Summerland Key, FL Homes

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  /37

  $850,000

  • 3 Beds
  • 2 Baths
  • 1,079 Sq Ft

  923 Indies Rd, Summerland Key, FL 33042

  This updated 3 bedroom, 2 bath canal front home is located on the desirable Oceanside of Ramrod Key with quick boating access and no bridges, making it a dream location for fishing, diving, and exploring Keys waters. From the covered porch, enjoy peaceful peek-a-boo views of the ocean while relaxing with the gentle breezes.Inside, the home features newer flooring, new central air conditioning,

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  (786) 761-5767

  923 Indies Rd, Summerland Key, FL 33042
• 

  

  

  /81

  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • House for Rent

  441 La Fitte Rd, Summerland Key, FL 33042

  ** SHORT-TERM RENTAL ** Stunning open water house with high ceilings, open floor plan, covered screen porch, and open deck for the sun lovers! New deck with a heavy-duty boat lift in place (15,000 pounds) in one of the cleanest waters in the FL Keys! Metal roof, New A/C, Water Heater, and a Front aluminum fence with beautiful landscaping This home is located in one of the best neighborhoods in

  Carolina Gil Caralex Intl Realty Group Corp

  441 La Fitte Rd, Summerland Key, FL 33042
• 

  

  

  /45

  $799,000 Sold Aug 29, 2025

  • 1,875 Sq Ft
  • $426/SF
  • 171 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1963

  17338 Dolphin St E, Summerland Key, FL 33042

  Nestled along a serene boating canal, this exceptional 2-bedroom, 2-bathroom home is a true masterpiece, crafted entirely from luxurious teak wood. With its timeless beauty and durable design, this home perfectly complements its natural surroundings, offering a tranquil retreat for water lovers.Step inside to find soaring cathedral ceilings that elevate the spacious living areas, flooding the

  Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
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  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  27772 Astrangia Ave, Summerland Key, FL 33042

  27772 Astrangia Ave, Summerland Key, FL 33042
• 

  

  

  /49

  $948,000

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft

  3667 S Seas St, Big Pine Key, FL 33043

  Discover your dream waterfront residence in the Florida Keys! Constructed with superior CBS building methods, featuring concrete floors, beams, and decorative railings, this home promises enduring quality. A full concrete seawall and robust 10k lb. boatlift offer convenient access to local sandbars, snorkeling spots, dining venues, and exceptional fishing grounds. The securely enclosed yard

  

  Scott Brisson

  KeyIsle Realty

  (833) 208-4500

  3667 S Seas St, Big Pine Key, FL 33043
• 

  /2

  $9,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  1540 Lantana Ln, Big Pine Key, FL 33043

  FISHERMANS DREAM HOUSE! BRING YOUR BOATS TO THIS AMAZING 3/2 HOUSE SECLUDED ON A CORNER LOT WITH 190FT OF SEAWALL. BOAT RAMP MINUTES AWAY. ICE MAKER AT THE OUTSIDE BAR.ENJOY THE POOL, OPEN DECKS, COCKTAILS AT THE OUTSIDE BAR, AND THE ADORABLE KEY DEER ROAMING THE NEIGHBORHOOD. SLEEPS 8. AVAILABLE FOR MONTHLY RENTALS TOO. DISCOUNTED PRICES FOR MULTIPLE MONTH RENTALS AND OFF SEASON.

  Andrea Lennon Vylla Home

  1540 Lantana Ln, Big Pine Key, FL 33043
• 

  

  /30

  $385,000 Sold Aug 29, 2025

  • 1,747 Sq Ft
  • $220/SF
  • 201 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1980

  27858 Lobster Tail Trail, Summerland Key, FL 33042

  Estate sale- Great opportunity to get a canal home in the Lower Keys. Very roomy floorplan with 1747 sq ft interior living , 3 bedrooms, 3 full bathrooms. Mobile home with addition on short stilts. 46' concrete seawall with great boating access. Neighborhood boat ramp. Fully deeded ownership. Sold in AS IS condition.

  Sandra Tuttle Island Welcome Real Estate

  27858 Lobster Tail Trail, Summerland Key, FL 33042
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  /2

  Est $911,352 Not Listed For Sale

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

  1581 State Rd Unit 4A, Little Torch Key, FL 33042

  1581 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  /12

  $299,000

  • Land

  20822 1st Ave, Cudjoe Key, FL 33042

  Located in the prestigious waterfront community of Cudjoe Gardens, this cleared and buildable 10,000 sq. ft. canal front lot offers an exceptional opportunity to create your dream home in the Lower Keys. With deep water, quick ocean access and no bridges, this property is perfect for boating enthusiasts and water lovers alike.Situated on a wide, clean canal just moments from the open ocean, the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 713-1031

  20822 1st Ave, Cudjoe Key, FL 33042
• 

  

  /21

  $1,000,000 Sold Aug 29, 2025

  • 1,050 Sq Ft
  • $952/SF
  • 250 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  419 Blackbeard Rd, Summerland Key, FL 33042

  2 Bed, 2 Bath Home on Double Lot with Full Seawall & Prime Boating Access Nestled in the serene beauty of Little Torch Key, this 2-bedroom, 2-bathroom home offers the ultimate in waterfront living. Situated on a spacious double lot with a full seawall, you'll enjoy peace of mind, privacy, and easy access to some of the best boating in the Florida Keys. The outdoor area is perfect for relaxation

  Karen Haack Coldwell Banker Schmitt RE Co.

  419 Blackbeard Rd, Summerland Key, FL 33042
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  /2

  Est $671,896 Not Listed For Sale

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  17172 Marlin Dr, Sugarloaf Shores, FL 33042
• 

  

  /4

  $285,000

  • Land

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 876-6382

  Unlisted Address
• 

  

  /35

  $560,000 Sold Aug 29, 2025

  • 1,129 Sq Ft
  • $496/SF
  • 196 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1953

  19616 Aztec St, Summerland Key, FL 33042

  Nestled in a quiet and charming neighborhood on Sugarloaf Key, this beautifully remodeled 2-bedroom, 2-bathroom home offers a perfect blend of modern updates and coastal charm. With plenty of natural light throughout and crown molding accenting every room, this home feels both elegant and welcoming. The kitchen features newer, stainless steel appliances and stylish finishes, making it ideal for

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  19616 Aztec St, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
• 

  

  /15

  $320,000

  • Land

  27345 Guadaloupe Ln, Ramrod Key, FL 33042

  Oceanside canal front lot with direct bridge free water access. Easy ride out to some of the Keys best fishing. Situated close to US 1 between Key West and Marathon. Restaurants, shopping and mini golf all nearby. Lot is currently in ROGO and the sewer meter is in place. Purchase a building right and start your dream home now or gather ROGO points and begin later. No HOA. Lot has been approved

  

  Scott Brisson

  KeyIsle Realty

  (786) 983-9662

  27345 Guadaloupe Ln, Ramrod Key, FL 33042
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  /40

  $635,000 Sold Aug 29, 2025

  • 1,272 Sq Ft
  • $499/SF
  • 212 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  31148 Avenue C, Big Pine Key, FL 33043

  Don't miss out on this amazing property. This property is a true delight. This turn key 3-bedroom, 2-bath home in a nice neighborhood. Main bathroom offers a relaxing Jacuzzi tub, while the kitchen features elegant granite countertops and modern stainless steel appliances. This home offers the luxury of marble tile flooring and carpet throughout the bedrooms. Fenced in backyard is the perfect

  Sandra Rodriguez Lokation Real Estate

  31148 Avenue C, Big Pine Key, FL 33043
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  /6

  Not Listed For Sale

  2 ROGO pts Gulf Blvd, Big Pine Key, FL 33043

  2 ROGO pts Gulf Blvd, Big Pine Key, FL 33043
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  /45

  $1,699,000

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  27314 Saint Lucie Ln, Ramrod Key, FL 33042

  Brand new concrete waterfront pool home on a corner canal lot with an exceptional 204' of water frontage, including the main canal, and just moments from open ocean access! This stunning home is built to withstand 180 mph winds, featuring impact-rated doors and windows, a metal roof, and solid concrete construction.Enjoy Florida Keys boating with a 40' concrete dock, 15,000 lb boat lift, and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 783-4784

  27314 Saint Lucie Ln, Ramrod Key, FL 33042
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  /43

  $1,170,000 Sold Aug 28, 2025

  • 1,232 Sq Ft
  • $950/SF
  • 29 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  1777 Pine Channel Dr, Summerland Key, FL 33042

  Built in 2022, this elevated Gulf-front home on Little Torch Key enjoys water on 2 sides offering lots of privacy and fantastic water views from all angels. Designed with storm-ready construction in mind, it features impact-resistant windows and doors, a metal roof, and Hardi board siding for lasting durability and peace of mind. Inside, the home is bright and welcoming, with high ceilings, crown

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  1777 Pine Channel Dr, Summerland Key, FL 33042
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  /2

  Est $229,999 Not Listed For Sale

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  825 Hawksbill Ln, Sugarloaf Key, FL 33042
• 

  

  /32

  $1,199,000

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

  27417 Tobago Ln, Ramrod Key, FL 33042

  This custom-built 3-bedroom, 2-bathroom residence on Ramrod Key offers a spacious, split floorplan, 1500 sq ft and is just 27 miles from Key West. The high quality 2010 construction features a hip metal roof, hardi plank siding, impact windows, and doors, ensuring durability and peace of mind. The heart of this home is its large kitchen, designed for both function and style. With an abundance of

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 822-7622

  27417 Tobago Ln, Ramrod Key, FL 33042
• 

  

  /71

  $3,150,000 Sold Aug 28, 2025

  • 4,976 Sq Ft
  • $633/SF
  • 118 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 2010

  225 Colson Dr, Summerland Key, FL 33042

  Experience the epitome of island luxury in this custom built 5,000 sq. ft. ICF (super energy efficient insulated concrete forms) constructed estate, where masterful design, refined finishes, and breathtaking ocean views come together in perfect harmony. Situated on over an acre of prime oceanfront land, this gated and walled compound offers the ultimate in privacy, serenity, and sophisticated

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  225 Colson Dr, Summerland Key, FL 33042
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  /2

  Est $3,138,085 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft

  999 Flagship Dr, Summerland Key, FL 33042

  999 Flagship Dr, Summerland Key, FL 33042
• 

  

  /16

  $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
• 

  

  /46

  $1,390,000 Sold Aug 26, 2025

  • 1,152 Sq Ft
  • $1,207/SF
  • 30 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  229 Caribbean Dr E, Summerland Key, FL 33042

  Welcome to a stunning coastal retreat on the gorgeous waters of Summerland Key. This beautifully appointed, concrete elevated waterfront home offers the ultimate in Keys living--designed for both relaxation and recreation with unmatched boating access.Step into an airy, light-filled interior where coastal elegance meets casual comfort. This 3 bedroom and 2 bath home is being sold fully furnished,

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  229 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042
• 

  

  /30

  $829,000

  • 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
• 

  

  /5

  $175,000 Sold Aug 21, 2025

  • Land

  • 9 Days On Market

  27313 Saint Martin Ln, Ramrod Key, FL 33042

  This is your chance to get your piece of the Keys and build your dream home on a canal corner lot with easy boating access to the ocean or bay. This is a Tier 3 cleared lot in Breezeswept Beach Estates with no active building or dock permit.

  Sandra Tuttle Island Welcome Real Estate

  27313 Saint Martin Ln, Ramrod Key, FL 33042
• 

  /2

  Est $1,166,374 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  29565 Ranger Ave, Big Pine Key, FL 33043

  29565 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /37

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  22954 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 230-1509

  22954 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /37

  $705,000 Sold Aug 21, 2025

  • 1,148 Sq Ft
  • $614/SF
  • 127 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  27312 Anguila Ln, Summerland Key, FL 33042

  Enjoy 185' of waterfront with quick ocean access at this 2 Bedroom 2 Bath 1,148 sq. ft. home custom designed and built by the current owner. Upon entering you'll be greeted with a spacious open concept Great Room boasting soaring tongue in groove wood ceilings and fantastic sunset views over the salt ponds. Large sliding glass doors allow for an abundance of natural light and welcome you to the

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  27312 Anguila Ln, Summerland Key, FL 33042
• 

  

  /14

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043
• 

  

  /37

  $995,000

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

  687 & 689 Crane Blvd, Sugarloaf Key, FL 33042

  A truly special offering for those who value strength, design, and the uncommon. Built to endure, this elevated solid poured concrete home features an insulated and Gaco coated, concrete roof, concrete floors, and an open, vault-like design with soaring ceilings--bringing an airy, artsy, and industrial-chic feel to island living.Located in highly desirable Sugarloaf Key, just 20 minutes from Key

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 807-6597

  687 & 689 Crane Blvd, Sugarloaf Key, FL 33042
• 

  

  /23

  $710,000 Sold Aug 20, 2025

  • 1,188 Sq Ft
  • $598/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2014

  19603 Seminole St, Summerland Key, FL 33042

  Discover your dream retreat on Upper Sugarloaf Key in the exclusive Indian Mounds subdivision. This impeccably maintained 3-bed, 2-bath home spans 1,188 sq ft with 9' ceilings, 5'' crown molding, and a spacious living-dining-kitchen area. Enjoy granite counters, stainless appliances, ample cabinets, two extra freezers, and a Samsung washer/dryer. Home is situated on a 5000 sq ft landscaped lot

  Steven Koleno Beycome of Florida, LLC

  19603 Seminole St, Summerland Key, FL 33042
• 

  /2

  Est $985,647 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft

  18954 Acosta Trail, Summerland Key, FL 33042

  18954 Acosta Trail, Summerland Key, FL 33042
• 

  

  /9

  $2,400,000

  • Land
  • 0.55 Acre
  • $4,356,000 per Acre

  24356 Overseas Hwy, Summerland Key, FL 33042

  Begin your Florida Keys venture at this exceptional waterfront Commercial property. The site consists of four lots measuring 60'x100' each, creating a 24,000-square-foot parcel with 240 feet of concrete seawall. The property comes equipped with water and electrical connections. Its strategic location offers excellent access to both the Atlantic and Gulf waters, including proximity to Looe Key

  

  Scott Brisson

  KeyIsle Realty

  (786) 937-2950

  24356 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /49

  $650,000 Sold Aug 20, 2025

  • 1,029 Sq Ft
  • $632/SF
  • 262 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2012

  27317 Cayman Ln, Summerland Key, FL 33042

  Welcome to Breezeswept Beach Estates, located on Ramrod Key MM 27. This home is situated on a large corner waterfront lot with an expansive outdoor entertainment area under this home. Enjoy beautiful Sunset Views from your living room and open porch area. The location includes excellent boating and fishing from this home with quick access to offshore fishing and diving sites. This home has a

  Diana Fiddes Coldwell Banker Schmitt Key Largo

  27317 Cayman Ln, Summerland Key, FL 33042
• 

  /2

  Est $453,103 Not Listed For Sale

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042

  520 Blackbeard Rd, Little Torch Key, FL 33042
• 

  

  /60

  $2,599,000

  • 4 Beds
  • 3 Baths
  • 2,886 Sq Ft

  1260 Sugarloaf Blvd, Summerland Key, FL 33042

  Fabulous Sunset Views over Sugarloaf Sound at this 4 Bedroom 3 Bath 2,886 sq. ft. open water concrete home in Sugarloaf Shores, an upscale coastal community of waterfront homes located just 15 minutes outside of Key West. Built by the current owner the home features a massive Great Room boasting stunning open water views from all angles and an open Kitchen highlighted by a center cooking island

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 855-6752

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /32

  $450,000 Sold Aug 20, 2025

  • 814 Sq Ft
  • $553/SF
  • 283 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  Charming Florida Keys Retreat at Venture Out on Cudjoe Key: Your Slice of Paradise Awaits! Welcome to your dream getaway nestled in the vibrant Venture Out community! This beautifully designed 2 BR, 2 BA home, built in 2016, is perfect for those seeking a blend of relaxation and adventure. Fully furnished and ready for you to move in or rent out nightly, this property is a true gem in the heart

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

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