Summerland Key, FL Homes

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  /53

  $2,650,000

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  1147 Flagship Dr, Summerland Key, FL 33042

  Located on the highly desired Flagship Drive in Summerland Cove Isles, this stunning 3 bedroom, 2 bath home plus a loft offers beautiful views of the salt ponds and open water. As you walk up the front steps, you're greeted by a grand porch that sets the tone for the coastal charm found throughout the home. The split floor plan provides ideal privacy, with two guest bedrooms on one side and a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 758-4228

  1147 Flagship Dr, Summerland Key, FL 33042
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  /81

  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • House for Rent

  441 La Fitte Rd, Summerland Key, FL 33042

  ** SHORT-TERM RENTAL ** Stunning open water house with high ceilings, open floor plan, covered screen porch, and open deck for the sun lovers! New deck with a heavy-duty boat lift in place (15,000 pounds) in one of the cleanest waters in the FL Keys! Metal roof, New A/C, Water Heater, and a Front aluminum fence with beautiful landscaping This home is located in one of the best neighborhoods in

  Carolina Gil Caralex Intl Realty Group Corp

  441 La Fitte Rd, Summerland Key, FL 33042
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  /59

  $860,300 Sold May 02, 2025

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $996/SF
  • 76 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
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  /2

  Est $2,190,438 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,096 Sq Ft

  17015 Wahoo Ln W, Summerland Key, FL 33042

  17015 Wahoo Ln W, Summerland Key, FL 33042
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  /42

  $1,895,000 Under Contract

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

  20771 2nd Ave W, Summerland Key, FL 33042

  Incredible Florida Keys living! High quality concrete construction, impact windows and doors and custom metal roof- this home is ABOVE FLOOD and has no stairs! Enjoy the ease of one level living, with the storm safety of being above flood. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool and tiki! Exceptional boating- the 100' concrete dock

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 952-5792

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

  $1,450 per month

  • Property for Rent

  29859 Overseas Hwy Unit A14, Big Pine Key, FL 33043

  🌴 Big Pine Key Lot for Rent - RV or Tiny Home Ready! 🌴Enjoy the Florida Keys lifestyle in this beautiful lot located in a desirable condominium community in Big Pine Key, just off U.S. 1 and close to everything!🏝️ Community Features:Heated pool for year-round enjoymentWasher/dryer available for tenantsSafe, friendly neighborhoodSteps from the bus stop, shops,

  Graciela Lozano KeysLifestyle Real Estate (KW)

  29859 Overseas Hwy Unit A14, Big Pine Key, FL 33043
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  /5

  $725,000 Sold Jul 30, 2025

  19462 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $520/SF
  • 3 Days On Market

  Current Estimated Value $719,609

  Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty

  19462 Canal Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042
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  /6

  $400,000

  • Land

  21865 Spain Blvd, Summerland Key, FL 33042

  Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (305) 614-8634

  21865 Spain Blvd, Summerland Key, FL 33042
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  /27

  $300,000 Sold Nov 26, 2025

  27983 Snapper Ln, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Below List Price
  • $446/SF
  • 60 Days On Market

  Last Listing Agent Sandra Dolowy KeyIsle Realty

  27983 Snapper Ln, Little Torch Key, FL 33042
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  /5

  Est $1,340,213 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,881 Sq Ft

  354 Airport Dr S, Summerland Key, FL 33042

  354 Airport Dr S, Summerland Key, FL 33042
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  /36

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,039 Sq Ft

  29048 Iris Dr, Big Pine Key, FL 33043

  Located on a 50-foot-wide canal, this updated 3-bedroom, 2-bath home provides good boating access to Pine Channel, the Atlantic Ocean, and the backcountry. The great room features a cathedral ceiling, abundant natural light from a south-facing picture window, and French doors opening to a covered porch with canal views. Upgrades include impact-resistant windows and doors, new stainless steel

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 528-3127

  29048 Iris Dr, Big Pine Key, FL 33043
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  /101

  $4,700,000 Sold Feb 21, 2025

  29433 Enterprise Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 5 Baths
  • 3,727 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $1,261/SF
  • 25 Days On Market

  Current Estimated Value $4,716,891

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  29433 Enterprise Ave, Big Pine Key, FL 33043
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  /11

  Not Listed For Sale

  0 4th St Unit A&B 608914, Summerland Key, FL 33042

  0 4th St Unit A&B 608914, Summerland Key, FL 33042
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  /17

  $999,000

  • Land

  21082 6th Ave, Summerland Key, FL 33042

  An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 300-6302

  21082 6th Ave, Summerland Key, FL 33042
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  /2

  $55,000 Sold Oct 22, 2025

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 2 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042
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  /49

  Est $815,194 Not Listed For Sale

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

  29765 Osprey Ln, Big Pine Key, FL 33043

  29765 Osprey Ln, Big Pine Key, FL 33043
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  /63

  $2,450,000

  • 3 Beds
  • 3 Baths
  • 2,486 Sq Ft

  30468 Oleander Blvd, Big Pine Key, FL 33043

  Discover the easygoing charm of the Lower Keys at this .81-acre waterfront estate, featuring a two-bedroom, two-bath main house and a one-bedroom, one-bath guest cottage with views over Bogie Channel. Enjoy leisurely days entertaining under the large poolside tiki hut or on the covered platform at the end of the 463-foot pier--perfect for relaxing with family and friends while watching sunsets

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (877) 796-4209

  30468 Oleander Blvd, Big Pine Key, FL 33043
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  /46

  $1,390,000 Sold Aug 26, 2025

  229 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $1,207/SF
  • 30 Days On Market

  Current Estimated Value $1,358,207

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

  229 Caribbean Dr E, Summerland Key, FL 33042
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  /2

  Est $311,309 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042
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  /66

  $539,000

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
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  /29

  $740,000 Sold Oct 31, 2025

  27138 Dolphin Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2022

  Last Sold Summary

  • 14% Below List Price
  • $561/SF
  • 181 Days On Market

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  27138 Dolphin Rd, Summerland Key, FL 33042
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  /2

  Est $552,361 Not Listed For Sale

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

  27188 Dolphin Rd, Ramrod Key, FL 33042

  27188 Dolphin Rd, Ramrod Key, FL 33042
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  /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
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  /47

  $1,100,000 Sold Jun 27, 2025

  21014 7th Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $808/SF
  • 102 Days On Market

  Current Estimated Value $1,093,941

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

  21014 7th Ave, Summerland Key, FL 33042
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  /3

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  27732 Astrangia Ave, Little Torch Key, FL 33042

  27732 Astrangia Ave, Little Torch Key, FL 33042
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  /34

  $695,000

  • 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 $695,000. 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
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  /52

  $1,130,000 Sold Feb 05, 2025

  1348 Ocean Dr, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 930 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $1,215/SF
  • 64 Days On Market

  Current Estimated Value $1,126,960

  Last Listing Agent Jennifer Chaney Chaney Homes

  1348 Ocean Dr, Summerland Key, FL 33042
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  /14

  Not Listed For Sale

  12, 13, 14 Cook Island, Cook Island Key, FL 33043

  12, 13, 14 Cook Island, Cook Island Key, FL 33043
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  /45

  $1,250,000

  • 4 Beds
  • 2.5 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 Real E

  (888) 284-4668

  30985 Hibiscus Dr, Big Pine Key, FL 33043
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  /32

  $700,000 Sold May 14, 2025

  226 Newfound Blvd, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 3% Below List Price
  • $729/SF
  • 17 Days On Market

  Current Estimated Value $706,339

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  226 Newfound Blvd, Big Pine Key, FL 33043
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  /20

  Est $653,876 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 552 Sq Ft

  31342 Avenue I, Big Pine Key, FL 33043

  31342 Avenue I, Big Pine Key, FL 33043
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  /40

  $1,300,000

  • 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
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  /24

  $485,000 Sold May 23, 2025

  1923 Narcissus Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 1,506 Sq Ft
  • Built 1974

  Last Sold Summary

  • 22% Below List Price
  • $322/SF
  • 74 Days On Market

  Current Estimated Value $545,661

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  1923 Narcissus Ave, Big Pine Key, FL 33043
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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
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  /37

  $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
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  /45

  $1,700,000 Sold Feb 13, 2025

  20942 6th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $613/SF
  • 42 Days On Market

  Current Estimated Value $1,771,629

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

  20942 6th Ave W, Summerland Key, FL 33042
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  /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
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  /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
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  /34

  $600,000 Sold Sep 22, 2025

  19557 Mayan St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $607/SF
  • 186 Days On Market

  Current Estimated Value $606,004

  Last Listing Agent Lola McKee eXp Realty LLC

  19557 Mayan St, Summerland Key, FL 33042

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