Summerland Key, FL Homes

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  /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
• 

  

  

  /13

  $4,550 per month

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Property for Rent

  2635 Koehns Ave, Big Pine Key, FL 33043

  Discover this charming 3-bedroom, 2-bathroom furnished home.2-year lease preferred but negotiable.The spacious, open floor plan features a gourmet kitchen with white quartz countertops and sleek, stainless-steel Bertazzoni appliances imported from Italy.Relax in the dining area, overlooking a screened-in patio with stunning views of the heated saltwater pool. The lush backyard is a tropical

  

  Karen Liskey

  Key Colony Beach Realty

  (866) 729-5076

  2635 Koehns Ave, Big Pine Key, FL 33043
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  /60

  $1,022,500 Sold Dec 01, 2025

  29490 Ranger Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $760/SF
  • 46 Days On Market

  Last Listing Agent Jennifer Sylvia Keller Williams Key West Compass Realty

  29490 Ranger Ave, Big Pine Key, FL 33043
• 

  

  

  /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
• 

  

  

  /32

  $939,000

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  31343 Avenue I, Big Pine Key, FL 33043

  Welcome to a boater's dream on Big Pine Key. Built in 2020 and still feels brand new, this beautifully maintained 3-bedroom, 2-bath home is offered fully furnished and ready to enjoy or generate rental income. A 75-foot concrete dock delivers outstanding boating access, placing you just minutes from premier fishing grounds and offering easy routes to both the Gulf and the Ocean. Designed for

  

  Sandra Tuttle

  Island Welcome Real Estate

  (877) 346-6985

  31343 Avenue I, Big Pine Key, FL 33043
• 

  

  /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
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  /6

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 480 Sq Ft

  31450 Avenue C, Big Pine Key, FL 33043

  31450 Avenue C, Big Pine Key, FL 33043
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  /66

  $539,000

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

  701 Spanish Main Dr Unit 154, 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
• 

  

  /58

  $3,750,000

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

  755 & 744 Sawyer Dr, Cudjoe 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

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe 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
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  /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
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  /51

  $1,250,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,166 Sq Ft

  30985 Hibiscus Dr, Big Pine Key, FL 33043

  CBS POOL HOME OFFERS 133 ft. along the 50 ft. wide canal, boat davits, a fish cleaning station and quick access to Bogie Channel, the Atlantic and back country. Dock multiple boats along the 60 ft. concrete seawall with the possibility of adding more dockage. The fenced 19,762 sq. ft. double lot provides a private, park-like setting featuring an inviting, heated pool, outdoor shower, grilling

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 284-4668

  30985 Hibiscus Dr, Big Pine Key, FL 33043
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  /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
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  /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
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  /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
• 

  

  /30

  $800,000

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

  630 Barry Ave, Summerland Key, FL 33042

  Set on a rare 0.68-acre property spanning four lots, this private canal-front home offers exceptional space, water access, and tranquility. With 204.5 feet of canal frontage, a 40-foot wood dock, and less than a 5-minute boat ride to Pine Channel, this location is ideal for boating enthusiasts. The 3-bedroom, 2-bath residence features a roof-covered deck perfect for entertaining friends and

  

  Brenda Thomas

  Island Welcome Real Estate

  (786) 822-8419

  630 Barry Ave, 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
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  /55

  Est $725,460 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,304 Sq Ft

  437 Palmetto Ave, Big Pine Key, FL 33043

  437 Palmetto Ave, Big Pine Key, FL 33043
• 

  

  /50

  $799,000 Open Sun 10AM - 12PM

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  1672 Pandorea Ln, Big Pine Key, FL 33043

  Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, an exceptional upgraded

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 410-2419

  1672 Pandorea Ln, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /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
• 

  

  /34

  $625,000

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

  27940 Lobster Tail Trail, Summerland Key, FL 33042

  Discover one of the best waterfront buying opportunities in the Lower Keys! This spacious and well-maintained 3-bedroom, 2-bath manufactured home offers incredible value and lifestyle at just $650,000. Inside, you'll find an open floor plan with updated laminate floors, a bright kitchen, and a large primary suite featuring a big bedroom and a relaxing bath with a soaking tub.Outdoors, enjoy 46

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 218-8749

  27940 Lobster Tail Trail, Summerland Key, FL 33042
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  /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
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  /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
• 

  

  /27

  Est $882,080 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 962 Sq Ft

  31111 Hibiscus Dr, Big Pine Key, FL 33043

  31111 Hibiscus Dr, Big Pine Key, FL 33043
• 

  

  /34

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 241-6029

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /17

  $3,500 per month

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

  30612 23rd Ln, Big Pine Key, FL 33043

  Property Id: 2240886Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can relax in comfort. Enjoy the convenience of WiFi, AC, and a washing machine during your stay. The 2 bathrooms are equipped with all of the conveniences of home. Located between the Back Bay and the Ocean. Property sits on an acre lot, enjoy the breezy,

  30612 23rd Ln, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /22

  Est $641,875 Not Listed For Sale

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

  30876 Malaga Ln, Big Pine Key, FL 33043

  30876 Malaga Ln, Big Pine Key, FL 33043
• 

  

  /40

  $1,300,000 Under Contract

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

  537 Heck Ave, Summerland Key, FL 33042

  Welcome to island living at its finest. This stunning 3-bedroom, 2-bath canal-front home is packed with every bell and whistle you could want in a Florida Keys retreat. Designed for both comfort and entertaining, the property features a private pool, tiki hut, 3 screened in porches boat lift with direct canal access and close to open water with no bridges. Perfect for days on the water and

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (786) 410-6602

  537 Heck Ave, Summerland Key, FL 33042
• 

  

  /42

  $5,490 per month

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

  31547 Avenue D, Big Pine Key, FL 33043

  Come see this immaculate 2 Bedroom 2 Bath Big Pine Key Waterfront home with its Wonderful Water Views! It is available for a seasonal rental, so come on down and enjoy the Florida winter weather! It has a well equipped kitchen for your convenience and is only 5 years old. Please see the attached photos. You'll be glad you did! Only 30 miles to Key West and all of the other Points of Interest in

  Philip Vias LoKation

  31547 Avenue D, Big Pine Key, FL 33043
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  /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
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  /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

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