Homes in ZIP Code 33042

• 

  

  

  /42

  $1,449,000

  New Construction Open Wed 12PM - 2PM

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  22872 Buccaneer Ln, Cudjoe Key, FL 33042

  *SWIMMING POOL BEING BUILT NOW! Construction process underway. * Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West! Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  22872 Buccaneer Ln, Cudjoe Key, FL 33042
• 

  

  

  /96

  $1,575,000

  Sold Mar 23, 2026

  17176 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $669/SF
  • 63 Days On Market

  Current Estimated Value $1,631,377

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

  17176 Bonita Ln W, Summerland Key, FL 33042
• 

  

  

  /37

  Est $1,773,608

  Not Listed For Sale

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 2008

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  Last Sold Summary

  • 42 Days On Market
• 

  

  

  /3

  $284,999

  $104K PRICE DROP

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

  0 Sunset Blvd Unit MFRA4697420, 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 REAL ESTATE

  0 Sunset Blvd Unit MFRA4697420, Summerland Key, FL 33042
• 

  

  

  /30

  $440,000

  Sold Apr 30, 2026

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 604 Sq Ft
  • Built 1976

  Last Sold Summary

  • 9% Below List Price
  • $728/SF
  • 170 Days On Market

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
• 

  

  /46

  Est $2,564,810

  Not Listed For Sale

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 2,371 Sq Ft
  • Built 1967

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  Last Sold Summary

  • 78 Days On Market
• 

  

  /40

  $894,000

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  28571 Buccaneer Rd, Summerland Key, FL 33042

  Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large

  Diane Corliss Coldwell Banker Schmitt RE Co.

  28571 Buccaneer Rd, Summerland Key, FL 33042
• 

  /2

  $1,400,000

  Sold Sep 17, 2025

  491 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 2020

  Last Sold Summary

  • $1,163/SF
  • 0 Days On Market

  Current Estimated Value $1,444,356

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  491 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /46

  Est $1,290,489

  Not Listed For Sale

  137 Caribbean Dr E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1986

  137 Caribbean Dr E, Summerland Key, FL 33042

  Last Sold Summary

  • 8 Days On Market
• 

  

  /42

  $1,049,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft

  27416 Cayman Ln, Ramrod Key, FL 33042

  Seller offering a buyer concession at closing--providing flexibility toward closing costs, an interest rate buy-down, prepaid expenses, or other allowable buyer costs. Now offered with this added value, this is an exceptional opportunity to own one of the Lower Keys' premier boating properties. Boater's dream waterfront on Ramrod Key with no-bridge ocean access, dual boat lifts, and open Atlantic

  Melissa Gibbins Expert Realty LLC (HQ)

  27416 Cayman Ln, Ramrod Key, FL 33042
• 

  

  /9

  $175,000

  Sold Apr 06, 2026

  Vacant Picard Ln, Cudjoe Key, FL 33042

  • Land
  • 6,000 Sq Ft
  • $1,270,500 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 219 Days On Market

  Last Listing Agent Lee Sanders/Sunnie SanLorenzo KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
• 

  /2

  Est $1,688,512

  Not Listed For Sale

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2005

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042
• 

  

  /51

  $1,725,000

  $174K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,440 Sq Ft

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living. Large impact glass doors and windows frame ocean views and invite natural light into every room. Soaring, 26' ceilings enhance the open-concept layout with rich wood beams amplifying the

  Lauren Dunn Coldwell Banker Schmitt Islamorada

  22542 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /30

  $430,000

  Sold May 11, 2026

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft
  • Built 1975

  Last Sold Summary

  • $1,036/SF
  • 94 Days On Market

  Current Estimated Value $452,438

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
• 

  /2

  Est $939,323

  Not Listed For Sale

  22842 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,326 Sq Ft
  • Built 1998

  22842 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /3

  $60,000

  • Land
  • 5,000 Sq Ft
  • $522,720 per Acre

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /23

  $710,000

  Sold Aug 20, 2025

  19603 Seminole St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $598/SF
  • 5 Days On Market

  Current Estimated Value $735,565

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  19603 Seminole St, Summerland Key, FL 33042
• 

  

  /115

  Est $7,033,207

  Not Listed For Sale

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  785 Sawyer Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • 44 Days On Market
• 

  

  /37

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  27732 Astrangia Ave, Little Torch Key, FL 33042

  Welcome to your own slice of the Florida Keys paradise. This beautifully remodeled and fully furnished 2-bedroom, 2-bath waterfront home is the definition of move-in ready--offered turnkey and decorated in charming coastal colors and beach-inspired décor that perfectly captures the relaxed island lifestyle. Ideally positioned just three homes from open water, this canal-front retreat offers

  Monika Rydzak eXp Realty LLC KW Branch

  27732 Astrangia Ave, Little Torch Key, FL 33042
• 

  

  /73

  $2,650,000

  Sold Jul 10, 2026

  23941 Henry St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $1,187/SF
  • 32 Days On Market

  Current Estimated Value $2,797,197

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  23941 Henry St, Summerland Key, FL 33042
• 

  

  /42

  Est $1,047,129

  Not Listed For Sale

  27330 Barbados Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1991

  27330 Barbados Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 79 Days On Market
• 

  

  /74

  $2,895,000

  $355K PRICE DROP Under Contract

  • 4 Beds
  • 4 Baths
  • 1,804 Sq Ft

  17385 Keystone Rd, Summerland Key, FL 33042

  Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. (24,662 sqft Upland & 12,477 submerged). These point lots are extremely limited and among the most

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17385 Keystone Rd, Summerland Key, FL 33042
• 

  

  /73

  $809,300

  Sold Aug 18, 2025

  547 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1991

  Last Sold Summary

  • $736/SF
  • 39 Days On Market

  Current Estimated Value $867,854

  Last Listing Agent Litney Ellis Dalton Wade Inc

  547 Heck Ave, Little Torch Key, FL 33042
• 

  

  /64

  Est $1,694,468

  Not Listed For Sale

  553 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft
  • Built 1996

  553 Indies Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 76 Days On Market
• 

  

  /78

  $1,490,000

  New Construction $110K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! This newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies, ideal for soaking in the sunrise or entertaining guests in true Keys style. Canal with direct access to the open ocean. No

  NON-MLS MEMBER MAR NON MLS MEMBER

  142 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /41

  $2,280,000

  Sold Apr 02, 2026

  1176 Thatch Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 1984

  Last Sold Summary

  • 24% Below List Price
  • $1,446/SF
  • 359 Days On Market

  Current Estimated Value $2,323,186

  Last Listing Agent Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  

  /62

  Est $5,194,680

  Not Listed For Sale

  1141 Ocean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 4.5 Baths
  • 3,421 Sq Ft
  • Built 2005

  1141 Ocean Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 22 Days On Market
• 

  

  /9

  $399,000

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

  27917 Coral Shores Rd, Summerland Key, FL 33042

  Located on a clean boating canal in Coral Shores Subdivision. This property is waiting for someone to tear it down and put up their brand-new home. With a full 46 foot seawall and a 5-minute boat ride to open water this is a boater's dream. The wooded lots across the street offer both privacy and beautiful wildlife where you can enjoy the peaceful sound of the many different types of birds. There

  Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

  27917 Coral Shores Rd, Summerland Key, FL 33042
• 

  

  /41

  $1,350,000

  Sold Aug 18, 2025

  20735 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 16 Days On Market

  Current Estimated Value $1,387,022

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20735 5th Ave W, Summerland Key, FL 33042
• 

  

  /39

  Est $671,979

  Not Listed For Sale

  25161 Center St, Summerland Key, FL 33042

  • 1 Bed
  • 1.5 Baths
  • 1,024 Sq Ft
  • Built 1958

  25161 Center St, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  /27

  $320,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

  Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
• 

  

  /37

  $725,000

  Sold Jan 14, 2026

  27394 Saint Lucie Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1994

  Last Sold Summary

  • $673/SF
  • 19 Days On Market

  Current Estimated Value $760,732

  Last Listing Agent Casey Arnold eXp Realty LLC

  27394 Saint Lucie Ln, Summerland Key, FL 33042
• 

  

  /40

  Est $2,227,481

  Not Listed For Sale

  20995 2nd Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft
  • Built 2007

  20995 2nd Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  /7

  $799,990

  • Land
  • 7,840 Sq Ft
  • $4,444,389 per Acre

  28525 Jolly Roger Dr, Little Torch Key, FL 33042

  RARE opportunity to own a build ready canal front lot in the heart of Little Torch Key. Tucked away on a quiet dead end road near the end of the island, this prime waterfront parcel offers the best of both worlds! Open water views from the front and a deep canal with seawall along the back. Enjoy unobstructed ocean and sky views from your front porch with no homes across the street ever, creating

  Fazana Haniff FL Home Group LLC

  28525 Jolly Roger Dr, Little Torch Key, FL 33042
• 

  

  /4

  $837,000

  Sold Jul 10, 2026

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 7% Below List Price
  • $943/SF
  • 37 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
• 

  

  /49

  Est $6,992,903

  Not Listed For Sale

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft
  • Built 1992

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 7 Days On Market
• 

  

  /50

  $1,199,000

  $226K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  27414 Guadaloupe Ln, Ramrod Key, FL 33042

  Pride of ownership makes this house a home buyer's dream. This 3 bed, 2 bath, 1492sf home sits on an oversized fully fenced lot with beautiful landscaping, 14x32 heated, saltwater pool, large screened porch w/stairs to the pool & outdoor living space offering a private retreat for you to enjoy the laid-back Florida Keys lifestyle. Located in Breezeswept Beach Estate in Ramrod Key, this home is

  Pamela Stangler Expert Realty LLC

  27414 Guadaloupe Ln, Ramrod Key, FL 33042
• 

  

  /49

  $750,000

  Sold Jul 24, 2025

  25121 Center St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $781/SF
  • 72 Days On Market

  Current Estimated Value $773,465

  Last Listing Agent Gregory Sullivan BYOWNER.COM

  25121 Center St, Summerland Key, FL 33042
• 

  

  /57

  Est $1,504,648

  Not Listed For Sale

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  468 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 215 Days On Market
• 

  

  /47

  $445,000

  $10K PRICE DROP

  • Land
  • 2,078 Sq Ft
  • $9,328,296 per Acre

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

  ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

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