Summerland Key, FL Homes

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  /46

  $998,000 Sold Sep 09, 2025

  1117 Basque Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft
  • Built 2013

  Last Sold Summary

  • $757/SF
  • 16 Days On Market

  Current Estimated Value $1,000,542

  Last Listing Agent Lynn Goodwin Coldwell Banker Schmitt Real Estate Co.

  1117 Basque Ln, Cudjoe Key, FL 33042
• 

  

  /2

  Est $883,002 Not Listed For Sale

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

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  53 Gold Boullion Rd, Cudjoe Key, FL 33042
• 

  

  

  /33

  $1,195,000

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

  17226 Jamaica Ln, Summerland Key, FL 33042

  Completely remodeled, turn key 3 bed 2 bath canal front home that.backs up to the nature's preserve. Home features large pool with a bar area and 300 square feet enclosed storage ,mature landscaping and concrete wall with automatic gate . Easy boating access from new concrete dock to Atlantic ocean side and the Gulf. Actively profitable Airbnb home

  Stephen Hachey

  17226 Jamaica Ln, Summerland Key, FL 33042
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  /30

  $2,100,000 Sold Mar 26, 2025

  15800 Old State Road 4a, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,548 Sq Ft
  • Built 2006

  Last Sold Summary

  • 19% Below List Price
  • $1,357/SF
  • 154 Days On Market

  Current Estimated Value $2,099,516

  Last Listing Agent Rodrigo Kirilauscas K & A Realty

  15800 Old State Road 4a, Summerland Key, FL 33042
• 

  

  

  /23

  Est $796,209 Not Listed For Sale

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

  27225 Mariposa Rd, Summerland Key, FL 33042

  27225 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /47

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  43 Venetian Way, Summerland Key, FL 33042

  Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

  Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
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  /6

  $14,500 Sold Sep 29, 2025

  0 Vacant Land Unit 616529, Sugarloaf Key, FL 33042

  • Land

  Last Sold Summary

  • 7% Above List Price
  • 4 Days On Market

  Last Listing Agent Sam Williams Coldwell Banker Schmitt Real Estate Co.

  0 Vacant Land Unit 616529, Sugarloaf Key, FL 33042
• 

  /2

  Est $782,329 Not Listed For Sale

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

  27087 Angelfish Rd, Summerland Key, FL 33042

  27087 Angelfish Rd, Summerland Key, FL 33042
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  /45

  $1,399,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  1185 Hakluyt Ln, Summerland Key, FL 33042

  Location, location, location!Situated on the desirable southern tip of Cudjoe Key, this exceptional oceanside property offers everything you could dream of in a true Florida Keys retreat. Enjoy breathtaking open-water views from every room and an inviting open floor plan featuring a newer kitchen, updated appliances, modern bathrooms, refreshed flooring, and upgraded impact windows and

  Greg MacLaren Internet Realty of the Florida Keys

  1185 Hakluyt 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

  Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

  923 Indies Rd, Summerland Key, FL 33042
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  /69

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

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

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

  

  /50

  $1,299,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,464 Sq Ft

  19749 Date Palm Dr, Summerland Key, FL 33042

  An incredible opportunity, especially for those looking for a spacious, 2464 sq ft well-equipped 12-foot stilted custom-built, waterfront home. 4 bedrooms, 3 baths plus a den with recent improvements and updates. Enormous Master bedroom and master bath with a gigantic tub. A huge breathtaking kitchen with stainless steel appliances. The combination of a large living area, open floor plan, modern

  Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

  19749 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /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 $552,974

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

  1620 Buttonwood Dr, Big Pine Key, FL 33043
• 

  

  /14

  Est $387,000 Not Listed For Sale

  29167 Cactus Ln, Big Pine Key, FL 33043

  29167 Cactus Ln, Big Pine Key, FL 33043
• 

  

  /40

  $1,250,000

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

  857 Caribbean Dr E, Summerland Key, FL 33042

  HOME is where the BOAT IS!Discover effortless access to world-class boating on one of the widest, deepest, and most desirable canals in the Lower Keys. Your 17,000-lb boat lift sits on a pristine flow-through canal--meaning clean, clear water and quick access. In just minutes, you can be fishing the Atlantic, exploring the backcountry in the Gulf, or gliding toward a perfect Key West sunset.This

  Donna Pezzi Keller Williams Key West Compass Realty

  857 Caribbean Dr E, Summerland Key, FL 33042
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  /47

  $520,000 Sold Sep 04, 2025

  27853 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $542/SF
  • 117 Days On Market

  Last Listing Agent Leah Scarborough Island Welcome Real Estate

  27853 Coral Shores Rd, Little Torch Key, FL 33042
• 

  /2

  Est $587,000 Not Listed For Sale

  • Studio

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  Lot 2 Egret Ln, Big Pine Key, FL 33043
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  /48

  $1,299,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  24347 Caribbean Dr W, Summerland Key, FL 33042

  Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-water canal with excellent boating access. Boaters will appreciate the new 17,000-lb boat lift and a quick ride to Looe Key, American Shoal, and the Adolf Bush wreck.The 1232 sq ft home sits on a 6,000 sq ft lot and features hurricane-impact windows, offering peace of mind and energy efficiency. The home has

  Shirley Carey Berkshire Hathaway HomeServices Knight & Gardner Realty

  24347 Caribbean Dr W, Summerland Key, FL 33042
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  /30

  $557,235 Sold Apr 11, 2025

  30053 Pine Channel Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,006 Sq Ft
  • Built 1977

  Last Sold Summary

  • 7% Below List Price
  • $554/SF
  • 196 Days On Market

  Current Estimated Value $568,809

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

  30053 Pine Channel Rd, Big Pine Key, FL 33043
• 

  

  /11

  Est $291,789 Not Listed For Sale

  Lot 3 Egret Ln, Big Pine Key, FL 33043

  Lot 3 Egret Ln, Big Pine Key, FL 33043
• 

  

  /45

  $1,249,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  17144 Coral Dr, Summerland Key, FL 33042

  Located in prestigious Sugarloaf Shores, a coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3-bedroom, 2-bath home, a massive Great Room with a cathedral ceiling will greet you, highlighted by remodeled cabinetry, kitchen, and stainless steel appliances, including a gas range, where friends and family can gather. Enjoy the full-length porch

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

  17144 Coral Dr, Summerland Key, FL 33042
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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 $1,028,825

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

  17425 Jamaica Ln, Summerland Key, FL 33042
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  /66

  Not Listed For Sale

  • 2 Beds

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

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

  

  /44

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  27426 Martinique Ln, Summerland Key, FL 33042

  Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

  Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27426 Martinique Ln, Summerland Key, FL 33042
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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

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  681 W Indies Dr, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

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

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

  

  /42

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  29662 Independence Ave, Big Pine Key, FL 33043

  Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads

  Karen Haack Coldwell Banker Schmitt RE Co.

  29662 Independence Ave, Big Pine Key, FL 33043
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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 $3,225,575

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

  23971 Henry St, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
• 

  

  /34

  $1,149,000

  • 3 Beds
  • 3 Baths
  • 2,143 Sq Ft

  1615 Fern Ave, Big Pine Key, FL 33043

  Don't settle for small spaces! Welcome to this spacious and beautifully updated 3-bedroom, 2.5-bath home nestled on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Fully renovated, this two-story home feels open, airy, and inviting throughout.Inside, you'll find a large living room filled with natural light, offering plenty of space for family gatherings. A versatile office/den

  Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1615 Fern Ave, Big Pine Key, FL 33043
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  /2

  $73,000 Sold Feb 21, 2025

  00 Valencia Rd, Cudjoe Key, FL 33042

  • Land
  • 1.01 Acres
  • $72,277 per Acre

  Last Sold Summary

  • 64% Below List Price
  • 36 Days On Market

  Last Listing Agent Jennifer Withers EXP REALTY LLC

  00 Valencia Rd, Cudjoe Key, FL 33042
• 

  /2

  Est $262,234 Not Listed For Sale

  • Studio

  281 Pelican Ln, Big Pine Key, FL 33043

  281 Pelican Ln, Big Pine Key, FL 33043
• 

  

  /21

  $1,269,000 New Construction

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

  325 Pirates Rd, Summerland Key, FL 33042

  **PRICE INCREASE REFLECTS INSTALLATION OF 8'X20' SWIMMING POOL, TO BE COMPLETED BY SUMMER 2026.***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

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  325 Pirates Rd, Summerland Key, FL 33042
• 

  

  /45

  $900,000 Sold Apr 03, 2025

  2250 San Remo Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1989

  Last Sold Summary

  • 9% Below List Price
  • $573/SF
  • 243 Days On Market

  Current Estimated Value $925,846

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

  2250 San Remo Dr, Big Pine Key, FL 33043
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  /35

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 849 Sq Ft

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042
• 

  

  /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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  /33

  $1,350,000 Sold Jul 24, 2025

  20883 4th Ave, Cudjoe Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,524 Sq Ft
  • Built 2011

  Last Sold Summary

  • 21% Below List Price
  • $535/SF
  • 215 Days On Market

  Current Estimated Value $1,619,297

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

  20883 4th Ave, Cudjoe Key, FL 33042
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  /58

  Est $1,726,076 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,548 Sq Ft

  1106 Thatch Ln, Summerland Key, FL 33042

  1106 Thatch Ln, Summerland Key, FL 33042
• 

  

  /33

  $949,000 Pending

  • 2 Beds
  • 3 Baths
  • 1,140 Sq Ft

  151 Cutthroat Dr, Summerland Key, FL 33042

  Move-in ready waterfront 2-bedroom, 2.5-bath home located in desirable Cudjoe Key. The open floor plan features a spacious living and dining area complemented by an upgraded kitchen with new cabinetry, granite countertops, and modern stainless-steel appliances. The main level offers two bedrooms and 1.5 baths, while a permitted full second bath is conveniently located downstairs with easy access

  Heather Bennett Keller Williams Key West Compass Realty

  151 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /39

  $1,725,000 Sold Apr 25, 2025

  474 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1973

  Last Sold Summary

  • 21% Below List Price
  • $1,037/SF
  • 127 Days On Market

  Current Estimated Value $1,721,912

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

  474 Caribbean Dr E, Summerland Key, FL 33042

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