Summerland Key, FL Homes

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  /40

  $1,350,000 Sold May 15, 2025

  31254 Hollerich Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,315 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Below List Price
  • $1,027/SF
  • 6 Days On Market

  Current Estimated Value $1,203,276

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  31254 Hollerich Dr, Big Pine Key, FL 33043
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  /37

  Est $1,714,767 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  1008 Buttonwood Dr E, Summerland Key, FL 33042
• 

  

  

  /9

  $3,500,000

  • Land

  19657 Seminole St, Sugarloaf Key, FL 33042

  Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

  Derek Epperly Engel & Volkers Key West

  19657 Seminole St, Sugarloaf Key, FL 33042
• 

  

  

  /23

  $710,000 Sold Aug 20, 2025

  19603 Seminole St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $598/SF
  • 5 Days On Market

  Current Estimated Value $710,827

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  19603 Seminole St, Summerland Key, FL 33042
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  /43

  Est $2,869,904 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,160 Sq Ft

  1619 Long Beach Dr, Big Pine Key, FL 33043

  1619 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /33

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,278 Sq Ft

  31525 Avenue A, Big Pine Key, FL 33043

  $525K Opportunity with so much potential. Privacy fence with 2 big double gates with access from both streets and no neighbor across the street. Unique CBS 3bd/2bth ground level home. Central AC, Tile Floors, Double corner lot. 100 X 100. Lots of parking, if you have work vehicles or an RV has rv elect, hook. Room for pool and entertaining. Patio deck area. Close to community park, public boat

  Rose Dell Keller Williams Key West Compass Realty

  31525 Avenue A, Big Pine Key, FL 33043
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  /30

  $628,000 Sold Sep 05, 2025

  31256 Avenue H, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $549/SF
  • 106 Days On Market

  Current Estimated Value $622,645

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  31256 Avenue H, Big Pine Key, FL 33043
• 

  /2

  Est $1,014,873 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  29552 Independence Ave, Big Pine Key, FL 33043

  29552 Independence Ave, Big Pine Key, FL 33043
• 

  

  /60

  $2,700,000

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft

  556 Caribbean Dr E, Summerland Key, FL 33042

  The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
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  /20

  $260,000 Sold Mar 21, 2025

  31048 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $442/SF
  • 151 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  31048 Avenue J, Big Pine Key, FL 33043
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  /40

  Est $661,357 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  29366 Lucrecia St, Big Pine Key, FL 33043

  29366 Lucrecia St, Big Pine Key, FL 33043
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  /24

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  853 Indies Rd, Summerland Key, FL 33042

  Move right into this well-maintained 3-bedroom, 2-bath canal front home, built in 2006 and cared for with pride. The bright, open layout features a split floor plan that offers comfortable space for everyday living and entertaining.The primary bedroom includes an en-suite bath and a versatile bonus room -- ideal for a home office, nursery, or cozy retreat. Step outside to enjoy peaceful canal

  Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  853 Indies Rd, Summerland Key, FL 33042
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  /34

  $695,000 Sold Aug 05, 2025

  1555 Watson Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,233 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Below List Price
  • $564/SF
  • 5 Days On Market

  Current Estimated Value $686,503

  Last Listing Agent Terrance Sullivan Ocean Sotheby's International Realty

  1555 Watson Blvd, Big Pine Key, FL 33043
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  /42

  Est $1,256,679 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  31040 Atlantis Dr, Big Pine Key, FL 33043

  31040 Atlantis Dr, Big Pine Key, FL 33043
• 

  

  /53

  $1,799,000

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  1481 Sugarloaf Blvd, Summerland Key, FL 33042

  Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy.Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
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  /41

  $1,350,000 Sold Aug 18, 2025

  20735 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 16 Days On Market

  Current Estimated Value $1,349,457

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20735 5th Ave W, Summerland Key, FL 33042
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  /46

  Est $2,774,656 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,371 Sq Ft

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  661 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /25

  $745,000

  • Land

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

  Barbara Eads Barbara Eads Realty

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042
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  /42

  $930,000 Sold Nov 19, 2025

  29012 Bigonia Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1993

  Last Sold Summary

  • 15% Below List Price
  • $881/SF
  • 92 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  29012 Bigonia Dr, Big Pine Key, FL 33043
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  /2

  Est $1,087,205 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft

  467 Almond Ln, Big Pine Key, FL 33043

  467 Almond Ln, Big Pine Key, FL 33043
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  /49

  $329,000 Open House 1/03

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
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  /36

  $1,215,000 Sold Apr 09, 2025

  17246 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $844/SF
  • 23 Days On Market

  Current Estimated Value $1,207,590

  Last Listing Agent Stephen Hachey

  17246 Jamaica Ln, Summerland Key, FL 33042
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  /46

  Est $1,281,511 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  137 Caribbean Dr E, Summerland Key, FL 33042

  137 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /43

  $925,000

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft

  3686 Gulfstream St, Big Pine Key, FL 33043

  Key Deer, Quick Access to Pine Channel, Canal Views & Updated Island Living: Your Florida Keys Dream Awaits!Imagine: breathtaking sunsets painting the sky, the gentle presence of Key Deer just outside your fence, and the tranquility of canal-front living in the heart of the National Key Deer Refuge. This charming 2-bedroom, 2-bathroom home offers a rare opportunity to live in harmony with nature

  Gidget Jackson Nicklaus Vance

  3686 Gulfstream St, Big Pine Key, FL 33043
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  /27

  $450,000 Sold Jan 28, 2025

  1537 Pandorea Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1973

  Last Sold Summary

  • $365/SF
  • 3 Days On Market

  Current Estimated Value $627,665

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  1537 Pandorea Ln, Big Pine Key, FL 33043
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  /36

  Est $2,407,626 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,224 Sq Ft

  333 Indies Rd, Ramrod Key, FL 33042

  333 Indies Rd, Ramrod Key, FL 33042
• 

  

  /15

  $644,500

  • Land

  132 Sugarloaf Dr, Summerland Key, FL 33042

  Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

  Heather Mason Coastal Collection Real Estate Inc.

  132 Sugarloaf Dr, Summerland Key, FL 33042
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  /47

  $945,000 Sold Oct 03, 2025

  29487 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $751/SF
  • 99 Days On Market

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  29487 Ranger Ave, Big Pine Key, FL 33043
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  /26

  Est $782,831 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,794 Sq Ft

  30946 Edward Rd, Big Pine Key, FL 33043

  30946 Edward Rd, Big Pine Key, FL 33043
• 

  

  /18

  $600,000

  • Land

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

  The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
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  /49

  $750,000 Sold Jul 24, 2025

  25121 Center St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $781/SF
  • 72 Days On Market

  Current Estimated Value $766,572

  Last Listing Agent Gregory Sullivan BYOWNER.COM

  25121 Center St, Summerland Key, FL 33042
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  /2

  Est $1,575,854 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042
• 

  

  /100

  $9,950,000

  • 6 Beds
  • 5 Baths
  • 5,208 Sq Ft

  16750 Old State Road 4a, Summerland Key, FL 33042

  Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

  Lisa Swanson The Agency Florida Keys

  16750 Old State Road 4a, Summerland Key, FL 33042
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  /5

  $150,000 Sold Jan 06, 2025

  29859 Overseas Hwy Unit A-2, Big Pine Key, FL 33043

  • Land

  Last Sold Summary

  • 14% Below List Price
  • 392 Days On Market

  Current Estimated Value $164,207

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  29859 Overseas Hwy Unit A-2, Big Pine Key, FL 33043
• 

  /2

  Est $883,588 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,326 Sq Ft

  22842 Buccaneer Ln, Summerland Key, FL 33042

  22842 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /16

  $775,000

  • Land

  28597 Peg Leg Rd, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3809 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom four-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house. Open Water View. House Permit SF-DUP-2025-0111, 41.5

  Barbara Eads Barbara Eads Realty

  28597 Peg Leg Rd, Little Torch Key, FL 33042
• 

  

  /46

  $540,000 Sold May 19, 2025

  31130 Avenue I, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1991

  Last Sold Summary

  • 14% Below List Price
  • $562/SF
  • 36 Days On Market

  Current Estimated Value $1,907,632

  Last Listing Agent Michael Sielicki Jr Real Broker, LLC

  31130 Avenue I, Big Pine Key, FL 33043
• 

  

  /24

  Est $953,778 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,482 Sq Ft

  19453 Seminole St, Sugarloaf Key, FL 33042

  19453 Seminole St, Sugarloaf Key, FL 33042
• 

  

  /19

  $475,000

  • Land

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

  Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
• 

  

  /21

  $642,500 Sold Feb 10, 2025

  19518 Caloosa St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Built 1992

  Last Sold Summary

  • 8% Below List Price
  • $562/SF
  • 159 Days On Market

  Current Estimated Value $661,881

  Last Listing Agent Wendy Holifield Berkshire Hathaway HomeServices Knight & Gardner Realty

  19518 Caloosa St, Summerland Key, FL 33042

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