Summerland Key, FL Homes

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  /68

  $2,985,000 Open Sun 11AM - 2PM

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

  23941 Henry St, Summerland Key, FL 33042

  Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (786) 686-4688

  23941 Henry St, Summerland Key, FL 33042
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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 $728,303

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

  19462 Canal Dr, Summerland Key, FL 33042
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  /63

  Est $2,002,545 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,366 Sq Ft

  17057 Bonita Ln W, Sugarloaf Key, FL 33042

  17057 Bonita Ln W, Sugarloaf Key, FL 33042
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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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  /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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  /9

  Not Listed For Sale

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Lot 8 Overseas Hwy, Summerland 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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  /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 $4,750,677

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  29433 Enterprise Ave, Big Pine Key, FL 33043
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  /51

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 167, Cudjoe 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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  /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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  /6

  Not Listed For Sale

  3 Rd Ave Unit 1, Big Pine Key, FL 33043

  3 Rd Ave Unit 1, Big Pine Key, FL 33043
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  /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
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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 $1,395,423

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

  229 Caribbean Dr E, Summerland Key, FL 33042
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  /14

  Est $473,333 Not Listed For Sale

  27391 W Indies Dr, Ramrod Key, FL 33042

  27391 W Indies Dr, Ramrod Key, FL 33042
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  /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
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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

  Current Estimated Value $748,492

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  27138 Dolphin Rd, Summerland Key, FL 33042
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  /21

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
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  /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
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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 $1,089,929

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

  21014 7th Ave, Summerland Key, FL 33042
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  /38

  Est $1,288,891 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042
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  /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
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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 $705,273

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  226 Newfound Blvd, Big Pine Key, FL 33043
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  /8

  Est $252,707 Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042
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  /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
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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 $559,379

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  1923 Narcissus Ave, Big Pine Key, FL 33043
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  /63

  Est $4,681,405 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 4,200 Sq Ft

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042
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  /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
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  /55

  $5,003,500 Sold Jan 05, 2026

  1151 Ocean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 6 Baths
  • 3,952 Sq Ft
  • Built 2007

  Last Sold Summary

  • 28% Below List Price
  • $1,266/SF
  • 47 Days On Market

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  1151 Ocean Dr, Summerland Key, FL 33042
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  /27

  Est $231,008 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
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  /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
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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 $1,821,365

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

  20942 6th Ave W, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042
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  /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
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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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  /30

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 392, Cudjoe 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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  /64

  $815,422 Sold Nov 06, 2025

  554 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • Built 1963

  Last Sold Summary

  • 9% Below List Price
  • $580/SF
  • 34 Days On Market

  Current Estimated Value $847,656

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  554 W Shore Dr, Summerland Key, FL 33042
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  /33

  Est $872,275 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  28120 County Rd, Little Torch Key, FL 33042

  28120 County Rd, Little Torch Key, FL 33042
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  /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

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