8,628

Summerland Key, FL Homes

Section Image
    • 273 Indies Rd, Summerland Key, FL 33042
      273 Indies Rd, Summerland Key, FL 33042
      273 Indies Rd, Summerland Key, FL 33042
      /16

      Est $865,252 Not Listed For Sale

      273 Indies Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,086 Sq Ft
      • Built 1996
      273 Indies Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 6% Above List Price
      • $852/SF
      • 237 Days On Market

      Last Sold Price $925,000

      Last Listing Agent Kathleen Gomez Coldwell Banker Schmitt RE Co.

  • 860 Lagoon Dr, Summerland Key, FL 33042
    860 Lagoon Dr, Summerland Key, FL 33042
    860 Lagoon Dr, Summerland Key, FL 33042
    /28

    $1,950,000

    • 3 Beds
    • 3 Baths
    • 1,797 Sq Ft

    860 Lagoon Dr, Summerland Key, FL 33042

    This stately concrete home has all the best of everything on one of the best boating areas in the Lower KeysThis home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's

    Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

    860 Lagoon Dr, Summerland Key, FL 33042
  • 3715 Pine St, Big Pine Key, FL 33043
    3715 Pine St, Big Pine Key, FL 33043
    3715 Pine St, Big Pine Key, FL 33043
    /32

    $825,000 Sold Apr 09, 2025

    3715 Pine St, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1993

    Last Sold Summary

    • 8% Below List Price
    • $859/SF
    • 4 Days On Market

    Current Estimated Value $839,328

    Last Listing Agent Maggie Beall Lokation Real Estate

    3715 Pine St, Big Pine Key, FL 33043
    • 1141 Ocean Dr, Summerland Key, FL 33042
      1141 Ocean Dr, Summerland Key, FL 33042
      1141 Ocean Dr, Summerland Key, FL 33042
      /62

      Est $4,766,488 Not Listed For Sale

      1141 Ocean Dr, Summerland Key, FL 33042

      • 5 Beds
      • 5 Baths
      • 3,421 Sq Ft
      • Built 2005
      1141 Ocean Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $1,473/SF
      • 22 Days On Market

      Last Sold Price $5,040,000

      Last Listing Agent Lisa Swanson The Agency Florida Keys

  • 3686 Gulfstream St, Big Pine Key, FL 33043
    3686 Gulfstream St, Big Pine Key, FL 33043
    3686 Gulfstream St, Big Pine Key, FL 33043
    /40

    $810,000

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

    3686 Gulfstream St, Big Pine Key, FL 33043

    Key Deer, Quick Access to Pine Channel, Canal Views & Updated Island Living: Your Florida Keys Dream Awaits!Imagine: breathtaking sunsets painting the sky, the gentle presence of Key Deer just outside your fence, and the tranquility of canal-front living in the heart of the National Key Deer Refuge. This charming 2-bedroom, 2-bathroom home offers a rare opportunity to live in harmony with nature

    Robert Smithwick Engel & Volkers Marathon

    3686 Gulfstream St, Big Pine Key, FL 33043
  • 28212 Gato Rd, Summerland Key, FL 33042
    28212 Gato Rd, Summerland Key, FL 33042
    28212 Gato Rd, Summerland Key, FL 33042
    /35

    $669,000 Sold Oct 24, 2025

    28212 Gato Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,077 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $621/SF
    • 80 Days On Market

    Current Estimated Value $671,131

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    28212 Gato Rd, Summerland Key, FL 33042
    • 716 Caribbean Dr E, Summerland Key, FL 33042
      716 Caribbean Dr E, Summerland Key, FL 33042
      716 Caribbean Dr E, Summerland Key, FL 33042
      /37

      Est $1,231,212 Not Listed For Sale

      716 Caribbean Dr E, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1983
      716 Caribbean Dr E, Summerland Key, FL 33042

      Last Sold Summary

      • 12% Above List Price
      • $803/SF
      • 19 Days On Market

      Last Sold Price $1,099,000

      Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  • 20844 4th Ave W, Summerland Key, FL 33042
    20844 4th Ave W, Summerland Key, FL 33042
    20844 4th Ave W, Summerland Key, FL 33042
    /61

    $2,795,000

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft

    20844 4th Ave W, Summerland Key, FL 33042

    FISHERMAN'S DREAM! BIG BOATS WELCOME! DEEP WATER! LARGE WATERFRONT HOME in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of luxury and comfort. All new impact windows &

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • 1659 Long Beach Dr, Big Pine Key, FL 33043
    1659 Long Beach Dr, Big Pine Key, FL 33043
    1659 Long Beach Dr, Big Pine Key, FL 33043
    /45

    $1,910,000 Sold Feb 26, 2026

    1659 Long Beach Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $1,146/SF
    • 7 Days On Market

    Current Estimated Value $1,988,398

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1659 Long Beach Dr, Big Pine Key, FL 33043
    • 20995 2nd Ave W, Summerland Key, FL 33042
      20995 2nd Ave W, Summerland Key, FL 33042
      20995 2nd Ave W, Summerland Key, FL 33042
      /40

      Est $2,177,676 Not Listed For Sale

      20995 2nd Ave W, Summerland Key, FL 33042

      • 3 Beds
      • 2.5 Baths
      • 2,184 Sq Ft
      • Built 2007
      20995 2nd Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Above List Price
      • $1,053/SF
      • 6 Days On Market

      Last Sold Price $2,300,000

      Last Listing Agent Gloria Sellers Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 28571 Buccaneer Rd, Summerland Key, FL 33042
    28571 Buccaneer Rd, Summerland Key, FL 33042
    28571 Buccaneer Rd, Summerland Key, FL 33042
    /40

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,034 Sq Ft

    28571 Buccaneer Rd, Summerland Key, FL 33042

    Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large island

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    28571 Buccaneer Rd, Summerland Key, FL 33042
  • 22882 Buccaneer Ln, Summerland Key, FL 33042
    22882 Buccaneer Ln, Summerland Key, FL 33042
    22882 Buccaneer Ln, Summerland Key, FL 33042
    /41

    $650,000 Sold Jul 01, 2025

    22882 Buccaneer Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1984

    Last Sold Summary

    • 19% Below List Price
    • $580/SF
    • 81 Days On Market

    Current Estimated Value $693,519

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

    22882 Buccaneer Ln, Summerland Key, FL 33042
    • 17279 Oleander Ln, Sugarloaf Key, FL 33042
      17279 Oleander Ln, Sugarloaf Key, FL 33042
      17279 Oleander Ln, Sugarloaf Key, FL 33042
      /49

      Est $6,696,546 Not Listed For Sale

      17279 Oleander Ln, Sugarloaf Key, FL 33042

      • 10 Beds
      • 11.5 Baths
      • 10,607 Sq Ft
      • Built 1992
      17279 Oleander Ln, Sugarloaf Key, FL 33042

      Last Sold Summary

      • 10% Above List Price
      • $698/SF
      • 7 Days On Market

      Last Sold Price $7,400,000

      Last Listing Agent Lisa Swanson The Agency Florida Keys

  • 29030 Iris Dr, Big Pine Key, FL 33043
    29030 Iris Dr, Big Pine Key, FL 33043
    29030 Iris Dr, Big Pine Key, FL 33043
    /26

    $625,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,353 Sq Ft

    29030 Iris Dr, Big Pine Key, FL 33043

    This 3BR spacious canal front home with quick open water access is nestled at the end of a quiet dead-end street. Amidst lush vegetation, this property offers the ultimate sanctuary for those seeking privacy and a connection to the Keys lifestyle. 50ft concrete seawall with 10,000lb boat lift. This home boasts an inviting shaded deck creating the perfect outdoor space for relaxation and

    Justyn Ewald Expert Realty LLC (HQ)

    29030 Iris Dr, Big Pine Key, FL 33043
  • 17177 Bonita Ln W, Summerland Key, FL 33042
    17177 Bonita Ln W, Summerland Key, FL 33042
    17177 Bonita Ln W, Summerland Key, FL 33042
    /42

    $1,450,000 Sold Jun 23, 2025

    17177 Bonita Ln W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft
    • Built 1978

    Last Sold Summary

    • 19% Below List Price
    • $1,018/SF
    • 362 Days On Market

    Current Estimated Value $1,465,004

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17177 Bonita Ln W, Summerland Key, FL 33042
    • 2035 Long Beach Dr, Big Pine Key, FL 33043
      2035 Long Beach Dr, Big Pine Key, FL 33043
      2035 Long Beach Dr, Big Pine Key, FL 33043
      /38

      Est $2,299,685 Not Listed For Sale

      2035 Long Beach Dr, Big Pine Key, FL 33043

      • 5 Beds
      • 3 Baths
      • 1,181 Sq Ft
      • Built 2016
      2035 Long Beach Dr, Big Pine Key, FL 33043

      Last Sold Summary

      • 4% Above List Price
      • $2,036/SF
      • 6 Days On Market

      Last Sold Price $2,405,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • 29678 Enterprise Ave, Big Pine Key, FL 33043
    29678 Enterprise Ave, Big Pine Key, FL 33043
    29678 Enterprise Ave, Big Pine Key, FL 33043
    /20

    $1,295,000

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    29678 Enterprise Ave, Big Pine Key, FL 33043

    Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean,

    Thomas Carden Keys to the Coast Real Estate LLC

    29678 Enterprise Ave, Big Pine Key, FL 33043
  • 23086 Snapper Ln, Summerland Key, FL 33042
    23086 Snapper Ln, Summerland Key, FL 33042
    23086 Snapper Ln, Summerland Key, FL 33042
    /52

    $2,300,000 Sold Sep 12, 2025

    23086 Snapper Ln, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,586 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $889/SF
    • 147 Days On Market

    Current Estimated Value $2,226,471

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    23086 Snapper Ln, Summerland Key, FL 33042
    • 31625 Warner St, Big Pine Key, FL 33043
      31625 Warner St, Big Pine Key, FL 33043
      31625 Warner St, Big Pine Key, FL 33043
      /30

      Est $942,036 Not Listed For Sale

      31625 Warner St, Big Pine Key, FL 33043

      • 1 Bed
      • 1 Bath
      • 650 Sq Ft
      • Built 1937
      31625 Warner St, Big Pine Key, FL 33043

      Last Sold Summary

      • 6% Below List Price
      • $1,538/SF
      • 3 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent Shane Wilson Cypress Realty, Inc.

  • 28177 Julia Ave, Little Torch Key, FL 33042
    28177 Julia Ave, Little Torch Key, FL 33042
    28177 Julia Ave, Little Torch Key, FL 33042
    /6

    $240,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    28177 Julia Ave, Little Torch Key, FL 33042

    Opportunity to purchase for land value in Little Torch Key. Large lot with existing mobile home on site that is not habitable. Property is being marketed as land only. Lot is zoned IS (Improved Subdivision District), which typically allows for single-family residential construction subject to Monroe County Land Development Code and applicable ROGO requirements. Conveniently located less than 5

    Maria Acosta Keller Williams Capital Realty

    28177 Julia Ave, Little Torch Key, FL 33042
  • 31129 Avenue G, Big Pine Key, FL 33043
    31129 Avenue G, Big Pine Key, FL 33043
    31129 Avenue G, Big Pine Key, FL 33043
    /32

    $455,000 Sold Feb 25, 2026

    31129 Avenue G, Big Pine Key, FL 33043

    • 3 Beds
    • 3 Baths
    • 844 Sq Ft
    • Built 1994

    Last Sold Summary

    • $539/SF
    • 52 Days On Market

    Last Listing Agent Ted Stewart Truman & Co. (KW)

    31129 Avenue G, Big Pine Key, FL 33043
    • 93 Venetian Way, Summerland Key, FL 33042
      93 Venetian Way, Summerland Key, FL 33042
      93 Venetian Way, Summerland Key, FL 33042
      /40

      Est $926,433 Not Listed For Sale

      93 Venetian Way, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1983
      93 Venetian Way, Summerland Key, FL 33042

      Last Sold Summary

      • 18% Above List Price
      • $481/SF
      • 11 Days On Market

      Last Sold Price $785,000

      Last Listing Agent Heather Mason Coastal Collection Real Estate Inc.

  • 29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
    /17

    $199,900 Under Contract

    • 2 Beds
    • 1 Bath
    • 300 Sq Ft

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043

    Live affordably or invest wisely in this 8 year old tiny home located on its own private lot in Big Pine Key, Lower Keys. This 24 ft Cornerstone model with two lofts is in perfect condition, thoughtfully maintained, and completely move in ready. The exterior has been newly repainted, and the interior is impeccably kept, showing pride of ownership throughout. The open living space includes a

    Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
  • 92 Frazier Ln, Summerland Key, FL 33042
    92 Frazier Ln, Summerland Key, FL 33042
    92 Frazier Ln, Summerland Key, FL 33042
    /42

    $630,000 Sold Jul 21, 2025

    92 Frazier Ln, Summerland Key, FL 33042

    • 2 Beds
    • 3 Baths
    • 768 Sq Ft
    • Built 1980

    Last Sold Summary

    • 9% Below List Price
    • $820/SF
    • 43 Days On Market

    Current Estimated Value $566,646

    Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    92 Frazier Ln, Summerland Key, FL 33042
    • 27018 Angelfish Rd, Summerland Key, FL 33042
      27018 Angelfish Rd, Summerland Key, FL 33042
      27018 Angelfish Rd, Summerland Key, FL 33042
      /48

      Est $620,278 Not Listed For Sale

      27018 Angelfish Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1992
      27018 Angelfish Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Below List Price
      • $651/SF
      • 15 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Monica Barrett Coldwell Banker Schmitt Real Estate Co.

  • 131 Doubloon Ln, Summerland Key, FL 33042
    131 Doubloon Ln, Summerland Key, FL 33042
    131 Doubloon Ln, Summerland Key, FL 33042
    /34

    $980,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    131 Doubloon Ln, Summerland Key, FL 33042

    3BR/2BA waterfront home on Doubloon Lane offering classic Florida Keys living and relaxation. Features include a pool, large covered patio, sun deck, and a 10,000-lb boat lift, ideal for boating and outdoor enjoyment. Upstairs living area includes impact windows and a new hot water heater (2024).The downstairs area includes two large storage rooms, one of which features a fully functioning

    Bea Evelyn Citron Compass Florida, LLC

    131 Doubloon Ln, Summerland Key, FL 33042
  • 27384 Barbuda Ln, Summerland Key, FL 33042
    27384 Barbuda Ln, Summerland Key, FL 33042
    27384 Barbuda Ln, Summerland Key, FL 33042
    /16

    $785,000 Sold Jul 25, 2025

    27384 Barbuda Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft
    • Built 1993

    Last Sold Summary

    • 17% Below List Price
    • $668/SF
    • 125 Days On Market

    Current Estimated Value $816,941

    Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

    27384 Barbuda Ln, Summerland Key, FL 33042
    • 221 Cutthroat Dr, Summerland Key, FL 33042
      221 Cutthroat Dr, Summerland Key, FL 33042
      221 Cutthroat Dr, Summerland Key, FL 33042
      /19

      Est $895,009 Not Listed For Sale

      221 Cutthroat Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1985
      221 Cutthroat Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 4% Above List Price
      • $881/SF
      • 498 Days On Market

      Last Sold Price $930,000

      Last Listing Agent Aryl and Pati Robison RE/MAX

  • Lot 10 Rainbow Beach, Big Torch Key, FL 33042
    Lot 10 Rainbow Beach, Big Torch Key, FL 33042
    Lot 10 Rainbow Beach, Big Torch Key, FL 33042
    /3

    $60,000

    • Land

    Lot 10 Rainbow Beach, Big Torch Key, FL 33042

    Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

    Shanti Cope Coldwell Banker Schmitt Key Largo

    Lot 10 Rainbow Beach, Big Torch Key, FL 33042
  • 365 Pirates Rd, Summerland Key, FL 33042
    365 Pirates Rd, Summerland Key, FL 33042
    365 Pirates Rd, Summerland Key, FL 33042
    /14

    $1,250,000 Sold Aug 11, 2025

    365 Pirates Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $893/SF
    • 47 Days On Market

    Current Estimated Value $1,232,194

    Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

    365 Pirates Rd, Summerland Key, FL 33042
    • 27310 W Indies Dr, Summerland Key, FL 33042
      27310 W Indies Dr, Summerland Key, FL 33042
      /2

      Est $1,118,149 Not Listed For Sale

      27310 W Indies Dr, Summerland Key, FL 33042

      • 2 Beds
      • 3 Baths
      • 1,120 Sq Ft
      • Built 1984
      27310 W Indies Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 6% Below List Price
      • $1,058/SF

      Last Sold Price $1,185,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
    /5

    $139,000

    • Land

    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

    Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

    Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
  • 28550 Doubloon Rd, Summerland Key, FL 33042
    28550 Doubloon Rd, Summerland Key, FL 33042
    28550 Doubloon Rd, Summerland Key, FL 33042
    /59

    $900,000 Sold Oct 31, 2025

    28550 Doubloon Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,371 Sq Ft
    • Built 1996

    Last Sold Summary

    • 18% Below List Price
    • $380/SF
    • 181 Days On Market

    Current Estimated Value $964,830

    Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

    28550 Doubloon Rd, Summerland Key, FL 33042
    • 27328 Jamaica Ln, Summerland Key, FL 33042
      27328 Jamaica Ln, Summerland Key, FL 33042
      27328 Jamaica Ln, Summerland Key, FL 33042
      /36

      Est $917,266 Not Listed For Sale

      27328 Jamaica Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,518 Sq Ft
      • Built 1979
      27328 Jamaica Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 23% Below List Price
      • $787/SF
      • 22 Days On Market

      Last Sold Price $1,195,000

      Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  • 17385 Keystone Rd, Summerland Key, FL 33042
    17385 Keystone Rd, Summerland Key, FL 33042
    17385 Keystone Rd, Summerland Key, FL 33042
    /74

    $2,995,000

    • 4 Beds
    • 4 Baths
    • 1,804 Sq Ft

    17385 Keystone Rd, Summerland Key, FL 33042

    Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. (24,662 sqft Upland & 12,477 submerged). These point lots are extremely limited and among the most

    Lisa Swanson The Agency Florida Keys

    17385 Keystone Rd, Summerland Key, FL 33042
  • 31120 Avenue J, Big Pine Key, FL 33043
    31120 Avenue J, Big Pine Key, FL 33043
    31120 Avenue J, Big Pine Key, FL 33043
    /24

    $710,000 Sold Dec 18, 2025

    31120 Avenue J, Big Pine Key, FL 33043

    • 2 Beds
    • 1.5 Baths
    • 864 Sq Ft
    • Built 2022

    Last Sold Summary

    • 9% Below List Price
    • $822/SF
    • 83 Days On Market

    Current Estimated Value $713,629

    Last Listing Agent David Kaufmann Century 21 Circle

    31120 Avenue J, Big Pine Key, FL 33043
    • 17153 Buttonwood Dr W, Summerland Key, FL 33042
      17153 Buttonwood Dr W, Summerland Key, FL 33042
      17153 Buttonwood Dr W, Summerland Key, FL 33042
      /61

      Est $1,993,494 Not Listed For Sale

      17153 Buttonwood Dr W, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,426 Sq Ft
      • Built 1998
      17153 Buttonwood Dr W, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Above List Price
      • $1,473/SF
      • 30 Days On Market

      Last Sold Price $2,100,000

      Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

  • 701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    /49

    $985,000

    • 2 Beds
    • 2 Baths
    • 888 Sq Ft

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

    Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
  • 28292 Dorothy Ave, Summerland Key, FL 33042
    28292 Dorothy Ave, Summerland Key, FL 33042
    28292 Dorothy Ave, Summerland Key, FL 33042
    /5

    $328,000 Sold Mar 27, 2026

    28292 Dorothy Ave, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 830 Sq Ft
    • Built 1975

    Last Sold Summary

    • $395/SF
    • 4 Days On Market

    Last Listing Agent Lauren Dunn Coldwell Banker Schmitt Islamorada

    28292 Dorothy Ave, Summerland Key, FL 33042
    • 17056 Wahoo Ln, Summerland Key, FL 33042
      17056 Wahoo Ln, Summerland Key, FL 33042
      17056 Wahoo Ln, Summerland Key, FL 33042
      /39

      Est $1,724,582 Not Listed For Sale

      17056 Wahoo Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2.5 Baths
      • 1,426 Sq Ft
      • Built 1992
      17056 Wahoo Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 24% Above List Price
      • $978/SF
      • 232 Days On Market

      Last Sold Price $1,395,000

      Last Listing Agent Lisa Swanson The Agency Florida Keys

Showing Results 481 - 520, Page 13 of 18

Florida Monroe County Summerland Key

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