Homes in ZIP Code 33042

• 

  

  /2

  Est $759,006

  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

  Last Sold Summary
• 

  

  

  /45

  $1,250,000

  Open Sat 10AM - 12PM

  • 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

  $870,000

  Sold Oct 10, 2025

  22818 Privateer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1997

  Last Sold Summary

  • $599/SF
  • 1 Day On Market

  Current Estimated Value $867,956

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  22818 Privateer Dr, Summerland Key, FL 33042
• 

  

  

  /77

  Est $5,806,243

  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
• 

  

  

  /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
• 

  

  /56

  $2,599,000

  Sold Jun 18, 2025

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft
  • Built 1975

  Last Sold Summary

  • $2,254/SF
  • 11 Days On Market

  Current Estimated Value $2,638,349

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  28595 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /41

  Est $1,421,647

  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
• 

  

  /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
• 

  

  /30

  $710,000

  Sold Dec 01, 2025

  701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2002

  Last Sold Summary

  • 25% Below List Price
  • $822/SF
  • 328 Days On Market

  Last Listing Agent Katrina Vanek Bluescape Real Estate

  701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
• 

  

  /45

  Est $1,538,895

  Not Listed For Sale

  622 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3.5 Baths
  • 2,156 Sq Ft
  • Built 1986

  622 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 156 Days On Market
• 

  /2

  $100,000

  $349K PRICE DROP Under Contract

  • Land
  • 14,810 Sq Ft
  • $294,118 per Acre

  Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

  Oversized lot in gorgeous Sugarloaf Key with 15,000 Square feet. Seller has done the Letter of Current Site Conditions with the County. Document available under the documents tab. Buyer to verify all information with Monroe County Planning and Building Department during due diligence period. House plans and extra lot removed, new price reflects that.

  Pamela Stangler Expert Realty LLC

  Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
• 

  

  /38

  $1,170,000

  Sold Mar 02, 2026

  218 Spanish Main Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $580/SF
  • 11 Days On Market

  Current Estimated Value $1,168,531

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  218 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /43

  Est $1,415,208

  Not Listed For Sale

  408 Sawyer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft
  • Built 1989

  408 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 16 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
• 

  

  /71

  $440,000

  $10K PRICE DROP Under Contract

  • Land
  • 2,613 Sq Ft
  • $7,333,333 per Acre

  701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042

  Ocean View Canal Front RV Lot in Venture Out - 35' Concrete SeawallBuild, park, invest, or simply pull in and start living the Keys lifestyle. This 35' x 69' beautiful, waterfront RV lot in the private, gated community of Venture Out offers ocean views, a 35' concrete seawall, and direct boating access to both the Atlantic and backcountry waters.The lot features a concrete pad and

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
• 

  

  /8

  Est $765,149

  Not Listed For Sale

  19514 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1995

  19514 Canal Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 76 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
• 

  

  /70

  $721,000

  Sold Jun 03, 2025

  22933 Buccaneer Ln, Summerland Key, FL 33042

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

  Last Sold Summary

  • 18% Below List Price
  • $663/SF
  • 74 Days On Market

  Current Estimated Value $763,559

  Last Listing Agent Bobby Baker Brightwild Real Estate

  22933 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /26

  Est $511,191

  Not Listed For Sale

  19910 Flamingo Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft
  • Built 1947

  19910 Flamingo Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 10 Days On Market
• 

  

  /18

  $255,000

  $10K PRICE DROP

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

  701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

  Welcome to RV Lot 642, located in the gated, waterfront community of Venture Out on Cudjoe Key. This well-positioned lot offers the perfect setup for your Florida Keys getaway, seasonal stay, or investment opportunity.Enjoy all the perks of a golf-cart-friendly community with resort-style amenities, including a large saltwater pool, marina with boat ramp, pickleball and tennis courts, bocce,

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
• 

  

  /47

  $350,000

  Sold Aug 14, 2025

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 675 Sq Ft
  • Built 1984

  Last Sold Summary

  • 22% Below List Price
  • $519/SF
  • 228 Days On Market

  Last Listing Agent Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042
• 

  

  /26

  Est $1,312,893

  Not Listed For Sale

  105 S Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1984

  105 S Point Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 31 Days On Market
• 

  

  /32

  $339,000

  $210K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

  Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
• 

  

  /44

  $870,000

  Sold Feb 05, 2026

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 779 Sq Ft
  • Built 2005

  Last Sold Summary

  • 13% Below List Price
  • $1,117/SF
  • 224 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
• 

  

  /32

  Est $1,853,632

  Not Listed For Sale

  17023 Allamanda Dr W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1979

  17023 Allamanda Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 77 Days On Market
• 

  

  /125

  $10,499,000

  $501K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 4,894 Sq Ft

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042

  Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key!This extraordinary new construction stunner is engineered as a rare modern fortress— built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
• 

  

  /37

  $765,000

  Sold Jul 28, 2025

  27255 Mariposa Rd, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $531/SF
  • 113 Days On Market

  Current Estimated Value $777,082

  Last Listing Agent Melissa Graham Bluescape Real Estate

  27255 Mariposa Rd, Ramrod Key, FL 33042
• 

  /2

  Est $1,826,963

  Not Listed For Sale

  17150 La Brisa Ct, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1980

  17150 La Brisa Ct, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /16

  $895,900

  $94K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Reduced over 100k for a quick sale. Boater's Paradise in Cudjoe Key under 1 million!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The

  Rayden Vega Casa Miami Real Estate

  22961 John Avery Ln, Summerland Key, FL 33042
• 

  

  /15

  $245,000

  Sold Feb 17, 2026

  27345 Guadaloupe Ln, Ramrod Key, FL 33042

  • Land
  • 6,000 Sq Ft
  • $1,778,700 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 56 Days On Market

  Current Estimated Value $243,895

  Last Listing Agent Scott Brisson KeyIsle Realty

  27345 Guadaloupe Ln, Ramrod Key, FL 33042
• 

  

  /40

  Est $987,575

  Not Listed For Sale

  17236 Keystone Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Built 1974

  17236 Keystone Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 184 Days On Market
• 

  

  /53

  $999,000

  $26K PRICE DROP

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

  24225 Caribbean Dr W, Summerland Key, FL 33042

  Sailor's Dream -- waterfront living at its best! Beautifully maintained tropical home with 3 bedrooms and 2 baths on a deep, wide canal with spectacular open-water views from the front porch and roof-height deck. The bright open living area flows effortlessly to screened front and screened back porches -- perfect for relaxing or entertaining. Primary ensuite and split-bedroom floor plan are ideal

  Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

  24225 Caribbean Dr W, Summerland Key, FL 33042
• 

  

  /38

  $785,000

  Sold Nov 04, 2025

  22464 La Fitte Dr, Summerland Key, FL 33042

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

  Last Sold Summary

  • 2% Below List Price
  • $913/SF
  • 41 Days On Market

  Current Estimated Value $775,674

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  22464 La Fitte Dr, Summerland Key, FL 33042
• 

  

  /42

  Est $934,871

  Not Listed For Sale

  17214 La Brisa Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • Built 1992

  17214 La Brisa Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 50 Days On Market
• 

  

  /63

  $1,124,900

  $74K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  417 Pirates Rd, Summerland Key, FL 33042

  Welcome to this beautifully updated canal-front home in the highly desirable Jolly Roger Estates on Little Torch Key! Offering 3 bedrooms, 2 baths, 1,170 sq ft of living space plus a 110 sq ft flex/office area, this meticulously maintained waterfront home features a desirable split floor plan with an open layout, remodeled kitchen with quartz countertops and LG ThinQ smart refrigerator and range,

  Maggie Beall Lokation Real Estate

  417 Pirates Rd, Summerland Key, FL 33042
• 

  

  /30

  $700,000

  Sold May 08, 2026

  26868 Mariposa Rd, Ramrod Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2023

  Last Sold Summary

  • 16% Below List Price
  • $481/SF
  • 202 Days On Market

  Current Estimated Value $773,141

  Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

  26868 Mariposa Rd, Ramrod Key, FL 33042
• 

  /2

  Est $968,000

  Not Listed For Sale

  17036 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1965

  17036 Wahoo Ln, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /75

  $875,000

  $64K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

  This is the house for your boat! Priced to sell! ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront home. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
• 

  /2

  $49,000

  Sold Jun 06, 2025

  Lot 7 Block 14, Cudjoe Key, FL 33042

  • Land
  • 6,767 Sq Ft
  • $315,419 per Acre

  Last Sold Summary

  • 29% Below List Price
  • 163 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 7 Block 14, Cudjoe Key, FL 33042
• 

  

  /37

  Est $2,220,828

  Not Listed For Sale

  17026 Bonita Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • Built 1989

  17026 Bonita Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 32 Days On Market

Showing Results 561 - 600, Page 15 of 18