Monroe, FL Homes

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  /44

  $1,595,000

  • 3 Beds
  • 3 Baths
  • 1,284 Sq Ft

  1211 Knowles Ln, Key West, FL 33040

  Discover the timeless charm of this beautifully remodeled historic home located in Old Town, Key West. This fully furnished 3 bedroom, 2.5 bath property boasts lovingly restored Dade County Pine, and combines classic craftsmanship with modern comforts. 1211 Knowles Ln features a 300 sq.ft. loft currently used as a 3rd bedroom, office and storage ! Both front and side porches invite you to relax

  Emily Lombard Ocean Sotheby's International Realty

  1211 Knowles Ln, Key West, FL 33040
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  /25

  $465,000 Sold Feb 21, 2025

  • 449 Sq Ft
  • $1,036/SF
  • 36 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1928

  623 Thomas St Unit C, Key West, FL 33040

  Located in the heart of Key West's historic Old Town, 623 Thomas St Unit C is a charming 1-bedroom, 1-bathroom condo offering 449 square feet of living space. Built in 1928, this residence exudes classic Key West architecture and ambiance. The condo boasts an open floor plan with vaulted ceilings, enhancing the sense of space. Italian Basalt tile flooring adds a touch of elegance throughout the

  Jimmy Lane Island Life Realty Experts

  623 Thomas St Unit C, Key West, FL 33040
• 

  

  

  /18

  Est $999,522 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 837 Sq Ft

  906 Frances St Unit B, Key West, FL 33040

  906 Frances St Unit B, Key West, FL 33040
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  /37

  $4,775,000

  • 4 Beds
  • 5 Baths
  • 2,716 Sq Ft

  709 Eaton St, Key West, FL 33040

  Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  709 Eaton St, Key West, FL 33040
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  /8

  $2,089,000 Sold Feb 14, 2025

  • 1,470 Sq Ft
  • $1,421/SF
  • 1 Day On Market

  • 4 Beds
  • 4 Baths
  • Built 1901

  619 Thomas St, Key West, FL 33040

  Welcome to Old Town Key West and this Lovely Historic Cigar Makers Home! MORE PICTURES COMING SOON of this Spacious 3 Bedroom, 3 Bath Main House , plus separate Cabana with additional 1 Bedroom, 1 Bath and outdoor shower. The main house sits nestled amongst its tropical vegetation with its white picket fence and inviting front porch waiting for you to enjoy people watching in this desirable

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  619 Thomas St, Key West, FL 33040
• 

  

  /14

  Est $676,182 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 601 Sq Ft

  714 Elizabeth St Unit A, Key West, FL 33040

  714 Elizabeth St Unit A, Key West, FL 33040
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  /26

  $650,000

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

  1105 Watson St, Key West, FL 33040

  Located in Key West's Historic District, this two-story, 2-bedroom, 2-bathroom home sits on a manageable lot, offering a unique renovation opportunity. Large primary bedroom, bathroom and sitting area located upstairs. Second bedroom and bathroom on the main floor along with the living, dining and kitchen.Located in the X Flood zone, centrally located on the island, close to downtown and

  Francesca Santiago Keller Williams Realty Professionals (KW)

  1105 Watson St, Key West, FL 33040
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  /58

  $1,800,000 Sold Feb 14, 2025

  • 2,003 Sq Ft
  • $899/SF
  • 9 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1928

  808 Fleming St, Key West, FL 33040

  This charming three-unit property at 808 Fleming Street represents an exceptional investment in one of Key West's most desirable neighborhoods. Located in the historic Old Town district, this versatile building offers multiple revenue streams and tremendous potential for savvy investors.This property is ideal for investors or multi-family living. With separate electric and water meters for each

  Barbara Crespo Keller Williams Key West Compass Realty

  808 Fleming St, Key West, FL 33040
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  /7

  Est $669,326 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 289 Sq Ft

  910 Simonton St Unit 2, Key West, FL 33040

  910 Simonton St Unit 2, Key West, FL 33040
• 

  

  /98

  $3,495,000

  • 5 Beds
  • 5 Baths
  • 2,721 Sq Ft

  1114 Packer St, Key West, FL 33040

  X FLOOD ZONE! Luxurious Old Town Key West Oasis with separate Guest House! Nestled in the heart of Key West's historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to discover a

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1114 Packer St, Key West, FL 33040
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  /36

  $835,000 Sold Feb 10, 2025

  • 953 Sq Ft
  • $876/SF
  • 44 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1915

  809 Southard St, Key West, FL 33040

  Welcome to 809 Southard Street, an exquisite Conch cottage nestled in the heart of Key West's historic district. This charming 3-bedroom, 1.5-bath home embodies timeless island elegance and modern convenience.Step inside to find gleaming hardwood floors and a thoughtful split floor plan, offering privacy and comfort. The stunning cathedral ceiling and Dade County pine accent wall create a warm,

  Jimmy Lane Island Life Realty Experts

  809 Southard St, Key West, FL 33040
• 

  

  /20

  Est $1,055,550 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 970 Sq Ft

  818 Whitehead St Unit 6, Key West, FL 33040

  818 Whitehead St Unit 6, Key West, FL 33040
• 

  

  /16

  $1,580,000

  • 8 Beds
  • 5 Baths
  • 1,830 Sq Ft

  928 Truman Ave Unit 101, Key West, FL 33040

  Old Town Multi-Use PropertyLocated on Truman Avenue, this versatile property offers both reliable income and future potential. Currently comprised of five legal long-term rental apartments, it's an excellent option for investors seeking steady cash flow or employee housing.Unit 101, a CBS structure, also offers potential for commercial conversion (buyer to verify), while the remaining apartments

  Allison Findlay Preferred Properties (KW)

  928 Truman Ave Unit 101, Key West, FL 33040
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  /39

  $1,800,000 Sold Feb 10, 2025

  • 2,160 Sq Ft
  • $833/SF
  • 48 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1997

  623 Simonton St Unit 9, Key West, FL 33040

  Hidden in the heart of Old Town Key West, this exceptional home in the Gardens of Key West combines privacy and prime location, just one block from vibrant Duval Street. Located in desirable Flood Zone X, this 3-bedroom, 3.5-bath residence offers off-street parking and a thoughtful layout perfect for relaxation or entertaining. The inviting open floor plan seamlessly connects the kitchen, dining,

  Terri Spottswood Truman & Co. (KW)

  623 Simonton St Unit 9, Key West, FL 33040
• 

  

  /21

  Est $1,005,856 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  120 Angela St Unit 202, Key West, FL 33040

  120 Angela St Unit 202, Key West, FL 33040
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  /47

  $2,195,000

  • 3 Beds
  • 4 Baths
  • 1,522 Sq Ft

  816 Ashe St, Key West, FL 33040

  This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within walking distance

  Bascom Grooms Bascom Grooms Real Estate (KW)

  816 Ashe St, Key West, FL 33040
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  /29

  $1,575,000 Sold Feb 07, 2025

  • 1,040 Sq Ft
  • $1,514/SF
  • 68 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1928

  624 Catholic Ln, Key West, FL 33040

  LOCATION CUBED! Located on one of Key West's most charming, quiet and private lanes, this home is perfect for entertaining guests with 2 separate guest cottages, flanking a 12' x 18' pool. The cottages have their own entry door from the off-street parking space through a faux wall, allowing for privacy for hosts and guests alike. The vaulted ceilings in the main house and in the cottages create

  Tyler Caudell Key West Realty, LLC (KW)

  624 Catholic Ln, Key West, FL 33040
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  /14

  Est $620,972 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 416 Sq Ft

  709 Emma St Unit 4, Key West, FL 33040

  709 Emma St Unit 4, Key West, FL 33040
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  /17

  $2,175,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  1115 Fleming St, Key West, FL 33040

  This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone else's overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890

  Derek Epperly Keys Atlantic Realty

  1115 Fleming St, Key West, FL 33040
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  /41

  $1,635,000 Sold Feb 06, 2025

  • 1,612 Sq Ft
  • $1,014/SF
  • 24 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1890

  1022 Grinnell St, Key West, FL 33040

  This beautifully updated historic home, originally built in the 1890s, combines vintage charm with modern conveniences. Featuring 3 bedrooms and 3 baths, it offers versatile living options, including the potential to function as a legal duplex with two electric meters.The open concept living room welcomes you with soaring cathedral ceilings, engineered wood floors, and impact glass windows

  Terri Spottswood Truman & Co. (KW)

  1022 Grinnell St, Key West, FL 33040
• 

  

  /11

  Est $621,651 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 416 Sq Ft

  709 Emma St Unit 3, Key West, FL 33040

  709 Emma St Unit 3, Key West, FL 33040
• 

  

  /23

  $990,000

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

  308 Peacon Ln, Key West, FL 33040

  Yes - not too good to be true or a misprint! Priced to sell for just $990,000 with this $400,000 price reduction. Rare 2 unit property in Old Town! Enjoy Key West living on one of our most picturesque Old Town lanes. Located in the heart of the historic district and near the seaport, everything you want in Key West is right out your door. Built in the early 1900s, over the years the home was

  Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  308 Peacon Ln, Key West, FL 33040
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  /24

  $805,500 Sold Feb 06, 2025

  • 577 Sq Ft
  • $1,396/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1938

  524 Margaret St Unit 103, Key West, FL 33040

  Incredible Old Town Key West location! Walk or bike to the Best of Old Town- steps from the Historic Seaport, neighborhood restaurants, Art Galleries and more!. Located pool side, this large 1 bedroom is gorgeous!. This condo was renovated over the last several years, and there are elements of Key West that have been used in the renovation. There are high ceilings throughout, and the kitchen

  Elaine Coyle Keller Williams Key West Compass Realty

  524 Margaret St Unit 103, Key West, FL 33040
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  /2

  Est $919,149 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 751 Sq Ft

  918 Southard St Unit 104, Key West, FL 33040

  918 Southard St Unit 104, Key West, FL 33040
• 

  

  /23

  $699,000

  • 2 Beds
  • 1 Bath
  • 643 Sq Ft

  409 Margaret St Unit 202 / B, Key West, FL 33040

  Close to the Historic Seaport, restaurants, art galleries, and more!. Recently renovated, this 2 bedroom, 1 bath condo has high impact windows and door, washer/ dryer, tankless hot water heater, new flooring, kitchen, mini splits, appliances, and is being sold furnished! Prime Old Town location, walk or bike to everything! This is easy island living- close to everything, and no need for a car.

  Elaine Coyle Keller Williams Key West Compass Realty

  409 Margaret St Unit 202 / B, Key West, FL 33040
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  /28

  $3,599,999 Sold Feb 04, 2025

  • 1,828 Sq Ft
  • $1,969/SF
  • 46 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2024

  522 Olivia St, Key West, FL 33040

  This newly built, exquisitely designed home, located in a prime location offers comfort and style to the highest standard.The architecture and gardens are designed by Key West's renowned designers. This 4 bedroom, 3.5 bath home embodies the pinnacle of luxury living. The open floor plan, introduces you to beautiful hand-finished walnut flooring, featuring 10-foot ceilings, an elegant half

  Key West Luxury Finders Preferred Properties (KW)

  522 Olivia St, Key West, FL 33040
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  /30

  Est $1,337,570 Not Listed For Sale

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

  626A Fleming St, Key West, FL 33040

  626A Fleming St, Key West, FL 33040
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  /32

  $5,500,000

  • 8 Beds
  • 11 Baths
  • 8,472 Sq Ft

  314 Simonton St, Key West, FL 33040

  Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  314 Simonton St, Key West, FL 33040
• 

  

  /19

  $518,000 Sold Feb 04, 2025

  • 648 Sq Ft
  • $799/SF
  • 217 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1928

  905 Pohalski St, Key West, FL 33040

  Discover a rare opportunity to bring your vision to life with this single-family home nestled in the heart of Old Town Key West. Steeped in history, this typical Conch cottage offers a historical charm, making it an ideal canvas for creating your dream residence. Embrace the rich heritage of Key West with this exceptional home, a true testament to the island's storied past. Originally part of the

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  905 Pohalski St, Key West, FL 33040
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  /67

  Est $4,144,867 Not Listed For Sale

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

  408 United St, Key West, FL 33040

  408 United St, Key West, FL 33040
• 

  

  /33

  $1,425,000

  • 3 Beds
  • 4 Baths
  • 1,464 Sq Ft

  415 Julia St, Key West, FL 33040

  At the best location in the heart of old town you will find this great duplex on Julia street in between Duval street and Whitehead street, 86 FOOTSTEPS TO DUVAL STREET. The back is a two bedroom two bathroom with a nice back yard. And in the front is a recently renovated one bedroom with two bathrooms with high ceilings and a great loft. It has an outdoor shower. A new A/C was installed 01/24.

  Annica Pedersen Key West Luxury Real Estate Inc (KW)

  415 Julia St, Key West, FL 33040
• 

  

  /24

  $1,420,555 Sold Feb 03, 2025

  • 1,064 Sq Ft
  • $1,335/SF
  • 21 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1943

  510 Amelia St, Key West, FL 33040

  Located in a transient license receiver zone, this delightful 1-bedroom, 1-bathroom Craftsman-style home offers a rare opportunity for short-term rentals in the heart of Old Town Key West. Just steps from the iconic Duval Street, this charming residence perfectly blends historic character with modern convenience.Inside, the open living space is bathed in natural light, with beautiful wood details

  Richard Haskins Buy The Keys

  510 Amelia St, Key West, FL 33040
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  /2

  Est $2,153,787 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,108 Sq Ft

  719 Chapman Ln, Key West, FL 33040

  719 Chapman Ln, Key West, FL 33040
• 

  

  /57

  $2,070,000

  • 3 Beds
  • 3 Baths
  • 1,473 Sq Ft

  1116 Packer St, Key West, FL 33040

  X FLOOD ZONE! Exquisite retreat in the heart of Old Town Key West--an ideal private sanctuary with rental income. This remarkable home offers refined style, privacy, and a proven rental history, appealing to buyers who value luxury and the allure of a tropical lifestyle. Behind an unassuming facade lies a sophisticated residence filled with high-end details. Restored in 2017, this home features

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1116 Packer St, Key West, FL 33040
• 

  

  /17

  $615,000 Sold Feb 03, 2025

  • 850 Sq Ft
  • $724/SF
  • 116 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2007

  634 Louisa St Unit 2, Key West, FL 33040

  Charming Old Town Key West TownhouseLocated just three blocks from the lively Duval Street, this 2-bedroom, 1.5-bathroom townhouse at 634 Louisa Street is the ideal Key West retreat. Priced to sell, this home blends modern amenities with classic island charm, offering a rare opportunity to own a piece of paradise.Prime Location & Modern ComfortsEnjoy the convenience of living in Old Town Key

  Scott Forman Royal Palms Realty (KW)

  634 Louisa St Unit 2, Key West, FL 33040
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  /6

  Est $1,316,022 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 969 Sq Ft

  1122 Virginia St, Key West, FL 33040

  1122 Virginia St, Key West, FL 33040
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  /33

  $2,000,000

  • 2 Beds
  • 2 Baths
  • 958 Sq Ft

  1401 Simonton St Unit 14, Key West, FL 33040

  This second-floor luxury condo is ideally situated just one block from the beach and the iconic Southernmost Point, offering the perfect balance of vacation living and income potential. As a high-demand rental property with an impressive occupancy rate, it presents an excellent opportunity for a 1031 exchange, especially with on-site management ensuring seamless service for guests.The property's

  Graciela Lozano KeysLifestyle Real Estate (KW)

  1401 Simonton St Unit 14, Key West, FL 33040
• 

  

  /24

  $980,000 Sold Feb 03, 2025

  • 975 Sq Ft
  • $1,005/SF
  • 169 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  918 Southard St Unit 202, Key West, FL 33040

  Discover the charm of this immaculate condo in the coveted Southard Square, located in the heart of Old Town, Key West. This bright and airy unit features two bedrooms, two bathrooms, and is offered fully furnished. The open-concept living area features abundant natural light, new appliances, and continues to the private porch surrounded by foliage offering privacy with local views.Rest easy

  Michelle Blades Realty Executives Florida Keys Old Town

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

  

  /14

  Est $2,151,823 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 917 Sq Ft

  210 Olivia St, Key West, FL 33040

  210 Olivia St, Key West, FL 33040
• 

  

  /19

  $2,095,000

  • 8 Beds
  • 4 Baths
  • 3,383 Sq Ft

  905 Grinnell St, Key West, FL 33040

  BIG TIME INVESTMENT OPPORTUNITY in the heart of the Historic District of Key West. Originally built as a former church, this 4 unit active rental property offers 3,383 square feet of living space, featuring 8 bedrooms and 4 bathrooms, and currently generates $10,908.50 in monthly rental income. (See below for a breakdown of beds and baths per unit) With versatile possibilities, it has the

  Team Kaufelt Truman & Co. (KW)

  905 Grinnell St, Key West, FL 33040

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