 bath

778 sqft

MLS# A4696940 · Listing courtesy of COLDWELL BANKER SARASOTA CENT.

Active

$469,900

1250 PORTOFINO DRIVE #202

SARASOTA, FL 34242

2 bed

2 bath

929 sqft

MLS# A4695140 · Listing courtesy of BECKMANN REAL ESTATE

Active Under Contract

$395,000

5830 MIDNIGHT PASS ROAD #32

SARASOTA, FL 34242

0 bed

1 bath

392 sqft

MLS# A4694962 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

915 SEASIDE DRIVE #402, Weeks 10-13, SARASOTA

Active

$80,000

915 SEASIDE DRIVE #402, Weeks 10-13

SARASOTA, FL 34242

2 bed

3 bath

1,750 sqft

MLS# A4694774 · Listing courtesy of DOUGLAS ELLIMAN

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

Homes Under $500K nearby

Questions about Siesta Key Homes Under $500K

How many homes under $500K are for sale in Siesta Key?

39 homes under $500K 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 under $500K in Siesta Key?

The median asking price is $399,000; most are listed between $59,000 and $476,000. 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 under $500K?

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

Call (941) 899-3045 Text George Send a message

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

Siesta Key Homes Under $500K

More in Siesta Key

Homes Under $500K nearby

Questions about Siesta Key Homes Under $500K

Want to see one of these homes under $500K?