Summerland Key, FL Homes

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  /35

  $669,000 Sold Oct 24, 2025

  28212 Gato Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Below List Price
  • $621/SF
  • 80 Days On Market

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  28212 Gato Rd, Summerland Key, FL 33042
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  /41

  Est $422,468 Not Listed For Sale

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042
• 

  

  

  /10

  $725,000

  • Land

  17220 Angelfish Ln, Sugarloaf Shores, FL 33042

  Build Your Dream Home in Sugarloaf Shores! Discover the rare opportunity to develop your very own piece of paradise in the exclusive Sugarloaf Shores! This 8,165 sq. ft. waterfront lot is high, dry, and cleared, offering a perfect blank slate for your dream home in the Florida Keys. With a full 70' concrete seawall, this property is a boater's paradise, providing direct access to both the

  The Spottswood Team Truman & Co. (KW)

  17220 Angelfish Ln, Sugarloaf Shores, FL 33042
• 

  

  

  /41

  $650,000 Sold Jul 01, 2025

  22882 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $580/SF
  • 81 Days On Market

  Current Estimated Value $685,138

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

  22882 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  

  /37

  Est $901,243 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  139 Le Grand Ln, Summerland Key, FL 33042

  139 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /14

  $299,000

  • Land

  27398 Jamaica Ln, Ramrod Key, FL 33042

  Great Location vacant lot with seawall and boat ramp. Minutes to Open Water. Just waiting for a perfect home. This is a great option to purchase 231 W. Indies Open Water Home and have great boating with this lot.Please look at MLS616482

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  27398 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  /28

  $598,000 Sold Feb 24, 2025

  33 E Cahill Ct, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $566/SF
  • 185 Days On Market

  Current Estimated Value $607,160

  Last Listing Agent Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  33 E Cahill Ct, Big Pine Key, FL 33043
• 

  

  /27

  Est $1,806,287 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft

  22836 Port Royal Ln, Summerland Key, FL 33042

  22836 Port Royal Ln, Summerland Key, FL 33042
• 

  

  /69

  $2,249,000 Pre-Foreclosure

  • 5 Beds
  • 3 Baths
  • 1,903 Sq Ft

  125 Colson Dr, Summerland Key, FL 33042

  THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' TRANSIENT LICENSE FOR NIGHTLY RENTALS ALLOWED! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! 5 bedrooms and 3 baths in this charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views, balconies from almost every room! Original hardwood floor, tons of character and warmth in this lovely home! Large

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  125 Colson Dr, Summerland Key, FL 33042
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  /42

  $1,450,000 Sold Jun 23, 2025

  17177 Bonita Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1978

  Last Sold Summary

  • 19% Below List Price
  • $1,018/SF
  • 362 Days On Market

  Current Estimated Value $1,442,116

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

  17177 Bonita Ln W, Summerland Key, FL 33042
• 

  

  /37

  Est $961,361 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,535 Sq Ft

  81 Coral Ave, Summerland Key, FL 33042

  81 Coral Ave, Summerland Key, FL 33042
• 

  

  /35

  $675,000

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

  31315 Avenue B, Big Pine Key, FL 33043

  Welcome to this elevated 3-bedroom, 2-bath home located in a quiet neighborhood in Big Pine Key. This well-maintained property features an open concept living and kitchen area, perfect for comfortable everyday living and entertaining. All three bedrooms are generously sized, and each includes its own walk-in closet. Impact-rated windows and doors provide added security and storm protection, while

  Keys Team Bryant and Kat Expert Realty LLC (HQ)

  31315 Avenue B, Big Pine Key, FL 33043
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  /52

  $2,300,000 Sold Sep 12, 2025

  23086 Snapper Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 147 Days On Market

  Current Estimated Value $2,262,159

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
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  /34

  Est $766,354 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 841 Sq Ft

  28551 Buccaneer Rd, Summerland Key, FL 33042

  28551 Buccaneer Rd, Summerland Key, FL 33042
• 

  

  /49

  $910,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  813 Hawksbill Ln, Summerland Key, FL 33042

  Charming 2BR/2BA PLUS A LOFT, Keys home on Upper Sugarloaf, the perfect blend of comfort and waterfront living. Built on sturdy concrete pilings with Hardie board siding and a metal roof, this three-story retreat of island living. with GENERAC Generator. Inside, you'll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys lifestyle. What truly

  Miguel Solis Douglas Elliman Florida, LLC - Sunset Drive

  813 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /42

  $630,000 Sold Jul 21, 2025

  92 Frazier Ln, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 768 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $820/SF
  • 43 Days On Market

  Current Estimated Value $619,509

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  92 Frazier Ln, Summerland Key, FL 33042
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  /43

  Est $1,186,022 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  17055 Kingfish Ln W, Summerland Key, FL 33042

  17055 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /29

  $925,000

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

  17245 Jamaica Ln, Summerland Key, FL 33042

  Tucked along a quiet canal in Sugarloaf Shores, 17245 Jamaica Lane captures the essence of easy Keys living. This waterfront retreat offers direct access to open water and all things salt life--paddleboarding, kayaking, the iconic jumping bridge, and world-class cycling right out your door. Set on a generous lot, this elevated 3-bedroom, 2-bath home blends laid-back island charm with modern

  Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
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  /16

  $785,000 Sold Jul 25, 2025

  27384 Barbuda Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1993

  Last Sold Summary

  • 17% Below List Price
  • $668/SF
  • 125 Days On Market

  Current Estimated Value $797,224

  Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

  27384 Barbuda Ln, Summerland Key, FL 33042
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  /50

  Est $930,520 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  17396 Jamaica Ln, Summerland Key, FL 33042

  17396 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /54

  $5,600,000

  • 4 Beds
  • 3.5 Baths
  • 5,608 Sq Ft

  974 Flagship Dr, Summerland Key, FL 33042

  Spectacular Open Water location, with fabulous views from this well-built Oceanfront concrete home. Direct Ocean access from the step down concrete seawall/dock that wraps around the waterside of the property, including the boat basin with two boat lifts and a fish cleaning station. Relax in large pool with over-spill hot tub & a big pool patio area and a covered patio for entertaining, which

  Lee Sanders KeyIsle Realty

  974 Flagship Dr, Summerland Key, FL 33042
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  /14

  $1,250,000 Sold Aug 11, 2025

  365 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $893/SF
  • 47 Days On Market

  Current Estimated Value $1,252,535

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  365 Pirates Rd, Summerland Key, FL 33042
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  /40

  Est $994,120 Not Listed For Sale

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

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  22983 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /34

  $890,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  726 Jamaica Ln, Summerland Key, FL 33042

  Boater's Dream & Handyman's Haven: Restore This Coastal Gem!Calling all boaters, handy enthusiasts, and investors! This 3-story home with a tool-lover's garage is brimming with potential and ready to shine again. Located on a prime waterfront lot, complete with a concrete seawall and davits, this property is perfect for anyone looking to create their dream home or secure a profitable investment.

  Natallie Liz Expert Realty LLC (HQ)

  726 Jamaica Ln, Summerland Key, FL 33042
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  /59

  $900,000 Sold Oct 31, 2025

  28550 Doubloon Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1996

  Last Sold Summary

  • 18% Below List Price
  • $380/SF
  • 181 Days On Market

  Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

  28550 Doubloon Rd, Summerland Key, FL 33042
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  /6

  Est $633,916 Not Listed For Sale

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

  79 Coral Ave, Summerland Key, FL 33042

  79 Coral Ave, Summerland Key, FL 33042
• 

  

  /26

  $1,180,000

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  27350 Barbados Ln, Ramrod Key, FL 33042

  Welcome to your slice of paradise in the Lower Florida Keys! This beautifully maintained 3-bedroom, 2-bath canal-front home offers everything you need for island living -- whether you're looking for a full-time residence, vacation getaway, or investment property. Nestled on a spacious 6,000 sq ft lot, this home boasts: - Direct Canal Access - Ideal for boaters! Navigate easily to open water.

  Jonathan Minerick Homecoin.com

  27350 Barbados Ln, Ramrod Key, FL 33042
• 

  

  /24

  $710,000 Sold Dec 18, 2025

  31120 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 864 Sq Ft
  • Built 2022

  Last Sold Summary

  • 9% Below List Price
  • $822/SF
  • 83 Days On Market

  Last Listing Agent David Kaufmann Century 21 Circle

  31120 Avenue J, Big Pine Key, FL 33043
• 

  /2

  Est $2,288,471 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  20820 7th Ave W, Summerland Key, FL 33042

  20820 7th Ave W, Summerland Key, FL 33042
• 

  

  /3

  $64,750

  • Land

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

  ROGO Lot. Letter on hand from Monroe County granting 2 points

  Jenna Stauffer Ocean Sotheby's International Realty

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
• 

  

  /30

  $540,000 Sold Mar 04, 2025

  31353 Avenue E, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 7% Below List Price
  • $662/SF
  • 256 Days On Market

  Current Estimated Value $548,540

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  31353 Avenue E, Big Pine Key, FL 33043
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  /48

  Est $993,124 Not Listed For Sale

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

  27342 Anguila Ln, Summerland Key, FL 33042

  27342 Anguila Ln, Summerland Key, FL 33042
• 

  

  /49

  $999,000 Open House 1/03

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  29559 Ranger Ave, Big Pine Key, FL 33043

  This well desired location and immaculately maintained home is 5 minutes from world class boating, fishing, diving and snorkeling. Located in Pine Channel Estates for the fastest and easiest direct access to the ocean or the endless options of bay-side boating adventures. Boasting a 75' concrete seawall with a 14K boat lift, davits, and drop-down on/off boat access, there is even a dive board for

  Donna Halstead Coldwell Banker Schmitt RE Co.

  29559 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /43

  $950,000 Sold Jun 25, 2025

  3881 Joyce Rd, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 1,428 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $665/SF
  • 69 Days On Market

  Current Estimated Value $963,878

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

  3881 Joyce Rd, Big Pine Key, FL 33043
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  /30

  Est $2,056,622 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,000 Sq Ft

  17082 Starfish Ln W, Summerland Key, FL 33042

  17082 Starfish Ln W, Summerland Key, FL 33042
• 

  

  /8

  $489,500

  • 3 Beds
  • 2 Baths
  • 704 Sq Ft

  3 W Cook, Cook Island Key, FL 33043

  Oceanfront home on offshore island only accessible by boat. This off grid rustic beachfront bungalow has two bedrooms, two baths, and an additional upstairs loft with panoramic views of Cook Island, Atlantic and Coupon Bight. The house amenities include solar power, generator hookup, hot and cold water from rain collecting cistern, inverter a/c units, permitted septic system. Repairable fully

  Stephen Hachey

  3 W Cook, Cook Island Key, FL 33043
• 

  

  /31

  $690,000 Sold May 30, 2025

  29393 Cypress Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1976

  Last Sold Summary

  • 16% Below List Price
  • $781/SF
  • 150 Days On Market

  Current Estimated Value $704,666

  Last Listing Agent Jennifer Weeks Select Properties of NWFL

  29393 Cypress Dr, Big Pine Key, FL 33043
• 

  /2

  Est $1,019,714 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,218 Sq Ft

  17174 Kingfish Ln W, Summerland Key, FL 33042

  17174 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /33

  $278,500

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
• 

  

  /35

  $902,500 Sold Apr 11, 2025

  346 Blackbeard Rd, Summerland Key, FL 33042

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

  Last Sold Summary

  • 8% Below List Price
  • $760/SF
  • 62 Days On Market

  Current Estimated Value $917,620

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  346 Blackbeard Rd, Summerland Key, FL 33042

Showing Results 561 - 600, Page 15 of 18