Homes in ZIP Code 33042

• 

  

  

  /39

  $750,000

  Sold May 11, 2026

  744 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 984 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Below List Price
  • $762/SF
  • 5 Days On Market

  Current Estimated Value $820,642

  Last Listing Agent Debra Farrell Island Welcome Real Estate

  744 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  

  /53

  Est $1,167,726

  Not Listed For Sale

  845 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1987

  845 Gulf Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 293 Days On Market
• 

  

  

  /9

  $2,400,000

  Pending

  • Land
  • 23,958 Sq Ft
  • $4,363,636 per Acre

  24356 Overseas Hwy, Summerland Key, FL 33042

  Begin your Florida Keys venture at this exceptional waterfront Commercial property. The site consists of four lots measuring 60'x100' each, creating a 24,000-square-foot parcel with 240 feet of concrete seawall. The property comes equipped with water and electrical connections. Its strategic location offers excellent access to both the Atlantic and Gulf waters, including proximity to Looe Key

  Scott Brisson KeyIsle Realty

  24356 Overseas Hwy, Summerland Key, FL 33042
• 

  

  

  /67

  $1,900,000

  Sold Nov 06, 2025

  17077 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $792/SF
  • 87 Days On Market

  Current Estimated Value $1,881,526

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17077 Bonita Ln W, Summerland Key, FL 33042
• 

  

  

  /31

  Est $1,341,417

  Not Listed For Sale

  27367 Martinique Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft
  • Built 2007

  27367 Martinique Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 12 Days On Market
• 

  

  /23

  $1,100,000

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft

  4276 Dorn Rd, Big Torch Key, FL 33042

  Welcome to your slice of paradise! Down in Big Torch Key, you'll feel a sense of solitude, satisfaction and serenity. Minimal, if any, noise or light pollution on this Key; look up at night and you will see stars you've never seen before! Quick and easy access to the Atlantic and Gulf of America, plenty of fishing spots and places to relax on the water without those big upper Key crowds. The

  Dylan Calhoun Luxe Properties

  4276 Dorn Rd, Big Torch Key, FL 33042
• 

  

  /5

  $175,000

  Sold Aug 21, 2025

  27313 Saint Martin Ln, Ramrod Key, FL 33042

  • Land
  • 6,500 Sq Ft
  • $1,172,769 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 9 Days On Market

  Current Estimated Value $175,955

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  27313 Saint Martin Ln, Ramrod Key, FL 33042
• 

  

  /32

  Est $773,119

  Not Listed For Sale

  519 Pirates Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1987

  519 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 263 Days On Market
• 

  

  /64

  $669,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042

  OCEANFRONT TRANSIENT RENTAL IN VENTURE OUT - CUDJOE KEYAmazing open water views of the sparkling Atlantic set the tone the moment you arrive. From this premier waterfront location, you'll enjoy sweeping vistas of the marina, lagoon, Tiki hut, and the iconic Bird Point sanctuary. Sunrise glows over endless blue water, creating a peaceful and ever-changing coastal backdrop.Positioned on a

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
• 

  

  /114

  $1,477,000

  Sold Sep 02, 2025

  153 Galleon Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Below List Price
  • $947/SF
  • 49 Days On Market

  Current Estimated Value $1,461,726

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  153 Galleon Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,119,546

  Not Listed For Sale

  321 W Indies Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • Built 1991

  321 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 24 Days On Market
• 

  

  /4

  $100,000

  Pending

  • Land
  • 1.01 Acres
  • $99,010 per Acre

  0 Mira Rd, Sugerloaf, FL 33042

  Vacant 1.01-acre parcel on Mira Rd in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, 5 miles to Cudjoe Key, and a short drive to local restaurants, marinas, and waterfront attractions throughout the Lower Florida Keys. Unimproved land offering future development or investment potential. Adjacent 1.01-acre lot on Acosta Trail (in front of subject

  Eugenia Hernandez Premium Properties R.E. Svc.

  0 Mira Rd, Sugerloaf, FL 33042
• 

  

  /59

  $2,175,000

  Sold Jun 20, 2025

  17346 Keystone Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,192 Sq Ft
  • Built 2019

  Last Sold Summary

  • 13% Below List Price
  • $992/SF
  • 41 Days On Market

  Current Estimated Value $2,244,935

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  17346 Keystone Rd, Summerland Key, FL 33042
• 

  

  /39

  Est $1,492,447

  Not Listed For Sale

  21076 3rd Ave, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft
  • Built 1992

  21076 3rd Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 33 Days On Market
• 

  

  /41

  $849,000

  $20K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  154 Cutthroat Dr, Summerland Key, FL 33042

  VA Assumable Loan for qualified buyers using VA benefits! Details available at buyer's request. Beautifully updated 2 bedroom, 2 bathroom home with spacious covered, screened porch overlooking the canal with access to both the Gulf of Mexico and the Atlantic Ocean in just a few minutes. With pride of ownership, this house has been upgraded and well maintained. Many upgrades include: 2024 - New

  Pamela Stangler Coldwell Banker Schmitt RE Co.

  154 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /19

  $505,000

  Sold Jul 30, 2025

  134 Tortuga Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 11% Below List Price
  • $478/SF
  • 4 Days On Market

  Current Estimated Value $651,114

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

  134 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /43

  Est $2,534,254

  Not Listed For Sale

  340 S Point Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,935 Sq Ft
  • Built 1973

  340 S Point Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 214 Days On Market
• 

  

  /28

  $928,000

  $92K PRICE DROP Under Contract

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

  27376 Tobago Ln, Summerland Key, FL 33042

  Nestled in Breezeswept Beach Estates, this fully remodeled canal-front home is the perfect Keys getaway. This 4-bed, 2-bath house features an open floor plan, vaulted ceilings, and a modern kitchen with granite countertops, new cabinets, and stainless steel appliances. The master suite offers a walk-in closet and spa-style bathroom, while the additional bedrooms provide plenty of space for family

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  27376 Tobago Ln, Summerland Key, FL 33042
• 

  

  /5

  $320,000

  Sold Apr 22, 2026

  248 Yardarm Rd, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $327/SF
  • 21 Days On Market

  Last Listing Agent Joe Ordini Keller Williams Key West Compass Realty

  248 Yardarm Rd, Cudjoe Key, FL 33042
• 

  

  /72

  Est $786,396

  Not Listed For Sale

  25083 Palm Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft
  • Built 1992

  25083 Palm Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 166 Days On Market
• 

  

  /30

  $430,000

  $67K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

  Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
• 

  

  /27

  $724,000

  Sold Oct 20, 2025

  25081 Overseas Hwy, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Above List Price
  • $633/SF
  • 75 Days On Market

  Current Estimated Value $733,991

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  25081 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /30

  Est $1,667,528

  Not Listed For Sale

  540 W Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Built 1989

  540 W Point Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 8 Days On Market
• 

  

  /74

  $2,950,000

  $550K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,812 Sq Ft

  16805 Tamarind Rd, Summerland Key, FL 33042

  OPEN WATER RESORT STYLE CONCRETE POOL home on sought after Southpoint, Sugarloaf Shores. This exceptional 4-bedroom, 3-bath concrete waterfront residence captures breathtaking open water views from nearly every room and delivers the ultimate Florida Keys lifestyle.Positioned on a generous, beautifully landscaped lot with mature palms and established tropical greenery, the property welcomes

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  16805 Tamarind Rd, Summerland Key, FL 33042
• 

  

  /52

  $1,006,000

  Sold Mar 19, 2026

  27360 Barbados Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Below List Price
  • $967/SF
  • 21 Days On Market

  Current Estimated Value $1,004,278

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27360 Barbados Ln, Summerland Key, FL 33042
• 

  

  /28

  Est $973,203

  Not Listed For Sale

  340 Spanish Main Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1997

  340 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market
• 

  

  /26

  $399,000

  Pending Pre-Foreclosure

  • 2 Beds
  • 1 Bath
  • 767 Sq Ft

  27942 Snapper Ln, Summerland Key, FL 33042

  Fantastic starter home in the stunning islands of the Florida Keys! This beautifully renovated home comes fully furnished including stainless steel appliances, microwave, 2 beds, dressers, TVs, couches, tables, and dishes. Located in an adorable and quiet community just over 26 miles from Key West. Bring your buyers!

  Nikki Tatum EXP Realty, LLC

  27942 Snapper Ln, Summerland Key, FL 33042
• 

  

  /39

  $1,100,000

  Sold Apr 27, 2026

  857 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 1987

  Last Sold Summary

  • 15% Below List Price
  • $914/SF
  • 112 Days On Market

  Current Estimated Value $1,193,128

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  857 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /36

  Est $1,548,802

  Not Listed For Sale

  20878 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1992

  20878 5th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 296 Days On Market
• 

  

  /25

  $569,700

  • 2 Beds
  • 1 Bath
  • 718 Sq Ft

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

  Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
• 

  /2

  $175,000

  Sold Dec 10, 2025

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 17% Below List Price
  • 23 Days On Market

  Last Listing Agent Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /41

  Est $897,144

  Not Listed For Sale

  24357 Caribbean Dr W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • Built 1977

  24357 Caribbean Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 54 Days On Market
• 

  /2

  $55,000

  • Land
  • 6,000 Sq Ft
  • $399,300 per Acre

  0 Vacant Land Unit 618301, Sugarloaf Key, FL 33042

  ROGO land dedication lot worth 2 points with paperwork completed and Monroe County letter of eligibility on file. No hidden expenses with this lot. Cost-effective way to get your permit faster! This lot is not buildable and is sold for land dedication purposes only.

  Nate Meyer Meyer and Boumerhi Realty LLC

  0 Vacant Land Unit 618301, Sugarloaf Key, FL 33042
• 

  

  /45

  $2,090,000

  Sold Jul 07, 2025

  23066 Tarpon Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3.5 Baths
  • 1,938 Sq Ft
  • Built 2025

  Last Sold Summary

  • 13% Below List Price
  • $1,078/SF
  • 65 Days On Market

  Current Estimated Value $1,996,745

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23066 Tarpon Ln, Summerland Key, FL 33042
• 

  /2

  Est $965,991

  Not Listed For Sale

  27285 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1990

  27285 Mariposa Rd, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /54

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,095 Sq Ft

  667 Caribbean Dr E, Summerland Key, FL 33042

  PILOTS and BOATERS will love this! Tucked away in the heart of Summerland Key, this charming 2-bedroom, 2-bath home captures the essence of true Florida Keys living. Surrounded by swaying palms and coastal breezes, the property features inviting wraparound balconies--perfect for morning coffee or unwinding after a day on the water. Designed with boaters in mind, you'll appreciate the deep,

  Donna Pezzi Keller Williams Key West Compass Realty

  667 Caribbean Dr E, Summerland Key, FL 33042
• 

  /2

  $2,030,000

  Sold Nov 17, 2025

  27450 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 4 Baths
  • 1,968 Sq Ft
  • Built 1984

  Last Sold Summary

  • 22% Below List Price
  • $1,032/SF
  • 273 Days On Market

  Current Estimated Value $2,047,913

  Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  27450 W Indies Dr, Summerland Key, FL 33042
• 

  

  /36

  Est $821,056

  Not Listed For Sale

  27392 Anguila Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft
  • Built 1979

  27392 Anguila Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 16 Days On Market
• 

  

  /46

  $487,000

  $88K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

  Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key—a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
• 

  

  /60

  $938,000

  Sold Dec 11, 2025

  460 Barry Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1985

  Last Sold Summary

  • 22% Below List Price
  • $651/SF
  • 196 Days On Market

  Current Estimated Value $955,187

  Last Listing Agent Noel Betancourt Tropic Shores Realty

  460 Barry Ave, Summerland Key, FL 33042

Showing Results 641 - 680, Page 17 of 18