Monroe, FL Homes

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  /44

  $1,349,995

  • 3 Beds
  • 3 Baths
  • 1,300 Sq Ft

  1118 Eaton St, Key West, FL 33040

  Step outside to your own slice of paradise - a private oasis that beckons you to unwind and rejuvenate. The sparkling pool, adorned with stunning blue mosaic tiles, creates a mesmerizing focal point, while the soothing sound of its waterfall feature transports you to a world of tranquility. Surrounding the pool, a spacious deck provides the perfect setting for sunbathing, alfresco dining, or

  

  Matthew Carlson

  Realty ONE Group Destination

  (786) 788-8481

  1118 Eaton St, Key West, FL 33040
• 

  Explore Old Town

• 

  

  

  /6

  $1,500 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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  /36

  $1,300,000 Sold Aug 29, 2025

  • 2,019 Sq Ft
  • $644/SF
  • 192 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1945

  1327 Duncan St, Key West, FL 33040

  Are you ready to build??? after talking with City Planning the new owner will be able to possibly renovate the main house and build a second new house Buyer to verify...Make your offer today.Welcome to 1327 Duncan Street, this property offers a 3 bedroom 1 bath single-family home plus a separate 1 bedroom 1 bath cottage with fenced in yard, laundry area, central air condition. The main

  Barbara Crespo Keller Williams Key West Compass Realty

  1327 Duncan St, Key West, FL 33040
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  /29

  Est $1,473,145 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
• 

  

  

  /27

  $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

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 560 Sq Ft
  • Condo for Rent

  1209 William St Unit 1, Key West, FL 33040

  This 2/1 Old Town apartment is in good condition with a new shower and combination window and ductless a/c units. Stack laundry in the unit and 1 off street parking spot included. Available August 1st. F/L/S to move in. Please contact David Austin, Anchor Line Realty, Licensed Real Estate Broker for showings.

  1209 William St Unit 1, Key West, FL 33040
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  /51

  $900,000 Sold Aug 25, 2025

  • 1,463 Sq Ft
  • $615/SF
  • 37 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1930

  318 Margaret St, Key West, FL 33040

  Historic charm meets modern comfort in this beautifully preserved 1930 Conch cottage nestled in Key West's sought-after Historic Seaport district. This two-story, 2-bedroom, 2-bath home (approximately 1,463 sq ft) boasts classic Key West architecture - wood siding and a metal roof - along with inviting outdoor spaces including an open front porch and a private backyard oasis. Inside, airy living

  Jose Wenzel, PA Preferred Properties (KW)

  318 Margaret St, Key West, FL 33040
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  /14

  Est $959,697 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
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  /20

  $1,750,000 Open Sun 12PM - 2PM

  • 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
• 

  

  /17

  $3,650 per month

  • 2 Beds
  • 2 Baths
  • Property for Rent

  726 Eaton St, Key West, FL 33040

  Step into Key West history with this beautifully updated two-bedroom, two-bathroom first-floor home tucked away behind the serene Freeman-Curry House, circa 1865, on Eaton Street. The Carriage House offers a quiet, private retreat while still being in the heart of Old Town.This apartment features two spacious bedrooms and two full bathrooms and includes a washer and dryer, refrigerator,

  Megan Mcdowell eXp Realty LLC

  726 Eaton St, Key West, FL 33040
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  /41

  $861,700 Sold Aug 19, 2025

  • 610 Sq Ft
  • $1,413/SF
  • 56 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1928

  611 Grinnell St Unit 6, Key West, FL 33040

  Old Town Key West, welcome to this adorable 2 Bedroom, 1 Bath historic cottage Tucked away in one of the most enchanting neighborhoods, 611 Grinnell Street,Home #6, is full of warmth, charm, and island character. A true hidden gem, this 610 sq ft home is part of a small, peaceful compound just a short stroll to Duval Street and the Historic Seaport. Close to wonderful restaurants, live music,

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  611 Grinnell St Unit 6, Key West, FL 33040
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  /45

  Est $2,141,161 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
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  /48

  $2,799,000

  • 3 Beds
  • 2 Baths
  • 1,223 Sq Ft

  626 Canfield Ln, Key West, FL 33040

  First time on the market in over 50 years! This property is a plant lovers paradise. The owner spent his entire life collecting plants and seeds from all over the world and created a quiet serene and private oasis in the middle of Old Town Key West, on a huge oversized lot. Some of the rare plants and palms are found nowhere else in the continental United States. The main house has many

  

  Cardenas & Krug Team

  Ocean Sotheby's International Realty

  (786) 983-5190

  626 Canfield Ln, Key West, FL 33040
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  /6

  $2,200 per month

  • Studio
  • 1 Bath
  • 252 Sq Ft
  • Condo for Rent

  908 Elizabeth St Unit 4, Key West, FL 33040

  Very cute little garden studio available Early August. Small but in the very HEART of it all! Walk to everything Old Town has to offer! Tenant pays electric and cable/internet. F/S/S. Sorry No Pets!

  908 Elizabeth St Unit 4, Key West, FL 33040
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  /40

  $1,880,000 Sold Aug 15, 2025

  • 1,600 Sq Ft
  • $1,175/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1923

  1212 Watson St, Key West, FL 33040

  1212 Watson Street, aka Island Bliss, is a quintessential Old Town Key West home. This beautiful one-and-a-half-story home has been thoughtfully restored with a mix of modern touches and traditional Key West influences. From the stylish LVT flooring throughout to the stunning kitchen to the new mini split ACs, there's isn't a bit of this home that hasn't been updated. The primary suite occupies

  Rodney Culiver Last Key Realty, Inc (KW)

  1212 Watson St, Key West, FL 33040
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  /31

  Est $1,777,512 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
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  /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
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  /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
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  /8

  $699,000 Sold Aug 15, 2025

  • 896 Sq Ft
  • $780/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  808 Virginia St Unit 5, Key West, FL 33040

  Here's a 2 bedroom/1.5 bath townhouse in historic old town Key West. Convenient to everything Key West has to offer. Only 6 units in the compound. Brand new shared pool on site in progress. Located in the X flood zone. Many recent upgrades including new central A/C in 2022. Renovated kitchen with cabinets and all appliances including washer & dryer..Deeded parking space # 5 and 1/6 interest in

  Michelle Kirby RE/MAX Keys Connection (KW)

  808 Virginia St Unit 5, Key West, FL 33040
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  /2

  Est $805,924 Not Listed For Sale

  • 1 Bed

  951 Caroline St Unit 5, Key West, FL 33040

  951 Caroline St Unit 5, Key West, FL 33040
• 

  

  /28

  $1,595,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  819 Elizabeth St, Key West, FL 33040

  Welcome to Casa Bella Petite le Bleu., an architectural gem in the heart of Old Town Key West, honored with a prestigious Ceramic Star for historic preservation. Nestled in the desirable X-Flood Zone, this home blends timeless charm with contemporary upgrades, off street parking and a private pool making it the perfect tropical retreat. From the moment you arrive, the classic front porch invites

  Paige Bethel Island Home Realty Inc.

  819 Elizabeth St, Key West, FL 33040
• 

  

  /14

  $2,854 - $3,961 per month

  Lofts at Bahama Village

  1 - 3 Beds

  750 Fort St, Key West, FL 33040

  Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a

  750 Fort St, Key West, FL 33040
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  /47

  $1,330,000 Sold Aug 13, 2025

  • 1,324 Sq Ft
  • $1,005/SF
  • 110 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2021

  317 Virginia St, Key West, FL 33040

  Modern Elegance in the Heart of Old Town Key West - Fully Furnished & Move-In ReadyWelcome to 317 Virginia Street, a stunning two-story residence built in 2021, perfectly situated in the heart of Old Town Key West. Just a few blocks from iconic Duval Street and the Southernmost Point, this home offers the ultimate blend of luxury, comfort, and island living.Elevated above flood level and

  Monique Thiel Sunshine State Realty Services

  317 Virginia St, Key West, FL 33040
• 

  

  /8

  Est $793,640 Not Listed For Sale

  • 1 Bed

  951 Caroline St Unit 1, Key West, FL 33040

  951 Caroline St Unit 1, Key West, FL 33040
• 

  

  /36

  $2,199,000

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  2 Aronovitz Ln, Key West, FL 33040

  Tucked away on a hidden lane just a half of block off of Duval Street, 1 and 2 Aronovitz Lane is a true diamond in the rough! A one of a kind opportunity that is being offered for the first time ever. This listing consists of two platted lots with a total of three development rights and 5,614 sq. ft. of land. The existing well maintained house at 2 Aronovitz Lane is a two bedroom/one bathroom

  Terry Garcia Keller Williams Key West Compass Realty

  2 Aronovitz Ln, Key West, FL 33040
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  /8

  $7,000 per month

  • 4 Beds
  • 2 Baths
  • Property for Rent

  417 Southard St Unit A, Key West, FL 33040

  Long term rental, 4 bedroom, 2-bathroom furnished apartment is conveniently located just steps away from Duval Street, Mile Marker 0, and within walking distance to the Southernmost Point, Fort Zachary Taylor Historic State Park. The apartment boasts Beautiful bathrooms with walk-in showers, spacious kitchens equipped with upgraded stainless steel appliances, a stunning waterfall kitchen counter

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  417 Southard St Unit A, Key West, FL 33040
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  /53

  $3,500,000 Sold Aug 08, 2025

  • 3,171 Sq Ft
  • $1,104/SF
  • 134 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 1964

  407-415 Olivia St, Key West, FL 33040

  Situated directly across from the iconic Ernest Hemingway House, this exceptional family compound combines the rich history of Old Town Key West with modern luxury and island charm. From the famous six-toed cats that roam next door to the vibrant energy of Duval Street just steps away, this location is as legendary as it is convenient. Spanning two addresses at 407 and 415 Olivia Street, this

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  407-415 Olivia St, Key West, FL 33040
• 

  

  /53

  Est $5,027,202 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,404 Sq Ft

  1006 & 1008 Fleming St, Key West, FL 33040

  1006 & 1008 Fleming St, Key West, FL 33040
• 

  

  /61

  $4,995,000

  • 4 Beds
  • 4 Baths
  • 3,026 Sq Ft

  1014 Southard St, Key West, FL 33040

  Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a world where classic charm meets modern elegance.With 4 bedrooms and 3.5 Baths and over 3,000 sq. ft. of interior space across two separate structures, enjoy an unparalleled gem in one of Key West's

  Suzanne Moore Suzanne Moore Real Estate

  1014 Southard St, Key West, FL 33040
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  /34

  $3,600 per month

  • 1 Bed
  • 1 Bath
  • 416 Sq Ft
  • House for Rent

  709 Emma St Unit 1, Key West, FL 33040

  Tropical and Islandy Bungalow Style Home In KEY WEST!! Cute As A Button! 1 Bedroom 1 Full Bath, Furnished, Very Modern, Remodeled, Single Family Home. Located In Old Town/Downtown Area. 3 Blocks From Duval St., Yet Far Enough Away To Enjoy Your Private, Quiet Lifestyle. Property Is Fenced. Large Front Porch, Spacious Side Yard For Entertaining. Assigned Off Street Parking. Central Air. Electric,

  Sabrina Liguori Premium Properties Real Estate

  709 Emma St Unit 1, Key West, FL 33040
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  /15

  $330,000 Sold Aug 07, 2025

  • 308 Sq Ft
  • $1,071/SF
  • 95 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1908

  1014 Varela St Unit 3, Key West, FL 33040

  Discover a unique opportunity to own a cozy 1-bedroom, 1-bath condominium ideally situated near vibrant downtown Key West, offering the perfect canvas for those with a vision to rejuvenate. While the property may need some TLC, its prime location allows for easy access to local shops, restaurants, and stunning beaches, making it an appealing option for both personal retreats and investment

  Letisia Powell Robert Slack LLC

  1014 Varela St Unit 3, Key West, FL 33040
• 

  

  /19

  Est $932,529 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 974 Sq Ft

  914-1/2 White St, Key West, FL 33040

  914-1/2 White St, Key West, FL 33040
• 

  

  /46

  $3,600,000 Under Contract

  • 3 Beds
  • 4 Baths
  • 1,890 Sq Ft

  715 Frances St, Key West, FL 33040

  Impeccably preserved historic residence located in the heart of Old Town Key West. Discover the enticing charm of Key West and stroll through the majestic tree lined streets from 715 Frances Street. A rare combination of Key West luxury and historic architecture, this beautiful eyebrow home is perfectly positioned on a large spacious lot on sought after X Flood zone keeping you high and

  Suzanne Moore Suzanne Moore Real Estate

  715 Frances St, Key West, FL 33040
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  /33

  $14,000 per month

  • 4 Beds
  • 4.5 Baths
  • 2,250 Sq Ft
  • House for Rent

  710 Caroline St, Key West, FL 33040

  This magnificent, historic, turn-key home is located on infamous Caroline Street, just a few blocks from Duval Street in the Historic Seaport area, making it one of the most ideal locations in Key West. The property underwent a multi-year complete renovation culminating in 2023, including being raised appx. 5 feet and impact glass windows & doors. The 2,250-square-foot home features a stunning

  jesse friedman Real Broker, LLC

  710 Caroline St, Key West, FL 33040
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  /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
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  311 Amelia St Unit B, Key West, FL 33040

  311 Amelia St Unit B, Key West, FL 33040
• 

  

  /41

  $1,699,000

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

  205 Virginia St, Key West, FL 33040

  Stunning Single Family Home located in the Heart of the Cultural Mecca of Key West.Built in 2019 with Elevation and Superior craftsmanship in mind featuring Hardie Board SIding, metal roof and Impact windows and doors, this home will provide you the modern & luxurious comforts you desire and safety and reassurance of your investment.An easy stroll to Duval St., Ft. Zach Beach and Amphitheatre

  Suzanne Moore Suzanne Moore Real Estate

  205 Virginia St, Key West, FL 33040
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  /43

  $2,900,000 Sold Aug 01, 2025

  • 2,697 Sq Ft
  • $1,075/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
• 

  

  /20

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,305 Sq Ft

  311 Amelia St Unit A, Key West, FL 33040

  311 Amelia St Unit A, Key West, FL 33040
• 

  

  /50

  $3,499,000

  • 5 Beds
  • 4 Baths
  • 2,349 Sq Ft

  1114 Grinnell St, Key West, FL 33040

  Exquisite Old Town residence just completed!Rare opportunity to own your Key West dream home designed to satisfy both peace of mind and self-indulging luxuries. This historic structure has been rebuilt from the foundation up to create the perfect harmony of historic restoration, structural integrity and custom design. Luxurious 5 bed/ 4 bath including a detached poolside cabana and off-street

  Wendy Zintsmaster Truman & Co. (KW)

  1114 Grinnell St, Key West, FL 33040

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