Summerland Key, FL Homes

• 

  

  

  /50

  $1,595,000

  $70K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,995 Sq Ft

  643 Indies Rd, Summerland Key, FL 33042

  Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for

  Greg MacLaren Internet Realty of the Florida Keys

  643 Indies Rd, Summerland Key, FL 33042
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  /44

  $853,000

  Sold Aug 12, 2025

  873 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $789/SF
  • 123 Days On Market

  Current Estimated Value $900,084

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  873 Indies Rd, Summerland Key, FL 33042
• 

  

  

  /14

  Est $434,000

  Not Listed For Sale

  29167 Cactus Ln, Big Pine Key, FL 33043

  29167 Cactus Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 121 Days On Market
• 

  

  

  /68

  $1,299,900

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft

  3746 Park Ave, Big Pine Key, FL 33043

  Welcome to your private paradise in the Lower Keys! This beautifully updated 2-bedroom, 2-bathroom two-story home offers the ultimate island escape with unmatched privacy -- no direct neighbors on any side, just peaceful surroundings, tropical landscaping, and the charm of the native Key Deer. Designed for true Florida Keys living, the outdoor space is a showstopper. Enjoy a brand-new heated

  Cabot Brown Compass Florida - Miami Beach

  3746 Park Ave, Big Pine Key, FL 33043
• 

  

  

  /31

  $925,000

  Sold Jan 30, 2026

  29178 Guava Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Below List Price
  • $602/SF
  • 5 Days On Market

  Current Estimated Value $962,197

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  29178 Guava Ln, Big Pine Key, FL 33043
• 

  /2

  Est $462,500

  Not Listed For Sale

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  • Studio

  Lot 2 Egret Ln, Big Pine Key, FL 33043
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  /44

  $1,065,000

  Open Sun 1PM - 3PM $35K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  29555 Enterprise Ave, Big Pine Key, FL 33043

  Accessibility elevator! Welcome to your Lower Keys retreat where comfort, and coastal living come together beautifully along with the convenience of an interior elevator. Situated on the desirable boating canal system of Pine Channel Estates, this 3 bedroom, 2 bath home is designed for those who appreciate the water based lifestyle. Inside, soaring vaulted ceilings create an open and airy

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  29555 Enterprise Ave, Big Pine Key, FL 33043
• 

  

  /18

  $480,000

  Sold Apr 01, 2026

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

  • Land
  • 2,307 Sq Ft
  • $9,059,272 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 126 Days On Market

  Current Estimated Value $521,003

  Last Listing Agent The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
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  /39

  $1,600,000

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  29667 Forrestal Ave, Big Pine Key, FL 33043

  LOOKING FOR A KEYS HOME WITH SOLID CONSTRUCTION? Check out this updated 3BD/2BA CBS home in desirable Pine Channel Estates, Big Pine Key -- just 30 miles from Key West and offering low-maintenance living at its finest. Step through the door into an open floor plan filled with natural light. Impact-resistant sliding glass doors blend indoor and outdoor living, while 32''x32'' porcelain tile runs

  Monika Rydzak eXp Realty LLC KW Branch

  29667 Forrestal Ave, Big Pine Key, FL 33043
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  /34

  $629,500

  Sold Sep 30, 2025

  31463 Avenue A, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $484/SF
  • 24 Days On Market

  Current Estimated Value $639,183

  Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt RE Co.

  31463 Avenue A, Big Pine Key, FL 33043
• 

  /2

  Est $194,932

  Not Listed For Sale

  281 Pelican Ln, Big Pine Key, FL 33043

  • Studio

  281 Pelican Ln, Big Pine Key, FL 33043
• 

  

  /30

  $649,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  29123 Rose Dr, Big Pine Key, FL 33043

  Welcome to your slice of paradise in the highly sought-after neighborhood of Eden Pines on Big Pine Key! This solid concrete construction home offers 2 bedrooms, 2 bathrooms, and 1,036 sq. ft. of comfortable living space, perfectly positioned on the water with a peaceful canal view. Enjoy the true Florida Keys lifestyle from your charming back porch that is ideal for morning coffee, evening

  Melissa Graham Bluescape Real Estate

  29123 Rose Dr, Big Pine Key, FL 33043
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  /34

  $580,000

  Sold Sep 15, 2025

  30868 Malaga Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $537/SF
  • 137 Days On Market

  Current Estimated Value $653,808

  Last Listing Agent Loren Rea Truman & Co. (KW)

  30868 Malaga Ln, Big Pine Key, FL 33043
• 

  

  /46

  Est $1,781,221

  Not Listed For Sale

  271 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 3.5 Baths
  • 2,358 Sq Ft
  • Built 2023

  271 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 342 Days On Market
• 

  

  /45

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  559 Powell Ave, Little Torch Key, FL 33042

  Built in 2019 on a 7,412 sq ft Lot! This modern home features three (3) bedrooms and two (2) bathrooms, offering everything you need. It's low maintenance yet packed with amenities. Enjoy a pool, a double lot, an extra-long dock, affordable insurance, a quiet, peaceful neighborhood, and excellent fishing opportunities. Step inside to an open-concept design that boasts a bright & fantastic living

  Bobby Coe RE/MAX Keys Connection (KW)

  559 Powell Ave, Little Torch Key, FL 33042
• 

  

  /40

  $640,000

  Sold Sep 15, 2025

  3806 Dyer Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $702/SF
  • 54 Days On Market

  Current Estimated Value $672,992

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

  3806 Dyer Rd, Big Pine Key, FL 33043
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  /35

  Not Listed For Sale

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 849 Sq Ft
  • Built 1992

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

  Last Sold Summary

  • 191 Days On Market
• 

  

  /20

  $6,500

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths

  1540 Lantana Ln, Big Pine Key, FL 33043

  FISHERMANS DREAM HOUSE! BRING YOUR BOATS TO THIS AMAZING 3/2 HOUSE SECLUDED ON A CORNER LOT WITH 190FT OF SEAWALL. BOAT RAMP MINUTES AWAY. ICE MAKER AT THE OUTSIDE BAR.ENJOY THE POOL, OPEN DECKS, COCKTAILS AT THE OUTSIDE BAR, AND THE ADORABLE KEY DEER ROAMING THE NEIGHBORHOOD. SLEEPS 8. AVAILABLE FOR MONTHLY RENTALS TOO. DISCOUNTED PRICES FOR MULTIPLE MONTH RENTALS AND OFF SEASON. 6500 through

  Andrea Lennon Vylla Home

  1540 Lantana Ln, Big Pine Key, FL 33043
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  /36

  $1,100,000

  Sold Jun 12, 2026

  22874 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,518 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $725/SF
  • 7 Days On Market

  Current Estimated Value $1,328,924

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  22874 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /58

  Est $1,808,482

  Not Listed For Sale

  1106 Thatch Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3.5 Baths
  • 2,548 Sq Ft
  • Built 2016

  1106 Thatch Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 50 Days On Market
• 

  /2

  $235,000

  $20K PRICE DROP

  • Land
  • 7.09 Acres
  • $33,145 per Acre

  Lot 7 Parcel 10, Cudjoe Key, FL 33042

  This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

  Pamela Stangler Expert Realty LLC

  Lot 7 Parcel 10, Cudjoe Key, FL 33042
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  /57

  $925,000

  Sold Mar 13, 2026

  2123 Spanish Channel Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $781/SF
  • 49 Days On Market

  Current Estimated Value $918,848

  Last Listing Agent Anne Press Lokation Real Estate

  2123 Spanish Channel Dr, Big Pine Key, FL 33043
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  /6

  Not Listed For Sale

  Lot 27 Angelfish Rd, Ramrod Key, FL 33042

  Lot 27 Angelfish Rd, Ramrod Key, FL 33042

  Last Sold Summary

  • 291 Days On Market
• 

  

  /15

  $1,395,000

  $55K PRICE DROP

  • Land
  • 2.29 Acres
  • $609,173 per Acre

  1261 Avenue A, Big Pine Key, FL 33043

  An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west

  Ally Kelley Ocean Sotheby's International

  1261 Avenue A, Big Pine Key, FL 33043
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  /9

  $100,000

  Sold Oct 29, 2025

  4W Cook Island, Big Pine Key, FL 33043

  • Land
  • 14,809 Sq Ft
  • $294,126 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 194 Days On Market

  Current Estimated Value $129,500

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

  4W Cook Island, Big Pine Key, FL 33043
• 

  

  /30

  Est $836,981

  Not Listed For Sale

  124 Yardarm Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2023

  124 Yardarm Rd, Cudjoe Key, FL 33042

  Last Sold Summary

  • 22 Days On Market
• 

  

  /24

  $259,000

  $6K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $5,180,000 per Acre

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

  RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
• 

  

  /47

  $1,399,000

  Sold Jun 17, 2026

  823 Indies Rd, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 2006

  Last Sold Summary

  • $925/SF
  • 5 Days On Market

  Current Estimated Value $1,396,669

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  823 Indies Rd, Ramrod Key, FL 33042
• 

  

  /41

  Not Listed For Sale

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft
  • Built 2004

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

  Last Sold Summary

  • 84 Days On Market
• 

  

  /28

  $465,000

  $10K PRICE DROP Under Contract

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

  29757 Henry Ln, Big Pine Key, FL 33043

  Enjoy the laid back Big Pine Key lifestyle. Situated on an expansive 11,500 square foot lot, this beautifully updated 2 bedroom, 2 bath home offers space, comfort, and the feel of a manufactured home while no longer functioning as a mobile home. The home is securely affixed to wood pilings and concrete blocks on a concrete pad, creating a more permanent structure. Inside, you'll find a large open

  Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  29757 Henry Ln, Big Pine Key, FL 33043
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  /37

  $800,000

  Sold Dec 19, 2025

  923 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $741/SF
  • 60 Days On Market

  Current Estimated Value $838,904

  Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

  923 Indies Rd, Summerland Key, FL 33042
• 

  

  /33

  Est $864,682

  Not Listed For Sale

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Built 2016

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • 175 Days On Market
• 

  

  /52

  $2,300,000

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  30995 Watson Blvd, Big Pine Key, FL 33043

  Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, durable metal roof, stainless steel appliances, quartz countertops, open-concept living areas, screened porch, private in-ground pool, and covered parking below. Built with modern coastal construction in mind, the CBS

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  30995 Watson Blvd, Big Pine Key, FL 33043
• 

  

  /25

  $500,000

  Sold Aug 19, 2025

  1620 Buttonwood Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft
  • Built 1974

  Last Sold Summary

  • 28% Below List Price
  • $490/SF
  • 265 Days On Market

  Current Estimated Value $527,081

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1620 Buttonwood Dr, Big Pine Key, FL 33043
• 

  /2

  Est $692,444

  Not Listed For Sale

  1547 Narcissus Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • Built 1991

  1547 Narcissus Ave, Big Pine Key, FL 33043
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  /71

  $1,379,000

  $16K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft

  16941 Driftwood Ln, Summerland Key, FL 33042

  There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key

  Coby Taylor Expert Realty LLC (HQ)

  16941 Driftwood Ln, Summerland Key, FL 33042
• 

  

  /42

  $1,750,000

  Sold Feb 26, 2026

  20771 2nd Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft
  • Built 2010

  Last Sold Summary

  • 17% Below List Price
  • $855/SF
  • 161 Days On Market

  Current Estimated Value $1,795,710

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  20771 2nd Ave W, Summerland Key, FL 33042
• 

  /2

  Est $671,706

  Not Listed For Sale

  1791 Narcissus Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • Built 1993

  1791 Narcissus Ave, Big Pine Key, FL 33043
• 

  

  /33

  $469,000

  • 1 Bed
  • 1.5 Baths
  • 735 Sq Ft

  701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

  Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

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