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3 bedsWith a pool
Homes Under $500K in Longboat Key, FL
77 listings

Homes Under $500K in Longboat Key, FL

Homes Under $500K in Longboat Key, FL

Show Map
24 of 77 Listings
Map

Homes Under $500K in Longboat Key, FL

24 of 77 Listings

  1. 693 Spanish Dr N #24 — photoNew82

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$423,750

2 bd · 2 ba · 1,429 sqft

693 Spanish Dr N #24, Longboat Key, FL

Andrew Vac · RE/MAX ALLIANCE GROUP

  • 2600 Harbourside Dr #Q8 — photo1Active

    $189,000

    — bd · 0 ba · — sqft

    2600 Harbourside Dr #Q8, Longboat Key, FL

    Daniel Treiman · MICHAEL SAUNDERS & COMPANY

  • 738 Spanish Dr S #98 — photo44Active

    $495,000

    2 bd · 2 ba · 1,140 sqft

    738 Spanish Dr S #98, Longboat Key, FL

    Geoff Scalera · AUM FLORIDA REAL ESTATE LLC

  • 845 Spanish Dr N #845 — photo58Active

    $450,000

    2 bd · 2 ba · 1,357 sqft

    845 Spanish Dr N #845, Longboat Key, FL

    Laura Rode · KW COASTAL LIVING III

  • 2600 Harbourside Drive — photo4Active

    $275,000

    0 bd · 0 ba · 1,302 sqft

    2600 Harbourside Drive, Longboat Key, FL

    STEVEN KOLENO · BEYCOME OF FLORIDA LLC

  • 554 Spanish Dr S — photo74Active

    $425,000

    2 bd · 2 ba · 1,326 sqft

    554 Spanish Dr S, Longboat Key, FL

    Kimberly Freiwald · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 4380 Exeter Dr #101 — photo82Active

    $389,500

    2 bd · 2 ba · 1,376 sqft

    4380 Exeter Dr #101, Longboat Key, FL

    Kimberly Freiwald · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 600 Sutton Pl #101B — photo53Active

    $319,000

    1 bd · 1 ba · 883 sqft

    600 Sutton Pl #101B, Longboat Key, FL

    Jill Baldwin · MARINA PARK REALTY LLC

  • 4485 Gulf Of Mexico Dr #402 — photoPrice ReducedOpen house Sun, Oct 18 · 1:00 PM51Active

    $456,789

    2 bd · 2 ba · 1,022 sqft

    4485 Gulf Of Mexico Dr #402, Longboat Key, FL

    Paula Van De Ree · NEAL VAN DE REE & ASSOCIATES

  • 408 Gulf Of Mexico Dr #1206 — photo5Active

    $65,000

    — bd · 0 ba · — sqft

    408 Gulf Of Mexico Dr #1206, Longboat Key, FL

    Daniel Treiman · MICHAEL SAUNDERS & COMPANY

  • 408 Gulf Of Mexico Dr #2207 — photo5Active

    $49,000

    — bd · 0 ba · — sqft

    408 Gulf Of Mexico Dr #2207, Longboat Key, FL

    Daniel Treiman · MICHAEL SAUNDERS & COMPANY

  • 408 Gulf Of Mexico Dr #2114 — photo5Active

    $39,000

    — bd · 0 ba · — sqft

    408 Gulf Of Mexico Dr #2114, Longboat Key, FL

    Daniel Treiman · MICHAEL SAUNDERS & COMPANY

  • 2800 Harbourside Dr #E-21 — photo17Active

    $385,000

    — bd · 0 ba · — sqft

    2800 Harbourside Dr #E-21, Longboat Key, FL

    Jennifer Wilson · LBRE LLC

  • 3453 Gulf Of Mexico Dr #237 — photo25Active

    $495,000

    0 bd · 1 ba · 368 sqft

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

    Rogers Moore · COLDWELL BANKER REALTY

  • 2800 Harbourside Drive Dr #M-10 — photo20Active

    $289,000

    — bd · 0 ba · — sqft

    2800 Harbourside Drive Dr #M-10, Longboat Key, FL

    Jennifer Wilson · LBRE LLC

  • 3802 Gulf Of Mexico Dr #a203 — photo69Active

    $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

  • 96 Twin Shores Blvd — photo9Active

    $399,000

    2 bd · 2 ba · 758 sqft

    96 Twin Shores Blvd, Longboat Key, FL

    Kyle Adams · EVENTIDE REALTY LLC

  • 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

  • 2600 Harbourside Dr #I-12 — photo16Active

    $200,000

    — bd · 0 ba · — sqft

    2600 Harbourside Dr #I-12, Longboat Key, FL

    Jennifer Wilson · LBRE 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 — photoPrice Reduced60Active

    $364,000

    1 bd · 1 ba · 630 sqft

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

    Kristy Gentile · RE/MAX ALLIANCE GROUP

  • 2600 Harbourside Dr #Q-10 — photo15Active

    $225,000

    — bd · 0 ba · — sqft

    2600 Harbourside Dr #Q-10, Longboat Key, FL

    Jennifer Wilson · LBRE LLC

  • 36 Twin Shores Blvd — photoPrice Reduced46Active

    $129,000

    1 bd · 1 ba · 564 sqft

    36 Twin Shores Blvd, Longboat Key, FL

    Sharon Austin · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 12…4

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    realMLS (Northeast Florida Multiple Listing Service)
    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by NEFMLS.
    Listing information ©2026 Northeast Florida Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-07 19:16:02 UTC
    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

    September 2026 · This period is still settling

    Selling at 93.8% of asking price

    Buyers here are paying below asking. MLS · 27 sales · as of Sep 30, 2026

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $995,500
    Homes for sale
    194
    Median days on market
    128 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,505 sq. ft.