Homes in ZIP Code 33042

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  /125

  $1,190,000

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  22748 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor living space is a dream with a new concrete pool & waterfall feature, 12k lb boat lift, 60' concrete seawall, & an expansive 10 foot deep back porch (total of nearly 700 sq ft of porches), all perfect for outdoor dining, lounging, &

  Lindsay Ryan EXP Realty LLC

  22748 Blackbeard Ln, Cudjoe Key, FL 33042
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  /61

  $1,636,000 Sold Aug 19, 2025

  227 La Fitte Rd, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,260 Sq Ft
  • Built 1982

  Last Sold Summary

  • 9% Below List Price
  • $1,298/SF
  • 6 Days On Market

  Current Estimated Value $1,640,704

  Last Listing Agent Jennifer Chaney Chaney Homes

  227 La Fitte Rd, Summerland Key, FL 33042
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  /30

  Est $1,654,465 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft

  540 W Point Dr, Summerland Key, FL 33042

  540 W Point Dr, Summerland Key, FL 33042
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  /4

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  24347 Caribbean Dr W, Summerland Key, FL 33042

  Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-water canal with excellent boating access. Boaters will appreciate the new 17,000-lb boat lift and a quick ride to Looe Key, American Shoal, and the Adolf Bush wreck.The 1232 sq ft home sits on a 6,000 sq ft lot and features hurricane-impact windows, offering peace of mind and energy efficiency. The home has

  Shirley Carey Berkshire Hathaway HomeServices Knight & Gardner Realty

  24347 Caribbean Dr W, Summerland Key, FL 33042
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  /39

  $1,116,000 Sold Jun 25, 2025

  591 Blackbeard Rd, Summerland Key, FL 33042

  • 4 Beds
  • 5 Baths
  • 2,512 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $444/SF
  • 25 Days On Market

  Current Estimated Value $1,190,796

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  591 Blackbeard Rd, Summerland Key, FL 33042
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  /28

  Est $937,863 Not Listed For Sale

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

  340 Spanish Main Dr, Summerland Key, FL 33042

  340 Spanish Main Dr, Summerland Key, FL 33042
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  /52

  $425,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

  Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
• 

  

  /46

  $1,900,000 Sold Mar 27, 2025

  271 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,358 Sq Ft
  • Built 2023

  Last Sold Summary

  • 36% Below List Price
  • $806/SF
  • 342 Days On Market

  Current Estimated Value $1,909,499

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  271 W Indies Dr, Ramrod Key, FL 33042
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  /36

  Est $1,476,165 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  20878 5th Ave W, Summerland Key, FL 33042

  20878 5th Ave W, Summerland Key, FL 33042
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  /60

  $175,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042
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  /2

  $49,000 Sold Sep 22, 2025

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042
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  /41

  Est $834,658 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  24357 Caribbean Dr W, Summerland Key, FL 33042

  24357 Caribbean Dr W, Summerland Key, FL 33042
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  /45

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  17144 Coral Dr, Summerland Key, FL 33042

  Located in prestigious Sugarloaf Shores, a coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3-bedroom, 2-bath home, a massive Great Room with a cathedral ceiling will greet you, highlighted by remodeled cabinetry, kitchen, and stainless steel appliances, including a gas range, where friends and family can gather. Enjoy the full-length porch

  Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  17144 Coral Dr, Summerland Key, FL 33042
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  /40

  $825,000 Sold Aug 04, 2025

  260 Airport Dr S, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 918 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $899/SF
  • 157 Days On Market

  Current Estimated Value $820,701

  Last Listing Agent Francesca Santiago Keller Williams Realty Professionals (KW)

  260 Airport Dr S, Summerland Key, FL 33042
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  /2

  Est $953,395 Not Listed For Sale

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

  27285 Mariposa Rd, Summerland Key, FL 33042

  27285 Mariposa Rd, Summerland Key, FL 33042
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  /16

  $989,999

  • 3 Beds
  • 3 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!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 lower

  Rayden Vega CASA MIAMI REAL ESTATE

  22961 John Avery Ln, Summerland Key, FL 33042
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  /74

  $3,300,000 Sold Feb 18, 2025

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  • 6 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1963

  Last Sold Summary

  • 27% Below List Price
  • $1,023/SF
  • 313 Days On Market

  Current Estimated Value $3,200,481

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  22572 Jolly Roger Dr, Summerland Key, FL 33042
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  /36

  Est $836,069 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  27392 Anguila Ln, Summerland Key, FL 33042

  27392 Anguila Ln, Summerland Key, FL 33042
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  /6

  $225,000

  • Land

  124 Cutthroat Dr, Cudjoe Key, FL 33042

  Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

  Jimmy Lane Island Life Realty Experts

  124 Cutthroat Dr, Cudjoe Key, FL 33042
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  /44

  $650,000 Sold Apr 17, 2025

  268 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $616/SF
  • 86 Days On Market

  Current Estimated Value $666,448

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  268 Spanish Main Dr, Summerland Key, FL 33042
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  /8

  Est $766,810 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  743 Indies Rd, Summerland Key, FL 33042

  743 Indies Rd, Summerland Key, FL 33042
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  /14

  $265,000

  • Land

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

  Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out--golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
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  /41

  $2,425,000 Sold Nov 21, 2025

  281 W Indies Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 2,914 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $832/SF
  • 203 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  281 W Indies Dr, Summerland Key, FL 33042
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  /31

  Est $1,347,692 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft

  949 Bay Dr, Summerland Key, FL 33042

  949 Bay Dr, Summerland Key, FL 33042
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  /43

  $625,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

  Affordable piece of paradise! Move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. All new furnishings included! It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and dehumidify! Plus, a 5

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
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  /31

  $800,000 Sold Jan 31, 2025

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 2001

  Last Sold Summary

  • 8% Below List Price
  • $794/SF
  • 146 Days On Market

  Current Estimated Value $803,690

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042
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  /2

  Est $1,505,775 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,552 Sq Ft

  28537 John Silver Rd, Summerland Key, FL 33042

  28537 John Silver Rd, Summerland Key, FL 33042
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  /32

  $1,689,000

  • 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
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  /82

  $1,800,000 Sold Jun 20, 2025

  17175 Allamanda Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $851/SF
  • 19 Days On Market

  Current Estimated Value $1,788,477

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17175 Allamanda Dr W, Summerland Key, FL 33042
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  /45

  Est $1,842,665 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft

  1126 Lagoon Dr, Summerland Key, FL 33042

  1126 Lagoon Dr, Summerland Key, FL 33042
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  /2

  $56,000 Pending

  • Land
  • 0.26 Acre
  • $217,064 per Acre

  0 State Rd Unit 4A, Little Torch Key, FL 33042

  ROGO land dedication lot worth 2 points with paperwork completed and Monroe County letter of eligibility on file. No hidden expenses with this lot. Cost-effective way to get your permit faster! This lot is not buildable and is sold for land dedication purposes only.

  Nate Meyer Meyer and Boumerhi Realty LLC

  0 State Rd Unit 4A, Little Torch Key, FL 33042
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  /33

  $725,000 Sold Feb 21, 2025

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $507/SF
  • 175 Days On Market

  Current Estimated Value $774,250

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22918 Cudjoe Dr, Cudjoe Key, FL 33042
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  /32

  Est $1,297,310 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,861 Sq Ft

  827 Caribbean Dr E, Summerland Key, FL 33042

  827 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /23

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,228 Sq Ft

  22815 Port Royal Ln, Summerland Key, FL 33042

  DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! INCOME PRODUCING!, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main

  Rhonda Gailey Gailey Enterprises Real Estate

  22815 Port Royal Ln, Summerland Key, FL 33042
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  /45

  $1,230,000 Sold Jan 31, 2025

  27379 Jamaica Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Below List Price
  • $894/SF
  • 44 Days On Market

  Current Estimated Value $1,188,032

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  27379 Jamaica Ln, Ramrod Key, FL 33042
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  /39

  Est $1,419,183 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,312 Sq Ft

  27380 Cayman Ln, Summerland Key, FL 33042

  27380 Cayman Ln, Summerland Key, FL 33042
• 

  

  /98

  $2,800,000

  • 3 Beds
  • 3 Baths
  • 3,013 Sq Ft

  680 Cruikshank Island, Summerland Key, FL 33042

  Welcome to 680 Cruikshank Isle, an extraordinary waterfront estate in the heart of Summerland Key that captures the essence of Florida Keys luxury living. Offering over 3,000 sq. ft. of interior space, this three-bedroom, three-bath residence is thoughtfully designed for both elegance and comfort, blending open living areas with timeless architectural details.Inside, soaring ceilings and

  Barbara Crespo Keller Williams Key West Compass Realty

  680 Cruikshank Island, Summerland Key, FL 33042
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  /38

  $900,000 Sold May 30, 2025

  22971 Hawkins Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,142 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $788/SF
  • 46 Days On Market

  Current Estimated Value $908,646

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  22971 Hawkins Ln, Summerland Key, FL 33042
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  /80

  Est $4,070,706 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,068 Sq Ft

  24826 Calle Real, Summerland Key, FL 33042

  24826 Calle Real, Summerland Key, FL 33042
• 

  

  /12

  $725,000

  • Land

  17230 Angelfish Ln, Sugarloaf Shores, FL 33042

  Build Your Dream Home in Sugarloaf Shores! Don't miss this rare opportunity to own a waterfront lot in the desirable Sugarloaf Shores! This high and dry, cleared 8,165 sq. ft. parcel offers a fresh canvas for your vision of paradise in the Florida Keys. The property features a brand-new concrete seawall, perfect for the boating enthusiast, with direct access to both the Atlantic Ocean and the

  The Spottswood Team Truman & Co. (KW)

  17230 Angelfish Ln, Sugarloaf Shores, FL 33042

Showing Results 641 - 680, Page 17 of 18