Monroe, FL Homes

• 

  

  

  /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
• 

  Explore Truman Annex

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /30

  $1,249,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  532 Porter Ln, Key West, FL 33040

  Charming townhouse situated on Porter Lane in Presidents Walk community of the Truman Annex. This bright and sunny end unit is in excellent condition and offers many renovations throughout. Enjoy an updated kitchen with stainless appliances, subway tile backsplash and granite countertops. Engineered wood-look LVT flooring is not only very attractive but also extremely durable. Impact doors

  Wendy Zintsmaster Truman & Co. (KW)

  532 Porter Ln, Key West, FL 33040
• 

  

  

  /30

  $1,800,000 Sold Jul 08, 2025

  • 1,312 Sq Ft
  • $1372/SF
  • 136 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1995

  214 Fleming St, Key West, FL 33040

  Experience the epitome of Key West living in this exquisitely renovated 2-bedroom, single family home nestled within the exclusive gated community of Truman Annex. The first floor of this beautifully renovated Coastal designed home features a gourmet kitchen with top-of-the-line appliances, a spacious sun-filled Living Room and Dining Room made for hosting unforgettable gatherings. The private

  Rodney Culiver Last Key Realty, Inc (KW)

  214 Fleming St, Key West, FL 33040
• 

  

  /17

  Est $919,502 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 646 Sq Ft

  620 Thomas St Unit 297, Key West, FL 33040

  620 Thomas St Unit 297, Key West, FL 33040
• 

  

  /65

  $2,700,000

  • 2 Beds
  • 3 Baths
  • 1,418 Sq Ft

  413 Emma St Unit A, Key West, FL 33040

  Welcome to 413 Emma Street, Unit A - a rare opportunity to own a piece of Key West history in the prestigious Truman Annex. This elegant two-story, 2-bedroom, 2.5-bath villa is located in the exclusive Mills Place Condominiums, a unique enclave of just 20 residences, thoughtfully designed within charming bungalows and the original 1844 hospital by architect Robert Mills. This beautifully

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

  413 Emma St Unit A, Key West, FL 33040
• 

  

  /21

  $675,000 Sold Jun 30, 2025

  • 513 Sq Ft
  • $1316/SF
  • 168 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1991

  208 Southard St Unit 3, Key West, FL 33040

  If you're looking for a wonderful and cozy pied a terre here in Key West, look no further than this exquisitely maintained upstairs Shipyard condominium in highly desirable Truman Annex. This one bedroom/one bathroom wonderfully furnished property incorporates indoor and outdoor living with a large covered porch, perfect for dining, entertaining or just relaxing. Security and safety are evident

  Mike Caron Keller Williams Key West Compass Realty

  208 Southard St Unit 3, Key West, FL 33040
• 

  

  /6

  Est $922,868 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 748 Sq Ft

  620 Thomas St Unit 287, Key West, FL 33040

  620 Thomas St Unit 287, Key West, FL 33040
• 

  

  /16

  $2,200,000

  • 2 Beds
  • 3 Baths
  • 1,210 Sq Ft

  105 Front St Unit 119, Key West, FL 33040

  SOLD TURN KEY! This beautiful two bedroom, 2.5 bath Harbour Place condominium is located on the desirable first level with one of the largest decks which includes plenty of room for entertaining, relaxing and watching the sunsets and boats coming in out of the Key West harbor. There are gorgeous views of the open water from the living and dining rooms as well as the kitchen. The spacious

  The Behmke Group Keller Williams Key West Compass Realty

  105 Front St Unit 119, Key West, FL 33040
• 

  

  /28

  $675,000 Sold Jun 26, 2025

  • 580 Sq Ft
  • $1164/SF
  • 52 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1991

  210 Southard St Unit 2, Key West, FL 33040

  WELCOME TO THE MOST UNIQUE ISLAND IN FLORIDA! Set in the most desirable Gated Community only 2 blocks to Duval St. You will love the walkability here, close to all amenities. You can walk or ride your bike to Fort Zachary and spend the day on the beach. Your 2nd Floor Condo offers Brand New Hurricane Windows 2024 ($20,000 upgrade), Beautiful Luxury Vinyl Flooring throughout, Tiled Bath, Solid

  Stephen Hachey

  210 Southard St Unit 2, Key West, FL 33040
• 

  

  /19

  Est $844,245 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 646 Sq Ft

  620 Thomas St Unit 250, Key West, FL 33040

  620 Thomas St Unit 250, Key West, FL 33040
• 

  

  /42

  $2,400,000

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

  107 Front St Unit 215, Key West, FL 33040

  Second floor Harbour Place condominium features 2 bedrooms and 2.5 baths. Relax on your private balcony and admire the beautiful sunsets and views of the ocean, gulf and all the activity in Key West harbor. Recently updated, this beautiful property is move-in ready and has spectacular views from the large windows and both bedrooms. Easily accessible by the conveniently located elevator. One of

  The Behmke Group Keller Williams Key West Compass Realty

  107 Front St Unit 215, Key West, FL 33040
• 

  /2

  $820,000 Sold Apr 01, 2025

  • 680 Sq Ft
  • $1206/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1991

  210 Southard St Unit 9, Key West, FL 33040

  Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex in a gated community! Unit Number 9.This quaint, well-appointed condo is located on the first floor and offers two bedrooms and one bathroom. It has a huge back deck with a seating area and is just steps to all the "must see" sites and activities in Key West!Upon arrival you are

  Daniel Fienman 360 REALTY OF TAMPA LLC

  210 Southard St Unit 9, Key West, FL 33040
• 

  /2

  Est $833,943 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 513 Sq Ft

  620 Thomas St Unit 261, Key West, FL 33040

  620 Thomas St Unit 261, Key West, FL 33040
• 

  

  /48

  $2,495,000

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

  105 Front St Unit 121, Key West, FL 33040

  Epitome of Paradise!There is an enveloping comfort, an ease and repose, that beckons one away from the world's cares and invites one to lounge, drift away, and dream in this gorgeous waterfront condominium.Enjoy a single level open floor plan with two bedrooms, two full baths and a convenient powder room.Exquisitely decorated to reflect the local island flavor with all new furniture and

  The Behmke Group Keller Williams Key West Compass Realty

  105 Front St Unit 121, Key West, FL 33040
• 

  

  /19

  $685,000 Sold Mar 24, 2025

  • 513 Sq Ft
  • $1335/SF
  • 50 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1991

  206 Southard St Unit 8, Key West, FL 33040

  This charming transient licensed condominium is nestled in the Shipyard community of Truman Annex, offering a tranquil retreat just a 5-minute walk from the vibrant Duval Street. With its transiently licensed upstairs unit, this property provides the perfect balance of relaxation and proximity to the city's action. The gated community boasts a deeded parking spot and a pool, while the nearby

  Justyn Ewald Expert Realty LLC (HQ)

  206 Southard St Unit 8, Key West, FL 33040
• 

  

  /21

  Est $899,320 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft

  620 Thomas St Unit 257, Key West, FL 33040

  620 Thomas St Unit 257, Key West, FL 33040
• 

  

  /52

  $2,495,000

  • 3 Beds
  • 3 Baths
  • 1,325 Sq Ft

  115 Front St Unit 101, Key West, FL 33040

  Step into a piece of history, reimagined for modern luxury. This stunning 3-bedroom, 3-bath condominium is located in the historic Naval Administration Building within the prestigious, award-winning Truman Annex. Completely renovated to the highest contemporary standards, this one-of-a-kind residence boasts soaring exposed beam ceilings, ultra-thick concrete walls and ceilings for unparalleled

  Jimmy Lane Island Life Realty Experts

  115 Front St Unit 101, Key West, FL 33040
• 

  

  /26

  $1,500,000 Sold Mar 18, 2025

  • 960 Sq Ft
  • $1562/SF
  • 1 Day On Market

  • 2 Beds
  • 3 Baths
  • Built 1994

  510 Porter Ln, Key West, FL 33040

  Located in the highly sought-after Truman Annex, 510 Porter Lane is a beautifully renovated 2-bedroom, 2.5-bathroom townhome, just steps from Duval Street, the Truman Waterfront Amphitheater, top restaurants, bars, and all the attractions of Old Town Key West. A deeded covered parking spot is conveniently located just a few steps from the unit. Fully renovated in 2023, this home blends historic

  Austin Kimbler Expert Realty LLC (HQ)

  510 Porter Ln, Key West, FL 33040
• 

  

  /7

  Est $888,376 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  620 Thomas St Unit 186, Key West, FL 33040

  620 Thomas St Unit 186, Key West, FL 33040
• 

  

  /45

  $1,395,000

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

  115 Front St Unit 202, Key West, FL 33040

  Second Floor Harbour Place Condo located in the historic Navy Administrative Building. Features high ceilings and tile floors throughout. One level living with 2 bedrooms and 2.5 Baths. Large primary bedroom ensuite with walk-in closet. The guest bedroom has French doors that open to the balcony with guest bathroom in the hall. Has one covered parking space, # 84.

  The Behmke Group Keller Williams Key West Compass Realty

  115 Front St Unit 202, Key West, FL 33040
• 

  

  /40

  $1,550,000 Sold Feb 18, 2025

  • 1,036 Sq Ft
  • $1496/SF
  • 10 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1991

  406 Porter Ln, Key West, FL 33040

  Escape to Paradise in this Turnkey Truman Annex Villa! Nestled within the exclusive gates of Porter Court at Truman Annex, this exquisite 2-bedroom, 2.5-bathroom villa at 406 Porter Lane offers the quintessential Key West lifestyle. Immerse yourself in tropical elegance with palm tree and bird motifs adorning the furnishings. The spacious interior living area flows seamlessly through French doors

  Rodney Culiver Last Key Realty, Inc (KW)

  406 Porter Ln, Key West, FL 33040
• 

  

  /25

  Est $896,096 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 610 Sq Ft

  620 Thomas St Unit 171, Key West, FL 33040

  620 Thomas St Unit 171, Key West, FL 33040
• 

  

  /18

  $1,450,000

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

  101 Front St Unit 8, Key West, FL 33040

  This beautifully updated Foundry townhome in the exclusive gated Truman Annex community is a dream come true! The floor to ceiling windows and doors at the entry allow sunshine to filter into the main floor living space creating a bright and airy space. The main floor has 11 foot ceilings and double French doors that open to the private front courtyard and porch. The open floor plan allows for an

  Shannon Maska Last Key Realty, Inc (KW)

  101 Front St Unit 8, Key West, FL 33040
• 

  

  /17

  $850,000 Sold Jan 03, 2025

  • 604 Sq Ft
  • $1407/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1991

  620 Thomas St Unit 151, Key West, FL 33040

  This first floor, corner unit in the beautiful and gated Truman annex has been an extremely successful vacation rental for the past 11 years. It comes as no surprise that it has gained rave reviews and repeat guests over the years who delight in the ideal location, functionality, beautiful grounds , amazing pool and privacy!

  Robert Donahue Key West Luxury Real Estate Inc (KW)

  620 Thomas St Unit 151, Key West, FL 33040
• 

  

  /6

  Est $836,581 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 604 Sq Ft

  620 Thomas St Unit 168, Key West, FL 33040

  620 Thomas St Unit 168, Key West, FL 33040
• 

  

  /36

  $879,000

  • 2 Beds
  • 1 Bath
  • 646 Sq Ft

  620 Thomas St Unit 176, Key West, FL 33040

  Ground floor end unit! Two-bedroom, one bath Shipyard condo. Updated kitchen with stainless steel appliances. Updated bath with shower. New impact windows and doors. The Shipyard is in the Truman Annex in Old Town Key West. Great location with easy walking and biking to all the action and great restaurants, beaches and sunsets that Key West offers.

  The Behmke Group Keller Williams Key West Compass Realty

  620 Thomas St Unit 176, Key West, FL 33040
• 

  

  /73

  $4,400,000 Sold Jan 02, 2025

  • 3,213 Sq Ft
  • $1369/SF
  • 74 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1989

  64 Front St, Key West, FL 33040

  Your DREAM home awaits.. Located in Truman Annex, where luxury meets island living. This stunning 5-bedroom, 5-bathroom residence boasts over 3000 sq ft of living space offering unparalleled comfort and elegance.As you step inside you are greeted by an expansive and open floor plan, featuring 11ft high ceilings and abundant natural light that illuminates the interior. The kitchen and dining area

  Matthew Sheehan Ocean Sotheby's International Realty

  64 Front St, Key West, FL 33040
• 

  

  /22

  Est $916,203 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  620 Thomas St Unit 163, Key West, FL 33040

  620 Thomas St Unit 163, Key West, FL 33040
• 

  

  /34

  $1,250,000

  • 2 Beds
  • 3 Baths
  • 960 Sq Ft

  212 Southard St, Key West, FL 33040

  Take a look at this picture perfect townhouse located in the prestigious Truman Annex . Nice end unit located just off Southard St is in excellent condition with many renovations throughout the house. Kitchen has been nicely updated with stainless steel appliances, custom cabinetry and granite countertops. Bamboo flooring throughout the first level leads to a cozy back brick patio and the

  Mike Caron Keller Williams Key West Compass Realty

  212 Southard St, Key West, FL 33040
• 

  

  /22

  $830,000 Sold Dec 19, 2024

  • 580 Sq Ft
  • $1431/SF
  • 88 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1991

  620 Thomas St Unit 286, Key West, FL 33040

  About this space:The Jewel of The Shipyard Annex in Truman AnnexCity of Key West Business License # 28224We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called 'The Writer's Retreat'.This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch

  Darrin Smith Key West Luxury Real Estate Inc (KW)

  620 Thomas St Unit 286, Key West, FL 33040
• 

  

  /16

  Est $922,279 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 646 Sq Ft

  620 Thomas St Unit 157, Key West, FL 33040

  620 Thomas St Unit 157, Key West, FL 33040
• 

  

  /60

  $4,850,000

  • 5 Beds
  • 4 Baths
  • 3,148 Sq Ft

  202 Admirals Ln, Key West, FL 33040

  Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and

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

  202 Admirals Ln, Key West, FL 33040
• 

  

  /20

  $800,000 Sold Dec 06, 2024

  • 646 Sq Ft
  • $1238/SF
  • 30 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1991

  620 Thomas St Unit 183, Key West, FL 33040

  Great 2 bedroom, 1 bath downstairs end unit in Shipyard Condominiums. This ground floor property is bright and airy. French doors open to the large rear deck with a permanent awning. Assigned parking space is handy to the front door. Currently a vacation rental that includes the special Truman Annex Transient Rental License with restrictions.

  Mike Caron Keller Williams Key West Compass Realty

  620 Thomas St Unit 183, Key West, FL 33040
• 

  /2

  Est $3,575,219 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  109 Front St Unit 111, Key West, FL 33040

  109 Front St Unit 111, Key West, FL 33040
• 

  

  /32

  $1,850,000

  • 2 Beds
  • 3 Baths
  • 1,420 Sq Ft

  212 Fleming St, Key West, FL 33040

  Nestled within the highly sought-after Truman Annex neighborhood, this exquisite 2 bedroom, 2.5 bathroom single-family home offers an unparalleled Key West living experience. Its prime location puts you within effortless walking distance to Old Town's most treasured restaurants, vibrant attractions, and historic sites. Upon entering, you'll be captivated by the inviting ambiance. The interior

  Rodney Culiver Last Key Realty, Inc (KW)

  212 Fleming St, Key West, FL 33040
• 

  

  /42

  $1,475,000 Sold Dec 05, 2024

  • 1,468 Sq Ft
  • $1005/SF
  • 106 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  411 Emma St Unit B, Key West, FL 33040

  Exclusive Mills Place Condo, a true Key West gem. Priced below appraised value, this Mills Place condo not only exudes charm but also represents an incredible opportunity to own a piece of Key West history at an unbeatable price. Welcome to one of Key West's most sought-after addresses in the prestigious Truman Annex. This charming 3-bedroom, 2-bath condo offers everything you've been searching

  Leigh Ann Roach Berkshire Hathaway HomeServices Knight & Gardner Realty

  411 Emma St Unit B, Key West, FL 33040
• 

  

  /23

  Est $1,774,247 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,292 Sq Ft

  101 Front St Unit 2, Key West, FL 33040

  101 Front St Unit 2, Key West, FL 33040
• 

  

  /39

  $2,425,000

  • 2 Beds
  • 3 Baths
  • 1,620 Sq Ft

  106 Admirals Ln, Key West, FL 33040

  This town house is in the award-winning Truman Annex and is located on a private lane surrounded by charming custom-built homes. The generous open floor plan features 10-foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with quartz countertops and stainless-steel appliances with a gas cook top. The large living and dining

  The Behmke Group Keller Williams Key West Compass Realty

  106 Admirals Ln, Key West, FL 33040

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