Homes in ZIP Code 33042

• 

  

  

  /49

  $1,998,000

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

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  SELLER FINANCING AVAILABLE! This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation . Offering Four generous size bedrooms with Three full

  

  Emily Lombard

  Ocean Sotheby's International Realty

  (786) 788-8217

  22542 Jolly Roger 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
• 

  

  

  /33

  $2,620,000 Sold Jan 29, 2025

  17279 Pinetree Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,016 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $2,579/SF
  • 288 Days On Market

  Current Estimated Value $2,546,875

  Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

  17279 Pinetree Ln, Summerland Key, FL 33042
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  /51

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
• 

  

  

  /6

  $499,000

  • Land

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042

  7049 sf Oceanfront Lot with beautiful views of Cudjoe Bay ! Build your dream home in Cudjoe Key ! Don't miss out on this great opportunity to build and live in one of the most desirable neighborhoods in the Keys !

  

  Emily Lombard

  Ocean Sotheby's International Realty

  (786) 659-1030

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /8

  $2,700 - $3,000 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
• 

  

  /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 $736,126

  Last Listing Agent Caroline Bauer Key West Sales, LLC

  27438 Haiti Ln, Summerland Key, FL 33042
• 

  

  /31

  Est $738,324 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft

  4245 Egret Ln, Summerland Key, FL 33042

  4245 Egret Ln, Summerland Key, FL 33042
• 

  

  /28

  $1,375,000 Open Sat 10AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  22974 Anne Bonny Ln, Summerland Key, FL 33042

  Welcome to 22974 Anne Bonny Lane in Cudjoe Key, a beautifully appointed, turn-key waterfront home designed for island living and ready for immediate enjoyment--whether as a full-time residence, second home, or income-producing vacation rental. This 3-bedroom, 2-bath coastal retreat is being offered fully furnished, with stylish furnishings purchased just two years ago, allowing a new owner to

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 869-3656

  22974 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /24

  $5,900 per month

  • 2 Beds
  • 1 Bath
  • 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
• 

  

  /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 $836,765

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

  27417 Cayman Ln, Summerland Key, FL 33042
• 

  

  /43

  Est $2,273,518 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,935 Sq Ft

  340 S Point Dr, Summerland Key, FL 33042

  340 S Point Dr, Summerland Key, FL 33042
• 

  

  /49

  $1,140,000

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042

  Welcome to your piece of paradise! This stunning high-rise is the largest square footage home in the exclusive gated community of Venture Out on Cudjoe Key. This property embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 891-5684

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042
• 

  

  /20

  $4,000 - $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
• 

  

  /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

  Last Listing Agent Cardenas & Krug Team Ocean Sotheby's International Realty

  76 W Shore Dr, Summerland Key, FL 33042
• 

  

  /28

  Est $870,936 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  168 Airport Dr S, Summerland Key, FL 33042

  168 Airport Dr S, Summerland Key, FL 33042
• 

  

  /39

  $495,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 551-4336

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
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  /7

  $5,000 per month

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • House for Rent

  Unlisted Address

  3 bedroom/3 bathroom 1500 sqft canal front home. This property includes 45' of dockage in addition to a 15,000 pound boat lift. Inside you will find two en suite bedrooms & baths, and an open living and kitchen. There is also a large sized screened in covered porch overlooking the yard and canal. Pets are allowed with an additional one time pet fee of $250. Utilities paid by tenant (water and

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  Unlisted Address
• 

  

  /35

  $217,000 Sold Jan 31, 2025

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

  • Land

  Last Sold Summary

  • 5% Below List Price
  • 22 Days On Market

  Current Estimated Value $219,771

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
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  /63

  Est $1,904,059 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,366 Sq Ft

  17057 Bonita Ln W, Sugarloaf Key, FL 33042

  17057 Bonita Ln W, Sugarloaf Key, FL 33042
• 

  

  /20

  $224,500

  • Land

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

  RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 418-4615

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
• 

  

  /20

  $8,250 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
• 

  /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
• 

  

  /9

  Not Listed For Sale

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Lot 8 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /71

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft

  16941 Driftwood Ln, Summerland Key, FL 33042

  There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key West,

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (855) 606-6133

  16941 Driftwood Ln, 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
• 

  

  /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 $1,670,102

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17159 Amberjack Ln, Summerland Key, FL 33042
• 

  

  /14

  Est $359,667 Not Listed For Sale

  27391 W Indies Dr, Ramrod Key, FL 33042

  27391 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /44

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21855 Spain Blvd, Summerland Key, FL 33042

  Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (786) 882-7957

  21855 Spain Blvd, Summerland Key, FL 33042
• 

  

  /19

  $4,700 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  486 Airport Dr S, Summerland Key, FL 33042

  Property Id: 2182502Enjoy Florida Keys living in a nice neighborhood on a wide 60 ft., flow-through boating canal with a concrete seawall and davits — perfect for your boat or water toys. relax on the 400 sq. ft. screened porch, or take advantage of the massive 1,300 sqft garage/airport hangar downstairs — plenty of room to park all your toys and gear. Upstairs offers 3 bedrooms, 2 baths,

  486 Airport Dr S, 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
• 

  

  /21

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
• 

  

  /48

  $1,499,000

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

  823 Indies Rd, Ramrod Key, FL 33042

  Fabulous sunset views over the salt ponds at this concrete 3 Bedroom 2 Bath home in Breezeswept Beach Estates. Located towards the end of a very quiet street this home offers a lot of privacy with beautiful views of the bird estuary in front and long views of the canal in the back. Boaters will appreciate the immediate ocean access with no bridges and easy turn around from the 60' step-down dock

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 614-6847

  823 Indies Rd, Ramrod Key, FL 33042
• 

  

  /13

  $5,143 per month

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

  28515 Channel View Dr, Little Torch Key, FL 33042

  This is a waterfront 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, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour community gym and

  Joseph Danieli AKT Realty LLC

  28515 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 $1,319,141

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  1050 Gulf Dr, Summerland Key, FL 33042
• 

  

  /38

  Est $1,178,412 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042
• 

  

  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 Sawyer Dr, Summerland Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /20

  $7,082 per month

  • 1 Bed
  • 1 Bath
  • 893 Sq Ft
  • Condo for Rent

  18954 Acosta Rd Unit ID1297838P, Summerland Key, FL 33042

  Escape to paradise and feel at home in this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key, accommodating up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails.This charming home features a spacious open-concept floor plan designed for relaxation and connection. Natural light pours into the airy interior,

  18954 Acosta Rd Unit ID1297838P, Summerland Key, FL 33042
• 

  

  /73

  $2,925,000 Sold Jun 10, 2025

  17018 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1991

  Last Sold Summary

  • 25% Below List Price
  • $1,987/SF
  • 122 Days On Market

  Current Estimated Value $2,865,725

  Last Listing Agent Coby Taylor Taylor & Assoc. RE, Inc.

  17018 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /8

  Est $242,544 Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

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