Homes in ZIP Code 33042

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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1987

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042
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  /43

  $899,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,036 Sq Ft

  420 W Indies Dr, Ramrod Key, FL 33042

  Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  420 W Indies Dr, Ramrod Key, FL 33042
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  /2

  $49,000

  Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land
  • 5,499 Sq Ft
  • $388,080 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
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  /5

  Est $1,395,415

  Not Listed For Sale

  354 Airport Dr S, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,881 Sq Ft
  • Built 2013

  354 Airport Dr S, Summerland Key, FL 33042

  Last Sold Summary

  • 2 Days On Market
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  /71

  $2,795,000

  $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
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  /61

  $2,675,000

  Sold Jun 01, 2026

  20844 4th Ave W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Below List Price
  • $906/SF
  • 10 Days On Market

  Current Estimated Value $2,755,509

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

  20844 4th Ave W, 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

  Last Sold Summary

  • 53 Days On Market
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  /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
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  /43

  $1,100,000

  Sold May 14, 2026

  1011 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $962/SF
  • 0 Days On Market

  Current Estimated Value $1,078,082

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1011 Caribbean Dr E, Summerland Key, FL 33042
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  /2

  Est $258,124

  Not Listed For Sale

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  • Studio
  • Built 1981

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042
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  /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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  /70

  $1,290,000

  Sold May 19, 2026

  403 Indies Rd, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1991

  Last Sold Summary

  • 4% Below List Price
  • $960/SF
  • 63 Days On Market

  Current Estimated Value $1,292,272

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  403 Indies Rd, Ramrod Key, FL 33042
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  /2

  Est $719,767

  Not Listed For Sale

  27188 Dolphin Rd, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1991

  27188 Dolphin Rd, Ramrod Key, FL 33042
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  /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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  /75

  $830,000

  Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $884,122

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
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  /8

  Not Listed For Sale

  0000 Dorn Rd, Big Torch Key, FL 33042

  0000 Dorn Rd, Big Torch Key, FL 33042

  Last Sold Summary

  • 103 Days On Market
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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

  21012 6th Ave, Summerland Key, FL 33042
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  /50

  $1,900,000

  Sold Mar 27, 2026

  711 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $950/SF
  • 62 Days On Market

  Current Estimated Value $1,839,083

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
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  /34

  Not Listed For Sale

  27772 Astrangia Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1978

  27772 Astrangia Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 44 Days On Market
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  /70

  $3,399,000

  • 3 Beds
  • 3 Baths
  • 3,056 Sq Ft

  21090 5th Ave, Cudjoe Key, FL 33042

  Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  21090 5th Ave, Cudjoe Key, FL 33042
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  /41

  $1,105,000

  Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Current Estimated Value $1,148,119

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

  22946 Bluegill Ln, Summerland Key, FL 33042
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  /2

  Est $1,057,833

  Not Listed For Sale

  1581 State Rd Unit 4A, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2007

  1581 State Rd Unit 4A, Little Torch Key, FL 33042
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  /77

  $1,300,000

  • 3 Beds
  • 2.5 Baths
  • 2,392 Sq Ft

  27395 Barbuda Ln, Ramrod Key, FL 33042

  Discover the ideal blend of comfort, space, and waterfront living in this beautifully maintained canal-front home on Ramrod Key. Offering 2,392 sq. ft. of living space with 3 bedrooms, 2.5 baths, a versatile bonus room, and loft, this spacious residence is perfectly suited for full-time living, a vacation getaway, or an investment property. With 60' of dockage and easy ocean access, boating

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  27395 Barbuda Ln, Ramrod Key, FL 33042
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  /47

  $1,075,000

  Sold May 13, 2026

  110 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 9 Days On Market

  Current Estimated Value $1,079,826

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  110 Doubloon Ln, Summerland Key, FL 33042
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  /2

  Est $480,342

  Not Listed For Sale

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, 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.

  0 Niles Rd, Summerland Key, FL 33042
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  /11

  $560,000

  Sold Jun 18, 2026

  22963 Anne Bonny Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 834 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Below List Price
  • $671/SF
  • 43 Days On Market

  Current Estimated Value $584,856

  Last Listing Agent Judith Exposito Luxe Properties

  22963 Anne Bonny Ln, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
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  /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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  /61

  $1,750,000

  Sold Mar 09, 2026

  876 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 1978

  Last Sold Summary

  • 20% Below List Price
  • $1,493/SF
  • 122 Days On Market

  Current Estimated Value $1,708,408

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

  876 Gulf Dr, Summerland Key, FL 33042
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  /2

  Est $209,258

  Not Listed For Sale

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042
• 

  

  /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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  /34

  $840,207

  Sold Jul 03, 2026

  131 Doubloon Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $577/SF
  • 61 Days On Market

  Current Estimated Value $981,778

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  131 Doubloon Ln, Summerland Key, FL 33042
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  /2

  Est $3,147,413

  Not Listed For Sale

  999 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft
  • Built 2024

  999 Flagship Dr, Summerland Key, FL 33042
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  /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

  17286 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /5

  $75,000

  Sold Jun 22, 2026

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  • Land
  • 14,810 Sq Ft
  • $220,588 per Acre

  Last Sold Summary

  • 46% Below List Price
  • 177 Days On Market

  Last Listing Agent Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
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  /34

  Not Listed For Sale

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1998

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  Last Sold Summary

  • 66 Days On Market
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  /54

  $1,049,000

  $50K PRICE DROP

  • 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

  22953 John Silver Ln, Summerland Key, FL 33042
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  /91

  $3,675,000

  Sold May 11, 2026

  493 Coral Ave, Ramrod Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $2,127/SF
  • 10 Days On Market

  Current Estimated Value $3,640,391

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  493 Coral Ave, Ramrod Key, FL 33042
• 

  /2

  Est $860,870

  Not Listed For Sale

  18954 Acosta Trail, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft
  • Built 2013

  18954 Acosta Trail, Summerland Key, FL 33042

Showing Results 121 - 160, Page 4 of 18