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3 bedsNew construction
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With a pool
Homes Under $500K in Longboat Key, FL
25 listings

Homes Under $500K in Longboat Key, FL

Homes Under $500K in Longboat Key, FL

Hide Map
24 of 25 Listings
Map

Homes Under $500K in Longboat Key, FL

24 of 25 Listings

  1. 3453 Gulf Of Mexico Dr #237 — photo25

Your local brokerage

TO

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

  • 3802 Gulf Of Mexico Dr #a203 — photo72Active

    $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

  • 3453 Gulf Of Mexico Dr #242 — photo29Active

    $489,900

    1 bd · 1 ba · 528 sqft

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

    Eileen Saunders · MICHAEL SAUNDERS & COMPANY

  • 4370 Chatham Dr #304 — photoPrice Reduced52Active

    $425,000

    2 bd · 2 ba · 1,072 sqft

    4370 Chatham Dr #304, Longboat Key, FL

    Kevin Tai · PREFERRED SHORE LLC

  • 3453 Gulf Of Mexico Dr #200 — photo30Active

    $390,000

    1 bd · 1 ba · 876 sqft

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

    Kelly Baldwin · COLDWELL BANKER REALTY

  • 707 Saint Judes Dr S #1 — photo60Active

    $399,000

    1 bd · 1 ba · 630 sqft

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

    Kristy Gentile · RE/MAX ALLIANCE GROUP

  • 711 Spanish Dr S #211 — photo31Active

    $450,000

    2 bd · 2 ba · 1,327 sqft

    711 Spanish Dr S #211, Longboat Key, FL

    Geoff Scalera · AUM FLORIDA REAL ESTATE LLC

  • 4340 Falmouth Dr #104 — photoPrice Reduced36Active

    $449,900

    2 bd · 2 ba · 1,072 sqft

    4340 Falmouth Dr #104, Longboat Key, FL

    Melissa Sherk · PREFERRED SHORE LLC

  • 4390 Exeter Dr #107 — photo90Active

    $425,000

    2 bd · 2 ba · 1,152 sqft

    4390 Exeter Dr #107, Longboat Key, FL

    Sharon Meier · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 683 Spanish Dr S #214 — photo37Active

    $450,000

    2 bd · 2 ba · 1,361 sqft

    683 Spanish Dr S #214, Longboat Key, FL

    Geoff Scalera · AUM FLORIDA REAL ESTATE LLC

  • 2850 Gulf Of Mexico Dr #4 — photo37Active

    $325,000

    1 bd · 1 ba · 532 sqft

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

    Michael Renick PLLC · MANGROVE REALTY ASSOCIATES

  • 1945 Gulf Of Mexico Dr #M2-402 — photoPrice 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

  • 4340 Falmouth Dr #D-204 — photo88Active

    $479,000

    2 bd · 2 ba · 1,072 sqft

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

    Jonna Humphries · WAGNER REALTY

  • 4350 Chatham Dr #105 — photoPrice Reduced54Active

    $307,000

    1 bd · 1 ba · 747 sqft

    4350 Chatham Dr #105, Longboat Key, FL

    Malihe Karimi · MICHAEL SAUNDERS & COMPANY

  • 3804 Gulf Of Mexico Dr #B204 — photo28Active

    $339,000

    1 bd · 1 ba · 761 sqft

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

    Shaun Cumston · STERLING REALTY

  • 1930 Harbourside Dr #122 — photoPrice Reduced63Active

    $497,000

    2 bd · 2 ba · 1,192 sqft

    1930 Harbourside Dr #122, Longboat Key, FL

    David Leventhal · COLDWELL BANKER REALTY

  • 6700 Gulf Of Mexico Dr #143 — photoPrice Reduced18Active

    $410,000

    1 bd · 1 ba · 936 sqft

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

    Brooke Moran · DALTON WADE INC

  • 1935 Gulf Of Mexico Dr #G7-304 — photoPrice Reduced36Active

    $449,000

    2 bd · 1 ba · 933 sqft

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

    Alie Espinoza · EATON REALTY

  • 3806 Gulf Of Mexico Dr #C310 — photo77Active

    $389,500

    2 bd · 2 ba · 1,046 sqft

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

    Len Scavron · LEN SCAVRON

  • 605 Sutton Pl #102 — photoPrice Reduced30Active

    $485,000

    2 bd · 2 ba · 992 sqft

    605 Sutton Pl #102, Longboat Key, FL

    Frank Golio Jr., PLLC · LEGACY BAY PARTNERS

  • 4420 Exeter Dr #303 — photoPrice Reduced42Active

    $499,000

    2 bd · 2 ba · 1,152 sqft

    4420 Exeter Dr #303, Longboat Key, FL

    Jerry Gemmecke · SMITH & ASSOCIATES REAL ESTATE

  • 5231 Gulf Of Mexico Dr #104 — photoPrice Reduced34Active

    $499,000

    1 bd · 1 ba · 720 sqft

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

    JoDene Moneuse, PA · MICHAEL SAUNDERS & COMPANY

  • 4380 Exeter Dr #H202 — photoPrice Reduced37Active

    $480,000

    2 bd · 2 ba · 1,152 sqft

    4380 Exeter Dr #H202, Longboat Key, FL

    Ryan Skrzypkowski · COLDWELL BANKER REALTY

  • 6700 Gulf Of Mexico Dr #118 — photo74Active

    $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

  • 12

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    Your local brokerage

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    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

    Longboat Key 12-month median sale price trend

    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%