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
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  /28

  $980,000

  • 4 Beds
  • 3 Baths
  • 1,457 Sq Ft

  31441 Avenue F, Big Pine Key, FL 33043

  This solid all-concrete home, situated on a generous 10,000 sq ft double lot, offers the perfect blend of comfort and style for a growing family. Step into the open-concept living area with vaulted ceilings, creating an airy, welcoming atmosphere. The chef-inspired kitchen features beautiful quartz countertops and stainless steel appliances, perfect for cooking and entertaining. Tile floors

  

  Austin Kimbler

  Expert Realty LLC (HQ)

  (844) 559-1544

  31441 Avenue F, 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
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  /49

  $695,000 Under Contract

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

  31134 Hollerich Dr, Big Pine Key, FL 33043

  Motivated Seller, estate sale, turn key, including boat!Don't Miss This Waterfront Opportunity in Big Pine Key! Enjoy the ultimate Florida Keys lifestyle in this spacious 3-bedroom, 2-bath home featuring terrazzo floors, impact-rated doors and windows, and a screened porch overlooking the canal. Boaters and anglers will love the 90-foot concrete, step down seawall, davits and easy access to Bogie

  

  Jennifer Weeks

  Select Properties of NWFL

  (866) 378-6961

  31134 Hollerich Dr, Big Pine Key, FL 33043
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  /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
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  /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
• 

  

  /44

  $1,150,000 Under Contract

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

  21855 Spain Blvd, Summerland Key, FL 33042

  Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (786) 882-7957

  21855 Spain Blvd, Summerland Key, FL 33042
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  /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
• 

  

  /48

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  823 Indies Rd, Ramrod Key, FL 33042

  Fabulous sunset views over the salt ponds at this concrete 3 Bedroom 2 Bath home in Breezeswept Beach Estates. Located towards the end of a very quiet street this home offers a lot of privacy with beautiful views of the bird estuary in front and long views of the canal in the back. Boaters will appreciate the immediate ocean access with no bridges and easy turn around from the 60' step-down dock

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 614-6847

  823 Indies Rd, Ramrod Key, FL 33042
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  /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
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  /62

  $5,200,000

  • 4 Beds
  • 4 Baths
  • 2,660 Sq Ft

  17013 Coral Dr, Summerland Key, FL 33042

  Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 882-3659

  17013 Coral Dr, Summerland Key, FL 33042
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  /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
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  /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
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  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 Sawyer Dr, Summerland 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 for.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
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  /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
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  /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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  /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
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  /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
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  /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
• 

  

  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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