Summerland Key, FL Homes

• 

  

  

  /22

  Est $780,199

  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
• 

  

  

  /24

  $580,175

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

  Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
• 

  

  

  /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 $1,363,708

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20735 5th Ave W, Summerland Key, FL 33042
• 

  

  /2

  Est $827,386

  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

  Last Sold Summary
• 

  

  

  /51

  $425,000

  • 2 Beds
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042

  Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile

  Justyn Ewald Expert Realty LLC

  701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042
• 

  

  /37

  $725,000

  Sold Jan 14, 2026

  27394 Saint Lucie Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1994

  Last Sold Summary

  • $673/SF
  • 19 Days On Market

  Current Estimated Value $732,212

  Last Listing Agent Casey Arnold eXp Realty LLC

  27394 Saint Lucie Ln, Summerland Key, FL 33042
• 

  

  /19

  Est $1,016,009

  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
• 

  

  /32

  $995,000

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  29131 Watson Blvd, Big Pine Key, FL 33043

  Peaceful serenity found on this 22,077 square foot property with a cozy two bedroom one and one-half bath. Open concept large kitchen and living room leading out to the expansive deck overlooking the canal. Both bedrooms also have doors leading to the wrap around deck! The cathedral ceilings and wood trims give this home beach cottage character! The lower level has an amazing amount of storage

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  29131 Watson Blvd, Big Pine Key, FL 33043
• 

  

  /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

  Current Estimated Value $1,022,575

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  29487 Ranger Ave, Big Pine Key, FL 33043
• 

  /2

  Est $902,625

  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

  Last Sold Summary
• 

  

  /25

  $649,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  31147 Avenue H, Big Pine Key, FL 33043

  MOTIVATED SELLER! STILTED pool home in Big Pine! Home is being sold unfurnished. Spring into summer with this gorgeous sparkling swimming pool! Enjoy snacks & meals poolside with handy outdoor kitchen which lends itself to awesome laid back island style entertaining! That's what we love about this remarkably well kept property! 3 comfortably sized bedrooms, 2 full bathrooms & a screened in porch

  Jamie Caudill Lokation Real Estate

  31147 Avenue H, Big Pine Key, FL 33043
• 

  

  /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 $754,204

  Last Listing Agent Gregory Sullivan BYOWNER.COM

  25121 Center St, Summerland Key, FL 33042
• 

  

  /15

  Est $185,961

  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
• 

  

  /12

  $599,000

  • Land
  • 11,950 Sq Ft
  • $2,183,468 per Acre

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042

  **Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

  Daiane Sardinas Carvalho Centennial Realty Group, LLC

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042
• 

  

  /62

  $720,000

  Sold May 18, 2026

  28151 Helen Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $511/SF
  • 51 Days On Market

  Current Estimated Value $755,690

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  28151 Helen Ave, Summerland Key, FL 33042
• 

  

  /35

  Est $934,555

  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
• 

  

  /42

  $1,095,000

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  27345 Barbuda Ln, Summerland Key, FL 33042

  Looking for brand-new waterfront construction with excellent boating access to both the Atlantic and Gulf? This custom home, completed in fall 2025 on the southern end of Ramrod Key, puts you exactly where you want to be; close to deep, open water and far enough from US-1 to enjoy true peace and quiet. Built with hurricane impact-rated construction for added peace of mind, the home offers 3

  Madeleine Lowe Expert Realty LLC (HQ)

  27345 Barbuda Ln, Summerland Key, FL 33042
• 

  

  /29

  $720,000

  Sold Apr 17, 2026

  630 Barry Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Built 2005

  Last Sold Summary

  • 28% Below List Price
  • $678/SF
  • 86 Days On Market

  Current Estimated Value $854,809

  Last Listing Agent Brenda Thomas Island Welcome Real Estate

  630 Barry Ave, Little Torch Key, FL 33042
• 

  /2

  Est $770,293

  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

  Last Sold Summary
• 

  

  /40

  $795,000

  $15K PRICE DROP Under Contract

  • 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

  Robert Smithwick Engel & Volkers Marathon

  3686 Gulfstream St, Big Pine Key, FL 33043
• 

  

  /45

  $710,000

  Sold Feb 05, 2026

  27163 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2018

  Last Sold Summary

  • 10% Below List Price
  • $477/SF
  • 238 Days On Market

  Current Estimated Value $749,434

  Last Listing Agent Jessica Roden Ocean Sotheby's International Realty

  27163 Mariposa Rd, Summerland Key, FL 33042
• 

  /2

  Est $617,416

  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

  Last Sold Summary
• 

  

  /61

  $2,795,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft

  20844 4th Ave W, Summerland Key, FL 33042

  FISHERMAN'S DREAM! BIG BOATS WELCOME! DEEP WATER! LARGE WATERFRONT HOME in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of luxury and comfort. All new impact windows &

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20844 4th Ave W, Summerland Key, FL 33042
• 

  

  /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
  • 295 Days On Market

  Current Estimated Value $3,709,622

  Last Listing Agent Karen Williams-deCastro LPT Realty, LLC

  815 E Shore Dr, Summerland Key, FL 33042
• 

  /2

  Est $4,029,325

  Not Listed For Sale

  1152 W Shore Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 4,030 Sq Ft
  • Built 2008

  1152 W Shore Dr, Big Pine Key, FL 33043

  Last Sold Summary
• 

  

  /40

  $894,000

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  28571 Buccaneer Rd, Summerland Key, FL 33042

  Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large

  Diane Corliss Coldwell Banker Schmitt RE Co.

  28571 Buccaneer Rd, Summerland Key, FL 33042
• 

  

  /32

  $450,000

  Sold Aug 20, 2025

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $553/SF
  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
• 

  

  /3

  Est $1,141,387

  Not Listed For Sale

  Unlisted Address

  • 5 Beds
  • 4 Baths
  • 1,702 Sq Ft
  • Built 1967

  Unlisted Address

  Last Sold Summary

  • 1 Day On Market
• 

  

  /33

  $4,300

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  3930 Gordon Rd, Big Pine Key, FL 33043

  BRAND NEW CONSTRUCTION.LONG-TERM RENTAL AVAILABLE NOW.Pets welcome!Let your clients be the first to live in this newly constructed home. This house has a large porch facing the canal, with over-dead fans to keep your family cool.This 1350 sq. ft. house is fully tiled throughout.The bedrooms and the closets are spacious, and the ceilings are 9 feet high throughout the

  Mark Peterson Mark F. Peterson Licensed Real Estate Broker

  3930 Gordon Rd, Big Pine Key, FL 33043
• 

  

  /14

  $225,000

  Sold Apr 01, 2026

  27398 Jamaica Ln, Ramrod Key, FL 33042

  • Land
  • 6,098 Sq Ft
  • $1,607,143 per Acre

  Last Sold Summary

  • 25% Below List Price
  • 173 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  27398 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  /55

  Est $1,444,417

  Not Listed For Sale

  266 Colson Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 1975

  266 Colson Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market
• 

  

  /20

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  29678 Enterprise Ave, Big Pine Key, FL 33043

  Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean,

  Thomas Carden Keys to the Coast Real Estate LLC

  29678 Enterprise Ave, Big Pine Key, FL 33043
• 

  

  /30

  $1,185,000

  Sold Nov 17, 2025

  478 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $1,062/SF
  • 0 Days On Market

  Current Estimated Value $1,168,083

  Last Listing Agent Jenny Perry Preferred Properties (KW)

  478 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /37

  Est $1,838,393

  Not Listed For Sale

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 2008

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  Last Sold Summary

  • 42 Days On Market
• 

  

  /10

  $580,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 834 Sq Ft

  22963 Anne Bonny Ln, Summerland Key, FL 33042

  Canal-front opportunity in desirable Cudjoe Key! Charming 3-bedroom, 2-bath home with boating access to open water, offering incredible potential for renovation, investment, vacation retreat, or primary residence. Situated in sought-after Cutthroat Harbor Estates on a canal, this property offers the true Florida Keys lifestyle. Ready for updates and priced for buyers looking to add value and make

  Judith Exposito Luxe Properties

  22963 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /29

  $825,000

  Sold Feb 27, 2026

  17245 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $661/SF
  • 104 Days On Market

  Current Estimated Value $855,173

  Last Listing Agent Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /43

  Est $3,041,119

  Not Listed For Sale

  1619 Long Beach Dr, Big Pine Key, FL 33043

  • 5 Beds
  • 5.5 Baths
  • 3,160 Sq Ft
  • Built 1977

  1619 Long Beach Dr, Big Pine Key, FL 33043

  Last Sold Summary

  • 2 Days On Market
• 

  

  /41

  $1,049,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft

  27416 Cayman Ln, Ramrod Key, FL 33042

  Welcome to Breezeswept Beach Estates in Ramrod Key--a canal-front Florida Keys retreat built for boating and island living. Enjoy no-bridge Atlantic access and a quick ride to open water, plus a 60' composite dock (2022) with 14,000 lb and 6,000 lb boat lifts, fillet station, and swim ladder--perfect for anglers and boating enthusiasts. Spend your days exploring Picnic Island, nearby sandbars,

  Melissa Gibbins Expert Realty LLC (HQ)

  27416 Cayman Ln, Ramrod Key, FL 33042
• 

  

  /40

  $1,300,000

  Sold Feb 26, 2026

  537 Heck Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • Built 1997

  Last Sold Summary

  • $914/SF
  • 29 Days On Market

  Current Estimated Value $1,288,318

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  537 Heck Ave, Summerland Key, FL 33042
• 

  /2

  Est $1,031,764

  Not Listed For Sale

  29552 Independence Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1976

  29552 Independence Ave, Big Pine Key, FL 33043

  Last Sold Summary

Showing Results 401 - 440, Page 11 of 18