Homes in ZIP Code 33042

• 

  

  

  /61

  $835,000

  Sold May 04, 2026

  27332 St Martin Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • Built 1974

  Last Sold Summary

  • 14% Below List Price
  • $487/SF
  • 195 Days On Market

  Current Estimated Value $845,143

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  27332 St Martin Ln, Ramrod Key, FL 33042
• 

  

  

  /45

  Est $2,509,926

  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
• 

  

  

  /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
• 

  

  

  /50

  $550,000

  Sold Jul 14, 2025

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2021

  Last Sold Summary

  • 18% Below List Price
  • $637/SF
  • 245 Days On Market

  Last Listing Agent Joe Sappington Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
• 

  

  

  /43

  Est $1,396,187

  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
• 

  

  /36

  $998,000

  Under Contract

  • 5 Beds
  • 3 Baths
  • 2,572 Sq Ft

  596 W Shore Dr, Summerland Key, FL 33042

  Waterfront duplex located on a wide, deep boating canal with excellent boating access and 60 ft. of dockage, split between both units, offering approximately 30 ft. per side. Situated at 594-596 W. Shore Drive, this two-story multifamily property features approximately 1,392 sq. ft. downstairs and approximately 1,180 sq. ft. upstairs, plus separate tiki huts for each unit to enjoy outdoor

  Miranda Dender Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  596 W Shore Dr, Summerland Key, FL 33042
• 

  

  /17

  $850,000

  Sold Mar 30, 2026

  17171 Seagrape Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft
  • Built 1982

  Last Sold Summary

  • 22% Below List Price
  • $607/SF
  • 132 Days On Market

  Current Estimated Value $906,346

  Last Listing Agent Marie Howe Century 21 Circle - Key West

  17171 Seagrape Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $1,009,027

  Not Listed For Sale

  1107 Hawksbill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1984

  1107 Hawksbill Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 54 Days On Market
• 

  

  /125

  $10,499,000

  New Construction $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
• 

  

  /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 $923,344

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  22818 Privateer Dr, Summerland Key, FL 33042
• 

  

  /8

  Est $762,171

  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
• 

  

  /42

  $1,299,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft

  21025 3rd Ave, Summerland Key, FL 33042

  Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining.A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows

  Diane Corliss Coldwell Banker Schmitt RE Co.

  21025 3rd Ave, Summerland Key, FL 33042
• 

  

  /3

  $82,500

  Sold Jul 09, 2026

  0 Palm Ln Unit A12024518, Summerland Key, FL 33042

  • Land
  • 7,405 Sq Ft
  • $485,294 per Acre

  Last Sold Summary

  • 31% Below List Price
  • 25 Days On Market

  Last Listing Agent Carmen David Xcellence

  0 Palm Ln Unit A12024518, Summerland Key, FL 33042
• 

  

  /26

  Est $484,238

  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
• 

  

  /13

  $595,000

  • Land
  • 6,969 Sq Ft
  • $3,718,750 per Acre

  28597 Peg Leg Rd, Little Torch Key, FL 33042

  Canal-front with Open Water Views on a corner lot vacant land with a building permit already in process -- Permit #SFDUP-2025-0111, holding 41.5 ROGO points. Plans are drawn for a 3,809 square-foot, four-bedroom, four-bathroom residence with open water views. A separate dock permit is also in process -- Permit #R-DOCK-2025-0302 -- along with full architectural plans, all included in the purchase.

  Claudette Mell Century 21 Circle- Islamorada

  28597 Peg Leg Rd, Little Torch 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
• 

  

  /26

  Est $1,263,090

  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
• 

  

  /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
• 

  

  /42

  $600,000

  Sold Jun 04, 2026

  22948 Drake Ln, Summerland Key, FL 33042

  • Land
  • 6,098 Sq Ft
  • $4,285,714 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 177 Days On Market

  Current Estimated Value $655,400

  Last Listing Agent Barbara Bowers Preferred Properties (KW)

  22948 Drake Ln, Summerland Key, FL 33042
• 

  

  /32

  Est $1,791,600

  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
• 

  

  /53

  $999,000

  $26K PRICE DROP Under Contract

  • 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

  $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 $1,173,547

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  218 Spanish Main Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,778,690

  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
• 

  

  /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
• 

  

  /47

  $525,000

  Sold May 28, 2026

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1995

  Last Sold Summary

  • 11% Below List Price
  • $643/SF
  • 204 Days On Market

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
• 

  

  /40

  Est $994,777

  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
• 

  

  /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
• 

  

  /71

  $420,000

  Sold May 26, 2026

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

  • Land
  • 2,613 Sq Ft
  • $7,000,000 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 75 Days On Market

  Current Estimated Value $435,330

  Last Listing Agent Kelly Gardner Bluescape Real Estate

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

  

  /59

  Est $2,231,289

  Not Listed For Sale

  17346 Keystone Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,192 Sq Ft
  • Built 2019

  17346 Keystone Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 41 Days On Market
• 

  

  /16

  $2,195,000

  • 5 Beds
  • 3 Baths
  • 1,903 Sq Ft

  125 Colson Dr, Summerland Key, FL 33042

  TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  125 Colson Dr, Summerland 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
• 

  

  /42

  Est $997,771

  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
• 

  

  /55

  $875,000

  $124K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  22978 Port Royal Ln, Summerland Key, FL 33042

  Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully

  Anne Press Lokation Real Estate

  22978 Port Royal Ln, Summerland 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
• 

  /2

  Est $727,000

  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
• 

  

  /3

  $120,000

  $15K PRICE DROP

  • Land
  • 15,000 Sq Ft
  • $348,480 per Acre

  19617 Date Palm Dr, Sugarloaf Key, FL 33042

  Now only $120,000. Best priced lot in popular Upper Sugarloaf Key and priced for immediate sale! Take advantage of this opportunity to develop this larger 150 x 100 Tier III platted lot (infill lot located in a developed subdivision with adequate infrastructure). With its prime location and desirable features, this property is a rare find in today's market. Convenient to the community boat ramp

  Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  19617 Date Palm Dr, 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 $800,959

  Last Listing Agent Melissa Graham Bluescape Real Estate

  27255 Mariposa Rd, Ramrod Key, FL 33042
• 

  

  /73

  Est $3,008,098

  Not Listed For Sale

  17018 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1991

  17018 Wahoo Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 122 Days On Market
• 

  

  /46

  $399,900

  $19K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 833 Sq Ft

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

  This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 2 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 140, Cudjoe 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 $248,891

  Last Listing Agent Scott Brisson KeyIsle Realty

  27345 Guadaloupe Ln, Ramrod Key, FL 33042

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