Homes in ZIP Code 33042

• 

  

  

  /4

  $50,000

  Sold Dec 19, 2025

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

  • Land
  • 7,450 Sq Ft
  • $292,349 per Acre

  Last Sold Summary

  • 41% Below List Price
  • 25 Days On Market

  Last Listing Agent Sabre Mendoza Coldwell Banker Schmitt RE Co.

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
• 

  

  

  /29

  Not Listed For Sale

  28131 Helen Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft
  • Built 1972

  28131 Helen Ave, Little Torch Key, FL 33042

  Last Sold Summary

  • 91 Days On Market
• 

  

  

  /4

  $400,000

  • Land
  • 1,400 Acres
  • $286 per Acre

  27378 Jamaica Ln, Summerland Key, FL 33042

  ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

  Patricia Borges Borges Realty Group LLC

  27378 Jamaica Ln, Summerland Key, FL 33042
• 

  

  

  /39

  $705,000

  Sold Sep 08, 2025

  181 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $647/SF
  • 7 Days On Market

  Current Estimated Value $768,255

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  181 Doubloon Ln, Summerland Key, FL 33042
• 

  

  /2

  Est $244,109

  Not Listed For Sale

  27328 St Vincent Ln, Ramrod Key, FL 33042

  • Studio

  27328 St Vincent Ln, Ramrod Key, FL 33042
• 

  

  /51

  $1,250,000

  • 1 Bed
  • 3 Baths
  • 1,234 Sq Ft

  27001 Overseas Hwy, Ramrod Key, FL 33042

  Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample

  Bobby Coe RE/MAX Keys Connection (KW)

  27001 Overseas Hwy, Ramrod Key, FL 33042
• 

  

  /42

  $550,000

  Sold Dec 01, 2025

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $637/SF
  • 125 Days On Market

  Current Estimated Value $605,856

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
• 

  

  /49

  Est $302,405

  Not Listed For Sale

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  Last Sold Summary

  • 27 Days On Market
• 

  

  /17

  $255,000

  $10K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $5,100,000 per Acre

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

  Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
• 

  

  /33

  $1,075,000

  Sold Feb 20, 2026

  17226 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1998

  Last Sold Summary

  • 10% Below List Price
  • $861/SF
  • 32 Days On Market

  Current Estimated Value $1,094,176

  Last Listing Agent Stephen Hachey

  17226 Jamaica Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,069,933

  Not Listed For Sale

  783 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2017

  783 Pirates Rd, Summerland Key, FL 33042
• 

  

  /21

  $550,800

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  96 John St Unit 2, Summerland Key, FL 33042

  Well-maintained 3-bedroom, 2-bath home offering 1,120 square feet of comfortable living space in a small, well-kept community in Summerland Key. This home is in excellent condition, offers ample parking, and provides a wonderful opportunity for affordable homeownership in the Lower Keys. Subject to affordable housing deed restrictions.

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  96 John St Unit 2, Summerland Key, FL 33042
• 

  

  /60

  $2,512,500

  Sold Oct 31, 2025

  1260 Sugarloaf Blvd, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,886 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Below List Price
  • $871/SF
  • 60 Days On Market

  Current Estimated Value $2,537,654

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  /2

  Est $769,682

  Not Listed For Sale

  1313 State Rd Unit 4A, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1977

  1313 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  /26

  $989,000

  • 3 Beds
  • 2 Baths
  • 1,329 Sq Ft

  673 Indies Rd, Summerland Key, FL 33042

  Elevated Coastal Living in Breezeswept Beach Estates. Skip the typical vacation rentals & step into a home designed specifically for the genuine Florida Keys lifestyle. Situated on a quiet street within Breezeswept Beach Estates, this well-maintained 3-bedroom, 2-bathroom stilt home perfectly balances premier boating access with a peaceful, scenic setting. The property's positioning is truly

  Gregory Sullivan BYOWNER.COM

  673 Indies Rd, Summerland Key, FL 33042
• 

  

  /61

  $1,900,000

  Sold Jun 15, 2026

  556 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft
  • Built 1974

  Last Sold Summary

  • 30% Below List Price
  • $877/SF
  • 155 Days On Market

  Current Estimated Value $2,192,662

  Last Listing Agent Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /31

  Est $863,515

  Not Listed For Sale

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 2001

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • 146 Days On Market
• 

  

  /58

  $269,000

  $26K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 316 Sq Ft

  701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

  $21,000+ Gross Rental Revenue so far in 2026!Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential.Currently operating as a successful vacation

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
• 

  

  /25

  $1,249,000

  Sold Apr 28, 2026

  17170 Amberjack Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1989

  Last Sold Summary

  • $1,183/SF
  • 0 Days On Market

  Current Estimated Value $1,242,727

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

  17170 Amberjack Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /45

  $7,000,000

  • 3 Beds
  • 3.5 Baths
  • 2,851 Sq Ft

  0 Melody Key Unit 616249, Summerland Key, FL 33042

  An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

  Scott Forman Royal Palms Realty (KW)

  0 Melody Key Unit 616249, Summerland Key, FL 33042
• 

  

  /51

  $975,000

  Sold Aug 01, 2025

  527 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2023

  Last Sold Summary

  • 17% Below List Price
  • $812/SF
  • 101 Days On Market

  Current Estimated Value $1,083,583

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  527 Heck Ave, Little Torch Key, FL 33042
• 

  

  /28

  Est $1,831,081

  Not Listed For Sale

  27385 St Lucie Ln, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,988 Sq Ft
  • Built 1987

  27385 St Lucie Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 0 Days On Market
• 

  

  /46

  $2,200,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1330 Sugarloaf Blvd, Summerland Key, FL 33042

  A quiet escape with million-dollar views. Situated on an expansive lot of over a quarter-acre, this three-bedroom, two-bathroom home is nestled within the sought-after shores of Sugarloaf Key--tucked away from the highway and just steps from scenic walking and bike paths. The interiors offer a crisp, modern take on coastal comfort, sold fully furnished with a curated collection of new decor and

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1330 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /44

  $1,550,000

  Sold Feb 27, 2026

  17094 Coral Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $776/SF
  • 265 Days On Market

  Current Estimated Value $1,573,261

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17094 Coral Dr, Summerland Key, FL 33042
• 

  

  /31

  Est $800,147

  Not Listed For Sale

  27373 Antigua Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2016

  27373 Antigua Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  /14

  $395,000

  • Land
  • 6,098 Sq Ft
  • $2,821,429 per Acre

  24285 Caribbean Dr, Summerland Key, FL 33042

  Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has

  Donna Pezzi Keller Williams Key West Compass Realty

  24285 Caribbean Dr, Summerland Key, FL 33042
• 

  

  /49

  $278,000

  Sold Apr 30, 2026

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft
  • Built 1986

  Last Sold Summary

  • 16% Below List Price
  • $377/SF
  • 149 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
• 

  /2

  Est $870,902

  Not Listed For Sale

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2016

  53 Gold Boullion Rd, Cudjoe Key, FL 33042
• 

  

  /3

  $284,999

  $104K PRICE DROP

  • Land
  • 23,958 Sq Ft
  • $518,180 per Acre

  00200670-000100 Sunset Blvd, Summerland Key, FL 33042

  Beautiful .55 acre lot in Summerland Key, FL. Summerland Key is a unique fly-in community with a private airstrip and marina close by. SUMMERLAND ESTATES SUMMERLAND KEY PB2-167 PT LT 25 (LOT A 90 FT X 264.75 FT). Buyer is responsible for conducting due diligence on the property prior to purchase.

  Sean Seward Keller Williams Island Life RE

  00200670-000100 Sunset Blvd, Summerland Key, FL 33042
• 

  

  /40

  $950,000

  Sold Sep 17, 2025

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $825/SF
  • 85 Days On Market

  Current Estimated Value $1,035,053

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
• 

  /2

  Est $805,708

  Not Listed For Sale

  27087 Angelfish Rd, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2020

  27087 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 145 Days On Market
• 

  

  /50

  $1,595,000

  $70K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,995 Sq Ft

  643 Indies Rd, Summerland Key, FL 33042

  Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for

  Greg MacLaren Internet Realty of the Florida Keys

  643 Indies Rd, Summerland Key, FL 33042
• 

  

  /11

  $405,000

  Sold May 04, 2026

  744 Trinidad Ln, Little Torch Key, FL 33042

  • 3 Beds
  • 1.5 Baths
  • 1,104 Sq Ft
  • Built 1967

  Last Sold Summary

  • 26% Below List Price
  • $367/SF
  • 62 Days On Market

  Current Estimated Value $427,554

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  744 Trinidad Ln, Little Torch Key, FL 33042
• 

  

  /69

  Not Listed For Sale

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft
  • Built 1988

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  Last Sold Summary

  • 461 Days On Market
• 

  

  /38

  $894,000

  $2K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  437 Pirates Rd, Little Torch Key, FL 33042

  MOTIVATED SELLER! Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living

  Jo Ann Cook Ocean Sotheby's International

  437 Pirates Rd, Little Torch Key, FL 33042
• 

  

  /53

  $2,725,000

  Sold Mar 11, 2026

  1147 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $1,324/SF
  • 103 Days On Market

  Current Estimated Value $2,671,280

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1147 Flagship Dr, Summerland Key, FL 33042
• 

  /2

  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
• 

  

  /45

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  559 Powell Ave, Little Torch Key, FL 33042

  Built in 2019 on a 7,412 sq ft Lot! This modern home features three (3) bedrooms and two (2) bathrooms, offering everything you need. It's low maintenance yet packed with amenities. Enjoy a pool, a double lot, an extra-long dock, affordable insurance, a quiet, peaceful neighborhood, and excellent fishing opportunities. Step inside to an open-concept design that boasts a bright & fantastic living

  Bobby Coe RE/MAX Keys Connection (KW)

  559 Powell Ave, Little Torch Key, FL 33042
• 

  /2

  $185,000

  Sold Mar 20, 2026

  1223 Rogers Ln, Cudjoe Key, FL 33042

  • Land
  • 6,969 Sq Ft
  • $1,156,250 per Acre

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $185,117

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  1223 Rogers Ln, Cudjoe Key, FL 33042

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