Longboat Key Homes Under $500K

79 homes under $500K for sale in Longboat Key, median asking price $364,000, mostly $131,000 – $486,000. Homes with an asking price under $500,000. All of Longboat Key (ZIP 34228). As of Oct 9, 2026.

845 SPANISH DRIVE #845, LONGBOAT KEY
Active

$450,000

845 SPANISH DRIVE #845

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,357 sqft

MLS# A4706553 · Listing courtesy of KW COASTAL LIVING III

554 SPANISH DRIVE, LONGBOAT KEY
Active

$425,000

554 SPANISH DRIVE

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,326 sqft

MLS# A4708871 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

600 SUTTON PLACE #101B, LONGBOAT KEY
Active

$319,000

600 SUTTON PLACE #101B

LONGBOAT KEY, FL 34228

1 bed
1 bath
883 sqft

MLS# C7531576 · Listing courtesy of MARINA PARK REALTY LLC

4380 EXETER DRIVE #101, LONGBOAT KEY
Active

$389,500

4380 EXETER DRIVE #101

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,376 sqft

MLS# A4707428 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

4485 GULF OF MEXICO DRIVE #402, LONGBOAT KEY
Active

$345,678

4485 GULF OF MEXICO DRIVE #402

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,022 sqft

MLS# N6146025 · Listing courtesy of NEAL VAN DE REE & ASSOCIATES

408 GULF OF MEXICO DRIVE #1206, LONGBOAT KEY
Active

$65,000

408 GULF OF MEXICO DRIVE #1206

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4706908 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

408 GULF OF MEXICO DRIVE #2207, LONGBOAT KEY
Active

$49,000

408 GULF OF MEXICO DRIVE #2207

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4707116 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

408 GULF OF MEXICO DRIVE #2114, LONGBOAT KEY
Active

$39,000

408 GULF OF MEXICO DRIVE #2114

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4707119 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

2800 HARBOURSIDE DRIVE #E-21, LONGBOAT KEY
Active

$385,000

2800 HARBOURSIDE DRIVE #E-21

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4706843 · Listing courtesy of LBRE LLC

3453 GULF OF MEXICO DRIVE #237, LONGBOAT KEY
Active

$495,000

3453 GULF OF MEXICO DRIVE #237

LONGBOAT KEY, FL 34228

0 bed
1 bath
368 sqft

MLS# A4706240 · Listing courtesy of COLDWELL BANKER REALTY

1932 HARBOURSIDE DRIVE #214, LONGBOAT KEY
Active Under Contract

$449,000

1932 HARBOURSIDE DRIVE #214

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,192 sqft

MLS# A4706187 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

2800 HARBOURSIDE DRIVE DRIVE #M-10, LONGBOAT KEY
Active

$289,000

2800 HARBOURSIDE DRIVE DRIVE #M-10

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4705272 · Listing courtesy of LBRE LLC

3802 GULF OF MEXICO DRIVE #A203, LONGBOAT KEY
Active

$399,000

3802 GULF OF MEXICO DRIVE #A203

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,007 sqft

MLS# A4704650 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

96 TWIN SHORES BOULEVARD, LONGBOAT KEY
Active

$399,000

96 TWIN SHORES BOULEVARD

LONGBOAT KEY, FL 34228

2 bed
2 bath
758 sqft

MLS# A4706247 · Listing courtesy of EVENTIDE REALTY LLC

3453 GULF OF MEXICO DRIVE #242, LONGBOAT KEY
Active

$489,900

3453 GULF OF MEXICO DRIVE #242

LONGBOAT KEY, FL 34228

1 bed
1 bath
528 sqft

MLS# A4706004 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

4370 CHATHAM DRIVE #304, LONGBOAT KEY
Active

$425,000

4370 CHATHAM DRIVE #304

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,072 sqft

MLS# A4704453 · Listing courtesy of PREFERRED SHORE LLC

2600 HARBOURSIDE DRIVE #I-12, LONGBOAT KEY
Active

$200,000

2600 HARBOURSIDE DRIVE #I-12

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4704169 · Listing courtesy of LBRE LLC

3453 GULF OF MEXICO DRIVE #200, LONGBOAT KEY
Active

$390,000

3453 GULF OF MEXICO DRIVE #200

LONGBOAT KEY, FL 34228

1 bed
1 bath
876 sqft

MLS# A4703638 · Listing courtesy of COLDWELL BANKER REALTY

707 SAINT JUDES DRIVE #1, LONGBOAT KEY
Active

$364,000

707 SAINT JUDES DRIVE #1

LONGBOAT KEY, FL 34228

1 bed
1 bath
630 sqft

MLS# A4704345 · Listing courtesy of RE/MAX ALLIANCE GROUP

2600 HARBOURSIDE DRIVE #Q-10, LONGBOAT KEY
Active

$225,000

2600 HARBOURSIDE DRIVE #Q-10

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4703861 · Listing courtesy of LBRE LLC

36 TWIN SHORES BOULEVARD, LONGBOAT KEY
Active

$139,000

36 TWIN SHORES BOULEVARD

LONGBOAT KEY, FL 34228

1 bed
1 bath
564 sqft

MLS# A4702801 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

408 GULF OF MEXICO DRIVE #2126, LONGBOAT KEY
Active

$39,900

408 GULF OF MEXICO DRIVE #2126

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4703429 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

2600 HARBOURSIDE DRIVE #O-07, LONGBOAT KEY
Active

$216,000

2600 HARBOURSIDE DRIVE #O-07

LONGBOAT KEY, FL 34228

0 bed
0 bath
0 sqft

MLS# A4703254 · Listing courtesy of LBRE LLC

711 SPANISH DRIVE #211, LONGBOAT KEY
Active

$450,000

711 SPANISH DRIVE #211

LONGBOAT KEY, FL 34228

2 bed
2 bath
1,327 sqft

MLS# A4702742 · Listing courtesy of AUM FLORIDA REAL ESTATE LLC

More in Longboat Key

Homes Under $500K nearby

Questions about Longboat Key Homes Under $500K

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

79 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 Longboat Key?

The median asking price is $364,000; most are listed between $131,000 and $486,000. These are asking prices, not sale prices.

Can George help me buy in Longboat 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) 899-3045Text GeorgeSend 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