Homes in ZIP Code 33042

• 

  

  

  /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
• 

  

  

  /50

  $815,000

  Sold Jun 10, 2026

  27369 Saint Vincent Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,592 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $512/SF
  • 67 Days On Market

  Current Estimated Value $856,698

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27369 Saint Vincent Ln, Summerland Key, FL 33042
• 

  

  

  /31

  Est $1,363,392

  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
• 

  

  

  /36

  $5,995,000

  $295K PRICE DROP

  • 13 Beds
  • 7 Baths
  • 5,022 Sq Ft

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest

  Jennifer Weeks Select Properties of NWFL

  21470 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  

  /32

  $540,000

  Sold Jun 10, 2026

  27059 Old State Road 4a, Summerland Key, FL 33042

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

  Last Sold Summary

  • 3% Above List Price
  • $549/SF
  • 2 Days On Market

  Current Estimated Value $520,666

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  27059 Old State Road 4a, Summerland Key, FL 33042
• 

  

  /32

  Est $793,116

  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
• 

  

  /49

  $1,449,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  27372 W Indies Dr, Summerland Key, FL 33042

  **Open House this Friday, July 3, from 11:00 AM to 1:00 PM at 27372 W. Indies Drive, Ramrod Key.**Come preview this custom-built 4 bedroom, 3 bathroom waterfront home, offered for the first time ever. Built in 2020, this exceptional property features magnificent ocean views, canal-front dockage with a boat lift, high-end finishes throughout, and thoughtfully designed coastal living.If you

  Sandra Dolowy KeyIsle Realty

  27372 W Indies Dr, Summerland Key, FL 33042
• 

  

  /4

  $175,000

  Sold Dec 23, 2025

  Lot 2 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 12,500 Sq Ft
  • $609,840 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 25 Days On Market

  Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 2 Overseas Hwy, Summerland Key, FL 33042
• 

  /2

  Est $1,075,042

  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
• 

  /2

  $52,000

  $3K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $371,429 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
• 

  

  /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 $778,047

  Last Listing Agent Debra Farrell Island Welcome Real Estate

  744 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /47

  Est $1,116,012

  Not Listed For Sale

  21014 7th Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1988

  21014 7th Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 102 Days On Market
• 

  

  /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
• 

  

  /67

  $1,900,000

  Sold Nov 06, 2025

  17077 Bonita Ln W, Summerland Key, FL 33042

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

  Last Sold Summary

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

  Current Estimated Value $1,953,072

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17077 Bonita Ln W, Summerland Key, FL 33042
• 

  

  /39

  Est $1,467,331

  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
• 

  

  /27

  $337,500

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft

  27965 Tarpon Terrace, Little Torch Key, FL 33042

  Great investment opportunity in Little Torch Key! This well-maintained home sits on a clean, clear swimming canal with direct access for paddle boarding, kayaking, and fishing right from your backyard. A boat ramp is less than a mile away, making it perfect for boating and fishing enthusiasts. The property features a large fenced lot with plenty of parking, trailer storage, and a storage shed.

  Deni Heintzelman KeyIsle Realty

  27965 Tarpon Terrace, Little 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 $193,424

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  27313 Saint Martin Ln, Ramrod Key, FL 33042
• 

  

  /43

  Est $2,459,167

  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
• 

  

  /31

  $540,000

  $310K PRICE DROP

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

  4099 Egret Ln, Summerland Key, FL 33042

  Excellent Investment Opportunity! Classic waterfront home in quiet Big Torch Key. This home features 2 bedrooms, two bathrooms and a spacious open living/dining/kitchen area. Water from a 12k gallon cistern with a reverse osmosis system. City water is available and the home is connected to sewer. This home is being sold as a life estate. The homeowner will remain in place after purchase of the

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  4099 Egret Ln, Summerland Key, FL 33042
• 

  

  /9

  $2,150,000

  Sold Jun 25, 2026

  24356 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 23,958 Sq Ft
  • $3,909,091 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 254 Days On Market

  Last Listing Agent Scott Brisson KeyIsle Realty

  24356 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /72

  Est $792,304

  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
• 

  

  /43

  $999,000

  $300K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft

  19267 Hansen Trail, Summerland Key, FL 33042

  Set on over an acre of land, 19267 Hansen Trail is a truly one-of-a-kind property where modern luxury meets refined homestead living. Offering nearly 2,000 square feet of beautifully remodeled living space, this 3-bedroom, 2-bathroom residence has been thoughtfully upgraded with high-end finishes, all new impact windows and doors, and smart-home conveniences throughout. The open-concept design

  Justyn Ewald Expert Realty LLC (HQ)

  19267 Hansen Trail, Summerland 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 $1,506,243

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  153 Galleon Ln, Summerland Key, FL 33042
• 

  

  /36

  Est $1,485,510

  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
• 

  

  /7

  $3,995,900

  New Construction $4K PRICE DROP Pending

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

  231 E Shore Dr Unit 1, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 1, Summerland Key, FL 33042
• 

  /2

  $50,000

  Sold May 07, 2026

  12 Trin Ln, Torch Key, FL 33042

  • Land
  • 6,098 Sq Ft
  • $357,143 per Acre

  Last Sold Summary

  • 0 Days On Market

  12 Trin Ln, Torch Key, FL 33042
• 

  

  /41

  Est $858,257

  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
• 

  

  /42

  $875,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  324 Airport Dr S, Summerland Key, FL 33042

  Rare opportunity to own a canal-front home directly on the private Summerland Cove Airport--where you can fly in, dock up, and be on open water in minutes. This solid CBS home offers 960 sq ft of elevated living space, currently configured as a spacious 1-bedroom, 1-bath upstairs (originally a 2-bedroom--easily converted back). Downstairs features a fully enclosed, permitted bonus area with an

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  324 Airport Dr S, 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 $661,767

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

  134 Tortuga Ln, Summerland Key, FL 33042
• 

  /2

  Est $991,628

  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
• 

  

  /55

  $2,299,999

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,288 Sq Ft

  17210 Angelfish Ln, Summerland Key, FL 33042

  Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence offers 2,288 square feet of modern coastal comfort. Situated on an expansive 16,445-square-foot lot, the property features a private seawall for direct boating access and a sparkling pool perfect for relaxing after a day on the

  The Spottswood Team Truman & Co. (KW)

  17210 Angelfish Ln, Summerland Key, FL 33042
• 

  

  /64

  $650,000

  Sold Jun 30, 2026

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

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $797/SF
  • 62 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

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

  

  /36

  Est $790,878

  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
• 

  

  /54

  $2,246,000

  • 3 Beds
  • 1.5 Baths
  • 2,016 Sq Ft

  848 Caribbean Dr E, Summerland Key, FL 33042

  Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about. Completely renovated from top to bottom, the property sits on a deep water canal with 60 feet of brand new concrete dockage and quick direct access to open water, making it ideal for larger center consoles, sportfish boats, and

  Jonathan Minerick Homecoin.com

  848 Caribbean Dr E, 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
• 

  

  /48

  Est $1,323,085

  Not Listed For Sale

  903 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,161 Sq Ft
  • Built 1999

  903 Indies Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 84 Days On Market
• 

  

  /52

  $487,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

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

  Seller is Motivated!Coastal Charm Meets Modern ComfortWelcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key.Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, 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 $770,108

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  25081 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /8

  Est $794,061

  Not Listed For Sale

  743 Indies Rd, Summerland Key, FL 33042

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

  743 Indies Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 49 Days On Market
• 

  

  /60

  $175,000

  New Construction

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

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this 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

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042

Showing Results 641 - 680, Page 17 of 18