Monroe, FL Homes

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  /21

  $380,000 Sold Jun 24, 2025

  • 552 Sq Ft
  • $688/SF
  • 248 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1971

  27848 Lobster Tail Trail, Little Torch Key, FL 33042

  Waterfront property in the Florida Keys under $400,000! This 2 bedroom 1 bath mobile home sits on an clean canal, just minutes from open water by boat. Large screened in patio and large TIKI hut (10' x 14') on the canal. Hot tub and a large workshop in the back for your fishing or dive gear, steps away from the 46 foot concrete seawall. Property is being sold unfurnished. No HOA, No lot Rent,

  Derrick Johnson Coco Plum Real Estate

  27848 Lobster Tail Trail, Little Torch Key, FL 33042
• 

  

  /2

  Est $473,810 Not Listed For Sale

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  20874 4th Ave, Cudjoe Key, FL 33042
• 

  

  

  /51

  $1,500,000

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

  30985 Hibiscus Dr, Big Pine Key, FL 33043

  NEARLY 1/2 ACRE OF CANAL-FRONT TROPICAL PARADISE! Boaters will appreciate 133 ft. of frontage; can dock mutliple boats along the 50 ft. wide canal and 25 ft. across the end of the canal. Approximately 60 ft. of concrete seawall with boat davits and fish cleaning station. Completely furnished, this 2,166 sf., 4-bedroom, 2.5-bath, CBS pool home is nestled on an impressive,19,762 sq. ft. double lot

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (844) 629-4607

  30985 Hibiscus Dr, Big Pine Key, FL 33043
• 

  

  

  /34

  $578,000 Sold Jun 23, 2025

  • 960 Sq Ft
  • $602/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  31142 Avenue I, Big Pine Key, FL 33043

  Cute as a button and move-in ready! This three bedroom and two bathroom charmer has had many recent updates including fresh paint and a newer roof. Impact resistant doors and windows, as well as great elevation ensure reasonable insurance rates. Full concrete slab under the home for parking and storage and fully fenced in yard makes this a perfect home for a family to enjoy. Make an appointment

  Jimmy Lane Island Life Realty Experts

  31142 Avenue I, Big Pine Key, FL 33043
• 

  

  /2

  Not Listed For Sale

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042
• 

  

  /50

  $1,699,000

  • 4 Beds
  • 3 Baths
  • 1,967 Sq Ft

  1068 Buttonwood Dr E, Summerland Key, FL 33042

  Tucked away in the prestigious Sugarloaf Shores neighborhood this exceptionally private canal front retreat sits high on the ground sprawling over 1/2 acre of lushly landscaped fenced and gated grounds. Step inside the Living Room where large impact windows greet you boasting picturesque pool and garden views while flooding the space with natural light, creating an airy, welcoming atmosphere.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 751-6658

  1068 Buttonwood Dr E, Summerland Key, FL 33042
• 

  

  /42

  $1,450,000 Sold Jun 23, 2025

  • 1,425 Sq Ft
  • $1018/SF
  • 362 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  17177 Bonita Ln W, Summerland Key, FL 33042

  Modern finishes and enviable boating at this Sugarloaf Shores pool home, nestled on over a quarter acre! Enjoy year-round temperate weather, this exceptional property comes equipped for enjoying the outdoors, offering a resort-style custom pool with heater, chiller, jetted spa, sitting ledge, sun deck, and paver pool deck! Just steps from the pool is a full-length, 100' concrete dock with davits,

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  17177 Bonita Ln W, Summerland Key, FL 33042
• 

  /2

  Est $1,098,790 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  21034 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /35

  $870,000

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  575 Caribbean Dr E, Summerland Key, FL 33042

  Best Price for a canal home in Summerland Cove. Here is great opportunity to get a location with premier boating access- 60' concrete seawall on a canal that is 60' wide and has a 4' control depth. 10k boat lift. The home features 2 bedrooms 1.5 baths, with a metal roof and covered porch overlooking the canal. Cute Island cottage with long time owner. Offered FURNISHED including kayaks and

  

  Sandra Tuttle

  Island Welcome Real Estate

  (855) 515-8896

  575 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /28

  $500,000 Sold Jun 20, 2025

  • 575 Sq Ft
  • $870/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1958

  30952 Baileys Ln, Big Pine Key, FL 33043

  WATERFRONT - FIXER UPPER - BIG PINE KEY.Direct access to open water, no bridge obstructions.Transform this Old Florida Fish Camp into your Florida Keys Paradise. CONCRETE BLOCK CONSTUCTION. No drywall, original concrete floors, dimensional cut wood ceiling. 2 bedroom/ 1 bathroom. Garage doors open to cut-in boat ramp. Cash only, or construction/rehab loan.

  Joyce Craul Expert Realty LLC (HQ)

  30952 Baileys Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042

  1138 Basque Ln, Summerland Key, FL 33042
• 

  

  /36

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,039 Sq Ft

  29048 Iris Dr, Big Pine Key, FL 33043

  SITUATED ON A 50 FT. WIDE CANAL, this updated 3 bedroom / 2 bath home offers very good boat access to Pine Channel, the Atlantic and back country. The great room is bright and airy with a cathedral ceiling, south facing picture window and French doors that lead to the covered porch overlooking the canal. Updates include impact-resistant windows and doors, new stainless steel kitchen appliances,

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 528-3127

  29048 Iris Dr, Big Pine Key, FL 33043
• 

  

  /82

  $1,800,000 Sold Jun 20, 2025

  • 2,116 Sq Ft
  • $851/SF
  • 19 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  17175 Allamanda Dr W, Summerland Key, FL 33042

  Gorgeous Tropical Waterfront Oasis! No detail was overlooked in this stunning 4 BR, 3 BA luxury canal front estate in the prestigious Sugarloaf Shores. Tucked behind a privacy fence and surrounded by lush landscaping, this tropical retreat invites you to unwind in style. The expansive backyard is your personal oasis, featuring a massive heated concrete pool and a fully equipped 10' x 14' tiki

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17175 Allamanda Dr W, Summerland Key, FL 33042
• 

  

  /61

  Est $2,652,466 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,042 Sq Ft

  20886 4th Ave W, Summerland Key, FL 33042

  20886 4th Ave W, Summerland Key, FL 33042
• 

  

  /41

  $1,172,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  22946 Bluegill Ln, Summerland Key, FL 33042

  If you are looking for the ''Island Life'' with the best boating access in the Keys, this is the property for you. This beautifully updated tropical Keys home on a lushly landscaped spacious 10,200 square foot lot, is located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable for its premier boating access to world class fishing and diving in both

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 787-3949

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /59

  $2,175,000 Sold Jun 20, 2025

  • 2,192 Sq Ft
  • $992/SF
  • 41 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2019

  17346 Keystone Rd, Summerland Key, FL 33042

  Welcome to this stunning 3-bedroom, 2-bathroom home perfectly situated on nearly half an acre, offering serene water views and direct canal access. Ideal for boaters and outdoor enthusiasts, the property features a concrete dock--your gateway to waterfront adventures.Step inside to an open floorplan designed for both comfort and entertaining. The heart of the home is a beautifully updated

  Matthew Sheehan Ocean Sotheby's International Realty

  17346 Keystone Rd, Summerland Key, FL 33042
• 

  

  /39

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042
• 

  

  /24

  $899,000 Open Fri 11AM - 1PM

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

  29153 Cedar Dr, Big Pine Key, FL 33043

  This beautiful home sits on TWO LOTS FULLY FENCED and has 100' of canal frontage with a concrete seawall and a #15,000 boat lift. Can easily be converted into a 3/2 with very little expense. Great boating access to both the Atlantic and Gulf. It is move in ready, just bring your boat. Impeccably maintained, this home includes impact windows and doors and a metal roof for EXTREMELY LOW INSURANCE

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 770-5969

  29153 Cedar Dr, Big Pine Key, FL 33043
• 

  

  /42

  $1,000,000 Sold Jun 20, 2025

  • 1,764 Sq Ft
  • $567/SF
  • 79 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  27330 Barbados Ln, Ramrod Key, FL 33042

  Looking for a FL Keys Home with space? This meticulously maintained home has it!This original-owner, lovingly cared-for coastal retreat offers more living space than other homes of a similar style in the area, providing comfortable living both indoors & out.Upgraded to receive maximum insurance discounts, the home includes FULL impact-rated windows/doors, a metal hip roof, & single wraps for roof

  Brian Kruszewski LoKation Real Estate

  27330 Barbados Ln, Ramrod Key, FL 33042
• 

  /2

  Est $782,000 Not Listed For Sale

  • Studio

  164 Newfound Blvd, Big Pine Key, FL 33043

  164 Newfound Blvd, Big Pine Key, FL 33043
• 

  

  /29

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  1541 Sunrise Dr, Big Pine Key, FL 33043

  Enjoy absolutely stunning open water views and spectacular sunrises every morning from this gorgeous open waterfront property in Tropical Bay Estates. This spacious 3-bedroom, 2-bath home was completely remodeled in 2020 with beautiful finishes throughout. Enjoy a chef's kitchen, with top of the line appliances, and an abundance of cabinets and counter space, ideal for entertaining. Flooded

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 890-8953

  1541 Sunrise Dr, Big Pine Key, FL 33043
• 

  

  /56

  $2,599,000 Sold Jun 18, 2025

  • 1,153 Sq Ft
  • $2254/SF
  • 11 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  This beautifully located property, situated on the tip of Little Torch Key oceanside at the end of Jolly Roger Drive, offers the ultimate island living experience. With breathtaking views from every vantage point, this 2-bedroom, 2-bath concrete home sits on a spacious 16,400 sq ft lot surrounded by water on 3 sides. Relax on the large patio and watch stunning sunrises or enjoy the endless views

  Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

  28595 Jolly Roger Dr, Summerland Key, FL 33042
• 

  /2

  Est $230,000 Not Listed For Sale

  • Studio

  2112 San Marco Dr, Big Pine Key, FL 33043

  2112 San Marco Dr, Big Pine Key, FL 33043
• 

  

  /48

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,193 Sq Ft

  30246 Watson Blvd, Big Pine Key, FL 33043

  Discover your dream home on Big Pine Key at this expansive 37,500 sq. ft., property totaling 6 lots that combines privacy, nature and convenience. Nestled in a serene setting with tropical landscaping and thoughtful features, this home offers a massive yard that goes from street to street and is surrounded by a 6' stockade fence allowing lots of safety and room for kids and pets to play and roam.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (877) 679-8817

  30246 Watson Blvd, Big Pine Key, FL 33043
• 

  

  /27

  $1,900,000 Sold Jun 18, 2025

  • 1,990 Sq Ft
  • $955/SF
  • 85 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  17022 Starfish Ln W, Summerland Key, FL 33042

  SPECTACULAR OPEN WATER POINT & SUNSET VIEW. Enjoy waterfront living in this Classic 3 Bed/2 Bath wood frame home featuring vaulted ceilings and panoramic views overlooking Lower Sugarloaf Sound. Desirable SW exposure, 250' of protected waterfrontage providing quick boating access to both Atlantic and Gulf. Large ground level covered carport and patio plus secured storage room. Highly

  Kieran Mahoney Century 21 Circle

  17022 Starfish Ln W, Summerland Key, FL 33042
• 

  /2

  Est $235,333 Not Listed For Sale

  • Studio

  2120 San Marco Dr, Big Pine Key, FL 33043

  2120 San Marco Dr, Big Pine Key, FL 33043
• 

  

  /26

  $899,000

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  31463 Avenue G, Big Pine Key, FL 33043

  Welcome to this coastal escape on Big Pine Key, in the Lower Florida Keys. This newly built 2022 home combines modern design with the rugged durability required for island living. This 2-bedroom, 2-bathroom residence offers 1,260 sq ft of stylish, open-concept living space designed to showcase the natural beauty of the surroundings. For those seeking life on the water, this property is a

  

  Sandra Tuttle

  Island Welcome Real Estate

  (877) 716-2796

  31463 Avenue G, Big Pine Key, FL 33043
• 

  

  /51

  $1,200,000 Sold Jun 16, 2025

  • 2,137 Sq Ft
  • $562/SF
  • 26 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1977

  1060 W Shore Dr, Big Pine Key, FL 33043

  Open Water CBS Home with Breathtaking Views!This 3-bedroom, 2.5-bath CBS home offers stunning open water views of Pine Channel and unbeatable boating access to both the Atlantic Ocean and the Gulf. Situated on a spacious 10,564 sq ft lot, the property features a concrete seawall with a cut-in boat slip, perfect for water enthusiasts.The home boasts an excellent floor plan and includes a garage

  Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

  1060 W Shore Dr, Big Pine Key, FL 33043
• 

  /2

  Est $507,000 Not Listed For Sale

  • Studio

  2078 San Marco Dr, Big Pine Key, FL 33043

  2078 San Marco Dr, Big Pine Key, FL 33043
• 

  

  /63

  $2,670,000

  • 3 Beds
  • 3 Baths
  • 2,486 Sq Ft

  30468 Oleander Blvd, Big Pine Key, FL 33043

  THE LAID-BACK LOWER KEYS ARE CALLING YOU ... experience life at a slower pace on this .81 acre open water estate with a 2-bedroom, 2-bath main house as well as a 1-bedroom, 1-bath guest cottage overlooking Bogie Channel. Entertain in the large, poolside tiki or on the covered platform at the end of the 463 ft. pier where family and friends can relax as they watch the sunset after a fun day on

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 705-6242

  30468 Oleander Blvd, Big Pine Key, FL 33043
• 

  

  /40

  $1,075,000 Sold Jun 16, 2025

  • 1,152 Sq Ft
  • $933/SF
  • 191 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1982

  791 W Indies Dr, Summerland Key, FL 33042

  Welcome to your dream oasis in the heart of the Florida Keys! Nestled in the sought-after neighborhood of Breezeswept Beach Estates, this exceptional 4-bedroom, 2-bathroom ocean-front pool home offers the perfect blend of luxury, comfort, and coastal living. With breathtaking open water views and blue hole dredge, this home offers excellent fishing for the whole family from your own back yard;

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  791 W Indies Dr, Summerland Key, FL 33042
• 

  /2

  Est $686,008 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 854 Sq Ft

  31441 Ave F, Big Pine Key, FL 33043

  31441 Ave F, Big Pine Key, FL 33043
• 

  

  /48

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  28560 Doubloon Rd, Summerland Key, FL 33042

  This Jolly Roger Estates treasure puts good times in the Atlantic and back-country waters within easy reach by boat; the owners of this custom-built home will consider all reasonable offers! The 2-story stilt home has exceptional character, multiple inviting porches and outdoor sitting areas. Abundant kitchen cabinets are topped with stunning quartzite counters and a full-length screened porch

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 703-2360

  28560 Doubloon Rd, Summerland Key, FL 33042
• 

  

  /36

  $1,225,000 Sold Jun 13, 2025

  • 1,696 Sq Ft
  • $722/SF
  • 104 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  165 Colson Dr, Cudjoe Key, FL 33042

  Welcome Home! As you step inside of this Brand New contemporary coastal designed Florida Keys home, you will discover what you have been looking for in today's market. This property was built to last by using the finest available materials and sits on over a half-acre of land. The main great room features 15 ft. vaulted ceilings, an open concept living area with a combined high-end kitchen with a

  Terry Garcia Keller Williams Key West Compass Realty

  165 Colson Dr, Cudjoe Key, FL 33042
• 

  /2

  Est $1,013,001 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  460 Les Rohde Dr, Ramrod Key, FL 33042

  460 Les Rohde Dr, Ramrod Key, FL 33042
• 

  

  /36

  $879,000

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

  27325 Barbuda Ln, Summerland Key, FL 33042

  Nestled in the tranquil Breeze Swept Beach Estates of Ramrod Key, this fully updated 2-bedroom, 2-bathroom waterfront home captures the essence of Florida Keys living. Designed with durability and comfort in mind, the home features impact-resistant doors and windows, providing safety and peace of mind. The brand-new metal roof and Hardi Board siding offer long-lasting protection from the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 981-1937

  27325 Barbuda Ln, Summerland Key, FL 33042
• 

  

  /58

  $3,335,000 Sold Jun 13, 2025

  • 2,950 Sq Ft
  • $1131/SF
  • 37 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1956

  23971 Henry St, Summerland Key, FL 33042

  This newly renovated Oceanfront Pool home seamlessly blends luxury, privacy, and comfort while enjoying quick and easy ocean access on Summerland Key. Enter into the massive Great Room featuring 24-foot EURO retractable doors that open to sparkling ocean views and fill the space with lots of natural light. The Chef's Kitchen stands out with custom cabinetry, soft-close drawers, pull-out

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  23971 Henry St, Summerland Key, FL 33042
• 

  

  /43

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft

  701 Spanish Main Dr Unit 256, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 256, 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) 977-3240

  26868 Mariposa Rd, Ramrod Key, FL 33042
• 

  

  /107

  $5,300,000 Sold Jun 13, 2025

  • 4,981 Sq Ft
  • $1064/SF
  • 165 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2025

  220 E Caribbean Dr, Summerland Key, FL 33042

  Experience unparalleled luxury in this 2025 Custom Built Smart Home. Concrete-constructed oceanfront home, situated in prestigious Summerland Key. With 90 feet of ocean frontage and breathtaking southwest views of the Atlantic Ocean, this home is the ultimate retreat for those seeking elegance, comfort, and adventure.The third floor is the heart of this home, featuring an infinity-edge pool and

  Stacy Shahan Island Real Estate Company Florida Keys

  220 E Caribbean Dr, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18