Homes in ZIP Code 33042

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  /3

  $300,000

  • Land

  0 Candice Ave, Little Torch Key, FL 33042

  Rare opportunity to acquire a 6-parcel assemblage totaling approx. 13.67 acres on Little Torch Key. Includes five 6,000 sq. ft. Mates Beach lots on Candice Avenue (two Tier 3 Infill) and a 12.97+/- acre tract with 2.61 acres upland and 10.36 acres environmentally sensitive land. Perfect for agricultural or beekeeping use, conservation project, or long-term investment. Located in a desirable Lower

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  0 Candice Ave, Little Torch Key, FL 33042
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  /56

  $2,599,000 Sold Jun 18, 2025

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft
  • Built 1975

  Last Sold Summary

  • $2,254/SF
  • 11 Days On Market

  Current Estimated Value $2,560,893

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  28595 Jolly Roger Dr, Summerland Key, FL 33042
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  /46

  Est $2,653,210 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,006 Sq Ft

  961 W Indies Dr, Summerland Key, FL 33042

  961 W Indies Dr, Summerland Key, FL 33042
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  /61

  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

  Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom home, built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
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  /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
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  /28

  Est $813,784 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 925 Sq Ft

  27378 Haiti Ln, Summerland Key, FL 33042

  27378 Haiti Ln, Summerland Key, FL 33042
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  /94

  $3,875,000

  • 4 Beds
  • 4 Baths
  • 2,766 Sq Ft

  414 Caribbean Dr E, Summerland Key, FL 33042

  Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft.

  Lisa Swanson The Agency Florida Keys

  414 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /34

  $735,000 Sold May 16, 2025

  27373 Anguila Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $682/SF
  • 117 Days On Market

  Current Estimated Value $763,769

  Last Listing Agent Tracy Shields KeyIsle Realty

  27373 Anguila Ln, Summerland Key, FL 33042
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  /41

  Est $889,527 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  27468 Haiti Ln, Summerland Key, FL 33042

  27468 Haiti Ln, Summerland Key, FL 33042
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  /4

  $100,000

  • Land
  • 1.01 Acres
  • $99,010 per Acre

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042

  Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042
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  /92

  $1,050,000 Sold May 14, 2025

  27436 Tobago Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 2020

  Last Sold Summary

  • 19% Below List Price
  • $852/SF
  • 129 Days On Market

  Current Estimated Value $1,056,768

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  27436 Tobago Ln, Summerland Key, FL 33042
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  /2

  Est $750,475 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  433 Indies Rd, Summerland Key, FL 33042

  433 Indies Rd, Summerland Key, FL 33042
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  /47

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  43 Venetian Way, Summerland Key, FL 33042

  Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

  Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
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  /70

  $721,000 Sold Jun 03, 2025

  22933 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1995

  Last Sold Summary

  • 18% Below List Price
  • $663/SF
  • 74 Days On Market

  Current Estimated Value $750,641

  Last Listing Agent Bobby Baker Brightwild Real Estate

  22933 Buccaneer Ln, Summerland Key, FL 33042
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  /45

  Est $1,177,627 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,280 Sq Ft

  23058 Sailfish Ln, Summerland Key, FL 33042

  23058 Sailfish Ln, Summerland Key, FL 33042
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  /3

  $849,000

  • Land
  • 10 Acres
  • $84,900 per Acre

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
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  /40

  $785,000 Sold Mar 12, 2025

  17236 Keystone Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Built 1974

  Last Sold Summary

  • 21% Below List Price
  • $680/SF
  • 184 Days On Market

  Current Estimated Value $831,110

  Last Listing Agent Everett Watkins Keller Williams Key West Compass Realty

  17236 Keystone Rd, Summerland Key, FL 33042
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  /16

  Est $1,781,186 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft

  23076 Tarpon Ln, Summerland Key, FL 33042

  23076 Tarpon Ln, Summerland Key, FL 33042
• 

  

  /39

  $949,000

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

  437 Pirates Rd, Little Torch Key, FL 33042

  Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for

  Jo Ann Cook Ocean Sotheby's International

  437 Pirates Rd, Little Torch Key, FL 33042
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  /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
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  /27

  Est $1,611,514 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft

  23092 Snapper Ln, Summerland Key, FL 33042

  23092 Snapper Ln, Summerland Key, FL 33042
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  /67

  $2,875,000

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft

  20844 4th Ave W, Summerland Key, FL 33042

  SOLD TURNKEY! INCLUDES FURNISHINGS, 2006 PONTOON BOAT & 2021 JET SKI! DEEP WATER! A remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20844 4th Ave W, Summerland Key, FL 33042
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  /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
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  /42

  Est $1,399,354 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  1172 Coates Ln, Summerland Key, FL 33042

  1172 Coates Ln, Summerland Key, FL 33042
• 

  

  /25

  $730,000

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

  180 Sugarloaf Dr, Summerland Key, FL 33042

  **Motivated Sellers, all reasonable offers considered**This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000sqft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a quaint patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen, bonus screened porch and outdoor seating

  Jenny Perry Preferred Properties (KW)

  180 Sugarloaf Dr, Summerland Key, FL 33042
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  /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 $794,039

  Last Listing Agent Melissa Graham Bluescape Real Estate

  27255 Mariposa Rd, Ramrod Key, FL 33042
• 

  /2

  Est $1,230,624 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  22943 Dirk Ln, Summerland Key, FL 33042

  22943 Dirk Ln, Summerland Key, FL 33042
• 

  

  /37

  $879,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  NEW YEAR, NEW PRICE on this heavily rented PROTECTED DOCKAGE property! LOOK AT THIS VIEW! You have open water views from this impeccably maintained, fully stilted 2BR/2 BATH unit! A 43' SEAWALL with heavy duty dock posts, cleats, fish cleaning table and swim ladder add to the allure of this home perfect for the avid boater! North winds are NO PROBLEM with this protected dockage! The oversized

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
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  /38

  $785,000 Sold Nov 04, 2025

  22464 La Fitte Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $913/SF
  • 41 Days On Market

  Current Estimated Value $780,217

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  22464 La Fitte Dr, Summerland Key, FL 33042
• 

  /2

  Est $868,494 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  22973 Anne Bonny Ln, Summerland Key, FL 33042

  22973 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /48

  $359,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  27945 Tarpon Terrace, Little Torch Key, FL 33042

  Lots of new upgrades : Remodeled* New 40 gallon Hot Water Heater, several new mini splits, New Tiled floors throughout, New kitchen, New bathroom , new cabinet in the Laundry room area lots of new shelving added throughout, New electric box on the exterior, most of the appliances kitchen and laundry are newly added upgrades completely newly painted interior. Lots of money put into this remodeled

  Anne Press Lokation Real Estate

  27945 Tarpon Terrace, Little Torch Key, FL 33042
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  /2

  $49,000 Sold Jun 06, 2025

  Lot 7 Block 14, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 29% Below List Price
  • 163 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 7 Block 14, Cudjoe Key, FL 33042
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  /44

  Est $739,908 Not Listed For Sale

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

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  22903 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /13

  $395,000

  • Land

  24285 Caribbean Dr, Summerland Key, FL 33042

  Purchase this deep draft canal front LOT in Summerland Key while the building permit is in-process for a 4 bedroom / 2 bath stilted single family residence (home is additional). The plans shown are for a 1920 sq ft' / 2 story Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment,

  Donna Pezzi Keller Williams Key West Compass Realty

  24285 Caribbean Dr, Summerland Key, FL 33042
• 

  

  /40

  $837,000 Sold Mar 12, 2025

  22994 Anne Bonny Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Below List Price
  • $707/SF
  • 62 Days On Market

  Current Estimated Value $848,101

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

  22994 Anne Bonny Ln, Summerland Key, FL 33042
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  /45

  Est $1,215,239 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  22820 Blackbeard Ln, Summerland Key, FL 33042

  22820 Blackbeard Ln, Summerland Key, FL 33042
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  /7

  $190,000

  • Land
  • 6,000 Acres
  • $32 per Acre

  1145 Hakluyt Ln, Cudjoe Key, FL 33042

  Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

  Daniel Pacheco United Realty Group Inc

  1145 Hakluyt Ln, Cudjoe Key, FL 33042
• 

  

  /43

  $910,000 Sold Mar 04, 2025

  447 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft
  • Built 1991

  Last Sold Summary

  • 7% Below List Price
  • $925/SF
  • 51 Days On Market

  Current Estimated Value $924,488

  Last Listing Agent Jennifer Newman Truman & Co. (KW)

  447 Pirates Rd, Summerland Key, FL 33042
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  /47

  Est $2,338,073 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  22684 Jolly Roger Dr, Summerland Key, FL 33042

  22684 Jolly Roger Dr, Summerland Key, FL 33042
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  /116

  $19,750,000

  • 6 Beds
  • 7 Baths
  • 4,402 Sq Ft

  15760 Old State Road 4a, Summerland Key, FL 33042

  Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

  Lisa Swanson The Agency Florida Keys

  15760 Old State Road 4a, Summerland Key, FL 33042

Showing Results 521 - 560, Page 14 of 18