Summerland Key, FL Homes

• 

  

  /2

  Not Listed For Sale

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042

  1138 Basque Ln, Summerland Key, FL 33042
• 

  

  

  /90

  $3,900,000

  • 4 Beds
  • 3.5 Baths
  • 2,050 Sq Ft

  680 Elma Ave, Big Pine Key, FL 33043

  RARE west-facing private estate offering sunset views, owned bay bottom, and exceptional boating access. Welcome to Tarpon Cove, an exclusive retreat located in Big Pine Key, surrounded by the Florida Key Deer Preserve for unmatched privacy and natural beauty.The concrete residence has been meticulously reconstructed through a down-to-the-studs renovation, resulting in a 2023 effective age and is

  

  Sandra Tuttle

  Island Welcome Real Estate

  (877) 359-5426

  680 Elma Ave, Big Pine Key, FL 33043
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  /11

  $231,000 Sold Sep 25, 2025

  30887 Hammock Dr, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft
  • Built 1966

  Last Sold Summary

  • 18% Below List Price
  • $479/SF
  • 225 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  30887 Hammock Dr, Big Pine Key, FL 33043
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  /61

  Est $2,762,544 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,042 Sq Ft

  20886 4th Ave W, Summerland Key, FL 33042

  20886 4th Ave W, Summerland Key, FL 33042
• 

  

  

  /48

  $299,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

  Income-Producing Gem in Venture Out! Affordable 2BR/1BA Getaway with Resort Amenities.Discover an incredible opportunity to own a piece of the highly sought-after, gated community of Venture Out. This charming 2-bedroom, 1-bathroom home is one of the community's most affordable properties, offering a perfect blend of cozy comfort and exceptional investment potential.Ready for you to move in

  

  Ian Calderwood

  Bluescape Real Estate

  (305) 570-4554

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
• 

  

  /16

  $165,000 Sold Feb 24, 2025

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 8% Below List Price
  • 212 Days On Market

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

  8 Calico Jack Cir, Cudjoe Key, FL 33042
• 

  

  /39

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042
• 

  

  /43

  $1,599,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  17152 Marlin Dr, Summerland Key, FL 33042

  Nestled on a very quiet street in the exclusive community Sugarloaf Shores, this beautifully remodeled CBS Pool Home offers the perfect blend of privacy, entertainment and island charm. Situated on a massive 12,700 sq. ft. lot, this property is a lush sanctuary for gardeners and boaters alike. The backyard is a true private resort, designed for the ultimate outdoor lifestyle featuring a heated

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 692-4942

  17152 Marlin Dr, Summerland Key, FL 33042
• 

  

  /17

  $395,000 Sold Sep 22, 2025

  10W Cooks Unit B, Cook Island Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 596 Sq Ft
  • Built 1948

  Last Sold Summary

  • 12% Below List Price
  • $663/SF
  • 13 Days On Market

  Current Estimated Value $398,000

  Last Listing Agent Greg Gordon Island Home Realty Inc.

  10W Cooks Unit B, Cook Island Key, FL 33043
• 

  /2

  Est $785,000 Not Listed For Sale

  • Studio

  164 Newfound Blvd, Big Pine Key, FL 33043

  164 Newfound Blvd, Big Pine Key, FL 33043
• 

  

  /45

  $1,199,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  30366 Falcon Ln, Big Pine Key, FL 33043

  Fantastic CBS canal front Pool home on a double lot in Tropical Bay Estates. Entering into the large Great Room you will find soaring wood ceilings and an open floor plan boasting a true chef's Kitchen with stainless steel Viking appliances, gas range, and large granite bar to gather around. The spacious screened in Porch overlooks the water and is the perfect place to enjoy outdoor dining.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 231-9107

  30366 Falcon Ln, Big Pine Key, FL 33043
• 

  

  /40

  $1,175,000 Sold Mar 24, 2025

  29541 Flying Cloud Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 988 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $1,189/SF
  • 134 Days On Market

  Current Estimated Value $1,192,061

  Last Listing Agent Nira Tocco Coldwell Banker Schmitt RE Co.

  29541 Flying Cloud Ave, Big Pine Key, FL 33043
• 

  /2

  Est $393,333 Not Listed For Sale

  • Studio

  2112 San Marco Dr, Big Pine Key, FL 33043

  2112 San Marco Dr, Big Pine Key, FL 33043
• 

  

  /71

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

  Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall.* Community

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 977-2397

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
• 

  

  /53

  $900,000 Sold Oct 15, 2025

  31507 Avenue E, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 2017

  Last Sold Summary

  • 8% Below List Price
  • $789/SF
  • 120 Days On Market

  Current Estimated Value $886,896

  Last Listing Agent Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  31507 Avenue E, Big Pine Key, FL 33043
• 

  /2

  Est $395,333 Not Listed For Sale

  • Studio

  2120 San Marco Dr, Big Pine Key, FL 33043

  2120 San Marco Dr, Big Pine Key, FL 33043
• 

  

  /44

  $1,699,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  17094 Coral Dr, Summerland Key, FL 33042

  This beautifully appointed home is located in prestigious Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3 Bedroom 2 Bath 2,000 sq. ft. home a massive Great Room greets you highlighted by a true chef's Kitchen offering lots of custom cabinetry, stainless appliances, 2 wine coolers and large center island for friends

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-7125

  17094 Coral Dr, Summerland Key, FL 33042
• 

  

  /54

  $915,000 Sold Aug 19, 2025

  29737 Newfound Blvd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $866/SF
  • 33 Days On Market

  Current Estimated Value $954,732

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  29737 Newfound Blvd, Big Pine Key, FL 33043
• 

  /2

  Est $941,546 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 854 Sq Ft

  31441 Ave F, Big Pine Key, FL 33043

  31441 Ave F, Big Pine Key, FL 33043
• 

  

  /55

  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  937 Gulf Dr, Summerland Key, FL 33042

  Step into island elegance with this beautifully remodeled 3-bedroom, 2. bath waterfront home in one of the Florida Keys' most coveted boating communities -- Summerland Key Cove. Originally built in 2008 and completely redesigned in 2024, this residence blends contemporary coastal design with the solid construction and storm-safe features that matter most.Modern Coastal Interiors:The interior

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 751-4617

  937 Gulf Dr, Summerland Key, FL 33042
• 

  

  /27

  $1,900,000 Sold Jun 18, 2025

  17022 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • Built 1994

  Last Sold Summary

  • 14% Below List Price
  • $955/SF
  • 85 Days On Market

  Current Estimated Value $1,932,880

  Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

  17022 Starfish Ln W, Summerland Key, FL 33042
• 

  /2

  Est $896,349 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  460 Les Rohde Dr, Ramrod Key, FL 33042

  460 Les Rohde Dr, Ramrod Key, FL 33042
• 

  

  /12

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  744 Trinidad Ln, Summerland Key, FL 33042

  Positioned to capture beautiful open water views of Pine Channel, this property sits in a quiet neighborhood that blends privacy with convenience. Spanning an impressive 12,000 sq ft, this double lot offers a rare opportunity to secure space, flexibility, and open water views in the Lower Keys. Enjoy being just minutes from shopping, restaurants, nightlife, the nature park, and the Big Pine

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 503-8190

  744 Trinidad Ln, Summerland Key, FL 33042
• 

  

  /60

  $2,512,500 Sold Oct 31, 2025

  1260 Sugarloaf Blvd, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,886 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Below List Price
  • $871/SF
  • 60 Days On Market

  Current Estimated Value $2,465,414

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

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  /2

  Est $1,181,658 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  29663 Saratoga Ave, Big Pine Key, FL 33043

  29663 Saratoga Ave, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /58

  $2,025,000 Sold May 13, 2025

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $1,567/SF
  • 85 Days On Market

  Current Estimated Value $2,021,525

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
• 

  /2

  Est $678,073 Not Listed For Sale

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

  31380 Ave G, Big Pine Key, FL 33043

  31380 Ave G, Big Pine Key, FL 33043
• 

  

  /47

  $629,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4104

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
• 

  

  /37

  $540,000 Sold Mar 04, 2025

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $750/SF
  • 9 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  27883 Coral Shores Rd, Little Torch Key, FL 33042
• 

  /2

  Est $240,758 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,087 Sq Ft

  31030 E Ave, Big Pine Key, FL 33043

  31030 E Ave, Big Pine Key, FL 33043
• 

  

  /31

  $430,000

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  Acre of Privacy, your Keys cottage/bungalow in the woods. Artist retreat, man cave or maybe just because you love privacy and want an escape. Horse stables nearby and you can ride horses in this area. Connected to the house by sidewalk and decking is a Screen porch 13 X 18 plus a storge room 9 X 12. Additionally, there are 2 carports, 3 sheds. Space in yard to park your cars, boats, RV. Property

  Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
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  /32

  $635,000 Sold Apr 25, 2025

  2682 Koehns Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Below List Price
  • $509/SF
  • 12 Days On Market

  Current Estimated Value $639,017

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  2682 Koehns Ave, Big Pine Key, FL 33043
• 

  /2

  Est $330,333 Not Listed For Sale

  • Studio

  27328 St Vincent Ln, Ramrod Key, FL 33042

  27328 St Vincent Ln, Ramrod Key, FL 33042
• 

  

  /32

  $975,000

  • 4 Beds
  • 3 Baths
  • 2,503 Sq Ft

  30451 Hibiscus Ln, Big Pine Key, FL 33043

  ONE-OF-A-KIND! Custom-built home '2010'on a large 125 X 250 property, 31,250 sq. ft. more than 1/2 acre. 4bd/3bth plus a bonus room for a total 2493 sqft. Perfect for 2 working professionals from home or a big family. Good size bedrooms. 2 are ensuite. Separate Kitchen Dining & Living Room and an extra room for office or hobbies, gym or guest. Concrete slab under house same size of house so lots

  Rose Dell Keller Williams Key West Compass Realty

  30451 Hibiscus Ln, Big Pine Key, FL 33043
• 

  

  /51

  $975,000 Sold Aug 01, 2025

  527 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2023

  Last Sold Summary

  • 17% Below List Price
  • $812/SF
  • 101 Days On Market

  Current Estimated Value $964,474

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

  527 Heck Ave, Little Torch Key, FL 33042
• 

  

  /49

  Est $351,493 Not Listed For Sale

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
• 

  

  /72

  $1,998,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,639 Sq Ft

  30980 Witters Ln, Big Pine Key, FL 33043

  MODERN ISLAND RETREAT ON BOGIE CHANNEL - BIG PINE KEY, FLDiscover the epitome of Lower Keys living in this luxurious 4-bedroom, 3.5-bath CBS pool home, ideally positioned on Bogie Channel with direct boating access. Built in 2022 and offered furnished, this elevated residence combines modern design, coastal charm, and unmatched functionality.Step inside to soaring ceilings, expansive windows, and

  Donna Pezzi Keller Williams Key West Compass Realty

  30980 Witters Ln, Big Pine Key, FL 33043
• 

  

  /41

  $689,000 Sold Jun 27, 2025

  29873 Journeys End Rd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Below List Price
  • $582/SF
  • 104 Days On Market

  Current Estimated Value $702,058

  Last Listing Agent Heather Bennett Keller Williams Key West Compass Realty

  29873 Journeys End Rd, Big Pine Key, FL 33043
• 

  

  /8

  Est $469,191 Not Listed For Sale

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  17256 Keystone Rd, Sugarloaf Key, FL 33042

Showing Results 281 - 320, Page 8 of 18