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Waterfront Homes in Longboat Key, FL
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Waterfront Homes in Longboat Key, FL

Waterfront Homes in Longboat Key, FL

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24 of 200 Listings
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Waterfront Homes in Longboat Key, FL

24 of 200 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. listing photoNew10Active

    $6,700,000

    6 bd · 6 ba · 6,390 sqft

    Address withheld · Longboat Key, FL

    Reid Murphy · DEVELOPERS REALTY LBK, INC

  2. 560 Harbor Point Rd — photo70Active

    $9,500,000

    4 bd · 5 ba · 5,245 sqft

    560 Harbor Point Rd, Longboat Key, FL

    Meghan Leiter · MICHAEL SAUNDERS & COMPANY

  3. 3010 Grand Bay Blvd #416 — photo55Active

    $2,495,000

    3 bd · 4 ba · 2,925 sqft

    3010 Grand Bay Blvd #416, Longboat Key, FL

    Roger Pettingell · COLDWELL BANKER REALTY

  4. 415 L Ambiance Dr #Ph-F — photo65Active

    $12,995,000

    4 bd · 4 ba · 4,912 sqft

    415 L Ambiance Dr #Ph-F, Longboat Key, FL

    Roger Pettingell · COLDWELL BANKER REALTY

  5. 4800 Gulf Of Mexico Dr #205 — photo71Active

    $759,000

    2 bd · 2 ba · 1,325 sqft

    4800 Gulf Of Mexico Dr #205, Longboat Key, FL

    Debby McCaig · COLDWELL BANKER REALTY

  6. 677 Lands End Dr — photo39Active

    $2,500,000

    3 bd · 3 ba · 4,182 sqft

    677 Lands End Dr, Longboat Key, FL

    Jennifer Linehan · MICHAEL SAUNDERS & COMPANY

  7. 5655 Gulf Of Mexico Dr #a107 — photo29Active

    $775,000

    2 bd · 2 ba · 1,274 sqft

    5655 Gulf Of Mexico Dr #a107, Longboat Key, FL

    Judy Mitchell · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  8. 6610 Gulf Of Mexico Dr — photo100Active

    $22,000,000

    4 bd · 7 ba · 6,891 sqft

    6610 Gulf Of Mexico Dr, Longboat Key, FL

    Reid Murphy · DEVELOPERS REALTY LBK, INC

  9. 660 Penfield St — photo53Active

    $2,693,000

    3 bd · 2 ba · 2,461 sqft

    660 Penfield St, Longboat Key, FL

    Cathy Meldahl, PA · MICHAEL SAUNDERS & COMPANY

  10. 615 Dream Island Pl #212 — photo44Active

    $1,089,000

    2 bd · 2 ba · 1,293 sqft

    615 Dream Island Pl #212, Longboat Key, FL

    Judy Mitchell · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  11. 775 Longboat Club Rd #304 — photo32Active

    $1,295,000

    2 bd · 2 ba · 1,602 sqft

    775 Longboat Club Rd #304, Longboat Key, FL

    Larry Brzostek · RE/MAX ALLIANCE GROUP

  12. 1920 Harbourside Dr #1003 — photo90Active

    $624,900

    2 bd · 3 ba · 1,690 sqft

    1920 Harbourside Dr #1003, Longboat Key, FL

    Keith Curcio · COLDWELL BANKER REALTY

  13. 1916 Harbourside Dr #804 — photo86Active

    $1,599,000

    4 bd · 3 ba · 2,846 sqft

    1916 Harbourside Dr #804, Longboat Key, FL

    Kathy Callahan · MICHAEL SAUNDERS & COMPANY

  14. 2055 Gulf Of Mexico Dr #G2-213 — photo66Active

    $595,000

    1 bd · 2 ba · 1,094 sqft

    2055 Gulf Of Mexico Dr #G2-213, Longboat Key, FL

    Derek Eisenberg · CONTINENTAL REAL ESTATE GROUP

  15. 2550 Harbourside Dr #334 — photo64Active

    $1,400,000

    3 bd · 3 ba · 3,083 sqft

    2550 Harbourside Dr #334, Longboat Key, FL

    Wendy Ross, PA · COLDWELL BANKER REALTY

  16. 3488 Mistletoe Ln — photo81Active

    $3,275,000

    3 bd · 3 ba · 3,341 sqft

    3488 Mistletoe Ln, Longboat Key, FL

    Kim Ogilvie · MICHAEL SAUNDERS & COMPANY

  17. 6529 Gulfside Rd — photo35Active

    $15,000,000

    5 bd · 5 ba · 6,500 sqft

    6529 Gulfside Rd, Longboat Key, FL

    Reid Murphy · DEVELOPERS REALTY LBK, INC

  18. 100 Sands Point Rd #219 — photo50Active

    $1,325,000

    2 bd · 2 ba · 1,492 sqft

    100 Sands Point Rd #219, Longboat Key, FL

    Diane Smith · KELLER WILLIAMS ON THE WATER S

  19. 3060 Grand Bay Blvd #162 — photo50Active

    $1,595,000

    3 bd · 4 ba · 2,250 sqft

    3060 Grand Bay Blvd #162, Longboat Key, FL

    Bruce Myer · COLDWELL BANKER REALTY

  20. 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

  21. 3710 Gulf Of Mexico Dr #a3 — photo58Active

    $525,000

    2 bd · 2 ba · 720 sqft

    3710 Gulf Of Mexico Dr #a3, Longboat Key, FL

    Sharon Austin · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  22. 2550 Harbourside Dr #333 — photoPrice Reduced44Active

    $1,395,000

    3 bd · 3 ba · 3,067 sqft

    2550 Harbourside Dr #333, Longboat Key, FL

    Lee Mirman · INVESTMENTS IN SARASOTA

  23. 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

  24. 340 Gulf Of Mexico Dr #136 — photo65Active

    $2,995,000

    3 bd · 4 ba · 2,880 sqft

    340 Gulf Of Mexico Dr #136, Longboat Key, FL

    Roger Pettingell · COLDWELL BANKER REALTY

12…9

About Waterfront Homes in Longboat Key, FL

Waterfront Homes in Longboat Key, FL: 200 active listings as of October 19, 2026, 00:17 UTC.

Property types among these 200 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
Condominium11155.5%
Single Family Residence4422.0%
Boat Slip3316.5%

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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

    Longboat Key 12-month median sale price trend

    Selling at 93.8% of asking price

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

    Homes that sold · County records, as of Sep 23, 2026

    Median sale price
    $887,500$655,000–$962,750 typical range
    Price per sq. ft.
    $516
    Sales
    10
    Paid in cash
    80.0%

    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

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    40.1%

    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.