Summerland Key, FL Homes

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  /2

  $570,000

  Sold Jul 17, 2025

  3767 Hibiscus St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $594/SF
  • 6 Days On Market

  Current Estimated Value $616,897

  Last Listing Agent Ryan Call REALTY ZOOM

  3767 Hibiscus St, Big Pine Key, FL 33043
• 

  

  

  /39

  Est $1,282,196

  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
• 

  

  

  /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
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  /2

  $1,650,000

  Sold Sep 03, 2025

  743 E Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $944/SF
  • 1 Day On Market

  Current Estimated Value $2,138,608

  Last Listing Agent Scott Brisson KeyIsle Realty

  743 E Shore Dr, Summerland Key, FL 33042
• 

  

  

  /31

  Est $746,588

  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
• 

  

  /66

  $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
• 

  

  /11

  $475,000

  Sold May 27, 2026

  19264 Acosta Trail, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 832 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $571/SF
  • 9 Days On Market

  Current Estimated Value $483,690

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  19264 Acosta Trail, Summerland Key, FL 33042
• 

  

  /82

  Est $1,849,994

  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
• 

  

  /45

  $499,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 758 Sq Ft

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

  4th of JULY PRICE REDUCTION!!! Price DROPPED 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 access to the

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
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  /4

  $700,000

  Sold Apr 23, 2026

  20963 7th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Below List Price
  • $450/SF

  Current Estimated Value $902,229

  Last Listing Agent Wyelda Bierman Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  20963 7th Ave W, Summerland Key, FL 33042
• 

  

  /29

  Est $873,387

  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
• 

  

  /46

  $759,000

  $16K 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
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  /49

  $995,000

  Sold Dec 23, 2025

  29462 Geraldine St, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 1991

  Last Sold Summary

  • 9% Below List Price
  • $444/SF
  • 65 Days On Market

  Current Estimated Value $1,041,933

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  29462 Geraldine St, Big Pine Key, FL 33043
• 

  

  /23

  Est $718,514

  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
• 

  

  /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
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  /42

  $925,000

  Sold May 29, 2026

  29664 Saratoga Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 2,129 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $434/SF
  • 46 Days On Market

  Current Estimated Value $1,009,341

  Last Listing Agent Halley Haack Coldwell Banker Schmitt RE Co.

  29664 Saratoga Ave, Big Pine Key, FL 33043
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  /2

  Est $747,957

  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
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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
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  /39

  $1,300,000

  Sold Jun 05, 2026

  20838 5th Ave W, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1987

  Last Sold Summary

  • 19% Below List Price
  • $669/SF
  • 187 Days On Market

  Current Estimated Value $1,443,071

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20838 5th Ave W, Cudjoe Key, FL 33042
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  /64

  Est $1,090,245

  Not Listed For Sale

  184 Cutthroat Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1963

  184 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 151 Days On Market
• 

  

  /31

  $925,000

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  31364 Avenue J, Big Pine Key, FL 33043

  Open Waterfront Double Lot with Protected Boating and Endless PossibilitiesDiscover the best of Florida Keys waterfront living on this spacious double lot located on a quiet street on the open water with 150 feet of protective canal frontage with seawall, this property offers direct boating access to both the backcountry and the Atlantic Ocean and is only one lot in from the mouth of the canal

  Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

  31364 Avenue J, Big Pine Key, FL 33043
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  /28

  $510,500

  Sold Aug 14, 2025

  31124 Avenue E, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $560/SF
  • 17 Days On Market

  Current Estimated Value $501,820

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  31124 Avenue E, Big Pine Key, FL 33043
• 

  

  /58

  Est $1,809,567

  Not Listed For Sale

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1988

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 85 Days On Market
• 

  

  /4

  $675,000

  • Land
  • 13,503 Sq Ft
  • $2,177,419 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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  /32

  $670,000

  Sold Jun 15, 2026

  27999 Lobster Tail Trail, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $570/SF
  • 148 Days On Market

  Current Estimated Value $692,165

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  27999 Lobster Tail Trail, Little Torch Key, FL 33042
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  /4

  Est $899,169

  Not Listed For Sale

  27456 Martinique Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,108 Sq Ft
  • Built 1976

  27456 Martinique Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 0 Days On Market
• 

  

  /53

  $2,375,000

  • 5 Beds
  • 4 Baths
  • 2,772 Sq Ft

  205 S Point Dr, Summerland Key, FL 33042

  Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views. The primary suite is a private

  Dawn McComish Lokation Real Estate

  205 S Point Dr, Summerland Key, FL 33042
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  /18

  $415,000

  Sold Jun 26, 2026

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  • Land
  • 2,178 Sq Ft
  • $8,300,000 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 228 Days On Market

  Current Estimated Value $442,778

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
• 

  

  /45

  Est $2,115,009

  Not Listed For Sale

  19527 Indian Mound Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,752 Sq Ft
  • Built 1996

  19527 Indian Mound Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 96 Days On Market
• 

  

  /41

  $849,000

  $120K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,277 Sq Ft

  29544 Independence Ave, Big Pine Key, FL 33043

  GREAT INVESTMENT OPPORTUNITY! $849,000 Best price property in Pine Channel Estates, Big Pine Key. Fully furnished. Remodeled 2 bdrm/2 full bath + BONUS room (3rd bdrm/office). 75' Canal frontage. Total sq.ft. 1934 w/heated sq.ft. 1277. All new SS appliances. Metal roof, impact windows and garage door, vinyl siding, tankless water heater, gutters, hurricane shutters, fence, covered patio, large

  Jennifer Sylvia Keller Williams Key West Compass Realty

  29544 Independence Ave, Big Pine Key, FL 33043
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  /62

  $1,185,000

  Sold Oct 06, 2025

  22915 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $882/SF
  • 37 Days On Market

  Current Estimated Value $1,228,912

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  22915 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /20

  Est $1,686,248

  Not Listed For Sale

  4244 Dorn Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1984

  4244 Dorn Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 368 Days On Market
• 

  

  /94

  $3,300,000

  $200K PRICE DROP Under Contract

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042

  Experience the ultimate island lifestyle in this breathtaking waterfront residence located in the prestigious Sugarloaf Shores subdivision. Situated on a massive 25,482 sq. ft. lot, this property offers rare privacy with plenty of room to breathe.Built with solid CBS construction, this 5-bedroom, 4-bath home is designed to capture the beauty of its surroundings. The open living space and

  Daniel Urban Expert Realty LLC (HQ)

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042
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  /34

  $1,300,000

  Sold Aug 18, 2025

  22822 John Silver Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 2002

  Last Sold Summary

  • 19% Below List Price
  • $619/SF
  • 214 Days On Market

  Current Estimated Value $1,392,458

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  22822 John Silver Ln, Summerland Key, FL 33042
• 

  

  /56

  Est $2,664,599

  Not Listed For Sale

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft
  • Built 1975

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market
• 

  

  /71

  $2,069,000

  • 3 Beds
  • 2 Baths
  • 1,849 Sq Ft

  1733 Sunrise Dr, Big Pine Key, FL 33043

  Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

  Norman De la Cruz Florida Realty of Miami Corp

  1733 Sunrise Dr, Big Pine Key, FL 33043
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  /42

  $749,000

  Sold Sep 19, 2025

  28009 Gulf Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $743/SF
  • 88 Days On Market

  Current Estimated Value $756,232

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  28009 Gulf Blvd, Big Pine Key, FL 33043
• 

  

  /52

  Est $1,291,577

  Not Listed For Sale

  570 La Fitte Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 2020

  570 La Fitte Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 126 Days On Market
• 

  

  /52

  $749,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  629 Powell Ave, Summerland Key, FL 33042

  Welcome to 629 Powell Drive in Little Torch Key, the lowest-priced fully stilted CBS home currently available in the Lower Florida Keys. This elevated 2-bedroom, 1-bath canal-front home offers the ideal combination of affordability, boating access, and island living. Built for peace of mind, the home features a 2018 metal roof, accordion shutters on the doors, and panel shutters for the windows.

  Coby Taylor Expert Realty LLC (HQ)

  629 Powell Ave, Summerland Key, FL 33042
• 

  /2

  $55,000

  Sold Dec 04, 2025

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

  • Land
  • 6,000 Sq Ft
  • $399,300 per Acre

  Last Sold Summary

  • 90% Above List Price
  • 73 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

Showing Results 601 - 640, Page 16 of 18