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

Homes Under $2.75M in Longboat Key, FL

Homes Under $2.75M in Longboat Key, FL

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24 of 227 Listings
Map

Homes Under $2.75M in Longboat Key, FL

24 of 227 Listings

  1. 2110 Harbourside Dr #523 — photoNew62

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$628,000

3 bd · 2 ba · 2,031 sqft

2110 Harbourside Dr #523, Longboat Key, FL

Judy Kepecz-Hays · COLDWELL BANKER REALTY

  • 5320 Gulf Of Mexico Dr #101 — photo39Active

    $999,000

    3 bd · 2 ba · 1,323 sqft

    5320 Gulf Of Mexico Dr #101, Longboat Key, FL

    Roger Pettingell · COLDWELL BANKER REALTY

  • 3060 Grand Bay Blvd #124 — photo56Active

    $1,699,000

    2 bd · 3 ba · 2,369 sqft

    3060 Grand Bay Blvd #124, Longboat Key, FL

    Steve Walter · MICHAEL SAUNDERS & COMPANY

  • 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

  • 693 Spanish Dr N #24 — photoOpen house Sun, Oct 25 · 1:00 PM82Active

    $423,750

    2 bd · 2 ba · 1,429 sqft

    693 Spanish Dr N #24, Longboat Key, FL

    Andrew Vac · RE/MAX ALLIANCE GROUP

  • 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

  • 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

  • 917 Spanish Dr N — photo75Active

    $675,000

    2 bd · 2 ba · 1,103 sqft

    917 Spanish Dr N, Longboat Key, FL

    Kimberly Freiwald · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 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

  • 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

  • 615 Dream Island Pl #212 — photo46Active

    $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

  • 2012 Harbourside Dr #2102 — photo34Active

    $795,000

    2 bd · 3 ba · 1,590 sqft

    2012 Harbourside Dr #2102, Longboat Key, FL

    Alex Larchenko · KELLER WILLIAMS ON THE WATER S

  • 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

  • 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

  • 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

  • 605 Sutton Pl #101 — photo45Active

    $595,000

    2 bd · 2 ba · 1,148 sqft

    605 Sutton Pl #101, Longboat Key, FL

    Gloria Bracciano · DOUGLAS ELLIMAN

  • 2141 Harbourside Dr #1203 — photoOpen house Sun, Oct 25 · 1:00 PM44Active

    $1,450,000

    3 bd · 3 ba · 2,204 sqft

    2141 Harbourside Dr #1203, Longboat Key, FL

    Judy Mitchell · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 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

  • 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

  • 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

  • 2550 Harbourside Dr #334 — photoPrice Reduced64Active

    $1,250,000

    3 bd · 3 ba · 3,083 sqft

    2550 Harbourside Dr #334, Longboat Key, FL

    Wendy Ross, PA · COLDWELL BANKER REALTY

  • 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

  • 6960 Poinsetta Avenue — photoPrice Reduced20Active

    $1,149,000

    2 bd · 2 ba · 1,461 sqft

    6960 Poinsetta Avenue, Longboat Key, FL

    Emma McLeod · Emerald Seascapes Properties LLC

  • 12…10

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Central Panhandle Association of REALTORS
    IDX information is provided exclusively for consumers’ personal, non-commercial use, that it 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 the MLS.
    Listing information ©2026 Central Panhandle Association of Realtors®. All Rights Reserved. Last Updated: 2026-10-19 06:42:49 UTC
    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

    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.