Summerland Key, FL Homes

• 

  

  

  /29

  $495,000

  Sold Feb 13, 2026

  31525 Avenue A, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,278 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $387/SF
  • 229 Days On Market

  Current Estimated Value $537,363

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  31525 Avenue A, Big Pine Key, FL 33043
• 

  

  

  /21

  Not Listed For Sale

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft
  • Built 1978

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  

  /45

  $7,000,000

  • 3 Beds
  • 3.5 Baths
  • 2,851 Sq Ft

  0 Melody Key Unit 616249, Summerland Key, FL 33042

  An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity—an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings

  Scott Forman Royal Palms Realty (KW)

  0 Melody Key Unit 616249, Summerland Key, FL 33042
• 

  

  

  /61

  $1,900,000

  Sold Jun 15, 2026

  556 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft
  • Built 1974

  Last Sold Summary

  • 30% Below List Price
  • $877/SF
  • 155 Days On Market

  Current Estimated Value $1,925,382

  Last Listing Agent Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  

  /31

  Est $843,482

  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

  • 174 Days On Market

  Last Listing Agent ANTHONY GUADALUPE Non Member Listing Office
• 

  

  /17

  $4,500

  • 3 Beds
  • 2 Baths
  • 1,565 Sq Ft

  24840 Park Dr, Summerland Key, FL 33042

  { WOW } Try and find a rental in the Lower Florida Keys! Then, yet again, one with 3 bedrooms, 2 Full baths and spacious Kitchen, Livingroom, Dinning open concept layout. Welcome to living in Summerland Key Cove. Live where others vacation — in Summerland Key Cove, just 25 miles from Key West. Whether you're a boater, pilot, fisherman, or someone who simply enjoys walking their dog by the water,

  Thomas Murphy LAER Realty

  24840 Park Dr, Summerland Key, FL 33042
• 

  

  /25

  $1,249,000

  Sold Apr 28, 2026

  17170 Amberjack Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1989

  Last Sold Summary

  • $1,183/SF
  • 0 Days On Market

  Current Estimated Value $1,243,030

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17170 Amberjack Ln, Summerland Key, FL 33042
• 

  /2

  Est $814,920

  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
• 

  

  /46

  $675,000

  $60K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  30920 Baileys Ln, Big Pine Key, FL 33043

  Discover the perfect blend of coastal living and convenience in this CBS-built home offering exceptional access to open water--just minutes to both the Gulf and the Atlantic. Situated on a spacious double lot, the property includes a 30 ft. Step down boat slip cut in, ideal for docking your boat and enjoying effortless days on the water.Designed for seamless indoor-outdoor living, the home

  Deni Heintzelman KeyIsle Realty

  30920 Baileys Ln, Big Pine Key, FL 33043
• 

  

  /100

  $3,300,000

  Sold Dec 01, 2025

  815 E Shore Dr, Summerland Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,531 Sq Ft
  • Built 1961

  Last Sold Summary

  • 26% Below List Price
  • $728/SF
  • 292 Days On Market

  Current Estimated Value $3,539,470

  Last Listing Agent NON-MLS MEMBER MAR NON MLS MEMBER

  815 E Shore Dr, Summerland Key, FL 33042
• 

  /2

  Est $737,340

  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
• 

  

  /14

  $395,000

  • Land
  • 6,098 Sq Ft
  • $2,821,429 per Acre

  24285 Caribbean Dr, Summerland Key, FL 33042

  Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has

  Donna Pezzi Keller Williams Key West Compass Realty

  24285 Caribbean Dr, Summerland Key, FL 33042
• 

  

  /34

  $740,000

  Sold Jul 10, 2026

  3672 Fox St, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 1,224 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $605/SF
  • 136 Days On Market

  Current Estimated Value $796,998

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  3672 Fox St, Big Pine Key, FL 33043
• 

  

  /22

  Est $888,840

  Not Listed For Sale

  29548 Enterprise Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 4 Baths
  • 2,232 Sq Ft
  • Built 1974

  29548 Enterprise Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 523 Days On Market

  Last Listing Agent Jennifer Weeks Select Properties of NWFL
• 

  

  /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
• 

  

  /44

  $1,550,000

  Sold Feb 27, 2026

  17094 Coral Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $776/SF
  • 265 Days On Market

  Current Estimated Value $1,582,281

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17094 Coral Dr, Summerland Key, FL 33042
• 

  /2

  Est $828,451

  Not Listed For Sale

  677 Heck Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 875 Sq Ft
  • Built 1977

  677 Heck Ave, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /49

  $278,000

  Sold Apr 30, 2026

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

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft
  • Built 1986

  Last Sold Summary

  • 16% Below List Price
  • $377/SF
  • 149 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

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

  

  /19

  Est $981,827

  Not Listed For Sale

  825 Pirates Rd, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,920 Sq Ft
  • Built 1982

  825 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.
• 

  

  /44

  $1,045,000

  $55K 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
• 

  

  /40

  $950,000

  Sold Sep 17, 2025

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $825/SF
  • 85 Days On Market

  Current Estimated Value $1,025,643

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
• 

  /2

  Est $845,508

  Not Listed For Sale

  337 46th St, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Built 1958

  337 46th St, Summerland Key, FL 33042
• 

  

  /39

  $1,650,000

  $50K PRICE INCREASE Under Contract

  • 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
• 

  

  /53

  $2,725,000

  Sold Mar 11, 2026

  1147 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $1,324/SF
  • 103 Days On Market

  Current Estimated Value $2,652,185

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1147 Flagship Dr, Summerland Key, FL 33042
• 

  

  /33

  Est $644,424

  Not Listed For Sale

  21161 Old State Road 4a, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 855 Sq Ft
  • Built 1975

  21161 Old State Road 4a, Summerland Key, FL 33042

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)
• 

  

  /30

  $649,000

  $25K PRICE DROP Under Contract

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

  29123 Rose Dr, Big Pine Key, FL 33043

  Accepting a Backup offer! 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

  Melissa Graham Bluescape Real Estate

  29123 Rose Dr, Big Pine Key, FL 33043
• 

  /2

  $185,000

  Sold Mar 20, 2026

  1223 Rogers Ln, Cudjoe Key, FL 33042

  • Land
  • 6,969 Sq Ft
  • $1,156,250 per Acre

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $185,105

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  1223 Rogers Ln, Cudjoe Key, FL 33042
• 

  

  /15

  Est $192,654

  Not Listed For Sale

  29859 Overseas Hwy Unit 54, Big Pine Key, FL 33043

  29859 Overseas Hwy Unit 54, Big Pine Key, FL 33043

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Cheryl Billings Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
• 

  

  /45

  $1,399,000

  Under Contract

  • 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

  Bobby Coe RE/MAX Keys Connection (KW)

  559 Powell Ave, Little Torch Key, FL 33042
• 

  

  /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 $947,651

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

  29178 Guava Ln, Big Pine Key, FL 33043
• 

  

  /35

  Est $953,129

  Not Listed For Sale

  346 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1996

  346 Blackbeard Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
• 

  /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
• 

  

  /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 $480,696

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

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

  /2

  Est $747,058

  Not Listed For Sale

  30827 Baileys Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 998 Sq Ft
  • Built 1980

  30827 Baileys Ln, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /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 $634,639

  Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt RE Co.

  31463 Avenue A, Big Pine Key, FL 33043
• 

  /2

  Est $579,041

  Not Listed For Sale

  30323 Poinciana Rd, Big Pine Key, FL 33043

  • 5 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1971

  30323 Poinciana Rd, Big Pine Key, FL 33043
• 

  

  /24

  $748,516

  Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,451 Sq Ft

  31357 Avenue C, Big Pine Key, FL 33043

  Bring your vision and make this Big Pine Key property your own! Situated on two spacious, fully fenced lots, this 3bedroom, 2bath home offers plenty of room, flexibility, and potential for the right buyer. The property features easy entry and access to both lots, providing ample space for vehicles, boats, trailers, recreational toys, and more. With the additional lot space, there is also room to

  Halley Haack Coldwell Banker Schmitt RE Co.

  31357 Avenue C, Big Pine Key, FL 33043
• 

  

  /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 $649,885

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

  30868 Malaga Ln, Big Pine Key, FL 33043

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