Monroe County, FL Homes

• 

  

  

  /15

  $2,899,000

  • Land

  94 Sunrise Dr, Marathon, FL 33050

  Build your dream oceanfront home in the prestigious gated community of Sunrise Isle, a coastal island of just 20 properties located next to beautiful Sombrero Beach in the heart of Marathon. Build anytime you like as the property comes with a deeded City of Marathon Transferrable Building Right subject to the conditions of the City of Marathon. Generous 40,249 sq. ft. ocean and canal front lot (a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 572-0195

  94 Sunrise Dr, Marathon, FL 33050
• 

  

  

  /23

  $4,000 per month

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Property for Rent

  220 Taylor Dr, Key Largo, FL 33037

  Newly updated and tastefully decorated, this canal-front fully furnished home is available for a 6+ month lease. The property offers direct canal frontage with 60 feet of dockage, includes use of a boat ramp located just steps away, and WiFi and yard maintenance are included, making it ideal for boating enthusiasts or anyone seeking the Florida Keys lifestyle. Only 30 minutes from Miami.The home

  Kimberly Hamilton Better Homes and Gardens Real Estate Destinations

  220 Taylor Dr, Key Largo, FL 33037
• 

  

  

  /25

  $685,000 Sold Jun 10, 2025

  2601 S Roosevelt Blvd Unit 603 A, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $908/SF
  • 25 Days On Market

  Current Estimated Value $701,952

  Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  2601 S Roosevelt Blvd Unit 603 A, Key West, FL 33040
• 

  

  

  /16

  Est $348,836 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  3312 Northside Dr Unit 105, Key West, FL 33040

  3312 Northside Dr Unit 105, Key West, FL 33040
• 

  

  

  /25

  $979,900

  • 4 Beds
  • 2 Baths
  • 1,943 Sq Ft

  160 Ridge St, Tavernier, FL 33070

  Beautiful corner-lot CBS home in the heart of Plantation Key. This 4-bedroom, 2-bath residence offers 1,964 sq. ft. of living space and is located in the desirable X flood zone. Notable features include impact windows and doors, a spacious open floor plan, and a bonus family room ideal for entertaining or additional living space.The bright interior is filled with natural light, with a functional

  

  Sandra Spaulding

  Coldwell Banker Schmitt Islamorada

  (877) 837-0467

  160 Ridge St, Tavernier, FL 33070
• 

  

  /20

  $17,240 per month

  • 2 Beds
  • 2 Baths
  • 2,023 Sq Ft
  • Condo for Rent

  536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040

  Experience the allure of this luxurious 2,000+ square foot penthouse, The Maloney, which occupies the entire second story of a historic red brick building at the corner of Fleming and Simonton. Originally constructed in 1908 as Key West's first pharmacy, this building now features two penthouse units and a first-floor boutique. The Maloney is available exclusively for monthly rentals, requiring a

  536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040
• 

  

  /34

  $1,550,000 Sold Jun 02, 2025

  1400 Virginia St, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Built 1923

  Last Sold Summary

  • 3% Below List Price
  • $1,160/SF
  • 124 Days On Market

  Current Estimated Value $1,607,291

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  1400 Virginia St, Key West, FL 33040
• 

  

  /24

  Est $1,036,930 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 975 Sq Ft

  918 Southard St Unit 202, Key West, FL 33040

  918 Southard St Unit 202, Key West, FL 33040
• 

  

  /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
• 

  

  /81

  $8,500 per month

  • 4 Beds
  • 4.5 Baths
  • 1 Sq Ft
  • House for Rent

  150 Azalea St, Tavernier, FL 33070

  6+ Month/Annual-- Rental--Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift. Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and

  Tracey Petrusha Venture Realty Group

  150 Azalea St, Tavernier, FL 33070
• 

  

  /3

  $1,090,000 Sold Jul 16, 2025

  83 Coco Plum Dr, Marathon, FL 33050

  • 6 Beds
  • 4 Baths
  • 2,072 Sq Ft
  • Built 2025

  Last Sold Summary

  • $526/SF
  • 0 Days On Market

  Last Listing Agent Kim Show Coldwell Banker Schmitt Real Estate Co.

  83 Coco Plum Dr, Marathon, FL 33050
• 

  

  /24

  Est $803,342 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 577 Sq Ft

  524 Margaret St Unit 103, Key West, FL 33040

  524 Margaret St Unit 103, Key West, FL 33040
• 

  

  /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
• 

  

  /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
• 

  

  /39

  $325,000 Sold Jul 11, 2025

  6099 Overseas Hwy Unit 107W, Marathon, FL 33050

  • 1 Bed
  • 1 Bath
  • 445 Sq Ft
  • Built 2003

  Last Sold Summary

  • 26% Below List Price
  • $730/SF
  • 493 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  6099 Overseas Hwy Unit 107W, Marathon, FL 33050
• 

  

  /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
• 

  

  /44

  $999,000

  • 3 Beds
  • 3 Baths
  • 1,548 Sq Ft

  108 Jamaica St, Marathon, FL 33050

  Looking for your Florida Keys dream home with space to spread out, soak up the sun, and maybe even tinker with a classic car or two? Welcome to 108 Jamaica Street on Duck Key, a tropical paradise on a double lot with a custom-built CBS home, screened pool, guest house, cistern for watering plants and washing cars, and epic garage. This place was built with love by the current owner and it shows.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 882-8610

  108 Jamaica St, Marathon, FL 33050
• 

  

  /35

  $5,900 per month

  • 2 Beds
  • 2 Baths
  • Townhouse for Rent

  169 Paradise Way, Islamorada, FL 33036

  Live your vacation year-round in this ocean-front townhome offering resort-style living. This recently constructed and furnished home features two-bedrooms and two-bathrooms. The first living level includes a guest bedroom and bathroom and an open-concept kitchen and living area, while the second level is dedicated to a private primary suite with a coffee and wet bar, ideal for a morning cup of

  Jocelyn Marzella Ocean Sotheby's International Realty

  169 Paradise Way, Islamorada, FL 33036
• 

  /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
• 

  

  /24

  Est $1,483,079 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,064 Sq Ft

  510 Amelia St, Key West, FL 33040

  510 Amelia St, Key West, FL 33040
• 

  

  /41

  $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
• 

  

  /83

  $24,233 per month

  • 4 Beds
  • 4.5 Baths
  • 2,594 Sq Ft
  • Condo for Rent

  811 104th St Unit ID1325586P, Marathon, FL 33050

  Experience the Florida Keys at its finest in this luxurious 4-bedroom, 4-bath tropical paradise nestled in a peaceful oceanfront neighborhood in Marathon, FL. This three-story waterfront estate was meticulously designed for the ultimate relaxation experience. Feel at home in this stunning retreat offering easy access to local shops, restaurants, beaches, and attractions.The open-concept

  811 104th St Unit ID1325586P, Marathon, FL 33050
• 

  

  /20

  $1,500,000 Sold Jul 31, 2025

  9922 Aviation Blvd, Marathon, FL 33050

  • 4 Beds
  • 4 Baths
  • 1,666 Sq Ft
  • Built 1980

  Last Sold Summary

  • 20% Below List Price
  • $900/SF
  • 137 Days On Market

  Current Estimated Value $1,543,080

  Last Listing Agent Stanley Rosen The Keyes Company

  9922 Aviation Blvd, Marathon, FL 33050
• 

  

  /30

  Est $1,283,416 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  70 Tamarind Dr, Key West, FL 33040

  70 Tamarind Dr, Key West, FL 33040
• 

  

  /38

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft

  153 Peg Leg Ln, Summerland Key, FL 33042

  Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 853-7147

  153 Peg Leg Ln, Summerland Key, FL 33042
• 

  

  /25

  $10,000 per month

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • House for Rent

  125 Gardenia St, Tavernier, FL 33070

  Experience luxury waterfront living in the heart of the Florida Keys! 4 bedrooms and 2 bathrooms. This stunning modern home offers sleek finishes, breathtaking canal views, and direct boating access. Enjoy the spacious outdoor entertainment area, complete with a private dock, lush synthetic turf, and a large jacuzzi—perfect for relaxing under the stars. The upper-level terrace provides an ideal

  Dahiana Rojas de Rojas Canvas Real Estate

  125 Gardenia St, Tavernier, FL 33070
• 

  

  /8

  $3,366,600 Sold Feb 25, 2025

  59720 Overseas Hwy, Marathon, FL 33050

  • 5 Beds
  • 4.5 Baths
  • 3,011 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Above List Price
  • $1,118/SF
  • 275 Days On Market

  Last Listing Agent Greg MacLaren Internet Realty of the Florida

  59720 Overseas Hwy, Marathon, FL 33050
• 

  

  /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
• 

  

  /37

  $3,600,000

  • 5 Beds
  • 6 Baths
  • 3,667 Sq Ft

  400 Aronovitz Ln, Key West, FL 33040

  Discover a rare investment and lifestyle opportunity at 'Zen Villa,' a prestigious compound anchored in the coveted X-Flood Zone of Old Town, Key West. Spanning a spacious 5,891 SF lot, this unique offering encompasses three distinct residences: the luxurious main estate at 400 Aronovitz Lane and two charming, income-generating cottages at 621 and 623 Whitehead Street.The main residence is a

  

  Damian Vantriglia

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  (786) 699-6375

  400 Aronovitz Ln, Key West, FL 33040
• 

  

  /20

  $6,835 per month

  • 3 Beds
  • 3 Baths
  • 2,518 Sq Ft
  • Condo for Rent

  8 Floral Ave Unit ID1297832P, Key West, FL 33040

  The Haven House is a truly heavenly retreat nestled on the quiet residential canals in Key Haven. This home boasts a modern waterfront private backyard with a dock and boat lift. With space-maximizing and luxury island touches from top to bottom, this monthly rental has it all. Stay just 15 minutes from downtown Duval Street in this one-of-a-kind island home.Seamless indoor-outdoor

  8 Floral Ave Unit ID1297832P, Key West, FL 33040
• 

  

  /40

  $1,100,000 Sold Apr 25, 2025

  88540 Overseas and Boat Slip 37 Hwy Unit 727, Plantation Key, FL 33070

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft
  • Built 1985

  Last Sold Summary

  • 26% Below List Price
  • $847/SF
  • 157 Days On Market

  Last Listing Agent Brett Newman Coldwell Banker Schmitt Islamorada

  88540 Overseas and Boat Slip 37 Hwy Unit 727, Plantation Key, FL 33070
• 

  

  /43

  Est $3,209,731 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 2,612 Sq Ft

  1711 Washington St, Key West, FL 33040

  1711 Washington St, Key West, FL 33040
• 

  

  /43

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,036 Sq Ft

  420 W Indies Dr, Summerland Key, FL 33042

  Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 666-1028

  420 W Indies Dr, Summerland Key, FL 33042
• 

  

  /24

  $6,995 per month

  • 3 Beds
  • 2 Baths
  • 2,272 Sq Ft
  • House for Rent

  125 3rd Ln, Key Largo, FL 33037

  This beautiful 3 bedroom, 2 bath canal front home is available for yearly rental. The home is fully furnished with a fully equipped kitchen. Situated on a double lot which includes a boat ramp to launch your boat, dockage and float for one or two jet skis. There is a beautiful pool including a hot tub. Located in a nice neighborhood close to restaurants, schools, John Pennekamp Park and is an

  Gladys Cornell RE/MAX All Keys Real Estate

  125 3rd Ln, Key Largo, FL 33037
• 

  

  /36

  $665,000 Sold Apr 07, 2025

  2027 Staples Ave, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft
  • Built 1958

  Last Sold Summary

  • $848/SF
  • 0 Days On Market

  Current Estimated Value $827,603

  Last Listing Agent Jessica Forsythe eXp Realty LLC

  2027 Staples Ave, Key West, FL 33040
• 

  

  /33

  Est $1,409,482 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,387 Sq Ft

  104 Geraldine St, Key West, FL 33040

  104 Geraldine St, Key West, FL 33040
• 

  

  /45

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  195 W Shore Dr, Summerland Key, FL 33042

  Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, this concrete block home offers the ultimate blend of sky, sea, and space. Featuring a 37' x 27' airplane hangar, 2-car garage, and expansive driveway, this 3-bedroom, 2-bathroom plus bonus/4th Bedroom residence is tailor-made for

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 998-8438

  195 W Shore Dr, Summerland Key, FL 33042
• 

  

  /19

  $4,994 per month

  • 2 Beds
  • 2 Baths
  • 1,348 Sq Ft
  • Townhouse for Rent

  202 Sanctuary Dr, Key Largo, FL 33037

  Beautiful Waterfront, FULLY FURNISHED One-Level FLAT, 2 Bedroom, 2 Bath Townhome for Rent at The Sanctuary at Key Largo, MM 100, Bayside. This rare rental opportunity offers the perfect combination of nature, history, and coastal living. Enjoy a serene lifestyle in one of Key Largo's most unique, treasured and Gated communities. Nestled on 24 acres of lush tropical hardwood hammock, this historic

  202 Sanctuary Dr, Key Largo, FL 33037
• 

  

  /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
• 

  

  /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

Showing Results 121 - 160, Page 4 of 18