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Luxury Homes in Big Pine Key, FL
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Luxury Homes in Big Pine Key, FL

Luxury Homes in Big Pine Key, FL

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16 Listings
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Luxury Homes in Big Pine Key, FL

16 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 545 Ixora Drive — photo30Active

    $1,300,000

    3 bd · 2 ba · 1,368 sqft

    545 Ixora Drive, Big Pine Key, FL

    Christina Noel Davis · Coldwell Banker Schmitt RE Co.

  2. 29466 Enterprise Avenue — photo55Active

    $1,150,000

    3 bd · 2 ba · 1,447 sqft

    29466 Enterprise Avenue, Big Pine Key, FL

    Patti Nickless · Coldwell Banker Schmitt Lower Keys (KW)

  3. 29038 Violet Drive — photo55Active

    $1,100,000

    3 bd · 2 ba · 1,064 sqft

    29038 Violet Drive, Big Pine Key, FL

    Christina Noel Davis · Coldwell Banker Schmitt RE Co.

  4. 1632 Bogie Drive — photo57Active

    $1,199,000

    3 bd · 4 ba · 1,508 sqft

    1632 Bogie Drive, Big Pine Key, FL

    Patti Nickless · Coldwell Banker Schmitt Lower Keys (KW)

  5. 1518 Sunrise Drive — photo56Active

    $1,400,000

    3 bd · 2 ba · 1,540 sqft

    1518 Sunrise Drive, Big Pine Key, FL

    Paul L. Rogers · Coldwell Banker Schmitt RE Co.

  6. 1657 Watson Boulevard — photo45Active

    $1,199,000

    3 bd · 2 ba · 1,330 sqft

    1657 Watson Boulevard, Big Pine Key, FL

    Christina Noel Davis · Coldwell Banker Schmitt RE Co.

  7. 31536 Avenue F — photo56Active

    $1,450,000

    3 bd · 2 ba · 1,026 sqft

    31536 Avenue F, Big Pine Key, FL

    Madeleine Young · Island Welcome Real Estate LLC

  8. 30525 Winifred Street — photoPrice Reduced32Active

    $1,150,000

    3 bd · 3 ba · 1,774 sqft

    30525 Winifred Street, Big Pine Key, FL

    Joyce Craul · Expert Realty LLC (HQ)

  9. 3746 Park Avenue — photoPrice Reduced68Active

    $1,199,900

    2 bd · 2 ba · 1,312 sqft

    3746 Park Avenue, Big Pine Key, FL

    Cabot Brown · Compass Florida - Miami Beach

  10. 29562 Saratoga Avenue — photoPrice Reduced71Active

    $1,435,000

    4 bd · 2 ba · 2,310 sqft

    29562 Saratoga Avenue, Big Pine Key, FL

    Ryan Gernaat · Coldwell Banker Schmitt Lower Keys (KW)

  11. 3742 Seagrape Street — photoPrice Reduced99Active

    $4,650,000

    3 bd · 3 ba · 4,687 sqft

    3742 Seagrape Street, Big Pine Key, FL

    Ally Kelley · Ocean Sotheby's International

  12. 29581 Richard Road — photoPrice Reduced78Active

    $2,499,000

    3 bd · 4 ba · 1,700 sqft

    29581 Richard Road, Big Pine Key, FL

    Diane Corliss · Coldwell Banker Schmitt Real Estate Co

  13. 30468 Oleander Boulevard — photoPrice Reduced63Active

    $2,150,000

    3 bd · 3 ba · 2,486 sqft

    30468 Oleander Boulevard, Big Pine Key, FL

    Patti Nickless · Coldwell Banker Schmitt Lower Keys (KW)

  14. 1607 Sunrise Drive — photo43Active

    $1,850,000

    2 bd · 2 ba · 1,980 sqft

    1607 Sunrise Drive, Big Pine Key, FL

    Lisa H Ferringo · Coldwell Banker Schmitt Real Estate Co

  15. 31473 Warner Road — photoPrice Reduced49Active

    $2,450,000

    3 bd · 4 ba · 2,087 sqft

    31473 Warner Road, Big Pine Key, FL

    Michele Adams · Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  16. 30995 Watson Boulevard — photo53Active

    $2,300,000

    4 bd · 3 ba · 2,400 sqft

    30995 Watson Boulevard, Big Pine Key, FL

    Banks G Prevatt · Coldwell Banker Schmitt RE Co.

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Listing data & MLS disclosures

Key West Association of REALTORS
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of The Key West Association of REALTORS®. MLS Real Estate listings held by brokerage firms other than this broker are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker's logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. Information deemed reliable but not guaranteed. Copyright ©2026 The Key West Association of REALTORS®. All Rights Reserved.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Big Pine Key, FL community profile

    Area
    79.9 sq. mi.

    Source: HJN community data

    Big Pine Key housing market

    September 2026 · This period is still settling

    Selling at 97.1% of asking price

    Buyers here are paying below asking. MLS · 11 sales · as of Sep 28, 2026

    Homes on the market · MLS, as of Sep 27, 2026–Sep 28, 2026

    Median list price
    $899,000
    Homes for sale
    85
    Median days on market
    96 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
    1,393 sq. ft.