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Homes Under $400K in Longboat Key, FL
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3 bedsWith a pool

Homes Under $400K in Longboat Key, FL

Homes Under $400K in Longboat Key, FL

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24 of 48 Listings
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Homes Under $400K in Longboat Key, FL

24 of 48 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 2600 Harbourside Dr #C3 — photoNew4Active

    $275,000

    1 bd · 1 ba · 1,302 sqft

    2600 Harbourside Dr #C3, Longboat Key, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  2. 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

  3. 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

  4. 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

  5. 2800 Harbourside Dr #E-21 — photo17Active

    $385,000

    — bd · 0 ba · — sqft

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

    Jennifer Wilson · LBRE LLC

  6. 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

  7. 3802 Gulf Of Mexico Dr #a203 — photoOpen house Sun, Oct 4 · 12:00 PM69Active

    $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

  8. 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

  9. 2600 Harbourside Dr #I-12 — photo16Active

    $200,000

    — bd · 0 ba · — sqft

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

    Jennifer Wilson · LBRE LLC

  10. 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

  11. 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

  12. 2600 Harbourside Dr #Q-10 — photo15Active

    $225,000

    — bd · 0 ba · — sqft

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

    Jennifer Wilson · LBRE LLC

  13. 36 Twin Shores Blvd — photoPrice Reduced46Active

    $139,000

    1 bd · 1 ba · 564 sqft

    36 Twin Shores Blvd, Longboat Key, FL

    Sharon Austin · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  14. 408 Gulf Of Mexico Dr #2126 — photo10Active

    $39,900

    — bd · 0 ba · — sqft

    408 Gulf Of Mexico Dr #2126, Longboat Key, FL

    Beverly St Hilaire · MICHAEL SAUNDERS & COMPANY

  15. 2600 Harbourside Dr #O-07 — photo3Active

    $216,000

    — bd · 0 ba · — sqft

    2600 Harbourside Dr #O-07, Longboat Key, FL

    Jennifer Wilson · LBRE LLC

  16. 2600 Harbourside Dr #P-05 — photo20Active

    $200,000

    — bd · 0 ba · — sqft

    2600 Harbourside Dr #P-05, Longboat Key, FL

    Heather Claridge · RIVER HILLS PROPERTIES, LLC B

  17. 71 Twin Shores Blvd — photo12Active

    $395,000

    2 bd · 2 ba · 758 sqft

    71 Twin Shores Blvd, Longboat Key, FL

    Kyle Adams · EVENTIDE REALTY LLC

  18. 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

  19. 2600 Harbourside Drive #R-13 — photo19Active

    $400,000

    — bd · 0 ba · — sqft

    2600 Harbourside Drive #R-13, Longboat Key, FL

    Jennifer Wilson · LBRE LLC

  20. 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

  21. 3710 Gulf Of Mexico Dr #E22 — photo37Active

    $310,000

    1 bd · 1 ba · 680 sqft

    3710 Gulf Of Mexico Dr #E22, Longboat Key, FL

    Bill Shuttleworth · EDGEWATER REAL ESTATE, INC

  22. 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

  23. 2600 Harbourside Dr #H06 — photo31Active

    $250,000

    — bd · 0 ba · — sqft

    2600 Harbourside Dr #H06, Longboat Key, FL

    Mike Warm, LLC · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  24. 408 Gulf Of Mexico Dr #2112 — photo5Active

    $39,500

    — bd · 0 ba · — sqft

    408 Gulf Of Mexico Dr #2112, Longboat Key, FL

    Daniel Treiman · MICHAEL SAUNDERS & COMPANY

12

About Homes Under $400K in Longboat Key, FL

Homes Under $400K in Longboat Key, FL: 48 active listings as of October 2, 2026, 11:08 UTC.

Property types among these 48 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Boat Slip3266.7%
Condominium1020.8%

Explore Longboat Key homes

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Listing data & MLS disclosures

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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.
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    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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 93.9% of asking price

    Buyers here are paying below asking. MLS · 23 sales · as of Sep 29, 2026

    Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

    Median list price
    $995,500
    Homes for sale
    194
    Median days on market
    148 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.