Summerland Key, FL Homes

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  /61

  $1,449,000

  • 2 Beds
  • 2 Baths
  • 1,372 Sq Ft

  21012 6th Ave, Summerland Key, FL 33042

  Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 666-1284

  21012 6th Ave, Summerland Key, FL 33042
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  /7

  $4,275,000

  Sold Mar 04, 2026

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $1,371/SF
  • 114 Days On Market

  Last Listing Agent Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042
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  /9

  Not Listed For Sale

  Lots 23-24 Coral Way, Big Pine Key, FL 33043

  Lots 23-24 Coral Way, Big Pine Key, FL 33043

  Last Sold Summary

  • 24 Days On Market
• 

  

  

  /12

  $789,900

  Under Contract

  • Land
  • 12,632 Sq Ft
  • $2,723,793 per Acre

  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 Real Estate Co

  (855) 297-2048

  0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
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  /41

  $775,000

  Sold May 01, 2026

  22939 Privateer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1988

  Last Sold Summary

  • $602/SF
  • 3 Days On Market

  Current Estimated Value $845,047

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  22939 Privateer Dr, Summerland 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

  Last Sold Summary

  • 20 Days On Market
• 

  

  /57

  $2,200,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  1631 Sunrise Dr, Big Pine Key, FL 33043

  Experience the pinnacle of Florida Keys waterfront living in this newly constructed (2023) open water home on Big Pine Key. Perfectly positioned to capture breathtaking sunrise views, this CBS-built residence offers a seamless blend of modern coastal design, durability, and effortless indoor-outdoor living. Spanning 1,834 square feet, the home features 3 Bedrooms and 2 Bathrooms, thoughtfully

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (866) 828-4958

  1631 Sunrise Dr, Big Pine Key, FL 33043
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  /36

  $1,120,000

  Sold Mar 24, 2026

  2148 Bahia Shores Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $933/SF
  • 1 Day On Market

  Current Estimated Value $1,193,071

  Last Listing Agent Anne Press Lokation Real Estate

  2148 Bahia Shores Rd, Big Pine Key, FL 33043
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  /11

  Not Listed For Sale

  LOT 38 W Indies Dr, Ramrod Key, FL 33042

  LOT 38 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 144 Days On Market
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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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  /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

  Current Estimated Value $5,337,716

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1151 Ocean Dr, Summerland Key, FL 33042
• 

  

  /20

  Not Listed For Sale

  31048 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft
  • Built 1967

  31048 Avenue J, Big Pine Key, FL 33043

  Last Sold Summary

  • 151 Days On Market
• 

  

  /53

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  29534 Geraldine St, Big Pine Key, FL 33043

  Discover the perfect blend of island lifestyle and income potential in this well-appointed waterfront home located in a desirable Big Pine Key boating community with Commercial Fishing District zoning--a rare advantage allowing marine-based business use, boat storage, and added flexibility.Situated on a 18,000 sq ft double lot with 150' of canal frontage, this solid concrete, single-level home

  

  Sandra Tuttle

  Island Welcome Real Estate

  (844) 697-1109

  29534 Geraldine St, Big Pine Key, FL 33043
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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 $643,990

  Last Listing Agent Lola McKee eXp Realty LLC

  19557 Mayan St, Summerland Key, FL 33042
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  /14

  Est $177,468

  Not Listed For Sale

  27391 W Indies Dr, Ramrod Key, FL 33042

  27391 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 2 Days On Market
• 

  

  /64

  $1,449,900

  $49K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  17215 Bonita Ln E, Sugarloaf Key, FL 33042

  Completely reimagined and absolutely stunning, this beautifully remodeled home in Sugarloaf Shores showcases a full renovation, including a brand new dock. The beautiful 3 Bedroom 2 Bathroom home features commercial grade luxury vinyl floors, beautiful new finishes, custom cabinetry, new appliances, and fresh paint inside and out. Every detail was thoughtfully selected, creating a clean, modern

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (866) 531-7954

  17215 Bonita Ln E, Sugarloaf Key, FL 33042
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  /2

  $48,000

  Sold Mar 13, 2026

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 26% Below List Price
  • 250 Days On Market

  Current Estimated Value $1,295,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
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  /21

  Not Listed For Sale

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

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft
  • Built 1978

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

  Last Sold Summary

  • 0 Days On Market
• 

  

  /74

  $1,750,000

  $40K PRICE DROP

  • 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

  

  Sandra Tuttle

  Island Welcome Real Estate

  (844) 795-0878

  30463 Hawk Ln, Big Pine Key, FL 33043
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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 $842,811

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  554 W Shore Dr, Summerland Key, FL 33042
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  /38

  Est $1,350,145

  Not Listed For Sale

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1994

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  Last Sold Summary

  • 15 Days On Market
• 

  

  /16

  $1,150,000

  $150K PRICE DROP

  • 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
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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 $3,257,763

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  225 Colson Dr, Summerland Key, FL 33042
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  /8

  Est $189,678

  Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 7 Days On Market
• 

  

  /47

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft

  30937 Baileys Ln, Big Pine Key, FL 33043

  Whether you enjoy fishing and diving or prefer kayaking and paddle boarding through the beautiful waters of the Lower Keys, this updated 'Old Keys' home offers the perfect base for quick access to Bogie Channel, the Atlantic, and the backcountry. Situated on a 50' x 100' lot, the 2-story, single-family residence features a cut-in boat slip with a boat lift beneath the expansive great room, along

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  (866) 810-8945

  30937 Baileys Ln, Big Pine Key, FL 33043
• 

  

  /20

  $207,000

  Sold Apr 09, 2026

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

  • Land
  • 1,742 Sq Ft
  • $5,175,000 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 375 Days On Market

  Current Estimated Value $224,910

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
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  /47

  Not Listed For Sale

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  Last Sold Summary

  • 194 Days On Market
• 

  

  /68

  $3,199,000

  • 3 Beds
  • 3 Baths
  • 1,586 Sq Ft

  1148 Big Pine Ave, Big Pine Key, FL 33043

  If you've been dreaming of the kind of place where the sunsets stop you in your tracks...this is it. Tucked away on a quiet road in Big Pine Key, this 2 Bedroom 2 Bath plus 1 Bedroom 1 Bath Guest Cottage one-of-a-kind point property delivers something incredibly rare in the Florida Keys, open water views and protected dockage, all wrapped into a private tropical setting on over an acre and a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (877) 703-1366

  1148 Big Pine Ave, Big Pine Key, FL 33043
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  /24

  $50,000

  Sold May 07, 2026

  13 Yuca Ln, Torch Key, FL 33042

  • Land
  • 5,000 Sq Ft
  • $435,540 per Acre

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Regine Mercier The Keyes Company

  13 Yuca Ln, Torch Key, FL 33042
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  /36

  Est $1,196,753

  Not Listed For Sale

  17246 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2020

  17246 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 23 Days On Market
• 

  

  /19

  $215,000

  $35K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $4,300,000 per Acre

  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

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  (645) 229-8475

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

  

  /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 $1,158,571

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1032 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /20

  Est $278,797

  Not Listed For Sale

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

  • Built 2001

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

  Last Sold Summary

  • 167 Days On Market
• 

  

  /39

  $1,399,000

  $200K PRICE DROP Under Contract

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

  20838 5th Ave W, Cudjoe 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 Real Estate Co

  (877) 473-4184

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

  

  /24

  $310,000

  Sold Apr 16, 2026

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

  • Land
  • 2,178 Sq Ft
  • $6,200,000 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 118 Days On Market

  Current Estimated Value $351,710

  Last Listing Agent Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
• 

  

  /63

  Est $4,572,277

  Not Listed For Sale

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  • 6 Beds
  • 7 Baths
  • 4,200 Sq Ft
  • Built 2023

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 9 Days On Market
• 

  

  /44

  $1,200,000

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  17286 Jamaica Ln, Summerland Key, FL 33042

  Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, fishing, and the easygoing Keys lifestyle right at their doorstep. Set on a quiet street just 15 minutes from Key West, this sturdy concrete 2 bedroom, 2 bath home offers southern exposure overlooking the canal, quick access to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 702-3934

  17286 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /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 $739,192

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  27312 Anguila Ln, Summerland Key, FL 33042
• 

  

  /27

  Est $245,034

  Not Listed For Sale

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

  • 1 Bed
  • Built 1974

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

  Last Sold Summary

  • 161 Days On Market
• 

  

  /51

  $1,099,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  22953 John Silver Ln, Summerland Key, FL 33042

  Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 241-8464

  22953 John Silver Ln, Summerland Key, FL 33042

Showing Results 81 - 120, Page 3 of 18