Homes in ZIP Code 33042

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  /63

  $1,325,000

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  28560 Doubloon Rd, Summerland Key, FL 33042

  Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 772-6030

  28560 Doubloon Rd, Summerland Key, FL 33042
• 

  

  

  /27

  $1,900,000 Sold Jun 18, 2025

  17022 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • Built 1994

  Last Sold Summary

  • 14% Below List Price
  • $955/SF
  • 85 Days On Market

  Current Estimated Value $1,977,344

  Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

  17022 Starfish Ln W, Summerland Key, FL 33042
• 

  

  /2

  Est $245,968 Not Listed For Sale

  27328 St Vincent Ln, Ramrod Key, FL 33042

  • Studio

  27328 St Vincent Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 92% Below List Price

  Last Sold Price $128,000

  Last Listing Agent Brian Kruszewski LoKation Real Estate
• 

  

  

  /17

  $599,900

  • Land

  17215 Keystone Rd, Sugarloaf Shores, FL 33042

  Cleared canal-front lot in Sugarloaf Shores with building permit in place and first inspection not due until December 2026! Positioned on the desirable no-bridge side, this expansive 27,716 sq. ft. residential parcel is surrounded by multi-million-dollar homes and offers easy access to the open water where days are enjoyed paddling and kayaking through mangrove-line creeks or heading out to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 957-7959

  17215 Keystone Rd, Sugarloaf Shores, FL 33042
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  /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 $2,458,790

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /49

  Est $441,520 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

  • 28% Above List Price
  • 27 Days On Market

  Last Sold Price $345,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
• 

  

  /47

  $559,000 Open Fri 10:30AM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

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

  Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 35 ft seawall.* Community Boat Ramp and boat washdown station.*

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 686-7983

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

  

  /58

  $2,025,000 Sold May 13, 2025

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $1,567/SF
  • 85 Days On Market

  Current Estimated Value $2,062,598

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /8

  Est $538,754 Not Listed For Sale

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 44% Above List Price
  • 248 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Al Barbosa One Sotheby's International Realty
• 

  

  /30

  $750,000 Under Contract

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

  26868 Mariposa Rd, Ramrod Key, FL 33042

  Presenting a newly built 2023 home on a spacious 12,250 sq. ft. lot in Ramrod Shores, designed with both efficiency and style in mind. This four-bedroom, two-bathroom property features durable construction elements like a metal roof and impact-resistant windows, optimizing insurance costs, with all 3 insurances combined under $5,000 total. The interior boasts an open-concept floor plan with high

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 783-4956

  26868 Mariposa Rd, Ramrod 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 $1,074,725

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  527 Heck Ave, Little Torch Key, FL 33042
• 

  /2

  Est $1,031,273 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

  Last Sold Summary

  • 3% Below List Price
  • $842/SF

  Last Sold Price $1,000,000

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys
• 

  

  /47

  $599,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4104

  701 Spanish Main Dr Unit 30, Cudjoe 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 $1,691,320

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17094 Coral Dr, Summerland Key, FL 33042
• 

  /2

  Est $695,788 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

  Last Sold Summary

  • 7% Below List Price
  • $659/SF

  Last Sold Price $652,410
• 

  

  /59

  $599,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4762

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
• 

  

  /3

  $49,000 Sold Jun 06, 2025

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 35% Below List Price
  • 206 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Vacant Land, Big Torch Key, FL 33042
• 

  

  /31

  Est $799,557 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

  • $794/SF
  • 146 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /107

  $2,999,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,538 Sq Ft

  747 La Fitte Rd, Summerland Key, FL 33042

  Spectacular open water location, with fabulous views from this newly constructed well-built oceanfront concrete home. Direct ocean or gulf access from massive dock that includes three boat lifts (one 15,000 pound, one 12,000 pound and a 10,000 pound double Waverunner lift). Relax in a large heated/chilled inground pool with a big covered pool patio area which drinks in the Ocean view. Home is

  John L. Markle Keller Williams Realty Premier Properties - Kendall

  747 La Fitte Rd, 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 $982,007

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
• 

  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  Last Sold Summary

  Last Sold Price $525,000

  Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC
• 

  

  /39

  $499,000

  • 2 Beds
  • 2 Baths
  • 618 Sq Ft

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042

  Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile home is located in Venture Out, a gated, resort-style community offering endless activities and true Island living at a price point rarely found on the water.Enjoy direct boating to open water, just minutes from the Atlantic and Gulf, making this a boaters dream. Located at Mile Marker 23, you're only 20

  Suzanne Moore Suzanne Moore Real Estate

  701 Spanish Main Dr Unit 411, Cudjoe 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 $2,561,769

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1147 Flagship Dr, Summerland Key, FL 33042
• 

  

  /28

  Est $1,854,845 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

  • 106% Above List Price
  • $452/SF
  • 0 Days On Market

  Last Sold Price $899,000

  Last Listing Agent Kathleen Gomez Coldwell Banker Schmitt RE Co.
• 

  

  /22

  $465,000

  • 1 Bed
  • 1 Bath
  • 799 Sq Ft

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

  A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

  Rose Dell Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
• 

  /2

  $185,000 Sold Mar 20, 2026

  1223 Rogers Ln, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $287,661

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  1223 Rogers Ln, Cudjoe Key, FL 33042
• 

  /2

  Est $792,625 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

  Last Sold Summary

  • 14% Below List Price
  • $495/SF

  Last Sold Price $695,000

  Last Listing Agent Mary Bryant Keller Williams Key West Compass Realty
• 

  

  /30

  $430,000

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  Acre Property! I've heard it said privacy is the ultimate luxury. Your Keys bungalow in the woods with a separate screened porch enclosure 13 X 18 plus a storge room 9 X 12. Connected to the house by a wood deck walkway. Artist retreat, man cave or maybe just because you love privacy and want an escape. Lots of potential. Are you handy! Additionally, there are 2 carports, Multiple storage areas.

  Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
• 

  

  /44

  $853,000 Sold Aug 12, 2025

  873 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $789/SF
  • 123 Days On Market

  Current Estimated Value $876,715

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  873 Indies Rd, Summerland Key, FL 33042
• 

  

  /23

  Est $844,752 Not Listed For Sale

  27225 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2017

  27225 Mariposa Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 10% Above List Price
  • $560/SF
  • 382 Days On Market

  Last Sold Price $764,500

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys
• 

  

  /62

  $2,599,000

  • 3 Beds
  • 2 Baths
  • 2,224 Sq Ft

  16843 E Point Dr, Summerland Key, FL 33042

  Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open water redefine the Lower Keys Lifestyle.Positioned along a crystal clear canal just moments from the Bay, this elevated residence offers over 2200 sq.ft of thoughtfully designed living space, featuring three spacious bedrooms and

  Suzanne Moore Suzanne Moore Real Estate

  16843 E Point Dr, Summerland Key, FL 33042
• 

  

  /29

  $510,000 Sold Apr 28, 2025

  1693 Bayview Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 917 Sq Ft
  • Built 1976

  Last Sold Summary

  • 13% Below List Price
  • $556/SF
  • 60 Days On Market

  Last Listing Agent Ana Tey-Guerra Trexy International Realty, Inc

  1693 Bayview Dr, Little Torch Key, FL 33042
• 

  /2

  Est $771,465 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

  • 1% Above List Price
  • $588/SF
  • 145 Days On Market

  Last Sold Price $765,000

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)
• 

  

  /29

  $800,000

  • 2 Beds
  • 2 Baths
  • 1,162 Sq Ft

  28452 Yucatan Ln, Summerland Key, FL 33042

  SATURDAY 28TH OPEN HOUSE 10AM-1PM Canal front home with quick exit out of the canal to Pine Channel for Atlantic or Gulf access. 7200 sq.ft. lot. Back yard big enough for a pool. Pack your toothbrush and your ready for your salt life to begin. Being sold mostly furnished 2bd/2bth 1162 sq.ft. Home, plus, southerly facing screen porch, which has accordian shutters,porch faces back yard and canal.

  Rose Dell Keller Williams Key West Compass Realty

  28452 Yucatan Ln, Summerland Key, FL 33042
• 

  

  /45

  $819,000 Sold May 19, 2025

  25093 Center St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Below List Price
  • $517/SF
  • 18 Days On Market

  Current Estimated Value $817,108

  Last Listing Agent Susan Hawkinson Bascom Grooms Real Estate (KW)

  25093 Center St, Summerland 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

  • $631/SF
  • 461 Days On Market

  Last Sold Price $265,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
• 

  

  /59

  $1,529,999 Open Sat 11AM - 2PM

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

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, 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

  Alejandro Perez Amerifirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /18

  $480,000 Sold Apr 01, 2026

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 20% Below List Price
  • 126 Days On Market

  Current Estimated Value $522,715

  Last Listing Agent The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
• 

  

  /66

  Not Listed For Sale

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 1978

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Last Sold Summary

  • $408/SF
  • 78 Days On Market

  Last Sold Price $284,500

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
• 

  

  /68

  $2,299,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,055 Sq Ft

  24266 Caribbean Dr W, Summerland Key, FL 33042

  A Private OCEANFRONT Retreat in Summerland Key. Nestled in the serene beauty of Summerland Key, this extraordinary 4-bedroom oceanfront residence offers a rare blend of architectural character, craftsmanship, and unobstructed open-water views. Designed for those who appreciate privacy and artistry, this is not a typical ''drive-by'' home - it's a destination.Thoughtfully configured in two

  Donna Pezzi Keller Williams Key West Compass Realty

  24266 Caribbean Dr W, Summerland Key, FL 33042

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