Monroe, FL Homes

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  /33

  $1,650,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  530 Grinnell St, Key West, FL 33040

  Situated in the heart of the Historic Seaport area, 530 Grinnell St is a charming property that perfectly encapsulates the island's unique character and vibrant lifestyle. This beautifully maintained home features a blend of classic architecture and modern amenities, making it an ideal retreat for both residents and vacationers alike. As you enter, you're greeted by an inviting open floor

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  (305) 676-8537

  530 Grinnell St, Key West, FL 33040
• 

  

  

  /6

  $1,000 per month

  • 1 Bed
  • 367 Sq Ft
  • Property for Rent

  600 Whitehead St Unit C-4, Key West, FL 33040

  Commercial office space in Old Town available for immediate use. Office is offered non-furnished, internet not included.

  

  Everett Watkins

  Keller Williams Key West Compass Realty

  (866) 823-0723

  600 Whitehead St Unit C-4, Key West, FL 33040
• 

  

  

  /42

  $797,000 Sold Aug 05, 2025

  • 1,677 Sq Ft
  • $475/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1963

  3739 Duck Ave, Key West, FL 33040

  Welcome to your tropical duplex opportunity in Key West which can be your slice of paradise. This beautifully duplex offers the perfect blend of charm, flexibility and opportunity in the Newtown section of Key West. The front home features 2 spacious bedrooms and 2 full bathrooms, filled with natural light and island charm. Enjoy the open living room, a well-appointed kitchen and dining area.

  Christopher Orth Berkshire Hathaway HomeServices Knight & Gardner Realty

  3739 Duck Ave, Key West, FL 33040
• 

  

  

  /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
• 

  

  

  /14

  $155,000

  • 1 Bed
  • 1.5 Baths
  • 500 Sq Ft

  1801 N Roosevelt Blvd Unit Tarpon 16, Key West, FL 33040

  Live the Key West Dream Aboard This 1989 Coastal 450 - Slip Included!Offered at $155,000, this rare LIVEABOARD opportunity puts you in the heart of paradise. Nestled in a desirable Key West marina, this spacious 1989 Coastal 450 comes as a boat-and-slip package, delivering the ultimate tropical lifestyle -- whether you're seeking a full-time residence or a weekend getaway.With a generous layout,

  

  Annie Rivera

  Berkshire Hathaway Florida Realty

  (786) 808-1586

  1801 N Roosevelt Blvd Unit Tarpon 16, Key West, FL 33040
• 

  

  /5

  $2,500 per month

  • 2,244 Sq Ft
  • Property for Rent

  2001 Flagler Ave, Key West, FL 33040

  Prime 2,244 SQFT Vacant Lot Available for Rent.A rare opportunity to lease a centrally located vacant lot in the heart of New Town! Whether you're looking to advertise your business, operate a food truck, start a new venture, or create a space uniquely your own--this versatile lot offers endless potential. Multiple possible uses (tenant to verify).Please do not walk the property without prior

  

  Everett Watkins

  Keller Williams Key West Compass Realty

  (786) 244-5194

  2001 Flagler Ave, Key West, FL 33040
• 

  

  /32

  $995,000 Sold Aug 05, 2025

  • 1,439 Sq Ft
  • $691/SF
  • 131 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2008

  1621 Rose St Unit 2, Key West, FL 33040

  Very spacious and elevated three bedroom/three bathroom (all ensuite) condo close to the Casa Marina area is now for sale. Built in 2008, this two story property has a first floor bedroom and bathroom with two generous sized bedrooms and bathrooms upstairs and a large laundry room with full size washer and dryer. Kitchen and bathrooms have granite countertops. Extra sized brand new back deck

  Mike Caron Keller Williams Key West Compass Realty

  1621 Rose St Unit 2, Key West, FL 33040
• 

  /2

  Est $1,618,877 Not Listed For Sale

  • Studio

  40 Sunset Key Dr, Key West, FL 33040

  40 Sunset Key Dr, Key West, FL 33040
• 

  

  /50

  $1,550,000

  • 3 Beds
  • 1.5 Baths
  • 1,251 Sq Ft

  1215 Margaret St, Key West, FL 33040

  Enjoy the perfect Key West location - Old Town bordering the Casa Marina neighborhood - in this 3 bedroom, 2.5 bath pool home. You'll have peace of mind knowing that the home was completely renovated from the ground up in 2019 while keeping with the historic style of the home's origins - tongue in groove ceilings, wood floors, pecky Cypress wall accent - but adding modern amenities such as impact

  

  Shane Wilson

  Cypress Realty, Inc.

  (786) 882-9251

  1215 Margaret St, Key West, FL 33040
• 

  

  /35

  $2,645 - $4,679 per month

  Ocean Walk

  Studio - 3 Beds

  3900 S Roosevelt Blvd, Key West, FL 33040

  Ocean Walk apartments are located on the peaceful Atlantic side of the island, nestled among lush natural vegetation, just steps away from the beach. Ideally located just minutes from the best dining, shopping and entertainment Key West has to offer, Ocean Walk Apartment Homes boast spacious one, two, and three bedroom apartments, spectacular views, and first-rate amenities. Each recently

  3900 S Roosevelt Blvd, Key West, FL 33040
• 

  

  /57

  $1,750,000 Sold Aug 05, 2025

  • 2,080 Sq Ft
  • $841/SF
  • 314 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1928

  704 Caroline St, Key West, FL 33040

  Triplex investment property! Prime location only 1 block from the historic Key West seaport and 2 blocks from Duval St. The downstairs offers 2 units which include a 1/1 with kitchenette and a 1/1 with full kitchen. Enjoy the front porch facing Caroline St. or spend a lazy afternoon lounging by the dip pool in the backyard. Ascend the gorgeous wooden staircase to the upstairs unit which

  LaReta Morrison eXp Realty LLC

  704 Caroline St, Key West, FL 33040
• 

  

  /37

  Est $2,322,246 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,581 Sq Ft

  1701 Laird St, Key West, FL 33040

  1701 Laird St, Key West, FL 33040
• 

  

  /28

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  3218 Harriet Ave, Key West, FL 33040

  Welcome to your island oasis in the heart of Key West! Nestled on a quiet tree lined street in the New Town neighborhood, this beautifully maintained 2 bedroom home offers the perfect balance of comfort, convenience, and Key West charm.Step inside and be greeted by a bright, open layout with impact-rated windows and doors that flood the space with natural light while offering peace of mind in our

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 981-0896

  3218 Harriet Ave, Key West, FL 33040
• 

  

  /15

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Property for Rent

  1114 White St Unit 2, Key West, FL 33040

  Old Town Key West- Large 2 bedroom, 2 bath , 12 foot ceilings. Spacious feeling throughout, large bedrooms, freshly painted, large bedrooms. The second bedroom is a large suite with private bathroom and additional storage. Upon entering , the open kitchen / living room is 40 feet long. No smoking on the property, no pets.

  Elaine Coyle Keller Williams Key West Compass Realty

  1114 White St Unit 2, Key West, FL 33040
• 

  

  /57

  $1,225,000 Sold Aug 04, 2025

  • 1,260 Sq Ft
  • $972/SF
  • 11 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1991

  115 Front St Unit 102, Key West, FL 33040

  **Prime Condo for Sale in the Exclusive Truman Annex**Discover your ideal Key West retreat in this stunning condo located within walking distance to the vibrant Duval Street and the beautiful Fort Zachary Taylor Beach. Nestled in the highly desirable Truman Annex, this property offers a perfect blend of convenience and tranquility in a prime location.Harbour Place was built to last with concrete

  Justyn Ewald Expert Realty LLC (HQ)

  115 Front St Unit 102, Key West, FL 33040
• 

  

  /29

  Est $1,497,452 Not Listed For Sale

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

  1219 Grinnell St Unit B, Key West, FL 33040

  1219 Grinnell St Unit B, Key West, FL 33040
• 

  

  /13

  $250,000

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  1801 N Roosevelt Blvd Unit M28, Key West, FL 33040

  LIVEABOARD Houseboat & Slip (Package) at Garrison Bight Marina (Houseboat Row). It's a Leasehold to the City of Key West and with the Transfer of Title to your name. NO RENTALS, VRBO/AIRBNB! This community is Historic. It's a TRUE KEY WEST LIFESTYLE... CASH ONLY! If your ready to enjoy life and have a crash pad in the Florida Keys, then come and see this one. Absolutely adorable.

  

  Annie Rivera

  Berkshire Hathaway Florida Realty

  (786) 822-8674

  1801 N Roosevelt Blvd Unit M28, Key West, FL 33040
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  /12

  $5,000 per month

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Condo for Rent

  1022 Fleming St Unit Lower, Key West, FL 33040

  Property Id: 1249660Fully Furnished, amazing 2 bedroom, 1 bathroom (upper level) newly furnished, gorgeous home in Key West on spectacular Fleming street in the old town, historic district, just a few blocks from famous Duval street. Amenities included: central air, central heat, deck, dishwasher, hardwood floors, stainless steel appliances, washer and dryer and pool. Small dog or two

  1022 Fleming St Unit Lower, Key West, FL 33040
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  /43

  $2,900,000 Sold Aug 01, 2025

  • 2,697 Sq Ft
  • $1075/SF
  • 124 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2017

  149 Simonton St, Key West, FL 33040

  Old Town Villas at Key West is a luxurious gated development just 1 block off of Duval Street. This townhome has 3 bedrooms, 3.5 baths on 4 floors. A private elevator in each unit takes you from the 2 car garage to the rooftop terrace. Just under 2,700 SF of solid concrete construction accompanied with high end appliances, a large community pool & cabana area.

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  149 Simonton St, Key West, FL 33040
• 

  

  /14

  Est $950,727 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 822 Sq Ft

  418 Amelia St Unit 2, Key West, FL 33040

  418 Amelia St Unit 2, Key West, FL 33040
• 

  

  /42

  $1,850,000

  • 3 Beds
  • 3 Baths
  • 1,804 Sq Ft

  846 Olivia St, Key West, FL 33040

  Welcome and bienvenidos to The Conch Corner in old town Key West. Surrounded by luxurious palms and a large Mango tree, originally built in the 1908 at the corner of Olivia and Packer. New 2022 detailed exterior and 2021 roofing system, this 3 bedroom, 3 bath home boasts 1,817 square feet of living space and off street parking. Cathedral ceiling in large, spacious living room downstairs, along

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  (305) 571-6027

  846 Olivia St, Key West, FL 33040
• 

  

  /13

  $3,800 per month

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Property for Rent

  2401 Patterson Ave Unit 102, Key West, FL 33040

  Spacious 2BD/1BA - Renovated Second-Floor Duplex in MidtownBe the first to enjoy this beautifully renovated 2-bedroom, 1-bath upstairs apartment in the heart of Key West's desirable Midtown neighborhood. This bright and airy home features a large open-concept living room and kitchen, complete with brand-new stainless steel appliances, modern finishes, and sleek countertops. Enjoy the convenience

  Jody Clark Key West Luxury Real Estate Inc (KW)

  2401 Patterson Ave Unit 102, Key West, FL 33040
• 

  

  /30

  $930,000 Sold Aug 01, 2025

  • 1,700 Sq Ft
  • $547/SF
  • 189 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1933

  608 Roberts Ln, Key West, FL 33040

  OLD TOWN CONCH HOUSE on a lovely Lane tucked away but close to all of your favorite shops, cafes and Key West attractions! First time on the market in over 45 years! This historic home built by the Roberts Family is located on a quiet cul-de-sac lane in Old Town Key West. Tucked away and just off Frances St, 608 Roberts Lane (formerly known as Cates Lane as well as Darwin Court dates back to the

  Bascom Grooms Bascom Grooms Real Estate (KW)

  608 Roberts Ln, Key West, FL 33040
• 

  

  /45

  Est $2,135,215 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,440 Sq Ft

  619 Simonton St Unit 7, Key West, FL 33040

  619 Simonton St Unit 7, Key West, FL 33040
• 

  

  /28

  $1,149,000

  • 2 Beds
  • 1 Bath
  • 852 Sq Ft

  1111 Watson St Unit C, Key West, FL 33040

  Nestled in the vibrant heart of Key West, 1111 Watson St C is a charming escape that embodies the essence of island living. This delightful abode offers a warm and inviting atmosphere, where the gentle sea breeze dances through palm trees and sunlight spills through large windows, casting a golden hue on the meticulously designed interiors.Imagine waking up in this cozy haven, surrounded by

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  (305) 419-1003

  1111 Watson St Unit C, Key West, FL 33040
• 

  

  /15

  $3,200 per month

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft
  • Condo for Rent

  3655 Seaside Dr Unit 128, Key West, FL 33040

  2 bed 2 bath condo located at the "Salt Ponds" condo complex. Convenient to everything Key West has to offer. Enjoy relaxing by the pool, playing tennis, and walking/jogging along the grounds. Restaurants, beaches and down town are easily accessible by bicycle or scooter. Amenities include pool, tennis court, 2 parking spaces -(including 1 covered space). Appliances: Dishwasher, Air Conditioning,

  3655 Seaside Dr Unit 128, Key West, FL 33040
• 

  

  /25

  $795,000 Sold Jul 30, 2025

  • 520 Sq Ft
  • $1529/SF
  • 8 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1938

  321 Julia St, Key West, FL 33040

  This beautifully renovated one bedroom conch cottage is a breath of fresh air and is in a prime Old Town location. This island retreat welcomes you through its white picket fence to a cozy front porch, inviting you to sit for a spell and breathe in your tropical surroundings. Inside you will find an open floor plan that boasts vaulted ceilings, LVT floors and Key West sunshine flooding through

  Wendy Zintsmaster Truman & Co. (KW)

  321 Julia St, Key West, FL 33040
• 

  

  /26

  Est $1,562,608 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,100 Sq Ft

  410 Porter Ln Unit 10, Key West, FL 33040

  410 Porter Ln Unit 10, Key West, FL 33040
• 

  

  /24

  $1,249,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  2525 Patterson Ave, Key West, FL 33040

  Wake up and smell the coffee! You should have bought ten years ago? You are going to say that again ten years from now! This is the house to buy because it has everything you want. Three bedroom two bathroom upstairs and ample useable space downstairs, plus a two car garage, plus off street parking, plus a huge privacy wall, plus a large pool, plus a pool house bar with a full kitchen in it! This

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  (305) 419-1662

  2525 Patterson Ave, Key West, FL 33040
• 

  

  /18

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 912 Sq Ft
  • Property for Rent

  2401 Patterson Ave Unit 101, Key West, FL 33040

  Spacious 3BD/2BA - Renovated First-Floor Duplex in MidtownThis fully renovated 3-bedroom, 2-bath apartment offers everything you need for comfortable long-term living in Key West's Midtown neighborhood. Located on the first floor of a freshly updated duplex, this home features a large open-concept living area and kitchen with all new appliances and high-end finishes. The unit includes a brand-new

  Jody Clark Key West Luxury Real Estate Inc (KW)

  2401 Patterson Ave Unit 101, Key West, FL 33040
• 

  

  /44

  $1,675,000 Sold Jul 30, 2025

  • 1,320 Sq Ft
  • $1269/SF
  • 116 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1999

  2605 Gulfview Dr, Key West, FL 33040

  Key West Waterfront Paradise - Private Dock & Pool!Welcome to one of the most exclusive waterfront homes in Key West, located in the prestigious gated community of Gulfview Pointe. This rare gem is one of the few properties in Key West offering both a private dock and private pool, making it the ultimate island retreat!Step inside to an open concept living and dining space, where ocean views of

  Paige Bethel Island Home Realty Inc.

  2605 Gulfview Dr, Key West, FL 33040
• 

  

  /31

  Est $1,853,518 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,440 Sq Ft

  603 Angela St Unit 2, Key West, FL 33040

  603 Angela St Unit 2, Key West, FL 33040
• 

  

  /21

  $729,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  3246 Duck Ave, Key West, FL 33040

  Nestled in lush greenery, this charming 2-bedroom, 2-bathroom townhouse is a private retreat in the heart of paradise. Enjoy a spacious deck overlooking a beautifully landscaped yard, complete with mature mango and avocado trees and vibrant tropical flowers.Inside, the updated kitchen shines with granite countertops, while modernized bathrooms add a touch of luxury. Impact doors and windows

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 640-0782

  3246 Duck Ave, Key West, FL 33040
• 

  

  /9

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  1800 Atlantic Blvd Unit 302A, Key West, FL 33040

  1800 Atlantic blvd. Has so much to offer, quiet location, fantastic apartment views, and a long list of amenities.

  1800 Atlantic Blvd Unit 302A, Key West, FL 33040
• 

  

  /25

  $975,000 Sold Jul 30, 2025

  • 1,613 Sq Ft
  • $604/SF
  • 85 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  2418 Linda Ave, Key West, FL 33040

  Start the New Year in this wonderful family home with a flexible floor plan. Located on a quiet street in mid town close to schools, shopping and walking trails through Little Hamaca Park nature preserve. Upon entering the home you will find an open concept living and kitchen area perfect for family gatherings. Impact rated French doors off the living room lead you to the tropically landscaped

  Tonya Cabanas Truman & Co. (KW)

  2418 Linda Ave, Key West, FL 33040
• 

  

  /19

  Est $581,207 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,070 Sq Ft

  3930 S Roosevelt Blvd Unit S208, Key West, FL 33040

  3930 S Roosevelt Blvd Unit S208, Key West, FL 33040
• 

  

  /20

  $1,750,000

  • 2 Beds
  • 1 Bath
  • 759 Sq Ft

  1020 Fleming St, Key West, FL 33040

  Discover your dream surfer's cottage on a tropical island! Built in 1918, this charming home still showcases elements of its historic architecture, blending timeless character with a unique coastal vibe. Located at 1020 Fleming Street in the Historic Seaport area of Old Town Key West, you'll be just a short walk from amazing restaurants, great bars, and some of the best fishing and diving

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  (305) 449-9943

  1020 Fleming St, Key West, FL 33040
• 

  

  /14

  $4,800 per month

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Property for Rent

  844 Olivia St, Key West, FL 33040

  AVAILABLE SEPTEMBER 1,2025 3 bedroom 2 bathroom in Old Town Key West with off street parking. Make an appointment to view this home and see all the possibilities this home has to offer. First room can be a bedroom or living area. Back room is a washer dryer room, it also has a small bathroom and shower. Upstairs loft is a great room for a bedroom along with seating area or bedroom and office, one

  Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

  844 Olivia St, Key West, FL 33040
• 

  

  /19

  $2,500,000 Sold Jul 30, 2025

  • 2,928 Sq Ft
  • $854/SF
  • 353 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1940

  1503 Washington St, Key West, FL 33040

  Welcome to your dream oasis in the heart of Key West! This stunning 4-bedroom, 4-bathroom home embodies luxury and entertainment, offering an unparalleled lifestyle in a prime, central location on the island.Stepping through Brazilian-Walnut Entry doors into this exquisitely updated residence, you are captivated by the lush courtyard and lured over the Pond bridge to the sounds of cascading

  Michelle Blades Realty Executives Florida Keys Old Town

  1503 Washington St, Key West, FL 33040
• 

  

  /18

  Not Listed For Sale

  • 2 Beds

  1801 N Roosevelt Blvd Unit Marlin 19, Key West, FL 33040

  1801 N Roosevelt Blvd Unit Marlin 19, Key West, FL 33040

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