Monroe, FL Homes

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  /59

  $4,695,000

  • 4 Beds
  • 5 Baths
  • 3,750 Sq Ft

  37 Cannon Royal Dr, Key West, FL 33040

  Hidden away in the exclusive enclave of Shark Key, 37 Cannon Royal Drive offers a rare balance of architectural elegance and coastal tranquility. This four-bedroom, four-and-a-half-bath home is perfectly positioned on over third an acre of waterfront property, where walls of glass frame sweeping views of the Gulf and fill the interiors with natural light.Inside, a series of exquisite arches adds

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (877) 350-8301

  37 Cannon Royal Dr, Key West, FL 33040
• 

  Explore Key West

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  /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
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  /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
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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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  /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
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  /34

  $6,000 per month

  • 3 Beds
  • 3 Baths
  • 1,380 Sq Ft
  • Property for Rent

  59 Palm Dr, Key West, FL 33040

  Enjoy the Keys lifestyle in this stunning canal-front 3-bedroom, 3-bathroom elevated modular home, located in the desirable Bay Point neighborhood, just behind Baby's Coffee. Available for $5,900 per month, this 2015-built home offers modern amenities and a spacious layout perfect for comfortable living.The lower level features a bedroom with a full bath, 9-foot ceilings, and access to a covered

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (645) 205-0832

  59 Palm Dr, Key West, FL 33040
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  /27

  $1,100,000 Sold Aug 01, 2025

  • 1,280 Sq Ft
  • $859/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  12 Aster Terrace, Key West, FL 33040

  Welcome to 12 Aster Terrace, a canalfront 3-bedroom 2-bathroom home located in the highly desirable Key Haven neighborhood--just minutes from downtown Key West. This single-level property features 60 feet of water frontage, 60-foot private seawall with boat lift, and excellent boating access to the Gulf and Atlantic. The home offers 1,280 sq. ft. of living space, a carport, and a spacious

  Connor Nelson Berkshire Hathaway HomeServices Knight & Gardner Realty

  12 Aster Terrace, Key West, FL 33040
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  /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
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  /37

  $665,000

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft

  2 Merganser Ln, Key West, FL 33040

  Spread your wings on Merganser Lane - nestled in the lush serenity of the Key West Golf Club, this townhouse is your ticket to island living with a graceful touch. This impeccably upgraded home boasts one of the most desirable locations in the community conveniently situated near the guard gate and just steps from one of the two inviting pools. The lush, private yard is a haven for pet owners and

  

  Nira Tocco

  Coldwell Banker Schmitt RE Co. Lower Keys Office

  (786) 396-5442

  2 Merganser Ln, Key West, FL 33040
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  /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
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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
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  /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
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  /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
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  /18

  $7,500 per month

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • Property for Rent

  6 Calle Dos, Key West, FL 33040

  The Rockland Key Resort is an amazing waterfront home only minutes from Key West. This beautifully renovated home is the perfect Keys oasis. Private fenced yard with mature landscape, new artificial turf, lanai, pool, and covered outdoor space. Ideal open floor plan with light-filled spaces overlooking the canal and pool. The kitchen offers stainless steel appliances, granite counters, &

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 964-3586

  6 Calle Dos, Key West, FL 33040
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  /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
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  /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
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  /47

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  26 Spoonbill Way, Key West, FL 33040

  Nestled within the prestigious Key West Golf Club, a rare opportunity beckons with this exceptional single-level home, one of only four of its kind in the golf course. Designed for effortless living and entertaining, this residence combines the ease of no interior steps with the luxury of a spacious layout and stunning views. Offering a unique blend of privacy, elegance, and serene golf course

  

  Leslie Howard

  Ocean Sotheby's International Realty

  (786) 422-9397

  26 Spoonbill Way, Key West, FL 33040
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  /18

  $3,600 per month

  Sunset Marina Apts

  2 Beds

  5555 College Rd, Key West, FL 33040

  5555 College Rd, 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
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  /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
• 

  

  /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
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  /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
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  /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
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  /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
• 

  

  /20

  $1,199,000

  • 4 Beds
  • 3 Baths
  • 1,504 Sq Ft

  806 Pearl St, Key West, FL 33040

  Unleash your vision and step into endless possibilities with this two-story duplex, a blank canvas located in the prestigious Meadows neighborhood of Key West. Packed with potential, this diamond in the rough is perfect for investors, developers, or dreamers looking to craft their masterpiece in one of Key West's most desirable areas. The property is a blank slate for your imagination to design

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 707-7124

  806 Pearl St, Key West, FL 33040
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  /14

  Call for Price

  Lofts at Bahama Village

  1 - 2 Beds

  750 Fort St, Key West, FL 33040

  750 Fort St, 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
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  /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
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  /28

  $1,280,000

  • 2 Beds
  • 3 Baths
  • 1,216 Sq Ft

  101 Front St Unit 15, Key West, FL 33040

  Located in the prestigious Truman Annex community, this town home in The Foundry is the perfect getaway offering the perfect blend of luxury, comfort, and convenience. This beautifully designed 2-bedroom, 2.5-bathroom home enjoys a highly desirable location with easy access to Key West's vibrant Old Town, while maintaining privacy and security within a gated community.As you step inside the

  Cardenas & Krug Team

  Ocean Sotheby's International Realty

  (786) 705-8652

  101 Front St Unit 15, 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
• 

  

  /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
• 

  

  /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
• 

  

  /30

  $1,299,000

  • 4 Beds
  • 2 Baths
  • 2,274 Sq Ft

  2809 Flagler Ave, Key West, FL 33040

  ***Property has 70k-120k worth of new windows that will be installed in phase III of the Airport Package*** Welcome to 2809 Flagler Ave, a beautifully updated residence that seamlessly blends classic charm with modern convenience. Originally built in 1953, this home has been enhanced with a thoughtfully designed two stories new addition in 2002 increasing both its space and functionality.The

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 964-2163

  2809 Flagler Ave, Key West, FL 33040
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  /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
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  /10

  $300,000 Sold Jul 29, 2025

  • Land

  • 8 Days On Market

  14 Dolphin Rd, Key West, FL 33040

  This proeprty has a rogo exempt letter. Build your island dream home on this spacious 6,772 square foot vacant lot located in a quiet residential neighborhood on Big Coppitt Key. Just 10 minutes from the heart of Key West, this lot offers the perfect blend of peaceful living and the natural beauty of the Lower Keys without the price tag of a waterfront property.Set in an established community,

  Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  14 Dolphin Rd, 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
• 

  

  /14

  $315,000

  • Land

  5555 College Rd Unit 4, Key West, FL 33040

  Discover your perfect docking solution with this 60 foot boat slip (65 foot LOA) located at the sheltered and protected Sunset Marina in Key West. Positioned on the Gulf side of Key West, this slip provides deep water access, ideal for both large and small vessels. At the entrance to the property owners will find an electric gate providing increased security. Owners will enjoy the exclusive

  Cardenas & Krug Team

  Ocean Sotheby's International Realty

  (305) 504-6479

  5555 College Rd Unit 4, 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
• 

  

  /21

  $578,000 Sold Jul 25, 2025

  • 886 Sq Ft
  • $652/SF
  • 1 Day On Market

  • 2 Beds
  • 1 Bath
  • Built 1959

  15 Cactus Dr, Key West, FL 33040

  Welcome to your beautifully renovated retreat! This bright and stylish 2-bedroom, 1-bathroom home sits on an beautiful 7,500 sqft lot, offering space, comfort, and potential rarely found in the Keys at this price point.Inside, enjoy modern finishes, an open-concept layout, and a thoughtfully updated kitchen. The home also features a metal roof and impact windows and doors keeping everything

  Richard Haskins Buy The Keys

  15 Cactus Dr, 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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