Summerland Key, FL Homes

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  $324,999

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

  This sale is for one 6000 square foot lot with a home in need of repairs or replacement.

  Joseph Ordini Keller Williams Key West Compass Realty

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
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  /43

  $975,000 Sold May 30, 2025

  17425 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2018

  Last Sold Summary

  • 19% Below List Price
  • $677/SF
  • 65 Days On Market

  Current Estimated Value $1,036,797

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

  17425 Jamaica Ln, Summerland Key, FL 33042
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  Est $1,660,936 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,942 Sq Ft

  25326 3rd St, Summerland Key, FL 33042

  25326 3rd St, Summerland Key, FL 33042
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  $980,000

  • 4 Beds
  • 3 Baths
  • 1,457 Sq Ft

  31441 Avenue F, Big Pine Key, FL 33043

  This solid all-concrete home, situated on a generous 10,000 sq ft double lot, offers the perfect blend of comfort and style for a growing family. Step into the open-concept living area with vaulted ceilings, creating an airy, welcoming atmosphere. The chef-inspired kitchen features beautiful quartz countertops and stainless steel appliances, perfect for cooking and entertaining. Tile floors

  Austin Kimbler Expert Realty LLC (HQ)

  31441 Avenue F, Big Pine Key, FL 33043
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  /58

  $3,335,000 Sold Jun 13, 2025

  23971 Henry St, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,950 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Below List Price
  • $1,131/SF
  • 37 Days On Market

  Current Estimated Value $3,254,444

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

  23971 Henry St, Summerland Key, FL 33042
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  /9

  Est $171,429 Not Listed For Sale

  29859 Overseas Hwy Unit B16, Big Pine Key, FL 33043

  29859 Overseas Hwy Unit B16, Big Pine Key, FL 33043
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  /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,

  Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  29678 Enterprise Ave, Big Pine Key, FL 33043
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  /2

  $73,000 Sold Feb 21, 2025

  00 Valencia Rd, Cudjoe Key, FL 33042

  • Land
  • 1.01 Acres
  • $72,277 per Acre

  Last Sold Summary

  • 64% Below List Price
  • 36 Days On Market

  Last Listing Agent Jennifer Withers EXP REALTY LLC

  00 Valencia Rd, Cudjoe Key, FL 33042
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  /15

  Est $194,101 Not Listed For Sale

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

  29859 Overseas Hwy Unit 54, Big Pine Key, FL 33043
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  $1,875,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  876 Gulf Dr, Summerland Key, FL 33042

  Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal

  Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
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  /45

  $900,000 Sold Apr 03, 2025

  2250 San Remo Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1989

  Last Sold Summary

  • 9% Below List Price
  • $573/SF
  • 243 Days On Market

  Current Estimated Value $915,744

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

  2250 San Remo Dr, Big Pine Key, FL 33043
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  /2

  Est $760,388 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  549 Powell Ave, Summerland Key, FL 33042

  549 Powell Ave, Summerland Key, FL 33042
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  /9

  $163,000

  • Land

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043

  ROGO EXEMPT - Buildable lot! Incredible opportunity to buy a piece of paradise in Florida keys! This residence offers a unique blend of coastal living and modern amenities. Appropriate for those seeking a tranquil retreat while still being conveniently close to local attractions and the beautiful waters of the Florida Keys. Discover the lifestyle you've been dreaming of here. Low HOA fee, just

  Steven Koleno Beycome of Florida, LLC

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
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  $1,350,000 Sold Jul 24, 2025

  20883 4th Ave, Cudjoe Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,524 Sq Ft
  • Built 2011

  Last Sold Summary

  • 21% Below List Price
  • $535/SF
  • 215 Days On Market

  Current Estimated Value $1,605,195

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

  20883 4th Ave, Cudjoe Key, FL 33042
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  /21

  Est $629,679 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,566 Sq Ft

  31011 Avenue C, Big Pine Key, FL 33043

  31011 Avenue C, Big Pine Key, FL 33043
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  $969,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  437 Pirates Rd, Little Torch Key, FL 33042

  Now offered in the sought after Jolly Roger Estates, this beautifully maintained one owner, free-flowing canal front home is just 10 years old and move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence features three bedrooms and two bathrooms with refined details such as crown molding, tray ceilings, tile showers, and an open-concept living area. A new metal roof was

  Jo Ann Cook Ocean Sotheby's International

  437 Pirates Rd, Little Torch Key, FL 33042
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  /39

  $1,725,000 Sold Apr 25, 2025

  474 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1973

  Last Sold Summary

  • 21% Below List Price
  • $1,037/SF
  • 127 Days On Market

  Current Estimated Value $1,684,471

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

  474 Caribbean Dr E, Summerland Key, FL 33042
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  /28

  Est $918,275 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  30887 Ortega Ln, Big Pine Key, FL 33043

  30887 Ortega Ln, Big Pine Key, FL 33043
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  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
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  $1,750,000 Sold Feb 13, 2025

  17194 Kingfish Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,073 Sq Ft
  • Built 2011

  Last Sold Summary

  • 17% Below List Price
  • $844/SF
  • 150 Days On Market

  Current Estimated Value $1,721,190

  Last Listing Agent Samantha Barrabeitg Taylor & Assoc. RE, Inc.

  17194 Kingfish Ln W, Summerland Key, FL 33042
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  /2

  Est $723,231 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 998 Sq Ft

  30827 Baileys Ln, Big Pine Key, FL 33043

  30827 Baileys Ln, Big Pine Key, FL 33043
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  /5

  $139,000

  • Land

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
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  /22

  $750,000 Sold Apr 10, 2025

  29548 Enterprise Ave, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 38% Below List Price
  • $336/SF
  • 523 Days On Market

  Current Estimated Value $758,945

  Last Listing Agent Jennifer Weeks Select Properties of NWFL

  29548 Enterprise Ave, Big Pine Key, FL 33043
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  /16

  Est $591,222 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,562 Sq Ft

  30323 Poinciana Rd, Big Pine Key, FL 33043

  30323 Poinciana Rd, Big Pine Key, FL 33043
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  $1,420,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  30890 Granada Ave, Big Pine Key, FL 33043

  Welcome to your tropical oasis--where the true spirit of the Florida Keys comes to life. This spacious 3-bedroom waterfront home blends casual island style with relaxed coastal living, offering 1,764 square feet designed for comfort and ease. High ceilings lined with tongue-and-groove wood immediately set the island tone as you enter the open living space. The kitchen flows seamlessly into the

  Sunnie San Lorenzo KeyIsle Realty

  30890 Granada Ave, Big Pine Key, FL 33043
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  /38

  $935,000 Sold Jun 30, 2025

  29374 Saratoga Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1986

  Last Sold Summary

  • 18% Below List Price
  • $835/SF
  • 150 Days On Market

  Current Estimated Value $938,388

  Last Listing Agent Dawn McComish Lokation Real Estate

  29374 Saratoga Ave, Big Pine Key, FL 33043
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  /2

  Est $3,373,682 Not Listed For Sale

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

  1152 W Shore Dr, Big Pine Key, FL 33043

  1152 W Shore Dr, Big Pine Key, FL 33043
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  /21

  $920,000

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

  27360 Saint Croix Ln, Summerland Key, FL 33042

  Enjoy the Keys lifestyle in one of the Lower Key's most desirable communities - Breezeswept! Here you'll enjoy island living with the convenience of being just a short drive to Key West. This waterfront home sits on a wide canal with 60 feet of concrete dock that includes one 15,000 boat lift, one davit set. The home is offered turnkey with all the furniture if you wish. The canal offers

  Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
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  /73

  $1,050,000 Sold Jan 03, 2025

  103 Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1989

  Last Sold Summary

  • 12% Below List Price
  • $931/SF
  • 24 Days On Market

  Current Estimated Value $1,046,630

  Last Listing Agent Stephany Duvall Engel & Volkers Marathon

  103 Shore Dr, Summerland Key, FL 33042
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  /42

  Est $1,192,788 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  29479 Ranger Ave, Big Pine Key, FL 33043

  29479 Ranger Ave, Big Pine Key, FL 33043
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  $725,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

  Priced to sell....Enjoy sweeping ocean views from this desirable 2-bed/2-bath residence, featuring a 35' dock on a pristine 60' wide canal, an exceptional setting for avid boaters with immediate access to both the Atlantic Ocean and the Gulf of Mexico. This charming home offers a wonderful canvas for personalized upgrades or serves perfectly as a serene vacation retreat. Additional highlights

  Holly Burger RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
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  $650,000 Sold Jun 30, 2025

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 4% Below List Price
  • $785/SF
  • 8 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042
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  /3

  Est $1,141,131 Not Listed For Sale

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

  Unlisted Address

  Unlisted Address
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  /51

  $837,500 Open House 1/03

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  29115 Rose Dr, Big Pine Key, FL 33043

  Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. Featuring an inviting open-concept floor plan, this home boasts three spacious bedrooms and two modern bathrooms, all enhanced by LVP flooring throughout. Built above flood level with just the right number of steps to climb, this home ensures both

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

  29115 Rose Dr, Big Pine Key, FL 33043
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  /51

  $1,100,000 Sold May 02, 2025

  27984 Barton Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,225 Sq Ft
  • Built 1993

  Last Sold Summary

  • 8% Below List Price
  • $898/SF
  • 126 Days On Market

  Current Estimated Value $1,097,869

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  27984 Barton Ave, Little Torch Key, FL 33042
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  Est $920,595 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  27322 Saint Martin Ln, Summerland Key, FL 33042

  27322 Saint Martin Ln, Summerland Key, FL 33042
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  $399,950

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  30170 Linda St, Big Pine Key, FL 33043

  Welcome to your charming new home! This delightful concrete 1-bedroom, 1-bathroom residence features a sturdy metal roof and is nestled on a generously sized, fully fenced lot, offering both comfort and privacy.Step inside to discover energy-efficient LED lighting throughout, complemented by an energy-efficient A/C system to keep you cool. The kitchen features a gas range, perfect for cooking

  Silvestri Team Jeanette & Janessa Silves Coldwell Banker Schmitt Key Largo

  30170 Linda St, Big Pine Key, FL 33043
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  $1,400,000 Sold Sep 17, 2025

  491 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 2020

  Last Sold Summary

  • $1,163/SF
  • 0 Days On Market

  Current Estimated Value $1,410,325

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  491 W Indies Dr, Ramrod Key, FL 33042
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  /55

  Est $1,337,107 Not Listed For Sale

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

  266 Colson Dr, Summerland Key, FL 33042

  266 Colson Dr, Summerland Key, FL 33042
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  $1,650,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  25368 2nd St, Summerland Key, FL 33042

  Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

  Ally Kelley Ocean Sotheby's International

  25368 2nd St, Summerland Key, FL 33042

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