Monroe, FL Homes

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  /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
• 

  

  

  /37

  $949,000

  • 2 Beds
  • 2 Baths
  • 1,052 Sq Ft

  273 Indies Rd, Summerland Key, FL 33042

  Welcome to this bright and modern 2-bedroom, 2-bath home located in the desirable Breezeswept Beach Estates on Ramrod Key. Completed in 2024 by the builder with high-quality features--including a metal roof, impact windows, new A/C, and durable Hardi board siding--this home was later purchased and further upgraded by the current owner, who is also the first to live in the home. Since purchasing,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 981-3223

  273 Indies Rd, Summerland Key, FL 33042
• 

  

  

  /50

  $550,000 Sold Jul 14, 2025

  • 864 Sq Ft
  • $637/SF
  • 245 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2021

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

  MOTIVATED SELLER. BRING THE OFFERS! BEST VALUE IN VENTURE OUT! HUGE PRICE DROP! NEGOTIABLE.! 2-YEAR HOME WARRANTY. TOTAL ELEGANCE! Experience the pinnacle of stilt-home living in this stunning residence at Venture Out, built just 3.5 years ago and meticulously designed with premium upgrades throughout. This 2-bedroom, 2-bathroom manufactured gem is move-in ready and fully furnished, offering a

  Joe Sappington Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
• 

  

  /2

  Est $1,177,658 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
• 

  

  

  /41

  $1,749,000

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

  25081 Overseas Hwy, Summerland Key, FL 33042

  So many opportunities at this 3 Bedroom 2 Bath canal front property located in the Commercial Fishing District boasting 240' of road frontage with excellent highway visibility and 240' of waterfront with full concrete dock and seawall, just one property in from the open water. Located in the Special Fishing District on Summerland Key where home businesses including commercial fishing and boat

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 526-7050

  25081 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /37

  $642,000 Sold Jul 11, 2025

  • 1,516 Sq Ft
  • $423/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  31067 Avenue C, Big Pine Key, FL 33043

  Spacious & Stylish 3/2 Home in Big Pine KeyWelcome to your slice of paradise! This beautifully remodeled 3-bedroom, 2-bath home sits on a 5,000 sq. ft. lot in Big Pine Key and has everything you need for relaxed Keys living. Inside, you'll find a bright, open layout with vaulted ceilings, fresh paint, bamboo wood floors, and a stunning kitchen with high-end appliances, a cooktop island, and

  Jared Chiagouris Island Welcome Real Estate LLC

  31067 Avenue C, Big Pine Key, FL 33043
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  /14

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043
• 

  

  /27

  $699,000

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

  25081 Overseas Hwy, Summerland Key, FL 33042

  So many opportunities at this 3 Bedroom 2 Bath canal front home located in the Special Fishing District on Summerland Key where home businesses including commercial fishing and boat mechanics are allowed. Boasting 60' of road frontage with excellent highway visibility and 60' of concrete canal dockage with quick and easy access to the gulf and ocean. The newly remodeled coastal style home

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 828-1613

  25081 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /54

  $615,000 Sold Jul 11, 2025

  • 864 Sq Ft
  • $712/SF
  • 194 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

  Are you dreaming of owning a piece of paradise in the Fabulous Florida Keys? Look no further than this gorgeous 2 bedroom, 2 bath waterfront home in the highly desired Venture Out Park in Cudjoe Key. This clean and updated home features a 35' concrete dock with whips, heavy duty aluminum posts, and easy access to enjoy both the gulf and ocean for world-class fishing and diving adventures. Inside,

  Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

  701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042
• 

  /2

  Est $1,049,961 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
• 

  

  /5

  $350,000

  • Land

  25091 Overseas Hwy, Summerland Key, FL 33042

  Attention all Commercial Fisherman and Marine Mechanics! Fantastic canal front commercial fishing district lot on Summerland Keys boasting 60' of road frontage with excellent highway visibility. 60' Concrete dock. Allowed uses include commercial fishing operations, boat repair and mechanic business and other home businesses.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 526-7517

  25091 Overseas Hwy, Summerland Key, FL 33042
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  /56

  $1,725,000 Sold Jul 11, 2025

  • 1,660 Sq Ft
  • $1039/SF
  • 258 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  17159 Amberjack Ln, Summerland Key, FL 33042

  Discover the pinnacle of Florida Keys living in this charming waterfront home on prestigious Sugarloaf Key, just 20 minutes from Key West! This stunning 3-bedroom, 2-bath, 1,660 sq. ft. stilted home is set on a spacious 12,500 sq. ft. lot along a crystal-clear wide canal, complete with a brand new gorgeous pool with a heater and chiller, a 32ft Dock and 12,000 lb. boat lift. Step inside and fall

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17159 Amberjack Ln, Summerland Key, FL 33042
• 

  /2

  Est $525,566 Not Listed For Sale

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042

  520 Blackbeard Rd, Little Torch Key, FL 33042
• 

  

  /6

  $350,000

  • Land

  24111 Overseas Hwy, Summerland Key, FL 33042

  Attention all Commercial Fisherman and Marine Mechanics! Fantastic canal front commercial fishing district lot on Summerland Keys boasting 60' of road frontage with excellent highway visibility. 60' Concrete dock. Allowed uses include commercial fishing operations, boat repair and mechanic business and other home businesses.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (866) 625-0494

  24111 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /83

  $3,300,000 Sold Jul 11, 2025

  • 3,086 Sq Ft
  • $1069/SF
  • 299 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2015

  16705 Tamarind Rd, Summerland Key, FL 33042

  Exquisite Open Water Estate on Prestigious Southpoint, Sugarloaf Key! Experience unparalleled luxury at this stunning solid concrete open water property, located just 20 minutes from the magic of Key West and Key West Airport. Situated on prestigious Southpoint, Sugarloaf Key, this magnificent estate offers breathtaking open water views and a lifestyle of elegance and comfort.Spanning 3,086

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  16705 Tamarind Rd, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042
• 

  

  /6

  $350,000

  • Land

  24101 Overseas Hwy, Summerland Key, FL 33042

  Attention all Commercial Fisherman and Marine Mechanics! Fantastic canal front commercial fishing district lot on Summerland Keys boasting 60' of road frontage with excellent highway visibility. 60' Concrete dock. Allowed uses include commercial fishing operations, boat repair and mechanic business and other home businesses.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (844) 620-9352

  24101 Overseas Hwy, Summerland Key, FL 33042
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  /27

  $837,000 Sold Jul 11, 2025

  • 1,085 Sq Ft
  • $771/SF
  • 274 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1975

  27417 Cayman Ln, Summerland Key, FL 33042

  This Breezeswept Beach Estates property is a must-see canalfront home. From the quick and easy open water access to the brand new 58-foot composite dock and a spacious fisherman's shed, anyone looking for an open water access property would be impressed! Unique curved concrete staircase leads to the main level that features a spacious living room, two roomy bedrooms and a large bathroom. Two sets

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

  27417 Cayman Ln, Summerland Key, FL 33042
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  /4

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042
• 

  

  /26

  $800,000

  • 3 Beds
  • 3 Baths
  • 1,360 Sq Ft

  23930 Overseas Hwy, Summerland Key, FL 33042

  2 units for the price of one! What an amazing opportunity to buy in the Florida Keys market without breaking the bank. Live in one unit & rent the other.Legal WATERFRONT duplex on Summerland Key just 25 minunets to Key West. Upper unit has 2B and 1Bath spacious living and dining space that opens onto a large deck overlooking the canal. Luxury vinyl floors, new lighting, new paint, new ceiling

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (888) 431-6038

  23930 Overseas Hwy, Summerland Key, FL 33042
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  /26

  $390,000 Sold Jul 10, 2025

  • 686 Sq Ft
  • $569/SF
  • 70 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1985

  27873 Coral Shores Rd, Little Torch Key, FL 33042

  Come get the Florida Keys sunrises and sunsets in the tranquil hidden Coral Shores Estates on Little Torch Key. Just a short cruise to the Gulf and Atlantic. There is a 46' wood dock which is a perfect place to keep your boat. Walk up just a few stairs to a screened in covered porch where you can enjoy the cool breeze. Step inside through the sliding glass doors and enjoy the view to the open

  Tracy Shields KeyIsle Realty

  27873 Coral Shores Rd, Little Torch Key, FL 33042
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  /2

  Est $885,534 Not Listed For Sale

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

  27434 Saint Lucie Ln, Ramrod Key, FL 33042

  27434 Saint Lucie Ln, Ramrod Key, FL 33042
• 

  

  /15

  $325,000

  • 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

  

  Scott Brisson

  KeyIsle Realty

  (866) 583-4634

  27345 Guadaloupe Ln, Ramrod Key, FL 33042
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  /45

  $2,090,000 Sold Jul 07, 2025

  • 1,938 Sq Ft
  • $1078/SF
  • 65 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  23066 Tarpon Ln, Summerland Key, FL 33042

  ''BRAND NEW' CBS Construction ready for occupancy!!! Amazing New Oceanside Home with 4 Bedrooms, 3.5 Baths, in Beautiful Cudjoe Ocean Shores, (Custom Built by Dream Builders of the Florida Keys). This home offers Open Water Views, Instant Deep Draft Boating for Big Boat Action, Protected Concrete step-down Dock, Open Floor plan, Dining Area, two Master Suites, High Ceilings, Chefs Kitchen with

  Greg MacLaren Internet Realty of the Florida Keys

  23066 Tarpon Ln, Summerland Key, FL 33042
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  /2

  Est $2,240,262 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft

  305 S Point Dr, Summerland Key, FL 33042

  305 S Point Dr, Summerland Key, FL 33042
• 

  

  /69

  $1,499,999

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  1667 Bogie Dr, Big Pine Key, FL 33043

  'Smuggler's Cove' is rich in history and a bit of mystery, as its name would suggest. Fast forward to the present and you'll discover that this 1948 home has kept much of its character with lots of hidden alcoves, while offering modern updates including a top-of-the-line appliances, USB electric outlets throughout, a 7.2 Yamaha surround-sound theatre system and so much more.Once inside the gated

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (844) 791-2437

  1667 Bogie Dr, Big Pine Key, FL 33043
• 

  

  /28

  $632,000 Sold Jul 03, 2025

  • 1,584 Sq Ft
  • $399/SF
  • 93 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1985

  28451 Gulf Blvd, Big Pine Key, FL 33043

  FULL DUPLEX on Big Pine Key - a RARE find! 2 bedrooms and 1 bath on each side with a private screened balcony.This stilted duplex sits on a corner lot of 9200 square feet located in a quiet subdivision. Across the street is non-buildable land so plenty of privacy. Appliances included for each side - range, fridge, and washer/dryer.Two 30 amp RV connections and ample room for parking boat

  Donna Pezzi Keller Williams Key West Compass Realty

  28451 Gulf Blvd, Big Pine Key, FL 33043
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  /2

  Est $1,306,970 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  22863 Bluegill Ln, Cudjoe Key, FL 33042
• 

  

  /49

  $1,749,000

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

  22865 Redfish Ln, Summerland Key, FL 33042

  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 the generous spacing between homes, as well as having

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 900-5290

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /33

  $650,000 Sold Jul 03, 2025

  • 1,008 Sq Ft
  • $645/SF
  • 429 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  30427 Hawk Ln, Big Pine Key, FL 33043

  Welcome to our cozy retreat nestled on Big Pine Key. This charming two bedroom one bath cottage offers a tranquil escape on a DOUBLE LOT fenced, providing privacy and security. Enjoy the picturesque waterfront views from your own back yard. Florida room with large impact windows to capture the water views. Impact windows through out. Approximately 273 feet of concrete seawall with davits,

  Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

  30427 Hawk Ln, Big Pine Key, FL 33043
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  /3

  Est $372,500 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042
• 

  

  /48

  $1,399,000 Open Sun 11AM - 2PM

  • 3 Beds
  • 3 Baths
  • 1,608 Sq Ft

  29457 Constitution Ave, Big Pine Key, FL 33043

  Solid, Spacious & Ready for Your Island Lifestyle! This 3 BD/3 BA concrete block home is just 3 houses in from Pine Channel, offering quick open water access and a short ride to Looe Key Reef, a world-famous spot for diving, snorkeling, and fishing. The 12,000 lb. boat lift is already installed and hard-wired for safety and convenience.Built Pre-FIRM, the home allows for renovation flexibility

  

  Nira Tocco

  Coldwell Banker Schmitt RE Co. Lower Keys Office

  (877) 806-2123

  29457 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /40

  $900,000 Sold Jul 01, 2025

  • 992 Sq Ft
  • $907/SF
  • 137 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  1342 Ocean Dr, Summerland Key, FL 33042

  Renovated Waterfront Gem! Welcome to your dream coastal retreat! This beautifully updated 2-bedroom, 2-bath home offers a 60-ft concrete dock along a 60-ft wide canal, providing the perfect setup for all your boating and water adventures. The property includes covered parking and a garage, ensuring convenience and plenty of storage for your vehicles and gear.Step inside to a bright and inviting

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  1342 Ocean Dr, Summerland Key, FL 33042
• 

  /2

  Est $339,000 Not Listed For Sale

  • Studio

  0 E Ave Unit 604969, Big Pine Key, FL 33043

  0 E Ave Unit 604969, Big Pine Key, FL 33043
• 

  

  /61

  $1,125,000

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft

  421 Ixora Dr, Big Pine Key, FL 33043

  Looking for great boating and a pool home that's already updated so you can spend time on the water? Look no further! This 2BD/3BA, CBS home is situated on a 50 ft. wide canal system that offers excellent access to the back country and Atlantic via Bogie Channel and Spanish Harbor. The 1120 sq. ft. living area has been completely renovated including the kitchen, bathrooms, impact-resistant

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 684-6607

  421 Ixora Dr, Big Pine Key, FL 33043
• 

  

  /41

  $650,000 Sold Jul 01, 2025

  • 1,120 Sq Ft
  • $580/SF
  • 81 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  22882 Buccaneer Ln, Summerland Key, FL 33042

  Coastal Paradise: 2-Bedroom, 2-Bath Canal-Front Home with Direct Ocean AccessThis stunning 2-bedroom, 2-bath home offers the ultimate canal-front lifestyle, minutes from open water with no bridges to navigate, perfect for boating enthusiasts. Located on the coveted Oceanside, the property features a spacious 60-foot dock ready for your vessel, offering convenient and quick access to the

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  22882 Buccaneer Ln, Summerland Key, FL 33042
• 

  /2

  Est $502,241 Not Listed For Sale

  • Studio
  • 1 Bath

  27418 Jamaica Ln, Ramrod Key, FL 33042

  27418 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  /42

  $999,000

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  29012 Bigonia Dr, Big Pine Key, FL 33043

  Get ready to fall in love with this beautifully remodeled 2-bedroom, 2-bath canal-front retreat, perfectly situated in the tranquil and desirable Eden Pines neighborhood of Big Pine Key. Nestled on a rare corner lot boasting an impressive 185 feet of water frontage, this home is a true boater's dream, offering two boat lifts (15,000 lb and 10,000 lb) and effortless access to open water for

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (844) 401-3365

  29012 Bigonia Dr, Big Pine Key, FL 33043
• 

  

  /44

  $650,000 Sold Jun 30, 2025

  • 828 Sq Ft
  • $785/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2002

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

  Turnkey Waterfront Vacation Rental with Ocean Views in Venture Out.Welcome to your Florida Keys escape--a fully furnished, income-producing 2-bedroom, 2-bath home ideally positioned on a wide canal with stunning ocean views and 35 feet of concrete seawall dockage. Located in the vibrant, gated community of Venture Out on Cudjoe Key, this well-maintained property is not just a serene coastal

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042

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