Homes in ZIP Code 33042

• 

  

  

  /37

  $1,195,000

  $94K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  22777 Jolly Roger Dr, Cudjoe Key, FL 33042

  Price Reduced! Motivated Seller... Stop dreaming and start packing. Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even have ample space for a chicken coop. A large saltwater pool is perfect for soaking

  Susan Halligan Live Local Realty of the Florida Keys

  22777 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  

  /51

  $990,000

  Sold Oct 28, 2025

  22841 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $516/SF
  • 139 Days On Market

  Current Estimated Value $1,099,290

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22841 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  

  /45

  Est $1,182,193

  Not Listed For Sale

  23058 Sailfish Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,280 Sq Ft
  • Built 1980

  23058 Sailfish Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 145 Days On Market
• 

  

  

  /59

  $535,000

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
• 

  

  

  /7

  $1,600,000

  Sold Nov 21, 2025

  23038 Overseas Hwy, Cudjoe Key, FL 33042

  • Land
  • 1.37 Acres
  • $1,164,531 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 141 Days On Market

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  23038 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /16

  Est $1,978,460

  Not Listed For Sale

  23076 Tarpon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1975

  23076 Tarpon Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 82 Days On Market
• 

  

  /3

  $799,000

  $50K PRICE DROP Pending

  • Land
  • 10 Acres
  • $79,934 per Acre

  0 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez Premium Properties R.E. Svc.

  0 Rocky Rd, Sugarloaf Key, FL 33042
• 

  

  /29

  $1,245,000

  Sold Jul 28, 2025

  17081 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $807/SF
  • 199 Days On Market

  Current Estimated Value $1,328,909

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  17081 Starfish Ln W, Summerland Key, FL 33042
• 

  

  /27

  Est $1,668,474

  Not Listed For Sale

  23092 Snapper Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Built 1985

  23092 Snapper Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 7 Days On Market
• 

  

  /50

  $289,000

  • 1 Bed
  • 1 Bath
  • 340 Sq Ft

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042

  Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect Florida Keys getaway, ideal as a vacation rental investment, seasonal escape, or personal retreat. Turn-key and ready to enjoy or rent immediately, this property offers excellent income potential with nightly rentals allowed in

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
• 

  

  /47

  $895,000

  Sold Dec 10, 2025

  22880 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,256 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $713/SF
  • 34 Days On Market

  Current Estimated Value $922,927

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22880 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /42

  Est $1,344,288

  Not Listed For Sale

  1172 Coates Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft
  • Built 2002

  1172 Coates Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 138 Days On Market
• 

  

  /63

  $3,295,000

  $400K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  24348 Caribbean Dr W, Summerland Key, FL 33042

  A stunning location with all attributes geared to the view of the beautiful open bay of Summerland Cove. This OCEANFRONT 3 bedroom 3 bath home is on the market for the first time since construction in 1996 and features an extensive renovation nearly complete. The property includes a stunning covered & heated pool with screened enclosure, a 28 foot concrete dock with davits, deep water boating

  Caroline Bauer Key West Sales, LLC

  24348 Caribbean Dr W, Summerland Key, FL 33042
• 

  

  /38

  $775,000

  Sold Sep 11, 2025

  22957 Drake Ln, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $769/SF
  • 7 Days On Market

  Current Estimated Value $833,933

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22957 Drake Ln, Cudjoe Key, FL 33042
• 

  /2

  Est $1,290,902

  Not Listed For Sale

  22943 Dirk Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • Built 1998

  22943 Dirk Ln, Summerland Key, FL 33042
• 

  

  /3

  $275,000

  • Land
  • 0 Sq Ft

  0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042

  Take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

  Pamela Stangler Expert Realty LLC

  0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042
• 

  

  /24

  $430,000

  Sold Nov 25, 2025

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

  • Land
  • 2,078 Sq Ft
  • $9,013,859 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 287 Days On Market

  Current Estimated Value $438,101

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042
• 

  

  /44

  Est $746,397

  Not Listed For Sale

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft
  • Built 1972

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 108 Days On Market
• 

  

  /70

  $950,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft

  123 Venetian Way, Summerland Key, FL 33042

  On a quiet dead-end street in the highly sought-after Sugarloaf Shores community, sits this fully renovated tropical retreat thats reminiscent of something straight out of a secret garden. Set on an oversized, gated and partially fenced parcel spanning over a quarter acre, this rare non-waterfront property offers the kind of lush green space that's nearly impossible to find in the Florida Keys.

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  123 Venetian Way, Summerland Key, FL 33042
• 

  

  /61

  $2,000,000

  Sold Mar 18, 2026

  743 Pattison Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 1997

  Last Sold Summary

  • 11% Below List Price
  • $1,195/SF
  • 135 Days On Market

  Current Estimated Value $2,022,704

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  743 Pattison Dr, Summerland Key, FL 33042
• 

  

  /70

  Est $777,646

  Not Listed For Sale

  22933 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1995

  22933 Buccaneer Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 74 Days On Market
• 

  

  /45

  $1,150,000

  $100K PRICE DROP

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

  20868 5th Ave W, Summerland Key, FL 33042

  Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man

  Karen Haack Coldwell Banker Schmitt RE Co.

  20868 5th Ave W, Summerland Key, FL 33042
• 

  

  /43

  $1,170,000

  Sold Aug 28, 2025

  1777 Pine Channel Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 2022

  Last Sold Summary

  • 10% Below List Price
  • $950/SF
  • 29 Days On Market

  Current Estimated Value $1,223,235

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1777 Pine Channel Dr, Summerland Key, FL 33042
• 

  /2

  Est $833,095

  Not Listed For Sale

  201 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1983

  201 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /7

  $3,650

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

  19525 Date Palm Dr, Summerland Key, FL 33042

  Enjoy island living in this beautiful 3-bedroom, 2-bathroom home located on a quiet street in desirable Sugarloaf Key. This is an unfurnished annual rental featuring a large deck and private yard with plenty of space to enjoy the outdoors. Background check first, last, security deposit required. Dogs okay upon approval.

  Cliff Glansen FlatFee.com

  19525 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /95

  $1,375,000

  Sold Oct 30, 2025

  241 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,888 Sq Ft
  • Built 2021

  Last Sold Summary

  • 10% Below List Price
  • $728/SF
  • 226 Days On Market

  Current Estimated Value $1,487,816

  Last Listing Agent Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  241 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /47

  Est $2,330,063

  Not Listed For Sale

  22684 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1977

  22684 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 17 Days On Market
• 

  

  /13

  $85,000

  • Land
  • 4 Acres
  • $21,250 per Acre

  LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042

  Offshore island 4 acre lot in the heart of the Great White Heron Wildlife refuge is suitable for temporary camping and exploration. World class flats fishing for bonefish, tarpon, permit and redfish nearby. Located on Southwest end of Little Knockemdown Key. Accessible by kayak, paddle board and shallow draft vessels. Privacy and nature abound here on Little Knockemdown Key - No roads or

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
• 

  

  /50

  $1,550,000

  Sold Feb 23, 2026

  56 Colson Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Built 1995

  Last Sold Summary

  • 3% Below List Price
  • $942/SF
  • 12 Days On Market

  Current Estimated Value $1,553,278

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  56 Colson Dr, Summerland Key, FL 33042
• 

  

  /34

  Est $819,157

  Not Listed For Sale

  191 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1963

  191 Doubloon Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 10 Days On Market
• 

  

  /55

  $329,000

  $98K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 748 Sq Ft

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

  Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
• 

  

  /55

  $1,800,000

  Sold Jul 18, 2025

  22925 John Avery Ln, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,638 Sq Ft
  • Built 1993

  Last Sold Summary

  • 21% Below List Price
  • $682/SF
  • 164 Days On Market

  Current Estimated Value $1,793,084

  Last Listing Agent Jonathan Minerick Homecoin.com

  22925 John Avery Ln, Summerland Key, FL 33042
• 

  /2

  Est $750,224

  Not Listed For Sale

  53 Treasure Chest Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1991

  53 Treasure Chest Dr, Summerland Key, FL 33042
• 

  

  /39

  $895,000

  $4K PRICE DROP

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

  437 Pirates Rd, Little Torch Key, FL 33042

  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 space ideal for

  Jo Ann Cook Ocean Sotheby's International

  437 Pirates Rd, Little Torch Key, FL 33042
• 

  

  /30

  $775,000

  Sold Sep 30, 2025

  24827 Park Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 2018

  Last Sold Summary

  • 14% Below List Price
  • $608/SF
  • 175 Days On Market

  Current Estimated Value $826,970

  Last Listing Agent Juan Benitez Benitez Keller Williams Key West Compass Realty

  24827 Park Dr, Summerland Key, FL 33042
• 

  

  /77

  Est $5,989,879

  Not Listed For Sale

  200 Erie Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 4,514 Sq Ft
  • Built 2002

  200 Erie Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 295 Days On Market
• 

  

  /45

  $1,300,000

  • 2 Beds
  • 2 Baths
  • 1,364 Sq Ft

  466 W Shore Dr, Summerland Key, FL 33042

  DOUBLE the Lot. DOUBLE the Waterfront. Endless Possibilities. Positioned on a rare spacious double lot near the Summerland Key airport, this waterfront property is tailor-made for boating enthusiasts and aviation lovers alike. Featuring 120 feet of concrete seawall on a desirable flow-through canal, you'll enjoy quick access to open water and some of the Lower Keys' best fishing, diving, and

  Donna Pezzi Keller Williams Key West Compass Realty

  466 W Shore Dr, Summerland Key, FL 33042
• 

  

  /17

  $320,000

  Sold Feb 20, 2026

  27977 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft
  • Built 1980

  Last Sold Summary

  • 20% Below List Price
  • $468/SF
  • 54 Days On Market

  Last Listing Agent Dasha Ray Conch Realty LLC (KW)

  27977 Coral Shores Rd, Little Torch Key, FL 33042
• 

  

  /41

  Est $1,425,778

  Not Listed For Sale

  20785 5th Ave W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1990

  20785 5th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 77 Days On Market
• 

  

  /55

  $1,650,000

  $150K PRICE DROP

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

  1163 de Lussan Ln, Summerland Key, FL 33042

  Are you dreaming of your own personal paradise? Look no further than this stunning property in the highly sought after Cutthroat Harbor Estates. With features that check off every box on your list, this home is truly a gem. Enjoy the luxury of CBS construction and a spacious 9000 sq. ft. lot. The 65' dock has been newly resurfaced with composite decking and comes equipped with a 10k lb boat lift

  Jan Fritz Coldwell Banker Schmitt RE Co.

  1163 de Lussan Ln, Summerland Key, FL 33042

Showing Results 521 - 560, Page 14 of 18