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Homes Under $2.75M in Longboat Key, FL
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3 bedsWith a pool

Homes Under $2.75M in Longboat Key, FL

Homes Under $2.75M in Longboat Key, FL

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24 of 212 Listings
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Homes Under $2.75M in Longboat Key, FL

24 of 212 Listings

Your local brokerage

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 5461 Gulf Of Mexico Dr #304 — photo50Active

    $1,495,000

    2 bd · 2 ba · 1,516 sqft

    5461 Gulf Of Mexico Dr #304, Longboat Key, FL

    Maggie Hicks · COLDWELL BANKER REALTY

  2. 546 Spanish Dr S — photoNew56Active

    $529,990

    2 bd · 2 ba · 1,393 sqft

    546 Spanish Dr S, Longboat Key, FL

    Jackie Griese · MICHAEL SAUNDERS & COMPANY

  3. 4485 Gulf Of Mexico Dr #402 — photoNewOpen house Sat, Oct 3 · 1:00 PM51Active

    $698,765

    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

  4. 1445 Gulf Of Mexico Dr #101 — photoNew43Active

    $1,090,000

    3 bd · 3 ba · 2,092 sqft

    1445 Gulf Of Mexico Dr #101, Longboat Key, FL

    Ryan Ackerman, PA · COLDWELL BANKER REALTY

  5. 1975 Gulf Of Mexico Dr #G4-203 — photoNew54Active

    $795,000

    2 bd · 2 ba · 1,257 sqft

    1975 Gulf Of Mexico Dr #G4-203, Longboat Key, FL

    Sandra Endres · COLDWELL BANKER REALTY

  6. 6330 Laguna Dr — photoOpen house Sat, Oct 3 · 3:00 PM87Active

    $1,999,000

    3 bd · 3 ba · 2,856 sqft

    6330 Laguna Dr, Longboat Key, FL

    Danielle Dietrich, PA · COLDWELL BANKER REALTY

  7. 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

  8. 3578 Fair Oaks Way — photoOpen house Sun, Oct 4 · 1:00 PM60Active

    $2,695,000

    3 bd · 4 ba · 3,118 sqft

    3578 Fair Oaks Way, Longboat Key, FL

    Bruce Myer · COLDWELL BANKER REALTY

  9. 3808 Gulf Of Mexico Dr #E412 — photo49Active

    $1,175,000

    3 bd · 3 ba · 2,544 sqft

    3808 Gulf Of Mexico Dr #E412, Longboat Key, FL

    Roger Pettingell · COLDWELL BANKER REALTY

  10. 775 Longboat Club Rd #405 — photo51Active

    $1,095,000

    2 bd · 2 ba · 1,602 sqft

    775 Longboat Club Rd #405, Longboat Key, FL

    Bruce Myer · COLDWELL BANKER REALTY

  11. 4525 Gulf Of Mexico Dr #204 — photo40Active

    $1,125,000

    2 bd · 2 ba · 1,362 sqft

    4525 Gulf Of Mexico Dr #204, Longboat Key, FL

    Roger Pettingell · COLDWELL BANKER REALTY

  12. 3617 Fair Oaks Pl — photoOpen house Sun, Oct 4 · 1:00 PM54Active

    $2,100,000

    3 bd · 4 ba · 2,950 sqft

    3617 Fair Oaks Pl, Longboat Key, FL

    Ryan Heers · COLDWELL BANKER REALTY

  13. 2525 Gulf Of Mexico Dr #7B — photo72Active

    $1,450,000

    2 bd · 2 ba · 1,491 sqft

    2525 Gulf Of Mexico Dr #7B, Longboat Key, FL

    Christine Green · COLDWELL BANKER REALTY

  14. 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

  15. 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

  16. 539 Forest Way #539 — photo62Active

    $639,000

    2 bd · 3 ba · 1,440 sqft

    539 Forest Way #539, Longboat Key, FL

    Sharon Austin · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  17. 760 Longboat Ct — photoOpen house Sun, Oct 4 · 12:00 PM34Active

    $840,000

    3 bd · 2 ba · 1,242 sqft

    760 Longboat Ct, Longboat Key, FL

    Jesse Griffin · CENTURY 21 BEGGINS ENTERPRISES

  18. 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

  19. 2800 Harbourside Dr #E-21 — photo17Active

    $385,000

    — bd · 0 ba · — sqft

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

    Jennifer Wilson · LBRE LLC

  20. 4600 Gulf Of Mexico Dr #301 — photoPrice Reduced28Active

    $660,000

    2 bd · 2 ba · 1,561 sqft

    4600 Gulf Of Mexico Dr #301, Longboat Key, FL

    Janice Buehl · FUTURE HOME REALTY INC

  21. 843 Bayport Way #843 — photo87Active

    $645,000

    2 bd · 2 ba · 1,260 sqft

    843 Bayport Way #843, Longboat Key, FL

    Jennifer Thompson, PA · COLDWELL BANKER REALTY

  22. 691 Tarawitt Dr — photo35Active

    $815,000

    2 bd · 2 ba · 1,490 sqft

    691 Tarawitt Dr, Longboat Key, FL

    JoDene Moneuse, PA · MICHAEL SAUNDERS & COMPANY

  23. 732 Bayport Way — photo42Active

    $1,050,000

    2 bd · 2 ba · 1,456 sqft

    732 Bayport Way, Longboat Key, FL

    Jennifer Kenna · EXP REALTY, LLC

  24. 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

12…9

About Homes Under $2.75M in Longboat Key, FL

Homes Under $2.75M in Longboat Key, FL: 212 active listings as of October 2, 2026, 18:53 UTC.

Property types among these 212 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
Condominium12358.0%
Boat Slip4119.3%
Single Family Residence2913.7%

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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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    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.