8,628

Summerland Key, FL Homes

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  • 28595 Jolly Roger Dr, Summerland Key, FL 33042
    28595 Jolly Roger Dr, Summerland Key, FL 33042
    28595 Jolly Roger Dr, Summerland Key, FL 33042
    /56

    $2,599,000 Sold Jun 18, 2025

    28595 Jolly Roger Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,153 Sq Ft
    • Built 1975

    Last Sold Summary

    • $2,254/SF
    • 11 Days On Market

    Current Estimated Value $2,612,934

    Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

    28595 Jolly Roger Dr, Summerland Key, FL 33042
    • 27468 Haiti Ln, Summerland Key, FL 33042
      27468 Haiti Ln, Summerland Key, FL 33042
      27468 Haiti Ln, Summerland Key, FL 33042
      /41

      Est $850,275 Not Listed For Sale

      27468 Haiti Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1979
      27468 Haiti Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Above List Price
      • $601/SF
      • 6 Days On Market

      Last Sold Price $830,000

      Last Listing Agent Emily Lombard Ocean Sotheby's International Realty

  • 831 W Indies Dr, Summerland Key, FL 33042
    831 W Indies Dr, Summerland Key, FL 33042
    831 W Indies Dr, Summerland Key, FL 33042
    /37

    $1,485,000

    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft

    831 W Indies Dr, Summerland Key, FL 33042

    Experience waterfront living in the highly desirable Breezeswept Beach Estates. This beautifully updated 2 bedroom, 2 bathroom home captures sweeping open water views and unforgettable sunrises right from your living room.Inside, the home features an airy open layout highlighted by vaulted wood beam ceilings and expansive impact windows that frame the water from nearly every angle. Both bedrooms

    Miranda Dender Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    831 W Indies Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
    /30

    $710,000 Sold Dec 01, 2025

    701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 2002

    Last Sold Summary

    • 25% Below List Price
    • $822/SF
    • 328 Days On Market

    Last Listing Agent Katrina Vanek Bluescape Real Estate

    701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
    • 433 Indies Rd, Summerland Key, FL 33042
      433 Indies Rd, Summerland Key, FL 33042
      /2

      Est $763,237 Not Listed For Sale

      433 Indies Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1991
      433 Indies Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Below List Price
      • $868/SF

      Last Sold Price $750,000

      Last Listing Agent Rick Servais Coldwell Banker Schmitt Real Estate Co.

  • 3836 No Name Rd, Big Pine Key, FL 33043
    3836 No Name Rd, Big Pine Key, FL 33043
    3836 No Name Rd, Big Pine Key, FL 33043
    /73

    $1,099,000

    • 5 Beds
    • 2 Baths
    • 1,888 Sq Ft

    3836 No Name Rd, Big Pine Key, FL 33043

    Introducing No Name Retreat - Rare waterfront opportunity with exceptional development potential featuring 140 feet of direct water frontage and expansive 14,420 sq ft lot. The property currently includes a full duplex plus an additional buildable vacant lot, offering endless possibilities for investors, builders, or someone looking for extra room next door. Live on the water while generating

    Saara Staten Engel & Volkers Marathon

    3836 No Name Rd, Big Pine Key, FL 33043
  • 27373 Anguila Ln, Summerland Key, FL 33042
    27373 Anguila Ln, Summerland Key, FL 33042
    27373 Anguila Ln, Summerland Key, FL 33042
    /34

    $735,000 Sold May 16, 2025

    27373 Anguila Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,077 Sq Ft
    • Built 2006

    Last Sold Summary

    • 11% Below List Price
    • $682/SF
    • 117 Days On Market

    Current Estimated Value $753,713

    Last Listing Agent Tracy Shields KeyIsle Realty

    27373 Anguila Ln, Summerland Key, FL 33042
    • 23058 Sailfish Ln, Summerland Key, FL 33042
      23058 Sailfish Ln, Summerland Key, FL 33042
      23058 Sailfish Ln, Summerland Key, FL 33042
      /45

      Est $1,115,203 Not Listed For Sale

      23058 Sailfish Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,280 Sq Ft
      • Built 1980
      23058 Sailfish Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $918/SF
      • 145 Days On Market

      Last Sold Price $1,175,000

      Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  • Lot 7 Hibiscus St, Big Pine Key, FL 33043
    Lot 7 Hibiscus St, Big Pine Key, FL 33043
    /2

    $95,000

    • Land

    Lot 7 Hibiscus St, Big Pine Key, FL 33043

    One of the cheapest waterfront lots in the Keys with great boating access directly from your property. Located in the beautiful nature preserve area of Big Pine Key, where nature and water actives are paramount. This lot is only 10 houses away from the open water, just minutes to our famous blue waters, fishing, diving and water actives that the Florida Keys are famous for. Many possibilities

    Pamela Stangler Expert Realty LLC

    Lot 7 Hibiscus St, Big Pine Key, FL 33043
  • 218 Spanish Main Dr, Summerland Key, FL 33042
    218 Spanish Main Dr, Summerland Key, FL 33042
    218 Spanish Main Dr, Summerland Key, FL 33042
    /38

    $1,170,000 Sold Mar 02, 2026

    218 Spanish Main Dr, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1994

    Last Sold Summary

    • 2% Below List Price
    • $580/SF
    • 11 Days On Market

    Current Estimated Value $1,184,579

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    218 Spanish Main Dr, Summerland Key, FL 33042
    • 23076 Tarpon Ln, Summerland Key, FL 33042
      23076 Tarpon Ln, Summerland Key, FL 33042
      23076 Tarpon Ln, Summerland Key, FL 33042
      /16

      Est $1,880,803 Not Listed For Sale

      23076 Tarpon Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,122 Sq Ft
      • Built 1975
      23076 Tarpon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 10% Above List Price
      • $1,872/SF
      • 82 Days On Market

      Last Sold Price $2,100,000

      Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  • 0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
    /3

    $64,750

    • Land

    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

    ROGO Lot. Letter on hand from Monroe County granting 2 points

    Jenna Stauffer Ocean Sotheby's International Realty

    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
  • 27436 Tobago Ln, Summerland Key, FL 33042
    27436 Tobago Ln, Summerland Key, FL 33042
    27436 Tobago Ln, Summerland Key, FL 33042
    /92

    $1,050,000 Sold May 14, 2025

    27436 Tobago Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2020

    Last Sold Summary

    • 19% Below List Price
    • $852/SF
    • 129 Days On Market

    Current Estimated Value $1,043,515

    Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

    27436 Tobago Ln, Summerland Key, FL 33042
    • 23092 Snapper Ln, Summerland Key, FL 33042
      23092 Snapper Ln, Summerland Key, FL 33042
      23092 Snapper Ln, Summerland Key, FL 33042
      /27

      Est $1,586,581 Not Listed For Sale

      23092 Snapper Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,645 Sq Ft
      • Built 1985
      23092 Snapper Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $957/SF
      • 7 Days On Market

      Last Sold Price $1,575,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • 28168 Julia Ave, Little Torch Key, FL 33042
    28168 Julia Ave, Little Torch Key, FL 33042
    /2

    $299,000

    • Land

    28168 Julia Ave, Little Torch Key, FL 33042

    ROGO EXEMPT LOT! Build Now, No Waiting, Water Meter On Site, 6000 SF, Boat Ramp Within Walking Distance, Live The Dream. Single family home next door going on the market soon, buy both!

    Doug Addeo Regional Trust Corporation

    28168 Julia Ave, Little Torch Key, FL 33042
  • 29185 Bougainvillea Ln, Big Pine Key, FL 33043
    29185 Bougainvillea Ln, Big Pine Key, FL 33043
    29185 Bougainvillea Ln, Big Pine Key, FL 33043
    /36

    $1,018,000 Sold Sep 26, 2025

    29185 Bougainvillea Ln, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1981

    Last Sold Summary

    • 7% Below List Price
    • $884/SF
    • 85 Days On Market

    Current Estimated Value $1,033,897

    Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

    29185 Bougainvillea Ln, Big Pine Key, FL 33043
    • 1172 Coates Ln, Summerland Key, FL 33042
      1172 Coates Ln, Summerland Key, FL 33042
      1172 Coates Ln, Summerland Key, FL 33042
      /42

      Est $1,269,952 Not Listed For Sale

      1172 Coates Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2.5 Baths
      • 1,794 Sq Ft
      • Built 2002
      1172 Coates Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $747/SF
      • 138 Days On Market

      Last Sold Price $1,340,000

      Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  • 22920 Privateer Dr, Summerland Key, FL 33042
    22920 Privateer Dr, Summerland Key, FL 33042
    22920 Privateer Dr, Summerland Key, FL 33042
    /41

    $790,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    22920 Privateer Dr, Summerland Key, FL 33042

    Unlock Instant Equity on this Waterfront Gem waiting for restoration! Rare opportunity to own a waterfront escape at an unbeatable price point. This diamond in the rough is priced strictly for its condition, allowing you to build custom equity from day one. With a solid foundation and a backyard leading straight to the water's edge, this is the ultimate project for a savvy investor or visionary

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, Summerland Key, FL 33042
  • 22933 Buccaneer Ln, Summerland Key, FL 33042
    22933 Buccaneer Ln, Summerland Key, FL 33042
    22933 Buccaneer Ln, Summerland Key, FL 33042
    /70

    $721,000 Sold Jun 03, 2025

    22933 Buccaneer Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • Built 1995

    Last Sold Summary

    • 18% Below List Price
    • $663/SF
    • 74 Days On Market

    Current Estimated Value $766,007

    Last Listing Agent Bobby Baker Brightwild Real Estate

    22933 Buccaneer Ln, Summerland Key, FL 33042
    • 22943 Dirk Ln, Summerland Key, FL 33042
      22943 Dirk Ln, Summerland Key, FL 33042
      /2

      Est $1,198,774 Not Listed For Sale

      22943 Dirk Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,598 Sq Ft
      • Built 1998
      22943 Dirk Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 6% Below List Price
      • $798/SF

      Last Sold Price $1,275,000

      Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

Showing Results 681 - 720, Page 18 of 18

Florida Monroe County Summerland Key

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