Homes in ZIP Code 33042

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  /27

  $225,000 Sold Jan 13, 2025

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 13% Below List Price
  • 161 Days On Market

  Current Estimated Value $230,278

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
• 

  

  

  /40

  Est $2,214,836 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  20995 2nd Ave W, Summerland Key, FL 33042

  20995 2nd Ave W, Summerland Key, FL 33042
• 

  

  

  /18

  $600,000

  • Land

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

  Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

  The Spottswood Team Truman & Co. (KW)

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

  

  

  /30

  $1,185,000 Sold Nov 17, 2025

  478 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $1,062/SF
  • 0 Days On Market

  Last Listing Agent Jenny Perry Preferred Properties (KW)

  478 Blackbeard Rd, Summerland Key, FL 33042
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  /49

  Est $6,954,565 Not Listed For Sale

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  17279 Oleander Ln, Sugarloaf Key, FL 33042
• 

  

  /100

  $9,950,000

  • 6 Beds
  • 5 Baths
  • 5,208 Sq Ft

  16750 Old State Road 4a, Summerland Key, FL 33042

  Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

  Lisa Swanson The Agency Florida Keys

  16750 Old State Road 4a, Summerland Key, FL 33042
• 

  

  /36

  $330,000 Sold Apr 17, 2025

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

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • Built 1983

  Last Sold Summary

  • 8% Below List Price
  • $453/SF
  • 63 Days On Market

  Last Listing Agent Frank Griffiths Lokation Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
• 

  /2

  Est $898,975 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  22974 John Avery Ln, Summerland Key, FL 33042

  22974 John Avery Ln, Summerland Key, FL 33042
• 

  

  /16

  $775,000

  • Land

  28597 Peg Leg Rd, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3809 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom four-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house. Open Water View. House Permit SF-DUP-2025-0111, 41.5

  Barbara Eads Barbara Eads Realty

  28597 Peg Leg Rd, Little Torch Key, FL 33042
• 

  

  /27

  $730,000 Sold Mar 21, 2025

  27230 Brown Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Below List Price
  • $588/SF
  • 102 Days On Market

  Current Estimated Value $771,636

  Last Listing Agent Amber DeBevec LoKation Real Estate

  27230 Brown Dr, Summerland Key, FL 33042
• 

  

  /40

  Est $826,082 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  93 Venetian Way, Summerland Key, FL 33042

  93 Venetian Way, Summerland Key, FL 33042
• 

  

  /19

  $475,000

  • Land

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

  Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
• 

  

  /45

  $799,000 Sold Aug 29, 2025

  17338 Dolphin St E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1963

  Last Sold Summary

  • 30% Below List Price
  • $426/SF
  • 171 Days On Market

  Current Estimated Value $857,668

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
• 

  

  /48

  Est $652,990 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  27018 Angelfish Rd, Summerland Key, FL 33042

  27018 Angelfish Rd, Summerland Key, FL 33042
• 

  

  /43

  $875,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  681 W Indies Dr, Summerland Key, FL 33042

  This charming 2-bedroom, 2-bath home is your slice of paradise in the Lower Keys. Nestled on the open water, the property offers ocean views that will take your breath away. Enjoy your morning coffee or evening cocktails on the screened-in porch, perfect for relaxing and soaking in the coastal breeze. With a swim dock right out back, you'll have easy access to the crystal-clear waters for a quick

  Karen Haack Coldwell Banker Schmitt RE Co.

  681 W Indies Dr, Summerland Key, FL 33042
• 

  

  /47

  $1,075,000 Sold Jul 30, 2025

  128 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1999

  Last Sold Summary

  • 16% Below List Price
  • $960/SF
  • 189 Days On Market

  Current Estimated Value $1,077,753

  Last Listing Agent Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

  128 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /19

  Est $876,834 Not Listed For Sale

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

  221 Cutthroat Dr, Summerland Key, FL 33042

  221 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /9

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

  Robin Nilsson Keller Williams Key West Compass Realty

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /40

  $940,000 Sold Jun 02, 2025

  763 Diane Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2012

  Last Sold Summary

  • 6% Below List Price
  • $791/SF
  • 15 Days On Market

  Current Estimated Value $947,373

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

  763 Diane Ave, Little Torch Key, FL 33042
• 

  /2

  Est $1,049,318 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft

  27310 W Indies Dr, Summerland Key, FL 33042

  27310 W Indies Dr, Summerland Key, FL 33042
• 

  

  /96

  $1,698,000

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft

  17176 Bonita Ln W, Summerland Key, FL 33042

  Experience island living in this 2,353 sq ft, 4-bed, 3-bath Sugarloaf Shores home on a 12,500 sq ft lot. The split-level design includes two ensuite bedrooms with balcony access, plus two guest rooms on the ground floor. Skylights brighten the open living areas, flowing seamlessly to a 44' screened balcony.Out back, enjoy a 22' x 10' pool, gazebo, private boat ramp, swim ladder, and dual lifts

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  17176 Bonita Ln W, Summerland Key, FL 33042
• 

  

  /23

  $690,000 Sold Feb 11, 2025

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  • Land

  Last Sold Summary

  • 7% Below List Price
  • 8 Days On Market

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

  17295 Keystone Rd, Sugarloaf Shores, FL 33042
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  /36

  Est $1,155,158 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,518 Sq Ft

  27328 Jamaica Ln, Summerland Key, FL 33042

  27328 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /64

  $3,199,000

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

  23941 Henry St, Summerland Key, FL 33042

  Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

  Stacy Shahan Island Real Estate Company Florida Keys

  23941 Henry St, Summerland Key, FL 33042
• 

  

  /40

  $1,115,000 Sold Sep 10, 2025

  28552 Maracaibo Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 988 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $1,129/SF
  • 8 Days On Market

  Current Estimated Value $1,097,878

  Last Listing Agent Teri Hiller Coldwell Banker Schmitt Real Estate Co.

  28552 Maracaibo Rd, Little Torch Key, FL 33042
• 

  

  /61

  Est $1,963,977 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  17153 Buttonwood Dr W, Summerland Key, FL 33042
• 

  

  /19

  $329,000

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft

  701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042

  NIGHTLY RENTALS ALLOWED! Welcome to this immaculate 2-bedroom, 1-bathroom vacation retreat nestled at the picturesque southern tip of Venture Out, where the land gracefully meets the sea. The attention to detail is evident with luxurious travertine flooring added to this home. Don't let the square footage fool you. This home offers an open floor plan with an open kitchen over looking the family

  Susan Halligan Live Local Realty of the Florida Keys

  701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042
• 

  

  /42

  $775,000 Sold Oct 01, 2025

  22988 Port Royal Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $691/SF
  • 68 Days On Market

  Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  22988 Port Royal Ln, Summerland Key, FL 33042
• 

  

  /39

  Est $1,718,053 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  17056 Wahoo Ln, Summerland Key, FL 33042

  17056 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /30

  $485,000

  • 2 Beds
  • 1.5 Baths
  • 604 Sq Ft

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

  Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
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  /77

  $2,500,000 Sold Jul 15, 2025

  943 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 2001

  Last Sold Summary

  • 7% Below List Price
  • $1,395/SF
  • 121 Days On Market

  Current Estimated Value $2,505,337

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  943 Flagship Dr, Summerland Key, FL 33042
• 

  

  /81

  Est $1,509,433 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  23041 Snapper Ln, Summerland Key, FL 33042

  23041 Snapper Ln, Summerland Key, FL 33042
• 

  

  /3

  $179,000 Pending

  • Land
  • 0.11 Acre
  • $1,627,273 per Acre

  Lot 32 Caloosa St, Sugarloaf, FL 33042

  Lot with ROGO letter for 5 points. Not ROGO exempt, use points towards building on another lot or contact the Monroe County Planning Department for information about building on this lot or how to use these points. Tier 3 AE11. Contact Monroe County to verify all information. ROGO letter available upon request.

  Pamela Stangler MMLS Assoc.-Inactive Member

  Lot 32 Caloosa St, Sugarloaf, FL 33042
• 

  

  /39

  $650,000 Sold Apr 25, 2025

  25161 Center St, Summerland Key, FL 33042

  • 1 Bed
  • 1.5 Baths
  • 1,024 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $635/SF
  • 6 Days On Market

  Current Estimated Value $628,434

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

  25161 Center St, Summerland Key, FL 33042
• 

  

  /19

  Est $806,158 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22910 Privateer Dr, Summerland Key, FL 33042

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /9

  $199,500

  • Land

  Vacant Picard Ln, Cudjoe Key, FL 33042

  Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desirable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity: apply for your permits to build your dream home, and complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open

  Sunnie San Lorenzo KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
• 

  

  /41

  $970,000 Sold May 27, 2025

  366 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $698/SF
  • 4 Days On Market

  Current Estimated Value $1,003,167

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

  366 Sawyer Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,538,850 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  27362 Anguila Ln, Summerland Key, FL 33042

  27362 Anguila Ln, Summerland Key, FL 33042
• 

  

  /11

  $650,000

  • Land

  775 Pirates Rd, Summerland Key, FL 33042

  Rare opportunity in Jolly Roger Estates on Little Torch Key. This 6,000 sq. ft. cleared and build-ready lot comes with two ROGO exemptions, allowing for immediate construction. The property features 60 feet of east-facing waterfront with a concrete dock, step-down, and davits already in place. Central sewer is connected. Located on a clean, deep canal (approx. 3 ft. control depth) with quick open

  Melissa Gibbins Expert Realty LLC (HQ)

  775 Pirates Rd, Summerland Key, FL 33042
• 

  /2

  $305,000 Sold Jan 29, 2025

  701 Spanish Main Dr Unit 502, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 0 Days On Market

  Current Estimated Value $304,016

  Last Listing Agent Susan Halligan Live Local Realty of the Florida Keys

  701 Spanish Main Dr Unit 502, Cudjoe Key, FL 33042

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