Homes in ZIP Code 33042

• 

  

  

  /31

  $795,000

  • 3 Beds
  • 1 Bath
  • 1,562 Sq Ft

  360 W Shore Dr, Summerland Key, FL 33042

  Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

  

  Brenda Thomas

  Island Welcome Real Estate

  (786) 949-3594

  360 W Shore Dr, Summerland Key, FL 33042
• 

  

  

  /70

  $12,500 per month

  • 4 Beds
  • 4 Baths
  • 2,952 Sq Ft
  • Property for Rent

  21640 Overseas Hwy, Summerland Key, FL 33042

  Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 442-3255

  21640 Overseas Hwy, Summerland Key, FL 33042
• 

  

  

  /18

  $738,000 Sold Mar 28, 2025

  27438 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1987

  Last Sold Summary

  • 8% Below List Price
  • $904/SF
  • 146 Days On Market

  Current Estimated Value $740,700

  Last Listing Agent Caroline Bauer Key West Sales, LLC

  27438 Haiti Ln, Summerland Key, FL 33042
• 

  

  

  /35

  Est $221,426 Not Listed For Sale

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
• 

  

  

  /71

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

  Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall.* Community

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 977-2397

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
• 

  

  /12

  $2,700 per month

  Coco Palms

  2 Beds

  21585 Overseas Hwy, Cudjoe Key, FL 33042

  Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

  21585 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /27

  $837,000 Sold Jul 11, 2025

  27417 Cayman Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,085 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $771/SF
  • 274 Days On Market

  Current Estimated Value $842,095

  Last Listing Agent Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  27417 Cayman Ln, Summerland Key, FL 33042
• 

  

  /31

  Est $809,040 Not Listed For Sale

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

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /44

  $1,699,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  17094 Coral Dr, Summerland Key, FL 33042

  This beautifully appointed home is located in prestigious Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3 Bedroom 2 Bath 2,000 sq. ft. home a massive Great Room greets you highlighted by a true chef's Kitchen offering lots of custom cabinetry, stainless appliances, 2 wine coolers and large center island for friends

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-7125

  17094 Coral Dr, Summerland Key, FL 33042
• 

  

  /22

  $3,600 per month

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • House for Rent

  201 Cutthroat Dr, Summerland Key, FL 33042

  LONG TERM RENTAL AVAILABLESpacious and well maintained unfurnished 2-BD, 2-BTH Stilted home for rent in Cudjoe Key. It has stainless steel appliances (stove/oven is brand new), and the Main Bedroom has it's own porch.A large deck overlooks the canal and is perfect for an evening adult beverage. This property is situated at the corner of Cutthroat Dr. and Blackbeard Ln. and has a large concrete

  Mark Peterson

  201 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /60

  $950,000 Sold Oct 17, 2025

  76 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,028 Sq Ft
  • Built 2001

  Last Sold Summary

  • 13% Below List Price
  • $924/SF
  • 369 Days On Market

  Current Estimated Value $960,265

  Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

  76 W Shore Dr, Summerland Key, FL 33042
• 

  

  /12

  Est $500,036 Not Listed For Sale

  • 2 Beds
  • 1,201 Sq Ft

  27007 Angelfish Rd, Summerland Key, FL 33042

  27007 Angelfish Rd, Summerland Key, FL 33042
• 

  

  /55

  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  937 Gulf Dr, Summerland Key, FL 33042

  Step into island elegance with this beautifully remodeled 3-bedroom, 2. bath waterfront home in one of the Florida Keys' most coveted boating communities -- Summerland Key Cove. Originally built in 2008 and completely redesigned in 2024, this residence blends contemporary coastal design with the solid construction and storm-safe features that matter most.Modern Coastal Interiors:The interior

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 751-4617

  937 Gulf Dr, Summerland Key, FL 33042
• 

  

  /20

  $5,537 - $15,000 per month

  Little Torch Cottages

  2 - 4 Beds

  28501 Channel View Dr, Little Torch Key, FL 33042

  In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

  28501 Channel View Dr, Little Torch Key, FL 33042
• 

  /2

  $1,030,000 Sold Nov 19, 2025

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft
  • Built 2010

  Last Sold Summary

  • $596/SF
  • 0 Days On Market

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

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /34

  Est $783,624 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft

  191 Doubloon Ln, Summerland Key, FL 33042

  191 Doubloon Ln, Summerland Key, FL 33042
• 

  

  /12

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  744 Trinidad Ln, Summerland Key, FL 33042

  Positioned to capture beautiful open water views of Pine Channel, this property sits in a quiet neighborhood that blends privacy with convenience. Spanning an impressive 12,000 sq ft, this double lot offers a rare opportunity to secure space, flexibility, and open water views in the Lower Keys. Enjoy being just minutes from shopping, restaurants, nightlife, the nature park, and the Big Pine

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 503-8190

  744 Trinidad Ln, Summerland Key, FL 33042
• 

  

  /19

  $4,900 per month

  • 2 Beds
  • 2 Baths
  • 884 Sq Ft
  • House for Rent

  27346 Martinique Ln, Summerland Key, FL 33042

  Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

  Alicia Rufino Island Living Realty, LLC

  27346 Martinique Ln, Summerland Key, FL 33042
• 

  

  /56

  $1,725,000 Sold Jul 11, 2025

  17159 Amberjack Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1989

  Last Sold Summary

  • 14% Below List Price
  • $1,039/SF
  • 258 Days On Market

  Current Estimated Value $1,677,377

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17159 Amberjack Ln, Summerland Key, FL 33042
• 

  

  /31

  Est $1,351,251 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft

  27367 Martinique Ln, Summerland Key, FL 33042

  27367 Martinique Ln, Summerland Key, FL 33042
• 

  

  /53

  $2,650,000

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  1147 Flagship Dr, Summerland Key, FL 33042

  Located on the highly desired Flagship Drive in Summerland Cove Isles, this stunning 3 bedroom, 2 bath home plus a loft offers beautiful views of the salt ponds and open water. As you walk up the front steps, you're greeted by a grand porch that sets the tone for the coastal charm found throughout the home. The split floor plan provides ideal privacy, with two guest bedrooms on one side and a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 758-4228

  1147 Flagship Dr, Summerland Key, FL 33042
• 

  

  /20

  $7,207 per month

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Condo for Rent

  886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042

  Loggerhead Lagoon is a stunning, tropically themed 3-bedroom 2-bathroom home located on a large private lot that offers covered parking, a boat dock, and direct access to the Gulf of Mexico. This rare find boasts a lush outdoor area full of beautiful palms, sun loungers, and tons of Florida sunshine. Located in Sugarloaf Key, just 19 miles from Key West and the world-famous Duval Street, this

  886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042
• 

  

  /45

  $1,550,000 Sold Jan 30, 2026

  28538 John Silver Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Below List Price
  • $1,242/SF
  • 164 Days On Market

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

  28538 John Silver Rd, Summerland Key, FL 33042
• 

  

  /52

  Est $1,131,346 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 930 Sq Ft

  1348 Ocean Dr, Summerland Key, FL 33042

  1348 Ocean Dr, Summerland Key, FL 33042
• 

  

  /42

  $1,845,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft

  20771 2nd Ave W, Summerland Key, FL 33042

  ACTIVELY SHOWING FOR OFFERS!!! Call to see! Incredible Florida Keys living! High quality concrete construction, impact windows and doors and custom metal roof- this home is ABOVE FLOOD and has no stairs! Enjoy the ease of one level living, with the storm safety of being above flood. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool and tiki!

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 952-5792

  20771 2nd Ave W, Summerland Key, FL 33042
• 

  

  /16

  $5,357 per month

  • 2 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • House for Rent

  53 Barry Ave, Summerland Key, FL 33042

  This is a 2 story furnished or unfurnished single family house with a private pool, fenced in yard, screened patio, 2 bedrooms, 2 bathrooms with showers, stainless steel appliances, hurricane windows, washer and dryer, tile and wood floors. You are also able to use the amenities at our property next door such as 24 hour community gym and sauna. marina with boat ramp, outdoor games, bbq, kayaks

  Joseph Danieli AKT Realty LLC

  53 Barry Ave, Summerland Key, FL 33042
• 

  

  /45

  $630,000 Sold Dec 08, 2025

  22970 Sharp Ln, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $1,094/SF
  • 4 Days On Market

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  22970 Sharp Ln, Summerland Key, FL 33042
• 

  

  /41

  Est $2,233,544 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,056 Sq Ft

  20864 4th Ave W, Summerland Key, FL 33042

  20864 4th Ave W, Summerland Key, FL 33042
• 

  

  /49

  $2,299,000

  • 4 Beds
  • 3 Baths
  • 2,440 Sq Ft

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  Welcome to coastal living in one of the most desirable neighborhoods in Cudjoe Key. This beautifully renovated 4-bedroom, 3-bath oceanfront residence sits proudly on a rare double lot, offering unmatched space, privacy, and breathtaking open-water views. Step inside to discover a bright, airy living space with stylish coastal finishes, vaulted ceilings, and walls of windows that frame the

  

  Emily Lombard

  Ocean Sotheby's International Realty

  (786) 952-5159

  22542 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /16

  $3,600 per month

  • 2 Beds
  • 1 Bath
  • 795 Sq Ft
  • House for Rent

  757 La Fitte Rd, Summerland Key, FL 33042

  We’re offering our Little Torch oceanside oceanfront home as a long-term rental.2 bedrooms, 1 bath.This is a comfortable, lived-in coastal home that reflects years of life by the water. It isn’t newly updated or polished, but it’s solid, welcoming, and easy to settle into. The home sits directly on the ocean, with wide-open water views that make everyday living feel

  757 La Fitte Rd, Summerland Key, FL 33042
• 

  

  /35

  $1,499,900 Sold May 27, 2025

  1082 Bay Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 1980

  Last Sold Summary

  • 25% Below List Price
  • $1,042/SF
  • 602 Days On Market

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

  1082 Bay Dr, Summerland Key, FL 33042
• 

  

  /18

  Est $1,685,729 Not Listed For Sale

  • 7 Beds
  • 4 Baths
  • 3,538 Sq Ft

  17042 Starfish Ln W, Summerland Key, FL 33042

  17042 Starfish Ln W, Summerland Key, FL 33042
• 

  

  /6

  $400,000

  • Land

  21865 Spain Blvd, Summerland Key, FL 33042

  Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (305) 614-8634

  21865 Spain Blvd, Summerland Key, FL 33042
• 

  

  /68

  $4,500 per month

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • House for Rent

  27316 Cayman Ln Unit 1,2, Summerland Key, FL 33042

  House in the Lower Keys Seasonal Rental. Available Sept 15, 2025 – Villa Marquesa, Lower Keys waterfront retreat! Spacious furnished home ideal for families, multi-gen living, or work-from-paradise. Corner lot on 2 wide canals with deep water access & 2 private docks (45’ & 15’). Upstairs: 3BR/1BA, 1,200 SQF, open kitchen, dining, living & TV rooms, water views. You can also rent downstairs unit,

  Hamlet Garcia Proxy Realty Group LLC

  27316 Cayman Ln Unit 1,2, Summerland Key, FL 33042
• 

  

  /60

  $930,000 Sold Jan 23, 2026

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2008

  Last Sold Summary

  • 2% Below List Price
  • $722/SF
  • 51 Days On Market

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
• 

  

  /33

  Est $2,559,800 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,016 Sq Ft

  17279 Pinetree Ln, Summerland Key, FL 33042

  17279 Pinetree Ln, Summerland Key, FL 33042
• 

  

  /16

  $999,000

  • Land

  21082 6th Ave, Summerland Key, FL 33042

  An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 300-6302

  21082 6th Ave, Summerland Key, FL 33042
• 

  

  /13

  $5,538 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28517 Channel View Dr, Little Torch Key, FL 33042

  This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished or furnished 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, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour

  Joseph Danieli AKT Realty LLC

  28517 Channel View Dr, Little Torch Key, FL 33042
• 

  

  /43

  $1,300,000 Sold Mar 14, 2025

  1050 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,171 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $1,110/SF
  • 24 Days On Market

  Current Estimated Value $1,323,845

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  1050 Gulf Dr, Summerland Key, FL 33042
• 

  

  /44

  Est $744,718 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  28233 Helen Ave, Little Torch Key, FL 33042

  28233 Helen Ave, Little Torch Key, FL 33042

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