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
• 

  

  

  /50

  $1,599,000 Under Contract

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

  56 Colson Dr, Summerland Key, FL 33042

  Exceptional waterfront living awaits at 56 Colson Drive in Cudjoe Gardens on Cudjoe Key--a fully renovated 3 Bedroom 2 Bathroom home offering 1,645 sq. ft. of thoughtfully planned interior space on a sprawling 11,900 sq. ft. lot. Built with CBS construction and impact doors and windows, this property combines durability with modern coastal appeal and is designed to take full advantage of the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 841-7430

  56 Colson Dr, Summerland 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
• 

  

  /52

  $1,335,000

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  28560 Doubloon Rd, Summerland Key, FL 33042

  Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 772-6030

  28560 Doubloon Rd, 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 $514,664 Not Listed For Sale

  • 2 Beds
  • 1,201 Sq Ft

  27007 Angelfish Rd, Summerland Key, FL 33042

  27007 Angelfish Rd, Summerland Key, FL 33042
• 

  

  /17

  $675,000

  • Land

  17215 Keystone Rd, Sugarloaf Shores, FL 33042

  Cleared canal-front lot in Sugarloaf Shores with building permit in place and first inspection not due until December 2026! Positioned on the desirable no-bridge side, this expansive 27,716 sq. ft. residential parcel is surrounded by multi-million-dollar homes and offers easy access to the open water where days are enjoyed paddling and kayaking through mangrove-line creeks or heading out to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 957-7959

  17215 Keystone Rd, Sugarloaf Shores, 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 $777,377 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
• 

  

  /38

  $1,200,000 Under Contract

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

  218 Spanish Main Dr, Summerland Key, FL 33042

  Welcome to 218 Spanish Main Dr., a turnkey, recently renovated Florida Keys waterfront home offering the perfect blend of coastal charm and modern comfort. This 2-story, 3 bed, 3 bath fully fenced retreat boasts 2,016 sq ft of thoughtfully designed space with water views from nearly every room. Enjoy porches on both levels, ideal for morning coffee or sunset cocktails. The main level features an

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 876-6037

  218 Spanish Main Dr, 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 $1,324,975 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
• 

  

  /47

  $569,900

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida 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 35 ft seawall.* Community Boat Ramp and boat washdown station.*

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 686-7983

  701 Spanish Main Dr Unit 510, Cudjoe 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 $1,163,203 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
• 

  

  /30

  $750,000

  • 4 Beds
  • 2 Baths
  • 1,456 Sq Ft

  26868 Mariposa Rd, Ramrod Key, FL 33042

  Presenting a newly built 2023 home on a spacious 12,250 sq. ft. lot in Ramrod Shores, designed with both efficiency and style in mind. This four-bedroom, two-bathroom property features durable construction elements like a metal roof and impact-resistant windows, optimizing insurance costs, with all 3 insurances combined under $5,000 total. The interior boasts an open-concept floor plan with high

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 783-4956

  26868 Mariposa Rd, Ramrod 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 $2,267,652 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
• 

  

  /41

  $1,899,000 Open Sun 11AM - 1PM

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

  28573 Le Grand Rd, Little Torch Key, FL 33042

  This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 527-2862

  28573 Le Grand Rd, Little Torch 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
• 

  

  /10

  $499,000

  • Land

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 834-4054

  63 Sugarloaf Dr, Sugarloaf Shores, 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
• 

  

  /86

  $5,999,000 Pending

  • 4 Beds
  • 4 Baths
  • 4,315 Sq Ft

  4500 Filer Cove Rd, Summerland Key, FL 33042

  Picture perfect Sunset Views over the open water at this 12-Acre waterfront compound located on Big Torch Key, a coastal community of large private estates located just 30 minutes outside of Key West. Driving down the gated 300' scenic driveway balmy breezes and tropical landscape lead you to the 4,315 sq. ft. open water residence. Once here you will enjoy world-class fishing and diving just

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 998-2623

  4500 Filer Cove Rd, 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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