Homes in ZIP Code 33042

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  /9

  Not Listed For Sale

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 543 Days On Market
• 

  

  

  /50

  $1,399,000

  $50K PRICE DROP

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

  845 Pirates Rd, Summerland Key, FL 33042

  **OPEN HOUSE HAS BEEN CANCELLED**- Discover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal-front home offers quick boating access to open water, making it ideal for fishing and island adventures.Designed for the Florida Keys lifestyle, the property features a private pool, tiki hut, and spacious outdoor entertaining areas

  Sandra Dolowy KeyIsle Realty

  845 Pirates Rd, Summerland Key, FL 33042
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  /39

  $705,000

  Sold Sep 08, 2025

  181 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $647/SF
  • 7 Days On Market

  Current Estimated Value $718,116

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  181 Doubloon Ln, Summerland Key, FL 33042
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  /2

  Est $494,568

  Not Listed For Sale

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  • Studio

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  Last Sold Summary
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  /58

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  885 Hawksbill Ln, Summerland Key, FL 33042

  Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Located at 885 Hawksbill Lane, this waterfront property sits on a 6,120 sq ft lot and features a concrete seawall with boat davits, pavers and a heated swimming pool and spa completed in 2022. Enjoy canal and mangrove views plus

  Tommy Mack Coastal Collection Real Estate Inc.

  885 Hawksbill Ln, Summerland Key, FL 33042
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  /31

  $735,000

  Sold Jun 06, 2025

  27373 Antigua Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2016

  Last Sold Summary

  • 2% Below List Price
  • $619/SF
  • 6 Days On Market

  Current Estimated Value $783,102

  Last Listing Agent Sandra Dolowy KeyIsle Realty

  27373 Antigua Ln, Ramrod Key, FL 33042
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  /2

  Not Listed For Sale

  430 Les Rohde Dr, Ramrod Key, FL 33042

  430 Les Rohde Dr, Ramrod Key, FL 33042

  Last Sold Summary
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  /48

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  22939 Gasparilla Ln, Summerland Key, FL 33042

  Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete

  Donna Pezzi Keller Williams Key West Compass Realty

  22939 Gasparilla Ln, Summerland Key, FL 33042
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  /42

  $550,000

  Sold Dec 01, 2025

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $637/SF
  • 125 Days On Market

  Current Estimated Value $581,777

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
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  /2

  Est $467,979

  Not Listed For Sale

  20874 4th Ave, Cudjoe Key, FL 33042

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  Last Sold Summary
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  /68

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  612 Blackbeard Rd, Summerland Key, FL 33042

  Stunning 3 Bedroom 2 Bath waterfront retreat in sought-after Jolly Rogers subdivision featuring a deep flow-through canal with quick boating access, a Trex dock, 15,000 lb boat lift, permitted cargo lift. Built for durability and peace of mind with impact windows and doors, Hardie board siding, aluminum railings, and low-maintenance Trex decking throughout, standing seam metal roof.Inside,

  Diane Corliss Coldwell Banker Schmitt RE Co.

  612 Blackbeard Rd, Summerland Key, FL 33042
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  /33

  $1,075,000

  Sold Feb 20, 2026

  17226 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1998

  Last Sold Summary

  • 10% Below List Price
  • $861/SF
  • 32 Days On Market

  Current Estimated Value $1,090,932

  Last Listing Agent Stephen Hachey

  17226 Jamaica Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,172,519

  Not Listed For Sale

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 2022

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  Last Sold Summary
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  /42

  $1,325,000

  • 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
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  /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 $1,997,714

  Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

  17022 Starfish Ln W, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  1138 Basque Ln, Summerland Key, FL 33042

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042

  Last Sold Summary
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  /38

  $1,349,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  335 Pirates Rd, Summerland Key, FL 33042

  *SWIMMING POOL TO BE BUILT IN SUMMER OF 2026*Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true for

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  335 Pirates Rd, Summerland Key, 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 $2,430,460

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
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  /61

  Est $2,930,906

  Not Listed For Sale

  20886 4th Ave W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 3,042 Sq Ft
  • Built 2008

  20886 4th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 66 Days On Market
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  /72

  $1,350,000

  Open Sat 11AM - 2PM

  • 5 Beds
  • 5 Baths
  • 2,258 Sq Ft

  4049 Egret Ln, Summerland Key, FL 33042

  Waterfront living meets comfort and functionality in this move-in ready canal front home. Offering 120 feet of concrete dockage in a deep water canal. Quick boating access to Niles Channel. Designed for the ultimate Florida Keys lifestyle, this property combines spacious indoor living with exceptional outdoor entertaining areas. The main home features 2 bedrooms and 2 bathrooms with an

  Deni Heintzelman KeyIsle Realty

  4049 Egret Ln, Summerland Key, FL 33042
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  /25

  $1,249,000

  Sold Apr 28, 2026

  17170 Amberjack Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1989

  Last Sold Summary

  • $1,183/SF
  • 0 Days On Market

  Current Estimated Value $1,264,151

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17170 Amberjack Ln, Summerland Key, FL 33042
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  /2

  Est $866,369

  Not Listed For Sale

  460 Les Rohde Dr, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2017

  460 Les Rohde Dr, Ramrod Key, FL 33042

  Last Sold Summary
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  /49

  $1,499,000

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  27372 W Indies Dr, Summerland Key, FL 33042

  Offered for the first time, this custom-built 4 bedroom, 3 bathroom waterfront residence on Ramrod Key showcases refined coastal design, exceptional craftsmanship, and magnificent ocean views. Completed in 2020, the two-story stilted home was thoughtfully designed to maximize light, views, and seamless indoor-outdoor living, with one master bedroom ensuite on each level for comfort and

  Sandra Dolowy KeyIsle Realty

  27372 W Indies Dr, Summerland Key, FL 33042
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  /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 $1,071,685

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  527 Heck Ave, Little Torch Key, FL 33042
• 

  /2

  Est $414,822

  Not Listed For Sale

  27328 St Vincent Ln, Ramrod Key, FL 33042

  • Studio

  27328 St Vincent Ln, Ramrod Key, FL 33042

  Last Sold Summary
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  /33

  $1,585,000

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  3167 Stewart Rd, Summerland Key, FL 33042

  SECLUDED SANCTUARY. This 3-bedroom, 2-bath home provides rare-to-find tranquility in a pristine natural setting. The two-story cottage embodies Old Florida-style with lovingly maintained stone accents and an expansive covered porch overlooking open water. The covered private deck extends your space to relax out to the water's edge. Inside, modern amenities enhance the home's charm and function.

  Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  3167 Stewart Rd, Summerland Key, FL 33042
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  /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 $1,587,504

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17094 Coral Dr, Summerland Key, FL 33042
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  /49

  Est $344,489

  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

  • 27 Days On Market
• 

  

  /38

  $1,490,000

  $109K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  1113 de Lussan Ln, Summerland Key, FL 33042

  Breathtaking Open Water Home in Cudjoe Key - Comes FULLY FURNISHED!Welcome to paradise! This stunning 2-bedroom, 2-bath home captures magnificent open water views and embodies the ultimate Florida Keys lifestyle.Main Living Area:Step inside to an open-concept kitchen, living room, and dining area bathed in natural light. Every detail is designed to highlight the beauty of the

  Diane Corliss Coldwell Banker Schmitt RE Co.

  1113 de Lussan Ln, Summerland Key, FL 33042
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  /49

  $278,000

  Sold Apr 30, 2026

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft
  • Built 1986

  Last Sold Summary

  • 16% Below List Price
  • $377/SF
  • 149 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
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  /2

  Est $1,041,179

  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
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  /78

  $1,490,000

  New Construction $110K PRICE DROP

  • 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

  Jose Cabrera AmeriFirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
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  /3

  $49,000

  Sold Jun 06, 2025

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  • Land
  • 5,499 Sq Ft
  • $388,080 per Acre

  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
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  /2

  Est $739,534

  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
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  /32

  $1,599,000

  $90K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,144 Sq Ft

  1151 Sugarloaf Blvd, Summerland Key, FL 33042

  Truly unique and private estate property on the desired Sugarloaf Blvd. in Sugarloaf Shores. Ground level CBS house sits on 2 waterfront lots. Totaling over 1.3 acres of land and approx. 400 ft. of canal front. Amazing view up the canal to the open water. The large floor plan featuring 3 bedrooms, 2 baths, den/office and fireplace. Kitchen has stainless appliances, quartz countertops and lots of

  Wendy Zintsmaster Truman & Co. (KW)

  1151 Sugarloaf Blvd, 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 $982,938

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
• 

  

  /31

  Est $834,914

  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

  • 146 Days On Market
• 

  

  /86

  $1,595,000

  $344K PRICE DROP

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

  16640 Cypress Rd, Summerland Key, FL 33042

  RARE Solar-Powered Waterfront Tropical Gem with TESLA Solar Storage Banks on Prestigious Sugarloaf Key! A rare opportunity to own a fully solar-powered waterfront residence featuring 26 solar panels and two Tesla Solar Powerwall storage banks, offering exceptionally low energy costs, backup power, and the potential to earn credits by supplying excess energy back to the grid. This elevated 3 BD, 2

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  16640 Cypress Rd, Summerland Key, FL 33042
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  /11

  $405,000

  Sold May 04, 2026

  744 Trinidad Ln, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1967

  Last Sold Summary

  • 26% Below List Price
  • $367/SF
  • 62 Days On Market

  Current Estimated Value $511,111

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  744 Trinidad Ln, Little Torch Key, FL 33042
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  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  Last Sold Summary

Showing Results 201 - 240, Page 6 of 18