Summerland Key, FL Homes

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  /3

  Not Listed For Sale

  Vacant Lot Diane Rd, Big Pine Key, FL 33043

  Vacant Lot Diane Rd, Big Pine Key, FL 33043
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  /26

  $1,250,000 Open Sun 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,364 Sq Ft

  466 W Shore Dr, Summerland Key, FL 33042

  Welcome to 466 W Shore Dr in prestigious Summerland Key. This 2 bedroom concrete home is situated on a 12,000 sg foot lot, located on a wide deep water boating canal. There is an RV hookup, as well as power at the dock. The home is a split bedroom and bathroom floor plan with beautiful terrazzo floors, updated kitchen, and baths. Enjoy the [Noseeum] screened porch off the living area, or the tiki

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  (786) 686-3066

  466 W Shore Dr, Summerland Key, FL 33042
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  /37

  $642,000 Sold Jul 11, 2025

  31067 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Above List Price
  • $423/SF
  • 9 Days On Market

  Current Estimated Value $673,184

  Last Listing Agent Jared Chiagouris Truman & Co. (KW)

  31067 Avenue C, Big Pine Key, FL 33043
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  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  27772 Astrangia Ave, Summerland Key, FL 33042

  27772 Astrangia Ave, Summerland Key, FL 33042
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  /50

  $1,599,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft

  56 Colson Dr, Summerland Key, FL 33042

  Exceptional waterfront living awaits at 56 Colson Drive in Cudjoe Gardens on Cudjoe Key--a fully renovated 3 Bedroom 2 Bathroom home offering 1,645 sq. ft. of thoughtfully planned interior space on a sprawling 11,900 sq. ft. lot. Built with CBS construction and impact doors and windows, this property combines durability with modern coastal appeal and is designed to take full advantage of the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 841-7430

  56 Colson Dr, Summerland Key, FL 33042
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  /2

  $49,000 Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
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  /2

  Est $1,021,853 Not Listed For Sale

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

  1581 State Rd Unit 4A, Little Torch Key, FL 33042

  1581 State Rd Unit 4A, Little Torch Key, FL 33042
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  /52

  $1,335,000

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

  28560 Doubloon Rd, Summerland Key, FL 33042

  Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 772-6030

  28560 Doubloon Rd, Summerland Key, FL 33042
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  /3

  $420,000 Sold Jun 27, 2025

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 488 Sq Ft
  • Built 1999

  Last Sold Summary

  • 13% Below List Price
  • $861/SF
  • 0 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  0 Vacant Unit 607262, Saddlebunch, FL 33040
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  /17

  $675,000

  • Land

  17215 Keystone Rd, Sugarloaf Shores, FL 33042

  Cleared canal-front lot in Sugarloaf Shores with building permit in place and first inspection not due until December 2026! Positioned on the desirable no-bridge side, this expansive 27,716 sq. ft. residential parcel is surrounded by multi-million-dollar homes and offers easy access to the open water where days are enjoyed paddling and kayaking through mangrove-line creeks or heading out to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 957-7959

  17215 Keystone Rd, Sugarloaf Shores, FL 33042
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  /38

  $840,000 Sold Sep 30, 2025

  3611 S Seas St, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $787/SF
  • 183 Days On Market

  Current Estimated Value $854,967

  Last Listing Agent Scott Brisson KeyIsle Realty

  3611 S Seas St, Big Pine Key, FL 33043
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  /14

  Est $410,963 Not Listed For Sale

  • 3 Beds

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  30919 Edward Rd Unit A, Big Pine Key, FL 33043
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  /38

  $1,200,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  218 Spanish Main Dr, Summerland Key, FL 33042

  Welcome to 218 Spanish Main Dr., a turnkey, recently renovated Florida Keys waterfront home offering the perfect blend of coastal charm and modern comfort. This 2-story, 3 bed, 3 bath fully fenced retreat boasts 2,016 sq ft of thoughtfully designed space with water views from nearly every room. Enjoy porches on both levels, ideal for morning coffee or sunset cocktails. The main level features an

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 876-6037

  218 Spanish Main Dr, Summerland Key, FL 33042
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  /75

  $830,000 Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $841,761

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
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  /2

  Est $562,218 Not Listed For Sale

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  17172 Marlin Dr, Sugarloaf Shores, FL 33042
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  /47

  $569,900

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 35 ft seawall.* Community Boat Ramp and boat washdown station.*

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 686-7983

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
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  /68

  $950,000 Sold Apr 11, 2025

  31670 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,227 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $774/SF
  • 28 Days On Market

  Current Estimated Value $929,000

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  31670 Avenue C, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
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  /79

  $615,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1258 Division St, Big Pine Key, FL 33043

  Welcome to Your Own Slice of Island Paradise in Big Pine Key! Tucked away in the heart of Big Pine, this picture-perfect 3-bedroom, 1-bath home invites you to slow down, breathe deep, & truly enjoy island living. Set on an oversized double lot totaling 12,500 sq ft, this property is truly a private tropical sanctuary: lush, peaceful, and full of life.From the moment you step inside, soaring beam

  

  Lindsay Ryan

  EXP Realty LLC

  (833) 721-7372

  1258 Division St, Big Pine Key, FL 33043
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  /41

  $1,105,000 Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Current Estimated Value $1,096,128

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

  22946 Bluegill Ln, Summerland Key, FL 33042
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  /2

  Est $200,159 Not Listed For Sale

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  825 Hawksbill Ln, Sugarloaf Key, FL 33042
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  /30

  $750,000

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

  26868 Mariposa Rd, Ramrod Key, FL 33042

  Presenting a newly built 2023 home on a spacious 12,250 sq. ft. lot in Ramrod Shores, designed with both efficiency and style in mind. This four-bedroom, two-bathroom property features durable construction elements like a metal roof and impact-resistant windows, optimizing insurance costs, with all 3 insurances combined under $5,000 total. The interior boasts an open-concept floor plan with high

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 783-4956

  26868 Mariposa Rd, Ramrod Key, FL 33042
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  /57

  $1,375,000 Sold Apr 17, 2025

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  Last Sold Summary

  • 19% Below List Price
  • $765/SF
  • 215 Days On Market

  Current Estimated Value $1,372,540

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
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  /2

  Est $3,379,420 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft

  999 Flagship Dr, Summerland Key, FL 33042

  999 Flagship Dr, Summerland Key, FL 33042
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  /41

  $1,899,000 Open Sun 11AM - 1PM

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

  28573 Le Grand Rd, Little Torch Key, FL 33042

  This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 527-2862

  28573 Le Grand Rd, Little Torch Key, FL 33042
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  /28

  $632,000 Sold Jul 03, 2025

  28451 Gulf Blvd, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $399/SF
  • 93 Days On Market

  Current Estimated Value $641,037

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  28451 Gulf Blvd, Big Pine Key, FL 33043
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  /17

  Est $305,961 Not Listed For Sale

  662 Blackbeard Rd, Little Torch Key, FL 33042

  662 Blackbeard Rd, Little Torch Key, FL 33042
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  /10

  $499,000

  • Land

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 834-4054

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042
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  /115

  $12,250,000 Sold May 07, 2025

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $2,506/SF
  • 44 Days On Market

  Current Estimated Value $4,507,572

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

  785 Sawyer Dr, Cudjoe Key, FL 33042
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  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042
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  /86

  $5,999,000 Pending

  • 4 Beds
  • 4 Baths
  • 4,315 Sq Ft

  4500 Filer Cove Rd, Summerland Key, FL 33042

  Picture perfect Sunset Views over the open water at this 12-Acre waterfront compound located on Big Torch Key, a coastal community of large private estates located just 30 minutes outside of Key West. Driving down the gated 300' scenic driveway balmy breezes and tropical landscape lead you to the 4,315 sq. ft. open water residence. Once here you will enjoy world-class fishing and diving just

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 998-2623

  4500 Filer Cove Rd, Summerland Key, FL 33042
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  $390,000 Sold Jul 10, 2025

  27873 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 686 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $569/SF
  • 70 Days On Market

  Last Listing Agent Tracy Shields KeyIsle Realty

  27873 Coral Shores Rd, Little Torch Key, FL 33042
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  /2

  Est $1,220,002 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  29565 Ranger Ave, Big Pine Key, FL 33043

  29565 Ranger Ave, Big Pine Key, FL 33043
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  /74

  $799,000

  • 2 Beds
  • 2 Baths
  • 766 Sq Ft

  701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042

  Canal Front Oasis with Resort Amenities!Nightly Rentals Allowed!Income Producing Gem!RARE-DOUBLE LOT!! Allows 2 cars with 2 separate driveways. Massive 69' Seawall!RARE-DAVITS for your boat!! Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom mid-rise home offers the ultimate Florida Keys

  

  Ian Calderwood

  Bluescape Real Estate

  (844) 482-8589

  701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
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  /64

  $809,000 Sold Nov 12, 2025

  3714 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $722/SF
  • 194 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  3714 Pine St, Big Pine Key, FL 33043
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  /14

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043
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  /45

  $1,599,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  17227 Allamanda Dr, Summerland Key, FL 33042

  Welcome to your own slice of paradise in the desirable Sugarloaf Shores neighborhood of the Lower Keys! This beautifully designed 3 bedroom, 2 bath home offers 1,788 sq. ft. of inviting living space that perfectly blends comfort, quality, and the laid-back island lifestyle. Located on the no-bridge side of Sugarloaf Shores, this property provides quick water access to world-class fishing, diving,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 803-0852

  17227 Allamanda Dr, Summerland Key, FL 33042
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  /2

  $144,000 Sold Mar 04, 2025

  Lot 15 Aztec St, Sugarloaf Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 2 Days On Market

  Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 15 Aztec St, Sugarloaf Key, FL 33042
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  /2

  Est $920,609 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft

  18954 Acosta Trail, Summerland Key, FL 33042

  18954 Acosta Trail, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18