Summerland Key, FL Homes

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  /70

  $1,435,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft

  29562 Saratoga Ave, Big Pine Key, FL 33043

  Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and

  

  Ryan Gernaat

  Coldwell Banker Schmitt Lower Keys (KW)

  29562 Saratoga Ave, Big Pine Key, FL 33043
• 

  

  

  /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 $1,404,471

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

  229 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  

  /3

  Not Listed For Sale

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  Last Sold Summary

  • 206 Days On Market
• 

  

  

  /34

  $1,575,000

  $20K PRICE DROP

  • 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 RE Co.

  22865 Redfish Ln, Summerland Key, FL 33042
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  /68

  $2,250,000

  Sold Apr 03, 2026

  24266 Caribbean Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Below List Price
  • $1,095/SF
  • 14 Days On Market

  Current Estimated Value $2,283,117

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  24266 Caribbean Dr W, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /71

  $2,795,000

  Open Sun 4PM - 6PM $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,913 Sq Ft

  20920 5th Ave W, Summerland Key, FL 33042

  Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

  

  Miriam Novotny

  Compass Florida, LLC

  20920 5th Ave W, Summerland Key, FL 33042
• 

  

  /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 $777,862

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  27138 Dolphin Rd, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /45

  $799,000

  $126K PRICE DROP

  • 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 Real Estate Co

  195 W Shore Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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
• 

  

  /70

  $2,800,000

  • 4 Beds
  • 3 Baths
  • 3,286 Sq Ft

  21640 Overseas Hwy, Summerland Key, FL 33042

  SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  21640 Overseas Hwy, Summerland 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 $772,519

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  22939 Privateer Dr, Summerland Key, FL 33042
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  /14

  Est $193,854

  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
• 

  

  /69

  $3,400,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft

  1083 Labat Ln, Cudjoe Key, FL 33042

  Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

  

  Sandra Tuttle

  Island Welcome Real Estate

  1083 Labat Ln, Cudjoe Key, FL 33042
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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 $1,130,535

  Last Listing Agent Anne Press Lokation Real Estate

  2148 Bahia Shores Rd, Big Pine Key, FL 33043
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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
• 

  

  /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

  3962 No Name Rd, Big Pine Key, FL 33043
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  /67

  $3,150,000

  Sold Jun 09, 2026

  270 E Caribbean Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,375 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $1,326/SF
  • 22 Days On Market

  Current Estimated Value $2,722,116

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  270 E Caribbean Dr, Summerland Key, FL 33042
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  /38

  Est $1,340,710

  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
• 

  

  /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

  21012 6th 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

  Current Estimated Value $5,352,024

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

  1151 Ocean Dr, Summerland Key, FL 33042
• 

  

  /8

  Est $206,393

  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
• 

  

  /48

  $899,000

  $51K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  29114 Cedar Dr, Big Pine Key, FL 33043

  Extra adjoining lot adds additional seawall frontage and provides plenty of room for a pool, extra recreational space, and additional parking at this beautifully updated waterfront property in Big Pine Key. This well-maintained home features impact-resistant windows and doors, along with a tranquil canal-side screened porch that creates the perfect setting to relax and enjoy the Florida Keys

  

  Lynn Goodwin

  Coldwell Banker Schmitt Real Estate Co.

  29114 Cedar Dr, Big Pine Key, FL 33043
• 

  

  /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 $648,925

  Last Listing Agent Lola McKee eXp Realty LLC

  19557 Mayan St, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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

  1631 Sunrise Dr, Big Pine Key, FL 33043
• 

  /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 $49,000

  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
• 

  

  /36

  Est $1,234,591

  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
• 

  

  /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.

  0 Niles Rd, 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 $916,582

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  554 W Shore Dr, Summerland Key, FL 33042
• 

  

  /20

  Est $275,480

  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
• 

  

  /16

  $549,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042

  Canal-front Paradise Awaits! Incredible view from your back deck!Unit 424 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

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042
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  /71

  $3,150,000

  Sold Aug 28, 2025

  225 Colson Dr, Summerland Key, FL 33042

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

  Last Sold Summary

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

  Current Estimated Value $3,381,094

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  225 Colson Dr, Summerland Key, FL 33042
• 

  

  /63

  Est $4,303,320

  Not Listed For Sale

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

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

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 9 Days On Market
• 

  

  /52

  $1,195,000

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

  29534 Geraldine St, Big Pine Key, FL 33043

  Turnkey and move-in ready, this exceptional waterfront home is being offered fully furnished--including furniture, dishes, cookware, and linens--so you can start enjoying the Florida Keys lifestyle from day one. Situated on an oversized 18,000 sq. ft. double lot with 150' of canal frontage in a quiet, peaceful Big Pine Key boating community, this solid concrete 3BD/2BA home features a desirable

  

  Sandra Tuttle

  Island Welcome Real Estate

  29534 Geraldine St, 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 $224,109

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

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

  

  /27

  Est $248,869

  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

  $2,499,000

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

  27348 Dominica Ln, Ramrod Key, FL 33042

  Welcome to your waterfront retreat on Ramrod Key, where beautiful open water views, quick ocean access, and exceptional outdoor living create the ultimate Florida Keys lifestyle. Built by renowned Tom Ryan in 2007, this well-maintained 3-bedroom, 2-bath home is designed for both relaxation and adventure. Step inside to a bright, open-concept living area featuring a spacious kitchen with ample

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  27348 Dominica Ln, Ramrod Key, FL 33042

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