Summerland Key, FL Homes

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  /41

  $1,099,990

  New Construction $69K PRICE DROP

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

  325 Pirates Rd, Summerland Key, FL 33042

  *POOL PLANS IN HAND FOR 12X22 POOL, WITH POOL QUOTE* Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  325 Pirates Rd, Summerland Key, FL 33042
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  /34

  $629,500

  Sold Sep 30, 2025

  31463 Avenue A, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $484/SF
  • 24 Days On Market

  Current Estimated Value $635,886

  Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt RE Co.

  31463 Avenue A, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  Last Sold Summary
• 

  

  

  /7

  $895,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  22817 Privateer Dr, Summerland Key, FL 33042

  Experience elevated island living in this beautifully renovated concrete home located in the heart of Cudjoe Key. Situated on desirable Privateer Drive, this stunning 4-bedroom, 1,800 square-foot residence perfectly combines modern upgrades, durable construction, and tropical outdoor luxury.Thoughtfully redesigned with stylish finishes and an open-concept layout, the home offers spacious

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  22817 Privateer Dr, Summerland Key, FL 33042
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  /34

  $580,000

  Sold Sep 15, 2025

  30868 Malaga Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $537/SF
  • 137 Days On Market

  Current Estimated Value $656,275

  Last Listing Agent Loren Rea Truman & Co. (KW)

  30868 Malaga Ln, Big Pine Key, FL 33043
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  /4

  Est $257,865

  Not Listed For Sale

  31373 Avenue C, Big Pine Key, FL 33043

  • 2 Beds
  • Built 1971

  31373 Avenue C, Big Pine Key, FL 33043

  Last Sold Summary

  • 116 Days On Market
• 

  

  /68

  $879,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

  This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
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  /51

  $1,200,000

  Sold Jun 16, 2025

  1060 W Shore Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2.5 Baths
  • 2,137 Sq Ft
  • Built 1977

  Last Sold Summary

  • 23% Below List Price
  • $562/SF
  • 26 Days On Market

  Current Estimated Value $1,514,929

  Last Listing Agent Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

  1060 W Shore Dr, Big Pine Key, FL 33043
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  /28

  Est $1,839,778

  Not Listed For Sale

  27385 St Lucie Ln, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,988 Sq Ft
  • Built 1987

  27385 St Lucie Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 0 Days On Market
• 

  

  /41

  $800,000

  • Land

  33000 Old State Road 4a, No Name Key, FL 33043

  YOU CAN HELP SAVE THE FLORIDA KEYS REEFS..!!THIS 20 ACRE PARCEL WITH A 17 ACRE SALTWATER LAKE WAS RECENTLY MARKETED AS A PRIVATE LAKE FOR PERSONAL USE. IT MAY STILL BE USED FOR THAT. THIS PROPERTY CANNOT BE DEVELOPED...!!!! NO HOME, NO COMMERCIAL USE. HOWEVER IN RECENT MONTHS RESEARCHERS FROM FLORIDA INTERNATIONAL UNIVERSITY HAVE BEEN STUDYING THE GROWTH OF SPIDER CRABS THAT THRIVE ON ALGAE. THE

  Tony Paterniti Tony Paterniti

  33000 Old State Road 4a, No Name Key, FL 33043
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  /40

  $640,000

  Sold Sep 15, 2025

  3806 Dyer Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $702/SF
  • 54 Days On Market

  Current Estimated Value $671,088

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

  3806 Dyer Rd, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  31119 Avenue I, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft
  • Built 1961

  31119 Avenue I, Big Pine Key, FL 33043

  Last Sold Summary
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  /35

  $530,000

  $10K PRICE DROP

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

  27967 Coral Shores Rd, Little Torch Key, FL 33042

  Canal-front living at its finest! This beautifully remodeled 2-bedroom, 2-bath home is truly a must-see. Step inside to discover a bright and inviting interior featuring new flooring, an updated kitchen, and stylishly renovated bathrooms. The home is enhanced with numerous impact windows, filling the space with natural light and added peace of mind.Relax and unwind on the screened patio, or

  Diane Corliss Coldwell Banker Schmitt RE Co.

  27967 Coral Shores Rd, Little Torch Key, FL 33042
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  /57

  $925,000

  Sold Mar 13, 2026

  2123 Spanish Channel Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $781/SF
  • 49 Days On Market

  Current Estimated Value $912,374

  Last Listing Agent Anne Press Lokation Real Estate

  2123 Spanish Channel Dr, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  29527 Constitution Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1982

  29527 Constitution Ave, Big Pine Key, FL 33043

  Last Sold Summary
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  /28

  $758,000

  $80K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  3856 Donna Rd, Big Pine Key, FL 33043

  30k Price Improvement, Priced to SELL, Motivated Seller, Bring all Offers. Sportsman Paradise. 2 Bedroom House with Permitted Concrete BOAT RAMP, concrete sea wall, concrete fish cleaning table with Permitted downstairs bathroom. Real short idle to open water. Back country fishing, lobster diving/snorkel and stone crabs right in your back yard. Easy access to to Atlantic & Looe Key. Lots of

  Alan Ballas Alan Ballas Realty

  3856 Donna Rd, Big Pine Key, FL 33043
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  /9

  $100,000

  Sold Oct 29, 2025

  4W Cook Island, Big Pine Key, FL 33043

  • Land
  • 14,809 Sq Ft
  • $294,126 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 194 Days On Market

  Current Estimated Value $129,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

  4W Cook Island, Big Pine Key, FL 33043
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  /2

  Est $857,184

  Not Listed For Sale

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2016

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  Last Sold Summary
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  /4

  $1,050,000

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  27403 Antigua Ln, Summerland Key, FL 33042

  Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light

  Sonia Petraitis Caffroni Capital Intl Realty LLC

  27403 Antigua Ln, Summerland Key, FL 33042
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  /37

  $800,000

  Sold Dec 19, 2025

  923 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $741/SF
  • 60 Days On Market

  Current Estimated Value $810,968

  Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

  923 Indies Rd, Summerland Key, FL 33042
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  /23

  Est $748,659

  Not Listed For Sale

  27225 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2017

  27225 Mariposa Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 382 Days On Market
• 

  

  /20

  $550,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  27910 Porgie Path, Summerland Key, FL 33042

  Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping.

  Alexis Seldin Xcellence

  27910 Porgie Path, Summerland Key, FL 33042
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  /25

  $500,000

  Sold Aug 19, 2025

  1620 Buttonwood Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft
  • Built 1974

  Last Sold Summary

  • 28% Below List Price
  • $490/SF
  • 265 Days On Market

  Current Estimated Value $570,959

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1620 Buttonwood Dr, Big Pine Key, FL 33043
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  /2

  Est $820,242

  Not Listed For Sale

  27087 Angelfish Rd, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2020

  27087 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 145 Days On Market
• 

  

  /25

  $615,000

  $35K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  31243 E Ave E, Big Pine Key, FL 33043

  **Price Improvement** Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is an ideal opportunity for families or first-time homebuyers seeking the quintessential Florida Keys lifestyle. Step inside to discover a comfortable and inviting living space, perfect for creating lasting memories. Outside, a small, fenced area provides a safe and convenient space for

  Sabre Mendoza Coldwell Banker Schmitt RE Co.

  31243 E Ave E, Big Pine Key, FL 33043
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  /42

  $1,750,000

  Sold Feb 26, 2026

  20771 2nd Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft
  • Built 2010

  Last Sold Summary

  • 17% Below List Price
  • $855/SF
  • 161 Days On Market

  Current Estimated Value $1,795,710

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  20771 2nd Ave W, Summerland Key, FL 33042
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  /69

  Not Listed For Sale

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft
  • Built 1988

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  Last Sold Summary

  • 461 Days On Market
• 

  /2

  $54,000

  $6K PRICE DROP

  • Land

  0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043

  ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

  Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043
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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 $1,006,025

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17425 Jamaica Ln, Summerland Key, FL 33042
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  /14

  Est $454,000

  Not Listed For Sale

  29167 Cactus Ln, Big Pine Key, FL 33043

  29167 Cactus Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 121 Days On Market
• 

  

  /39

  $698,000

  $1K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  30881 Witters Ln, Big Pine Key, FL 33043

  Updated cottage with all the necessities you need with minimal maintenance. This CBS home has a newer metal roof, mini split A/c, updated kitchen on 3 lots only a very short ride to Boggie Channel, the only market channel to the Atlantic and Gulf in the Lower Keys. This is a great opportunity for boaters and naturalist as this is only a short walk or kayak to No Name Key and surrounding waters

  John Nazzaro Keller Williams Realty Premier Properties - Kendall

  30881 Witters Ln, Big Pine Key, FL 33043
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  /43

  $815,000

  Sold Jan 23, 2026

  681 W Indies Dr, Summerland Key, FL 33042

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

  Last Sold Summary

  • 18% Below List Price
  • $894/SF
  • 211 Days On Market

  Current Estimated Value $806,912

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  681 W Indies Dr, Summerland Key, FL 33042
• 

  /2

  Est $344,667

  Not Listed For Sale

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  • Studio

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  Last Sold Summary
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  /4

  $400,000

  • Land
  • 1,400 Acres
  • $286 per Acre

  27378 Jamaica Ln, Summerland Key, FL 33042

  ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

  Patricia Borges Borges Realty Group LLC

  27378 Jamaica Ln, Summerland Key, FL 33042
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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 $3,197,257

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  23971 Henry St, Summerland Key, FL 33042
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  /66

  Not Listed For Sale

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

  • 2 Beds
  • Built 1978

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

  Last Sold Summary

  • 78 Days On Market
• 

  

  /17

  $255,000

  $10K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $5,100,000 per Acre

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

  Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
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  /24

  $360,000

  Sold Apr 27, 2026

  27735 Sea Whip St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Built 1978

  Last Sold Summary

  • 16% Below List Price
  • $349/SF
  • 12 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  27735 Sea Whip St, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2001

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  Last Sold Summary
• 

  

  /65

  $4,000

  $1K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 888 Sq Ft

  30361 Hardin Rd, Big Pine Key, FL 33043

  270' OF CANAL FRONTAGE & TWO CONCRETE DOCKS (70' + 54') - Welcome to the Blue Heron Estate, the ultimate waterfront compound for the serious boater and nature lover. Nestled on an expansive, fenced 15,045-square-foot lot within the tranquil National Key Deer Refuge, this newly renovated contemporary masterpiece offers a level of scale and privacy rarely found in a rental. With two massive

  Maris Delgado LoKation Real Estate - Key Largo

  30361 Hardin Rd, Big Pine Key, FL 33043

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