Homes Under $500K in Longboat Key, FL

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24 of 25 Listings

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24 of 25 Listings

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25 listings

Homes Under $500K in Longboat Key, FL

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24 of 25 Listings

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Homes Under $500K in Longboat Key, FL

24 of 25 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

25

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$495,000

0 bd · 1 ba · 368 sqft

3453 Gulf Of Mexico Dr #237, Longboat Key, FL

Rogers Moore · COLDWELL BANKER REALTY

72Active

$399,000

2 bd · 2 ba · 1,007 sqft

3802 Gulf Of Mexico Dr #a203, Longboat Key, FL

Holly Switow · PREMIER SOTHEBY'S INTERNATIONAL REALTY

29Active

$489,900

1 bd · 1 ba · 528 sqft

3453 Gulf Of Mexico Dr #242, Longboat Key, FL

Eileen Saunders · MICHAEL SAUNDERS & COMPANY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced52Active

$425,000

2 bd · 2 ba · 1,072 sqft

4370 Chatham Dr #304, Longboat Key, FL

Kevin Tai · PREFERRED SHORE LLC

30Active

$390,000

1 bd · 1 ba · 876 sqft

3453 Gulf Of Mexico Dr #200, Longboat Key, FL

Kelly Baldwin · COLDWELL BANKER REALTY

60Active

$399,000

1 bd · 1 ba · 630 sqft

707 Saint Judes Dr S #1, Longboat Key, FL

Kristy Gentile · RE/MAX ALLIANCE GROUP

31Active

$450,000

2 bd · 2 ba · 1,327 sqft

711 Spanish Dr S #211, Longboat Key, FL

Geoff Scalera · AUM FLORIDA REAL ESTATE LLC

Price Reduced36Active

$449,900

2 bd · 2 ba · 1,072 sqft

4340 Falmouth Dr #104, Longboat Key, FL

Melissa Sherk · PREFERRED SHORE LLC

90Active

$425,000

2 bd · 2 ba · 1,152 sqft

4390 Exeter Dr #107, Longboat Key, FL

Sharon Meier · PREMIER SOTHEBY'S INTERNATIONAL REALTY

37Active

$450,000

2 bd · 2 ba · 1,361 sqft

683 Spanish Dr S #214, Longboat Key, FL

Geoff Scalera · AUM FLORIDA REAL ESTATE LLC

37Active

$325,000

1 bd · 1 ba · 532 sqft

2850 Gulf Of Mexico Dr #4, Longboat Key, FL

Michael Renick PLLC · MANGROVE REALTY ASSOCIATES

Price Reduced28Active

$485,000

2 bd · 2 ba · 933 sqft

1945 Gulf Of Mexico Dr #M2-402, Longboat Key, FL

Stephen Hachey · FLAT FEE MLS REALTY

88Active

$479,000

2 bd · 2 ba · 1,072 sqft

4340 Falmouth Dr #D-204, Longboat Key, FL

Jonna Humphries · WAGNER REALTY

Price Reduced54Active

$307,000

1 bd · 1 ba · 747 sqft

4350 Chatham Dr #105, Longboat Key, FL

Malihe Karimi · MICHAEL SAUNDERS & COMPANY

28Active

$339,000

1 bd · 1 ba · 761 sqft

3804 Gulf Of Mexico Dr #B204, Longboat Key, FL

Shaun Cumston · STERLING REALTY

Price Reduced63Active

$497,000

2 bd · 2 ba · 1,192 sqft

1930 Harbourside Dr #122, Longboat Key, FL

David Leventhal · COLDWELL BANKER REALTY

Price Reduced18Active

$410,000

1 bd · 1 ba · 936 sqft

6700 Gulf Of Mexico Dr #143, Longboat Key, FL

Brooke Moran · DALTON WADE INC

Price Reduced36Active

$449,000

2 bd · 1 ba · 933 sqft

1935 Gulf Of Mexico Dr #G7-304, Longboat Key, FL

Alie Espinoza · EATON REALTY

77Active

$389,500

2 bd · 2 ba · 1,046 sqft

3806 Gulf Of Mexico Dr #C310, Longboat Key, FL

Len Scavron · LEN SCAVRON

Price Reduced30Active

$485,000

2 bd · 2 ba · 992 sqft

605 Sutton Pl #102, Longboat Key, FL

Frank Golio Jr., PLLC · LEGACY BAY PARTNERS

Price Reduced42Active

$499,000

2 bd · 2 ba · 1,152 sqft

4420 Exeter Dr #303, Longboat Key, FL

Jerry Gemmecke · SMITH & ASSOCIATES REAL ESTATE

Price Reduced34Active

$499,000

1 bd · 1 ba · 720 sqft

5231 Gulf Of Mexico Dr #104, Longboat Key, FL

JoDene Moneuse, PA · MICHAEL SAUNDERS & COMPANY

Price Reduced37Active

$480,000

2 bd · 2 ba · 1,152 sqft

4380 Exeter Dr #H202, Longboat Key, FL

Ryan Skrzypkowski · COLDWELL BANKER REALTY

74Active

$387,561

1 bd · 1 ba · 990 sqft

6700 Gulf Of Mexico Dr #118, Longboat Key, FL

Gerald Cunningham · KELLER WILLIAMS ON THE WATER S

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Longboat Key housing market

August 2026

Selling at 95.0% of asking price

Buyers here are paying below asking. MLS · 38 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 27, 2026

Median sale price: $1,800,000$597,500–$2,651,000 typical range
Price per sq. ft.: $656
Sales: 19
Paid in cash: 63.2%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 110 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -12.7%

Longboat Key, FL community profile

Population: 8,489
Median income: $133,076
Housing units: 10,273
People per sq. mi.: 1,179
Area: 7.2 sq. mi.

Source: HJN community data

Explore Longboat Key homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Longboat Key, FL community profile

Population: 8,489
Median income: $133,076
Housing units: 10,273
People per sq. mi.: 1,179
Area: 7.2 sq. mi.

Source: HJN community data

Longboat Key housing market

August 2026

Selling at 95.0% of asking price

Buyers here are paying below asking. MLS · 38 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 27, 2026

Median sale price: $1,800,000$597,500–$2,651,000 typical range
Price per sq. ft.: $656
Sales: 19
Paid in cash: 63.2%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 110 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -12.7%

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Longboat Key housing market

Homes that sold · County records, as of Aug 27, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Longboat Key, FL community profile

Explore Longboat Key homes

Your local brokerage

Listing data & MLS disclosures

Longboat Key, FL community profile

Longboat Key housing market

Homes that sold · County records, as of Aug 27, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026