Summerland Key, FL Homes

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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /13

  $475,000

  • 4 Beds
  • 3 Baths
  • 1,620 Sq Ft

  31052 Avenue H, Big Pine Key, FL 33043

  Investment opportunity on 10,000 sq. ft. double lot near the Big Pine Community Park; the location offers easy access to US1, local shopping and more; Marathon and Key West are within easy reach. **DO NOT WALK THE PROPERTY WITHOUT APPOINTMENT** 2 units, 2 tenants; pets on premises. 1,060 sq. ft. mobile home has 3BD/2BA, exterior wood siding; interior has been updated. CBS garage has 560 sq. ft.

  

  Patti Nickless

  Coldwell Banker Schmitt Real E

  (844) 542-1790

  31052 Avenue H, Big Pine Key, FL 33043
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  /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
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  /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
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  /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
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  /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
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  /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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  /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
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  /47

  Est $1,197,672 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  3827 Dyer Rd, Big Pine Key, FL 33043

  3827 Dyer Rd, Big Pine Key, FL 33043
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  /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
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  /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
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  /6

  $235,000 Sold Feb 05, 2025

  31450 Avenue C, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 480 Sq Ft
  • Built 1963

  Last Sold Summary

  • $490/SF
  • 19 Days On Market

  Last Listing Agent Kirksten Irick Preferred Properties (KW)

  31450 Avenue C, Big Pine Key, FL 33043
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  /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
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  /43

  $1,699,000

  • 2 Beds
  • 2 Baths
  • 1,980 Sq Ft

  1607 Sunrise Dr, Big Pine Key, FL 33043

  Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 301-2387

  1607 Sunrise Dr, Big Pine Key, FL 33043
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  /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
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  /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
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  /44

  Est $1,496,657 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  29667 Forrestal Ave, Big Pine Key, FL 33043

  29667 Forrestal Ave, Big Pine Key, FL 33043
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  /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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  /20

  $3,525 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • House for Rent

  29822 Frostproof Rd, Big Pine Key, FL 33043

  Property Id: 2218567Enjoy comfort and privacy in this elevated 2-bedroom, 2-bath home featuring an extra bedroom, open floor plan and vaulted ceilings for a bright, airy feel. The living room and master bedroom each open through French doors onto a balcony, while the bonus bedroom offers its own private sliding door access. Central A/C and heat keep the home comfortable year-round. Relax

  29822 Frostproof Rd, Big Pine Key, FL 33043
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  /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
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  /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
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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
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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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  /9

  Not Listed For Sale

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Lot 8 Overseas Hwy, Summerland Key, FL 33042
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  /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
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  /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
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  /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
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  /6

  Not Listed For Sale

  3 Rd Ave Unit 1, Big Pine Key, FL 33043

  3 Rd Ave Unit 1, Big Pine Key, FL 33043
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  /43

  $1,089,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  29039 Cedar Dr, Big Pine Key, FL 33043

  100 ft. canal-frontage, 15K boat lift, tiki hut and pool..... this Lower Keys property feels like your own private mini resort along the 50 ft. wide canal. The 10,000 sq. ft. double lot is strategically fenced to allow easy parking for multiple vehicles including boat trailer and RV parking. Picture yourself relaxing under the 12' x 18' poolside tiki or in one of numerous sitting areas amidst the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 368-1692

  29039 Cedar Dr, Big Pine Key, FL 33043
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  /13

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • House for Rent

  1540 Lantana Ln, Big Pine Key, FL 33043

  Fishermans Dream House!Bring your boats to this beautiful canal front home in Big Pine Key. Secluded on a corner lot with 190 ft of seawall. Boat ramp is less than a mile away. Enjoy swimming in the pool, relaxing on the deck, cocktails at the outside bar, or meeting the adorable friendly Key Deer roaming the neighborhood.Sleeps 8Available February 1st for monthly rentalCall Andrea for bookings

  Andrea Lennon Vylla Home

  1540 Lantana Ln, Big Pine Key, FL 33043
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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
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  /14

  Est $359,667 Not Listed For Sale

  27391 W Indies Dr, Ramrod Key, FL 33042

  27391 W Indies Dr, Ramrod Key, FL 33042

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