Homes in ZIP Code 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

  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 $449,078 Not Listed For Sale

  • Studio

  24397 W Caribbean Dr, Summerland Key, FL 33042

  24397 W Caribbean Dr, Summerland Key, FL 33042
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  /45

  $1,550,000

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

  28538 John Silver Rd, Summerland Key, FL 33042

  Experience the best of the Keys lifestyle in this beautifully appointed 3-bedroom, 2-bath home, ideally positioned on a premium corner lot with approximately 236 feet of waterfront along a wide canal. Offering direct and easy access to open water, this property is a dream for boaters and water lovers alike.Step inside to a bright, open layout where expansive windows frame stunning views of

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  28538 John Silver Rd, Summerland Key, FL 33042
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  /16

  $165,000 Sold Feb 24, 2025

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 8% Below List Price
  • 212 Days On Market

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

  8 Calico Jack Cir, Cudjoe Key, FL 33042
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  /2

  Est $706,205 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  1313 State Rd Unit 4A, Little Torch Key, FL 33042

  1313 State Rd Unit 4A, Little Torch Key, FL 33042
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  /60

  $1,490,000 New Construction

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

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your 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 impact-rated windows & doors,

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, 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 $1,910,354

  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

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /88

  $750,000

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

  40 Munson Ave, Summerland Key, FL 33042

  Welcome home to your peaceful island retreat! This stunning 3-bed, 2-bath home is move-in ready & full of charm. Enjoy soaring vaulted ceilings, an open layout, & a bright kitchen with Quartz countertops, stainless steel appliances, & large island with ample seating. Recent updates include new luxury vinyl plank flooring, new upgraded refrigerator, & new outdoor bar & sitting area perfect for

  Lindsay Ryan EXP Realty LLC

  40 Munson Ave, 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

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

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 925 Sq Ft

  1669 Pine Channel Dr, Little Torch Key, FL 33042

  1669 Pine Channel Dr, Little Torch Key, FL 33042
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  /60

  $949,900

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  Soak up the Keys lifestyle from this bright, modern 3-bed/2-bath home in the coveted oceanside community of Breezeswept Beach Estates on Ramrod Key. Built in 2008 with high-end finishes--sleek cabinetry, quality flooring, and fresh, airy decor--this turnkey residence is neat, clean, and move-in ready.Outdoor living shines here: two open decks (front and back) capture breezes and sunset glow,

  Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
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  /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 $1,989,947

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
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  /28

  Est $1,074,024 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,988 Sq Ft

  27385 St Lucie Ln, Ramrod Key, FL 33042

  27385 St Lucie Ln, Ramrod Key, FL 33042
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  /54

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 1,440 Sq Ft

  1082 Bay Dr, Summerland Key, FL 33042

  Rare Yacht-Ready Waterfront? It doesn't get better than this in the Lower Florida Keys! Embraced by the emerald waters of the American Caribbean, pristine, wide and flow-through canals, and nearly 200 feet of concrete seawall sits this extraordinary opportunity to own prime waterfront. A prized combination coveted by the most discerning boating enthusiasts. Sitting on an oversized 7,900 sq. ft.

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  1082 Bay Dr, Summerland Key, FL 33042
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  /37

  $540,000 Sold Mar 04, 2025

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $750/SF
  • 9 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  27883 Coral Shores Rd, Little Torch Key, FL 33042
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  /14

  Est $454,559 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
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  /59

  $1,569,999 New Construction

  • 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
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  /30

  $740,000 Sold Jan 21, 2025

  124 Yardarm Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $695/SF
  • 22 Days On Market

  Current Estimated Value $735,941

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

  124 Yardarm Rd, Cudjoe Key, FL 33042
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  /2

  Est $827,905 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  53 Gold Boullion Rd, Cudjoe Key, FL 33042
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  /45

  $7,000,000

  • 3 Beds
  • 4 Baths
  • 2,851 Sq Ft

  0 Melody Key Unit 616249, Summerland Key, FL 33042

  An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

  Scott Forman Royal Palms Realty (KW)

  0 Melody Key Unit 616249, 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 $959,050

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

  527 Heck Ave, Little Torch Key, FL 33042
• 

  

  /23

  Est $797,061 Not Listed For Sale

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

  27225 Mariposa Rd, Summerland Key, FL 33042

  27225 Mariposa Rd, Summerland Key, FL 33042
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  /30

  $362,000

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft

  27960 Porgie Path, Little Torch Key, FL 33042

  Canal Front Coral Shores Estates! This 3 Bedroom home with Open Water views of South Pine Channel has a wonderful Swimming Canal ,perfect for kayaking, SUP, and can be easily accessed from the beautiful large new deck- with ladder access to the water. The front of the yard has new fencing, and room to park several cars off street. The inside has 3 bedrooms and a bath, and 2 living room areas.

  Elaine Coyle Keller Williams Key West Compass Realty

  27960 Porgie Path, Little Torch Key, FL 33042
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  /48

  $975,000 Sold Jan 21, 2025

  22940 Gasparilla Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,465 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $666/SF
  • 50 Days On Market

  Current Estimated Value $943,041

  Last Listing Agent Bobby Krug Ocean Sotheby's International Realty

  22940 Gasparilla Ln, Summerland Key, FL 33042
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  /2

  Est $788,219 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft

  27087 Angelfish Rd, Summerland Key, FL 33042

  27087 Angelfish Rd, Summerland Key, FL 33042
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  /7

  $4,325,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042
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  /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
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  /69

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042
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  /43

  $1,125,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  22837 Calico Jack Cir, Summerland Key, FL 33042

  Seller says Bring Offers....Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking

  Beata Sharpe Coldwell Banker Vanguard Realty

  22837 Calico Jack Cir, Summerland Key, FL 33042
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  /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 $999,533

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
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  /66

  Not Listed For Sale

  • 2 Beds

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

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

  

  /56

  $6,995,000 Pending

  • 5 Beds
  • 6 Baths
  • 3,952 Sq Ft

  1151 Ocean Dr, Summerland Key, FL 33042

  This luxe, oceanfront estate will be sold at Luxury AUCTION Without Reserve on December 4, 2025! List price for REFERENCE ONLY. Offered in co-op. with Platinum Luxury Auctions. Inquire for details.Trophy Oceanfront Estate in THE PRIME location on Ocean Dr Summerland Key - surrounded by multi million dollar estates favored by celebrities and business leaders. Fly in and boat out! Located in one of

  Lisa Swanson The Agency Florida Keys

  1151 Ocean Dr, Summerland Key, FL 33042
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  /48

  $940,000 Sold Feb 28, 2025

  184 Cutthroat Dr, Summerland Key, FL 33042

  • 6 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • Built 1963

  Last Sold Summary

  • 22% Below List Price
  • $405/SF
  • 184 Days On Market

  Current Estimated Value $1,040,966

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  184 Cutthroat Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042
• 

  /2

  $52,000

  • Land

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

  Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
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  /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 $851,012

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  873 Indies Rd, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
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  /7

  $195,000

  • Land
  • 1.02 Acres
  • $191,177 per Acre

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042

  Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. It is a special lot that features mature trees. Near Sugarloaf School. 25 minutes to Key West.

  Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042
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  /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

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