Summerland Key, FL Homes

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  /42

  $1,900,000 Sold Jun 29, 2025

  20867 5th Ave W, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 2011

  Last Sold Summary

  • 5% Below List Price
  • $1,116/SF
  • 17 Days On Market

  Current Estimated Value $1,897,096

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

  20867 5th Ave W, Cudjoe Key, FL 33042
• 

  

  /2

  Est $1,086,543 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  17277 Dolphin St E, Summerland Key, FL 33042

  17277 Dolphin St E, Summerland Key, FL 33042
• 

  

  

  /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
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  /75

  $950,000 Sold Apr 30, 2025

  529 W Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1991

  Last Sold Summary

  • 21% Below List Price
  • $990/SF
  • 75 Days On Market

  Current Estimated Value $1,061,034

  Last Listing Agent Everett Smith Ocean Sotheby's International Realty

  529 W Shore Dr, Summerland Key, FL 33042
• 

  

  /2

  Est $1,161,785 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft

  421 W Indies, Ramrod Key, FL 33042

  421 W Indies, Ramrod Key, FL 33042
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  /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
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  /71

  $3,150,000 Sold Aug 28, 2025

  225 Colson Dr, Summerland Key, FL 33042

  • 6 Beds
  • 7 Baths
  • 4,976 Sq Ft
  • Built 2010

  Last Sold Summary

  • 10% Below List Price
  • $633/SF
  • 118 Days On Market

  Current Estimated Value $3,193,088

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

  225 Colson Dr, Summerland Key, FL 33042
• 

  /2

  Est $2,151,514 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
• 

  

  /43

  $1,999,000

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

  1659 Long Beach Dr, Big Pine Key, FL 33043

  Experience refined coastal living at this newly renovated oceanfront residence on prestigious Long Beach Drive in Big Pine Key. Perfectly positioned along a rare stretch of natural shoreline, this property offers an expansive private sandy beach that feels like your own secluded escape, paired with sweeping sunrise to sunset views over the Atlantic Ocean. This 3 bedroom, 2 bathroom home showcases

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 389-9201

  1659 Long Beach Dr, Big Pine Key, FL 33043
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  /32

  $450,000 Sold Mar 19, 2025

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 256 Days On Market

  Current Estimated Value $443,650

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 609, Cudjoe 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
• 

  

  /12

  $789,900

  • Land

  0 Dominica Ln Unit 615842, Ramrod Key, FL 33042

  Gorgeous Open Ocean location totaling 4 lots, boasting over a quarter acre of land with sheltered canal and private beach; an incredible investment opportunity! Build your dream home in paradise with a transferable building right, which are readily available on the market and provide an easy path to development. This unique opportunity is in the ideal location, on one of the last remaining Open

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 744-6884

  0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
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  /32

  $1,830,000 Sold Apr 02, 2025

  17023 Allamanda Dr W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $1,658/SF
  • 77 Days On Market

  Current Estimated Value $1,787,980

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17023 Allamanda Dr W, Summerland Key, FL 33042
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  /5

  Est $1,368,015 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

  $750,000

  • Land
  • 9.26 Acres
  • $80,995 per Acre

  0 Niles Rd, Summerland Key, FL 33042

  Discover the perfect opportunity to build your dream home in the Lower Keys on this desirable parcel located on Summerland Key, FL. Set within a peaceful residential neighborhood, this property offers an inviting blend of tranquility and convenience—just minutes from US-1, local marinas, boat ramps, dining, beaches, and world-class fishing. Enjoy the relaxed island lifestyle, tropical breezes,

  

  Javier Santana

  Sunland Real Estate, LLC.

  (786) 504-0768

  0 Niles Rd, Summerland Key, FL 33042
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  /43

  $1,150,000 Sold Sep 22, 2025

  1032 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1990

  Last Sold Summary

  • 18% Below List Price
  • $833/SF
  • 175 Days On Market

  Current Estimated Value $1,142,264

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1032 Caribbean Dr E, Summerland Key, FL 33042
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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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  /48

  $1,999,999

  • 3 Beds
  • 4 Baths
  • 2,100 Sq Ft

  23087 Sailfish Ln, Summerland Key, FL 33042

  Designed for those who live by the tides, this extraordinary waterfront residence captures everything that defines the Florida Keys lifestyle. Situated on a rare 15,625 sq ft double lot with 175 feet of deep-water dockage, the home enjoys a premier location one in from open water, delivering sweeping open water views while remaining protected within a wide 50-foot canal. Architecturally striking,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 807-9315

  23087 Sailfish Ln, Summerland Key, FL 33042
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  /37

  $705,000 Sold Aug 21, 2025

  27312 Anguila Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $614/SF
  • 127 Days On Market

  Current Estimated Value $734,941

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

  27312 Anguila Ln, Summerland Key, FL 33042
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  /33

  Est $628,706 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 888 Sq Ft

  30361 Harding Rd, Big Pine Key, FL 33043

  30361 Harding Rd, Big Pine Key, FL 33043
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  /64

  $1,790,000

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft

  30463 Hawk Ln, Big Pine Key, FL 33043

  Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living.Outdoors, the home transforms into a

  

  Sandra Tuttle

  Island Welcome Real Estate

  (844) 795-0878

  30463 Hawk Ln, Big Pine Key, FL 33043
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  /39

  $912,250 Sold Apr 03, 2025

  22879 Blackbeard Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $679/SF
  • 43 Days On Market

  Current Estimated Value $935,603

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22879 Blackbeard Ln, Summerland Key, FL 33042
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  /49

  Est $832,882 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
• 

  

  /16

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  715 Caribbean Dr E, Summerland Key, FL 33042

  Experience the ultimate Florida Keys lifestyle at 715 Caribbean Drive East in Summerland Key. Located in a desirable boating and aviation community, this property offers rare access to a private neighborhood airstrip, ideal for pilots and aviation enthusiasts. Designed for boaters, the home features a 60-foot dock and a 15,000-lb boat lift, providing easy access to open water, nearby sandbars,

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  (844) 920-0831

  715 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /29

  $800,000 Sold Feb 27, 2025

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $966/SF
  • 14 Days On Market

  Last Listing Agent Susan Rich Select Properties of NWFL

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
• 

  /2

  Est $306,879 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
• 

  

  /19

  $225,000

  • Land

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

  Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 761-5180

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
• 

  

  /31

  $725,000 Sold Jan 05, 2026

  27235 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $532/SF
  • 127 Days On Market

  Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

  27235 Mariposa Rd, Summerland Key, FL 33042
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  /2

  Est $570,623 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
• 

  

  /39

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  20838 5th Ave W, Summerland Key, FL 33042

  Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 952-7261

  20838 5th Ave W, Summerland Key, FL 33042
• 

  

  /35

  $817,500 Sold Dec 01, 2025

  22878 Privateer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $862/SF
  • 133 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22878 Privateer Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /60

  $490,000

  • 2 Beds
  • 1 Bath
  • 667 Sq Ft

  701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 981-9841

  701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
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  /83

  $3,300,000 Sold Jul 11, 2025

  16705 Tamarind Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 3,086 Sq Ft
  • Built 2015

  Last Sold Summary

  • 27% Below List Price
  • $1,069/SF
  • 299 Days On Market

  Current Estimated Value $3,191,925

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  16705 Tamarind Rd, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /66

  $799,000

  • 2 Beds
  • 2 Baths
  • 842 Sq Ft

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

  Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 841-6970

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
• 

  

  /3

  $75,000 Sold Oct 10, 2025

  0 Asturias Rd, Cudjoe Key, FL 33042

  • Land
  • 1.01 Acres
  • $74,124 per Acre

  Last Sold Summary

  • 62% Below List Price
  • 41 Days On Market

  Last Listing Agent Maryann Warren Coldwell Banker - Ft. Lauderdale

  0 Asturias Rd, Cudjoe Key, FL 33042
• 

  

  /20

  Est $673,958 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
• 

  

  /55

  $1,500,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042

  Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (866) 528-5667

  21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042
• 

  /2

  $600,000 Sold Jul 14, 2025

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 14% Below List Price
  • $735/SF
  • 56 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

Showing Results 121 - 160, Page 4 of 18