Summerland Key, FL Homes

• 

  

  

  /3

  Not Listed For Sale

  Vacant Lot Diane Rd, Big Pine Key, FL 33043

  Vacant Lot Diane Rd, Big Pine Key, FL 33043
• 

  

  

  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
• 

  

  

  /37

  $642,000 Sold Jul 11, 2025

  31067 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Above List Price
  • $423/SF
  • 9 Days On Market

  Current Estimated Value $673,184

  Last Listing Agent Jared Chiagouris Truman & Co. (KW)

  31067 Avenue C, Big Pine Key, FL 33043
• 

  

  

  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  27772 Astrangia Ave, Summerland Key, FL 33042

  27772 Astrangia Ave, Summerland Key, FL 33042
• 

  

  

  /51

  $1,250,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,166 Sq Ft

  30985 Hibiscus Dr, Big Pine Key, FL 33043

  CBS POOL HOME OFFERS 133 ft. along the 50 ft. wide canal, boat davits, a fish cleaning station and quick access to Bogie Channel, the Atlantic and back country. Dock multiple boats along the 60 ft. concrete seawall with the possibility of adding more dockage. The fenced 19,762 sq. ft. double lot provides a private, park-like setting featuring an inviting, heated pool, outdoor shower, grilling

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 284-4668

  30985 Hibiscus Dr, Big Pine Key, FL 33043
• 

  /2

  $49,000 Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
• 

  /2

  Est $1,021,853 Not Listed For Sale

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

  1581 State Rd Unit 4A, Little Torch Key, FL 33042

  1581 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  /30

  $800,000

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft

  630 Barry Ave, Summerland Key, FL 33042

  Set on a rare 0.68-acre property spanning four lots, this private canal-front home offers exceptional space, water access, and tranquility. With 204.5 feet of canal frontage, a 40-foot wood dock, and less than a 5-minute boat ride to Pine Channel, this location is ideal for boating enthusiasts. The 3-bedroom, 2-bath residence features a roof-covered deck perfect for entertaining friends and

  

  Brenda Thomas

  Island Welcome Real Estate

  (786) 822-8419

  630 Barry Ave, Summerland Key, FL 33042
• 

  

  /3

  $420,000 Sold Jun 27, 2025

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 488 Sq Ft
  • Built 1999

  Last Sold Summary

  • 13% Below List Price
  • $861/SF
  • 0 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  0 Vacant Unit 607262, Saddlebunch, FL 33040
• 

  

  /50

  $799,000 Open Sun 10AM - 12PM

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  1672 Pandorea Ln, Big Pine Key, FL 33043

  Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, an exceptional upgraded

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 410-2419

  1672 Pandorea Ln, Big Pine Key, FL 33043
• 

  

  /38

  $840,000 Sold Sep 30, 2025

  3611 S Seas St, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $787/SF
  • 183 Days On Market

  Current Estimated Value $854,967

  Last Listing Agent Scott Brisson KeyIsle Realty

  3611 S Seas St, Big Pine Key, FL 33043
• 

  

  /14

  Est $410,963 Not Listed For Sale

  • 3 Beds

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  30919 Edward Rd Unit A, Big Pine Key, FL 33043
• 

  

  /34

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  27940 Lobster Tail Trail, Summerland Key, FL 33042

  Discover one of the best waterfront buying opportunities in the Lower Keys! This spacious and well-maintained 3-bedroom, 2-bath manufactured home offers incredible value and lifestyle at just $650,000. Inside, you'll find an open floor plan with updated laminate floors, a bright kitchen, and a large primary suite featuring a big bedroom and a relaxing bath with a soaking tub.Outdoors, enjoy 46

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 218-8749

  27940 Lobster Tail Trail, Summerland Key, FL 33042
• 

  

  /75

  $830,000 Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $841,761

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  /2

  Est $562,218 Not Listed For Sale

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  17172 Marlin Dr, Sugarloaf Shores, FL 33042
• 

  

  /34

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 241-6029

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /68

  $950,000 Sold Apr 11, 2025

  31670 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,227 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $774/SF
  • 28 Days On Market

  Current Estimated Value $929,000

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

  31670 Avenue C, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
• 

  

  /40

  $1,300,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft

  537 Heck Ave, Summerland Key, FL 33042

  Welcome to island living at its finest. This stunning 3-bedroom, 2-bath canal-front home is packed with every bell and whistle you could want in a Florida Keys retreat. Designed for both comfort and entertaining, the property features a private pool, tiki hut, 3 screened in porches boat lift with direct canal access and close to open water with no bridges. Perfect for days on the water and

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (786) 410-6602

  537 Heck Ave, Summerland Key, FL 33042
• 

  

  /41

  $1,105,000 Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Current Estimated Value $1,096,128

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  /2

  Est $200,159 Not Listed For Sale

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  825 Hawksbill Ln, Sugarloaf Key, FL 33042
• 

  

  /41

  $999,000

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

  22954 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 230-1509

  22954 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /57

  $1,375,000 Sold Apr 17, 2025

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  Last Sold Summary

  • 19% Below List Price
  • $765/SF
  • 215 Days On Market

  Current Estimated Value $1,372,540

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
• 

  /2

  Est $3,379,420 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft

  999 Flagship Dr, Summerland Key, FL 33042

  999 Flagship Dr, Summerland Key, FL 33042
• 

  

  /38

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft

  153 Peg Leg Ln, Summerland Key, FL 33042

  Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 853-7147

  153 Peg Leg Ln, Summerland Key, FL 33042
• 

  

  /28

  $632,000 Sold Jul 03, 2025

  28451 Gulf Blvd, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $399/SF
  • 93 Days On Market

  Current Estimated Value $641,037

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  28451 Gulf Blvd, Big Pine Key, FL 33043
• 

  

  /17

  Est $305,961 Not Listed For Sale

  662 Blackbeard Rd, Little Torch Key, FL 33042

  662 Blackbeard Rd, Little Torch Key, FL 33042
• 

  

  /43

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,036 Sq Ft

  420 W Indies Dr, Summerland Key, FL 33042

  Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 666-1028

  420 W Indies Dr, Summerland Key, FL 33042
• 

  

  /115

  $12,250,000 Sold May 07, 2025

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $2,506/SF
  • 44 Days On Market

  Current Estimated Value $4,507,572

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

  785 Sawyer Dr, Cudjoe Key, FL 33042
• 

  

  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042
• 

  

  /45

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  195 W Shore Dr, Summerland Key, FL 33042

  Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, this concrete block home offers the ultimate blend of sky, sea, and space. Featuring a 37' x 27' airplane hangar, 2-car garage, and expansive driveway, this 3-bedroom, 2-bathroom plus bonus/4th Bedroom residence is tailor-made for

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 998-8438

  195 W Shore Dr, Summerland Key, FL 33042
• 

  

  /26

  $390,000 Sold Jul 10, 2025

  27873 Coral Shores Rd, Little Torch Key, FL 33042

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

  Last Sold Summary

  • 19% Below List Price
  • $569/SF
  • 70 Days On Market

  Last Listing Agent Tracy Shields KeyIsle Realty

  27873 Coral Shores Rd, Little Torch Key, FL 33042
• 

  /2

  Est $1,220,002 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  29565 Ranger Ave, Big Pine Key, FL 33043

  29565 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /27

  $987,500

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  3962 No Name Rd, Big Pine Key, FL 33043

  Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (888) 275-1086

  3962 No Name Rd, Big Pine Key, FL 33043
• 

  

  /64

  $809,000 Sold Nov 12, 2025

  3714 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $722/SF
  • 194 Days On Market

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

  3714 Pine St, Big Pine Key, FL 33043
• 

  

  /14

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043
• 

  

  /47

  $1,099,000

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  29051 Magnolia Ln, Big Pine Key, FL 33043

  Welcome to 29051 Magnolia Ln, Big Pine Key, FL! This home offers a 2-bedroom, 2-bath main area and a pre-FIRM permitted 480 sq. ft. studio/MIL suite with a full bath. Nestled on a 5,100 sq. ft. lot, this concrete home is ideal for island living. The chef's kitchen features stainless steel appliances, premium counters, and breakfast bar. Enjoy a screened porch overlooking the canal, complete with

  

  Yvette Toledo-Baste

  Compass Florida, LLC

  (866) 971-5749

  29051 Magnolia Ln, Big Pine Key, FL 33043
• 

  /2

  $144,000 Sold Mar 04, 2025

  Lot 15 Aztec St, Sugarloaf Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 2 Days On Market

  Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 15 Aztec St, Sugarloaf Key, FL 33042
• 

  /2

  Est $920,609 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft

  18954 Acosta Trail, Summerland Key, FL 33042

  18954 Acosta Trail, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18