Homes in ZIP Code 33042

• 

  

  

  /66

  $799,000

  $50K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 842 Sq Ft

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

  Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
• 

  

  

  /8

  $340,000

  Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 12,500 Sq Ft
  • $1,184,832 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 328 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  0 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /2

  Est $557,076

  Not Listed For Sale

  520 Blackbeard Rd, Little Torch Key, FL 33042

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042
• 

  

  

  /59

  $649,000

  New Construction $5K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 29, 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- Venture

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
• 

  

  

  /21

  $775,000

  Sold Mar 23, 2026

  27360 Saint Croix Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $673/SF
  • 272 Days On Market

  Current Estimated Value $795,894

  Last Listing Agent Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042
• 

  

  /47

  $649,000

  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- Venture

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

  

  /58

  $760,000

  Sold Aug 19, 2025

  640 Carolyn Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $896/SF
  • 66 Days On Market

  Current Estimated Value $772,279

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
• 

  /2

  Est $924,912

  Not Listed For Sale

  27434 Saint Lucie Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2022

  27434 Saint Lucie Ln, Ramrod Key, FL 33042
• 

  

  /22

  $899,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft

  23940 Overseas Hwy, Summerland Key, FL 33042

  Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern design & trim. A durable metal roof, Hardie-board siding, impact windows and doors. Enjoy relaxing or entertaining on the covered porch, step out on the composite dock and be on the open ocean or Gulf in minutes, perfect for boating,

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  23940 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /14

  $205,000

  Sold May 20, 2026

  701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

  • Land
  • 1,742 Sq Ft
  • $5,125,000 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 56 Days On Market

  Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

  701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
• 

  /2

  Est $2,306,292

  Not Listed For Sale

  305 S Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft
  • Built 1986

  305 S Point Dr, Summerland Key, FL 33042
• 

  

  /36

  $949,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,052 Sq Ft

  273 Indies Rd, Summerland Key, FL 33042

  Welcome to this bright and modern 2-bedroom, 2-bath home located in the desirable Breezeswept Beach Estates on Ramrod Key. Completed in 2024 by the builder with high-quality features including a metal roof, impact windows, new A/C, and durable Hardi board siding. This home was later purchased and further upgraded by the current owner, who is also the first to live in the home. Since purchasing,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  273 Indies Rd, Summerland Key, FL 33042
• 

  

  /43

  $1,700,000

  Sold Jan 30, 2026

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $820/SF
  • 140 Days On Market

  Current Estimated Value $1,712,484

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /23

  Not Listed For Sale

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 8 Days On Market
• 

  

  /29

  $775,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,162 Sq Ft

  28452 Yucatan Ln, Summerland Key, FL 33042

  Must be sold after Jan 1, 2027. Canal front home with quick exit out of the canal to Pine Channel for Atlantic or Gulf access. 7200 sq.ft. lot. Back yard big enough for a pool. Pack your toothbrush and your ready for your salt life to begin. Being sold mostly furnished 2bd/2bth 1162 sq.ft. Home, plus, southerly facing screen porch, which has accordian shutters,porch faces back yard and canal.

  Rose Dell Keller Williams Key West Compass Realty

  28452 Yucatan Ln, Summerland Key, FL 33042
• 

  

  /57

  $2,800,000

  Sold Oct 30, 2025

  22967 Redfish Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 3.5 Baths
  • 3,747 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $747/SF
  • 37 Days On Market

  Current Estimated Value $2,970,244

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22967 Redfish Ln, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Crane Blvd, Sugarloaf Key, FL 33042

  0 Crane Blvd, Sugarloaf Key, FL 33042
• 

  

  /21

  $430,000

  $35K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 799 Sq Ft

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

  A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

  Rose Dell Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
• 

  

  /44

  $700,000

  Sold Jan 09, 2026

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $810/SF
  • 23 Days On Market

  Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
• 

  /2

  Est $477,031

  Not Listed For Sale

  390 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1958

  390 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /36

  $750,000

  • Land
  • 9.25 Acres
  • $81,081 per Acre

  0 Niles Rd Unit MLS A11925960, 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 Unit MLS A11925960, Summerland Key, FL 33042
• 

  

  /57

  $1,250,000

  Sold Jun 30, 2026

  25368 2nd St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1958

  Last Sold Summary

  • 24% Below List Price
  • $898/SF
  • 241 Days On Market

  Current Estimated Value $1,513,000

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  25368 2nd St, Summerland Key, FL 33042
• 

  

  /9

  Not Listed For Sale

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 543 Days On Market
• 

  

  /59

  $3,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,409 Sq Ft

  17387 E Dolphin St, Sugarloaf Key, FL 33042

  Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or

  17387 E Dolphin St, Sugarloaf Key, FL 33042
• 

  

  /48

  $291,000

  Sold Mar 03, 2026

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

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $404/SF
  • 133 Days On Market

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

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

  /2

  Not Listed For Sale

  430 Les Rohde Dr, Ramrod Key, FL 33042

  430 Les Rohde Dr, Ramrod Key, FL 33042
• 

  

  /68

  $879,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

  This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
• 

  

  /43

  $1,410,000

  Sold Apr 30, 2026

  17152 Marlin Dr, Sugarloaf Key, FL 33042

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

  Last Sold Summary

  • 12% Below List Price
  • $1,175/SF
  • 70 Days On Market

  Current Estimated Value $1,428,779

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17152 Marlin Dr, Sugarloaf Key, FL 33042
• 

  /2

  Est $542,521

  Not Listed For Sale

  20874 4th Ave, Cudjoe Key, FL 33042

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042
• 

  

  /35

  $530,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  27967 Coral Shores Rd, Little Torch Key, FL 33042

  Canal-front living at its finest! This beautifully remodeled 2-bedroom, 2-bath home is truly a must-see. Step inside to discover a bright and inviting interior featuring new flooring, an updated kitchen, and stylishly renovated bathrooms. The home is enhanced with numerous impact windows, filling the space with natural light and added peace of mind.Relax and unwind on the screened patio, or

  Diane Corliss Coldwell Banker Schmitt RE Co.

  27967 Coral Shores Rd, Little Torch Key, FL 33042
• 

  /2

  $255,000

  Sold Oct 20, 2025

  150 Coral Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1993

  Last Sold Summary

  • $232/SF
  • 0 Days On Market

  Current Estimated Value $652,631

  Last Listing Agent User Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  150 Coral Ave, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  1138 Basque Ln, Summerland Key, FL 33042

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042
• 

  

  /4

  $1,050,000

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  27403 Antigua Ln, Summerland Key, FL 33042

  Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light

  Sonia Petraitis Caffroni Capital Intl Realty LLC

  27403 Antigua Ln, Summerland Key, FL 33042
• 

  

  /51

  $420,000

  Sold Nov 21, 2025

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $515/SF
  • 185 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
• 

  

  /61

  Est $2,864,337

  Not Listed For Sale

  20886 4th Ave W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 3,042 Sq Ft
  • Built 2008

  20886 4th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 66 Days On Market
• 

  

  /20

  $550,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  27910 Porgie Path, Summerland Key, FL 33042

  Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping.

  Alexis Seldin Xcellence

  27910 Porgie Path, Summerland Key, FL 33042
• 

  

  /84

  $1,600,000

  Sold Apr 09, 2026

  17125 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • Built 1982

  Last Sold Summary

  • $971/SF
  • 8 Days On Market

  Current Estimated Value $1,570,095

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

  17125 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /107

  Est $5,033,269

  Not Listed For Sale

  220 E Caribbean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 7 Baths
  • 4,981 Sq Ft
  • Built 2025

  220 E Caribbean Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 165 Days On Market
• 

  

  /64

  $1,480,000

  New Construction $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and impact-rated windows &

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18