11,029

Summerland Key, FL Homes

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    • /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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

    Agent Photo

    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

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