Homes in ZIP Code 33042

• 

  

  

  /62

  $720,000

  Sold May 18, 2026

  28151 Helen Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $511/SF
  • 51 Days On Market

  Current Estimated Value $738,252

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  28151 Helen Ave, Summerland Key, FL 33042
• 

  

  

  /40

  Est $920,561

  Not Listed For Sale

  93 Venetian Way, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1983

  93 Venetian Way, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market
• 

  

  

  /23

  $1,050,000

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  1331 Hudgins Dr, Summerland Key, FL 33042

  Construction Location Orientation. A Beautifully Appointed Canal Front Fortress All Concrete: Floors Walls Stairs Walk Around Ramp Driveway Deck & Seawall. All Solar Glazed and Insulated Impact windows Enter the Unique Palm Tree Stained-glass Impact door to 24-inch Travertine floors and Nine-foot ceilings throughout. Master Bedroom has French doors with a Tropical Stained-Glass Floral Cascade

  Camilo Perez Home Sold Realty, LLC

  1331 Hudgins Dr, Summerland Key, FL 33042
• 

  

  

  /29

  $720,000

  Sold Apr 17, 2026

  630 Barry Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Built 2005

  Last Sold Summary

  • 28% Below List Price
  • $678/SF
  • 86 Days On Market

  Current Estimated Value $887,114

  Last Listing Agent Brenda Thomas Island Welcome Real Estate

  630 Barry Ave, Little Torch Key, FL 33042
• 

  

  

  /48

  Est $695,528

  Not Listed For Sale

  27018 Angelfish Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1992

  27018 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 15 Days On Market
• 

  

  /10

  $725,000

  • Land
  • 8,276 Sq Ft
  • $3,815,789 per Acre

  17220 Angelfish Ln, Sugarloaf Shores, FL 33042

  Build Your Dream Home in Sugarloaf Shores! Discover the rare opportunity to develop your very own piece of paradise in the exclusive Sugarloaf Shores! This 8,165 sq. ft. waterfront lot is high, dry, and cleared, offering a perfect blank slate for your dream home in the Florida Keys. With a full 70' concrete seawall, this property is a boater's paradise, providing direct access to both the

  The Spottswood Team Truman & Co. (KW)

  17220 Angelfish Ln, Sugarloaf Shores, FL 33042
• 

  

  /45

  $710,000

  Sold Feb 05, 2026

  27163 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2018

  Last Sold Summary

  • 10% Below List Price
  • $477/SF
  • 238 Days On Market

  Current Estimated Value $742,790

  Last Listing Agent Jessica Roden Ocean Sotheby's International Realty

  27163 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /19

  Est $909,825

  Not Listed For Sale

  221 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1985

  221 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 498 Days On Market
• 

  

  /53

  $1,710,000

  $89K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  1481 Sugarloaf Blvd, Summerland Key, FL 33042

  Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy. Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /100

  $3,300,000

  Sold Dec 01, 2025

  815 E Shore Dr, Summerland Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,531 Sq Ft
  • Built 1961

  Last Sold Summary

  • 26% Below List Price
  • $728/SF
  • 295 Days On Market

  Current Estimated Value $4,119,742

  Last Listing Agent Karen Williams-deCastro LPT Realty, LLC

  815 E Shore Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,143,816

  Not Listed For Sale

  27310 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft
  • Built 1984

  27310 W Indies Dr, Summerland Key, FL 33042
• 

  

  /14

  $3,900

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  28528 Channel View Dr, Little Torch Key, FL 33042

  Current resident moving out on 6/30/26.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community pools, gym, sauna,

  Joseph Danieli AKT Realty LLC

  28528 Channel View Dr, Little Torch Key, FL 33042
• 

  

  /32

  $450,000

  Sold Aug 20, 2025

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $553/SF
  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
• 

  

  /36

  Est $952,743

  Not Listed For Sale

  27328 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,518 Sq Ft
  • Built 1979

  27328 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 22 Days On Market
• 

  

  /86

  $3,199,000

  $500K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,744 Sq Ft

  17183 Coral Dr, Summerland Key, FL 33042

  Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

  Jan Fritz Coldwell Banker Schmitt RE Co.

  17183 Coral Dr, Summerland Key, FL 33042
• 

  

  /14

  $225,000

  Sold Apr 01, 2026

  27398 Jamaica Ln, Ramrod Key, FL 33042

  • Land
  • 6,098 Sq Ft
  • $1,607,143 per Acre

  Last Sold Summary

  • 25% Below List Price
  • 173 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  27398 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  /61

  Est $1,834,585

  Not Listed For Sale

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1998

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 30 Days On Market
• 

  

  /66

  $2,795,000

  • 4 Beds
  • 5.5 Baths
  • 3,224 Sq Ft

  333 Indies Rd, Ramrod Key, FL 33042

  Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 51/2 bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis.This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a

  Greg MacLaren Internet Realty of the Florida Keys

  333 Indies Rd, Ramrod Key, FL 33042
• 

  

  /36

  $1,200,000

  Sold Jun 05, 2026

  831 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1980

  Last Sold Summary

  • 19% Below List Price
  • $1,038/SF
  • 87 Days On Market

  Current Estimated Value $1,439,667

  Last Listing Agent Miranda Dender Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  831 W Indies Dr, Summerland Key, FL 33042
• 

  

  /81

  Est $1,282,354

  Not Listed For Sale

  23041 Snapper Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1992

  23041 Snapper Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market
• 

  

  /32

  $2,100,000

  New Construction

  • 5 Beds
  • 4 Baths
  • 2,886 Sq Ft

  662 Blackbeard Rd, Little Torch Key, FL 33042

  Pre-Construction Luxury Home | Jolly Roger EstatesIntroducing a rare pre-construction opportunity in the desirable waterfront community of Jolly Roger Estates. This CBS-built, fortress-like home is designed for durability, efficiency, and modern coastal living. The two-story floor plan offers 5 bedrooms, 4 bathrooms, and 2,886 square feet of living space, along with a spacious downstairs storage

  Lanny Gardner Bluescape Real Estate

  662 Blackbeard Rd, Little Torch 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

  Current Estimated Value $1,221,646

  Last Listing Agent Jenny Perry Preferred Properties (KW)

  478 Blackbeard Rd, Summerland Key, FL 33042
• 

  /2

  Est $885,782

  Not Listed For Sale

  22910 Privateer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1988

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /15

  $644,500

  • Land
  • 15,200 Sq Ft
  • $1,847,001 per Acre

  132 Sugarloaf Dr, Summerland Key, FL 33042

  Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

  Heather Mason Coastal Collection Real Estate Inc.

  132 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /29

  $825,000

  Sold Feb 27, 2026

  17245 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $661/SF
  • 104 Days On Market

  Current Estimated Value $864,869

  Last Listing Agent Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,405,979

  Not Listed For Sale

  27362 Anguila Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 1975

  27362 Anguila Ln, Summerland Key, FL 33042
• 

  

  /100

  $8,995,000

  $955K PRICE DROP

  • 6 Beds
  • 4.5 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 Berkshire Hathaway HomeServices Knight & Gardner Realty

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

  

  /40

  $1,300,000

  Sold Feb 26, 2026

  537 Heck Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • Built 1997

  Last Sold Summary

  • $914/SF
  • 29 Days On Market

  Current Estimated Value $1,282,502

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  537 Heck Ave, Summerland Key, FL 33042
• 

  

  /12

  Est $711,622

  Not Listed For Sale

  27007 Angelfish Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1,201 Sq Ft
  • Built 1967

  27007 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 281 Days On Market
• 

  

  /50

  $3,495,000

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

  414 Caribbean Dr E, Summerland Key, FL 33042

  OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  414 Caribbean Dr E, Summerland 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 $905,045

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
• 

  

  /34

  Est $957,407

  Not Listed For Sale

  320 Spanish Main Dr, Summerland Key, FL 33042

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

  320 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 18 Days On Market
• 

  

  /9

  $225,000

  • Land
  • 7,405 Sq Ft
  • $1,323,529 per Acre

  26837 Overseas Hwy, Summerland Key, FL 33042

  Rare opportunity to acquire a commercially zoned, vacant land parcel, fronting on U.S. Highway 1 in Ramrod Key, Florida. The subject property is 7,340 square foot vacant parcel with 50 feet of direct Overseas Highway frontage. Zoned Suburban Commercial (SC) under the Monroe County Land Development Code.

  Casey Prindle Nicklaus Vance

  26837 Overseas Hwy, 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 $1,097,784

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

  128 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /37

  Est $933,974

  Not Listed For Sale

  139 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1994

  139 Le Grand Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 48 Days On Market
• 

  

  /55

  $3,025,000

  New Construction

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

  17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042

  A rare double-parcel waterfront opportunity in Lower Sugarloaf Key - offering a newly constructed home plus an adjacent buildable lot, creating the ultimate private boating compound.The newly built 3BD/2.5BA residence with an office/den & laundry/utility room spans 2,288sf on a 16,445sf lot and is thoughtfully designed with an open-concept layout, abundant natural light, and sweeping water

  The Spottswood Team Truman & Co. (KW)

  17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042
• 

  

  /42

  $920,000

  Sold Jun 18, 2026

  22954 Buccaneer Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $657/SF
  • 30 Days On Market

  Current Estimated Value $935,625

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22954 Buccaneer Ln, Cudjoe Key, FL 33042
• 

  

  /27

  Est $1,658,196

  Not Listed For Sale

  22836 Port Royal Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • Built 1987

  22836 Port Royal Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  /19

  $430,000

  $45K PRICE DROP

  • Land
  • 2,078 Sq Ft
  • $9,013,859 per Acre

  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

  Lanny Gardner Bluescape Real Estate

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

  

  /37

  $830,000

  Sold Jun 10, 2026

  153 Peg Leg Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $690/SF
  • 91 Days On Market

  Current Estimated Value $903,644

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  153 Peg Leg Ln, Cudjoe Key, FL 33042

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