Summerland Key, FL Homes

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  /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

  Current Estimated Value $694,391

  Last Listing Agent David Kaufmann Century 21 Circle

  31120 Avenue J, Big Pine Key, FL 33043
• 

  

  

  /44

  Est $886,348

  Not Listed For Sale

  873 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 2002

  873 Indies Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 123 Days On Market

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.
• 

  

  

  /58

  $1,299,000

  $100K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  885 Hawksbill Ln, Summerland Key, FL 33042

  Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Located at 885 Hawksbill Lane, this waterfront property sits on a 6,120 sq ft lot and features a concrete seawall with boat davits, pavers and a heated swimming pool and spa completed in 2022. Enjoy canal and mangrove views plus

  Tommy Mack Coastal Collection Real Estate Inc.

  885 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  

  /5

  $328,000

  Sold Mar 27, 2026

  28292 Dorothy Ave, Summerland Key, FL 33042

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

  Last Sold Summary

  • $395/SF
  • 4 Days On Market

  Last Listing Agent Lauren Dunn Coldwell Banker Schmitt Islamorada

  28292 Dorothy Ave, Summerland Key, FL 33042
• 

  

  

  /49

  Est $1,841,504

  Not Listed For Sale

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft
  • Built 1989

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty
• 

  

  /45

  $1,269,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  116 Spanish Main Dr, Summerland Key, FL 33042

  Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

  Tina Fingerman Beaches MLS

  116 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /61

  $750,000

  Sold Jul 31, 2026

  17326 Jamaica Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1987

  Last Sold Summary

  • 18% Below List Price
  • $493/SF
  • 115 Days On Market

  Current Estimated Value $862,948

  Last Listing Agent Stephanie Wise Keller Williams Key West Compass Realty

  17326 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $1,772,526

  Not Listed For Sale

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • Built 1963

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  Last Sold Summary

  • 275 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /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
• 

  

  /64

  $1,425,000

  Sold May 28, 2026

  17215 Bonita Ln E, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 2008

  Last Sold Summary

  • 5% Below List Price
  • $933/SF
  • 71 Days On Market

  Current Estimated Value $1,397,797

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17215 Bonita Ln E, Sugarloaf Key, FL 33042
• 

  /2

  Est $1,257,321

  Not Listed For Sale

  19563 Canal Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 1990

  19563 Canal Dr, Summerland Key, FL 33042
• 

  

  /41

  $590,000

  $200K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

  Jeff Shapiro Global Luxury Realty LLC

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /26

  $335,000

  Sold May 12, 2026

  31042 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1987

  Last Sold Summary

  • 16% Below List Price
  • $372/SF
  • 8 Days On Market

  Current Estimated Value $365,933

  Last Listing Agent John Nazzaro Keller Williams Realty Premier Properties - Kendall

  31042 Avenue J, Big Pine Key, FL 33043
• 

  

  /14

  Est $1,264,825

  Not Listed For Sale

  365 Pirates Rd, Summerland Key, FL 33042

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

  365 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.
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  /26

  $465,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft

  30461 Poinciana Rd, Big Pine Key, FL 33043

  Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 bath home, with an office, features a vaulted ceiling, new mini split air condition units, abundance of natural lighting, French doors leading to a large screened in porch, great entertaining area. A large primary bedroom has another screened in porch off the back that is shared with separate1/1 guest suite.

  Dorothy Santiago Keller Williams Realty Professionals (KW)

  30461 Poinciana Rd, Big Pine Key, FL 33043
• 

  

  /36

  $700,000

  Sold Jan 29, 2026

  24830 Park Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2015

  Last Sold Summary

  • 3% Below List Price
  • $589/SF
  • 7 Days On Market

  Current Estimated Value $710,752

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

  24830 Park Dr, Summerland Key, FL 33042
• 

  

  /56

  Est $1,697,564

  Not Listed For Sale

  17159 Amberjack Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1989

  17159 Amberjack Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 258 Days On Market

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty
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  /38

  $1,185,000

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

  706 Caribbean Dr E, Summerland Key, FL 33042

  OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With canal frontage, a 10,000-pound boat lift, and quick ocean access, this property is built for life on the water. The massive 1,188-square-foot garage below is a dream setup for serious boaters, offering space for storage, a workshop,

  Donna Pezzi Keller Williams Key West Compass Realty

  706 Caribbean Dr E, Summerland Key, FL 33042
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  /32

  $1,282,100

  Sold Nov 04, 2025

  32857 Tortuga Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1994

  Last Sold Summary

  • 8% Below List Price
  • $916/SF
  • 23 Days On Market

  Current Estimated Value $1,338,169

  Last Listing Agent Madeleine Young Island Welcome Real Estate LLC

  32857 Tortuga Ln, Big Pine Key, FL 33043
• 

  

  /29

  Est $908,745

  Not Listed For Sale

  27359 Jamaica Ln, Summerland Key, FL 33042

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

  27359 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Fred Mullins Coldwell Banker Schmitt Real Estate Co. (KW)
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  /64

  $1,499,000

  • 3 Beds
  • 3 Baths
  • 1,596 Sq Ft

  21007 4th Ave, Summerland Key, FL 33042

  Wake up to breathtaking Florida Keys sunrises from this exceptional oceanside waterfront home in Cudjoe Key. Offering 1,596 square feet of living space on an 8,920-square-foot lot, this CBS-built residence features 3 bedrooms and 3 bathrooms, + Office/beddroom,combining durability, comfort, and the relaxed island lifestyle you've been dreaming of.Designed for both everyday living and

  Diane Corliss Coldwell Banker Schmitt RE Co.

  21007 4th Ave, Summerland Key, FL 33042
• 

  /2

  $357,000

  Sold Nov 07, 2025

  31145 Hibiscus Dr, Big Pine Key, FL 33043

  • Land
  • 5,399 Sq Ft
  • $2,879,800 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 222 Days On Market

  Current Estimated Value $359,651

  Last Listing Agent Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  31145 Hibiscus Dr, Big Pine Key, FL 33043
• 

  

  /39

  Est $1,430,738

  Not Listed For Sale

  591 Blackbeard Rd, Summerland Key, FL 33042

  • 4 Beds
  • 4.5 Baths
  • 2,512 Sq Ft
  • Built 1989

  591 Blackbeard Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC
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  /56

  $1,150,000

  • 4 Beds
  • 3 Baths
  • 960 Sq Ft

  29565 Flying Cloud Ave, Big Pine Key, FL 33043

  Waterfront retreat with excellent boating access in the heart of Big Pine Key! Home has 15k boat lift, fish cleaning table and clear deep canal. This elevated home features a private dock, canal frontage, and plenty of room for boats, trailers outdoor entertaining and out door showers. Open-concept living areas, abundant natural light, and spacious porches create the perfect Keys getaway or

  Frank Kowalski Metro Dade Realty, Inc.

  29565 Flying Cloud Ave, Big Pine Key, FL 33043
• 

  

  /35

  $560,000

  Sold Aug 29, 2025

  19616 Aztec St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,129 Sq Ft
  • Built 1953

  Last Sold Summary

  • 20% Below List Price
  • $496/SF
  • 196 Days On Market

  Current Estimated Value $593,934

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  19616 Aztec St, Summerland Key, FL 33042
• 

  

  /31

  Est $770,711

  Not Listed For Sale

  4245 Egret Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2002

  4245 Egret Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
• 

  

  /45

  $493,000

  $36K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 758 Sq Ft

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

  MINI LOBSTER SEASON PRICE REDUCTION!!! Price DROPPED AGAIN below 500k! This is THE lowest 2BR/BA priced home in Venture Out on Cudjoe Key! MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
• 

  

  /36

  $840,000

  Sold Jun 26, 2026

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $976/SF
  • 159 Days On Market

  Last Listing Agent Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
• 

  

  /82

  Est $1,880,869

  Not Listed For Sale

  17175 Allamanda Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 1999

  17175 Allamanda Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty
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  /49

  $755,000

  $20K PRICE DROP

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

  19543 Navajo St, Cudjoe Key, FL 33042

  3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

  Pamela Stangler Expert Realty LLC

  19543 Navajo St, Cudjoe Key, FL 33042
• 

  

  /68

  $1,200,000

  Sold Aug 21, 2026

  612 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $745/SF
  • 85 Days On Market

  Current Estimated Value $1,275,257

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  612 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /29

  Est $843,123

  Not Listed For Sale

  22774 Cudjoe Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 1987

  22774 Cudjoe Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  /6

  $1,775,000

  • 4 Beds
  • 4 Baths
  • 1,671 Sq Ft

  193 Galleon Ln, Cudjoe Key, FL 33042

  Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new

  Joaquin Merlo-Garzon CRANELUXE

  193 Galleon Ln, Cudjoe Key, FL 33042
• 

  

  /90

  $1,075,000

  Sold May 11, 2026

  21855 Spain Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $733/SF
  • 28 Days On Market

  Current Estimated Value $1,079,435

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

  21855 Spain Blvd, Summerland Key, FL 33042
• 

  

  /23

  Est $753,411

  Not Listed For Sale

  283 Pirates Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1964

  283 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 148 Days On Market

  Last Listing Agent Cheryl Billings Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
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  /48

  $1,399,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  22939 Gasparilla Ln, Summerland Key, FL 33042

  Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete

  Donna Pezzi Keller Williams Key West Compass Realty

  22939 Gasparilla Ln, Summerland Key, FL 33042
• 

  

  /40

  $635,000

  Sold Aug 29, 2025

  31148 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Built 2003

  Last Sold Summary

  • 9% Below List Price
  • $499/SF
  • 212 Days On Market

  Current Estimated Value $642,355

  Last Listing Agent Sandra Rodriguez Lokation Real Estate

  31148 Avenue C, Big Pine Key, FL 33043
• 

  /2

  Est $783,918

  Not Listed For Sale

  19720 Date Palm Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • Built 1958

  19720 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /4

  $595,000

  $80K PRICE DROP

  • Land
  • 13,503 Sq Ft
  • $1,919,355 per Acre

  2080 Coral Way, Big Pine Key, FL 33043

  Rare opportunity to own a stunning ocean view double lot with 107 feet of canal frontage in sought-after Big Pine Key! Currently #5 in ROGO, this prime property comes with approved building plans—available upon request. The spacious lot offers ample room for your dream home with direct canal access and breathtaking open-water views. Buyers may have the ability to modify the existing plans—please

  Kelly Acosta ARGO GROUP PROPERTIES LLC

  2080 Coral Way, Big Pine Key, FL 33043
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  /58

  $1,164,000

  Sold Dec 12, 2025

  164 Tortuga Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $831/SF
  • 27 Days On Market

  Current Estimated Value $1,156,148

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  164 Tortuga Ln, Summerland Key, FL 33042

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