Monroe, FL Homes

• 

  

  

  /17

  Est $646,859 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  3029 N Roosevelt Blvd Unit 9, Key West, FL 33040

  3029 N Roosevelt Blvd Unit 9, Key West, FL 33040
• 

  

  

  /36

  $887,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 415, Key West, FL 33040

  Experience the pinnacle of island sophistication with these beautifully appointed courtyard residences at the sought-after Beachside Condominiums in Key West. With two TRANSIENT RENTAL LICENSES, this turnkey property offers exceptional flexibility as a personal retreat, full-time residence, or lucrative vacation rental. WITH 50% SELLER FINANCING OFFERED = AN EXCEPTIONAL OPPORTUNITY! Thoughtfully

  Michelle Blades Realty Executives Florida Keys Old Town

  3841 N Roosevelt Blvd Unit 415, Key West, FL 33040
• 

  

  

  /40

  $2,250,000 Sold Mar 21, 2025

  • 1,444 Sq Ft
  • $1558/SF
  • 118 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1889

  827 Elizabeth St, Key West, FL 33040

  Experience the quintessential Key West lifestyle in this beautifully transformed gem in the heart of Old Town's Solaris Hill. Restored and reimagined in 2022, this unique home seamlessly blends modern comfort with the historic charm of an 1889 cigar maker's factory, as noted in Key West Sanborn maps. Enter through an inviting white picket fence to a spacious front porch, perfect for enjoying lazy

  John Zaharakis Coldwell Banker Schmitt Real Estate Co. (KW)

  827 Elizabeth St, Key West, FL 33040
• 

  

  /2

  Est $3,135,754 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,586 Sq Ft

  3841 N Roosevelt Blvd Unit 114, Key West, FL 33040

  3841 N Roosevelt Blvd Unit 114, Key West, FL 33040
• 

  

  

  /38

  $6,500,000

  • 6 Beds
  • 8 Baths
  • 3,010 Sq Ft

  421-423 Simonton St, Key West, FL 33040

  Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  421-423 Simonton St, Key West, FL 33040
• 

  

  /29

  $1,650,000 Sold Mar 21, 2025

  • 1,876 Sq Ft
  • $880/SF
  • 120 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2007

  807 Washington St Unit 102, Key West, FL 33040

  Perfectly situated in the heart of Casa Marina! This 3-story townhome is being sold FULLY FURNISHED! Ideal for year round living or ready-to-go as a vacation rental!Recently renovated, open floor plan features a designer kitchen with custom Hansen & Bringle cabinets, quartz countertop, farm sink, Viking stove, refrigerator, dishwasher and custom-cut Carlisle Lumber pine floors. Two en suite

  Kelli Houze Berkshire Hathaway HomeServices Knight & Gardner Realty

  807 Washington St Unit 102, Key West, FL 33040
• 

  

  /20

  Est $1,244,288 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,351 Sq Ft

  833 Eisenhower Dr Unit 101, Key West, FL 33040

  833 Eisenhower Dr Unit 101, Key West, FL 33040
• 

  

  /12

  $865,000

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft

  3711 Eagle Ave, Key West, FL 33040

  On a beautiful street this duplex is located on the desirable upper end of Eagle Avenue. The main house is a full renovation project, offering a prime opportunity for customization or redevelopment. This property comes with a build-back letter from the City of Key West, offering a rare chance to create a custom home in a prime residential area. The property can also be purchased with the

  Terri Spottswood Truman & Co. (KW)

  3711 Eagle Ave, Key West, FL 33040
• 

  

  /49

  $5,250,000 Sold Mar 20, 2025

  • 1,912 Sq Ft
  • $2746/SF
  • 19 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2006

  291 Sunset Key Dr, Key West, FL 33040

  Here is the perfect Sunset Key island getaway home with stunning panoramic Key West Harbor and Gulf views. Lounge by your pool and spa or on your four covered porches with IPE decking while you enjoy the sites of open water where the Gulf meets the Atlantic. This home is in absolute mint condition with an open flow throughout. This 3 bedroom, 3 bath quality home needs nothing more. Elegant and

  Mike Caron Keller Williams Key West Compass Realty

  291 Sunset Key Dr, Key West, FL 33040
• 

  /2

  Est $1,355,325 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 115, Key West, FL 33040

  3841 N Roosevelt Blvd Unit 115, Key West, FL 33040
• 

  

  /3

  $865,000

  • Land

  3705 Eagle Ave, Key West, FL 33040

  Excellent opportunity to purchase a vacant, buildable 6,000 square foot lot in the heart of Key West's desirable New Town neighborhood. Located on prestigious Eagle Avenue it offers a rare chance to create a custom home in a prime residential area - beneficial use allocation granted from the City of Key West Planning Department. This lot can also be purchased with the adjacent property at 3711

  Terri Spottswood Truman & Co. (KW)

  3705 Eagle Ave, Key West, FL 33040
• 

  

  /28

  $3,280,000 Sold Mar 20, 2025

  • 3,417 Sq Ft
  • $960/SF
  • 136 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2008

  719 Eisenhower Dr Unit 7, Key West, FL 33040

  Luxury Waterfront Condo with Transient License - Key West, FL. More pictures and videos coming soon.This stunning 5-bedroom, 4-bathroom waterfront condo in Old Town Key West offers luxury and investment potential with a coveted transient nightly rental license. Enjoy breathtaking marina views from double balconies, a private pool, and a boat dock with deep water access. The home features an

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  719 Eisenhower Dr Unit 7, Key West, FL 33040
• 

  /2

  Est $1,007,217 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,586 Sq Ft

  3841 N Roosevelt Blvd Unit 232, Key West, FL 33040

  3841 N Roosevelt Blvd Unit 232, Key West, FL 33040
• 

  

  /18

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 1,451 Sq Ft

  314 Southard St, Key West, FL 33040

  Located in the heart of Old Town, this historic property offers a rare chance to restore a true gem to its original splendor. Set on a 5,025 sq ft lot in the desirable X flood zone, the home was originally built as two separate residences, now connected by a breezeway. Owned by the same family for generations, the property sits less than two blocks from Duval Street, three blocks from the

  Terri Spottswood Truman & Co. (KW)

  314 Southard St, Key West, FL 33040
• 

  

  /4

  $1,925,000 Sold Mar 20, 2025

  • 2,171 Sq Ft
  • $887/SF
  • 148 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1958

  2711 Seidenberg Ave, Key West, FL 33040

  Discover this beautifully renovated mid-century modern home in New Town, Key West. Located at the end of a quiet street, this 4 bedroom, 3 bathroom residence sits on a 9,000+ square foot lot with exceptional privacy, blended with sophisticated indoor-outdoor living.High-end finishes are thoughtfully integrated throughout the home, from sleek surfaces to custom cabinetry. The open concept design

  Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  2711 Seidenberg Ave, Key West, FL 33040
• 

  

  /21

  Est $539,340 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft

  3635 Seaside Dr Unit 310, Key West, FL 33040

  3635 Seaside Dr Unit 310, Key West, FL 33040
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  /36

  $970,000

  • 3 Beds
  • 2 Baths
  • 1,049 Sq Ft

  716 Elizabeth St Unit Rear, Key West, FL 33040

  Tucked away in the heart of historic Old Town Key West near Solares Hill, this enchanting property is a rare treasure that perfectly captures the charm and allure of Island Living. The front unit, a delightful two-bedroom, one-bath haven, features an inviting porch that exudes timeless Key West charm and affords the perfect perch to unwind amidst the vibrant tropical surroundings. Beyond, a

  Leigh Ann Roach Berkshire Hathaway HomeServices Knight & Gardner Realty

  716 Elizabeth St Unit Rear, Key West, FL 33040
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  /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
• 

  

  /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
• 

  

  /24

  $1,299,000

  • 3 Beds
  • 3 Baths
  • 2,080 Sq Ft

  611 Simonton St, Key West, FL 33040

  NEW PRICE! Fantastic Key West location in the heart of Old Town Key West. Close to famous Duval Street, Historic Seaport, fine dining, galleries and more. Spacious two story home with 2,080 sq ft of living space. Three bedrooms and three full baths. Fenced yard. Patio Space. French Doors. Lanai area. Seller financing possible with minimum 30% down! Competitive interest rate!

  Bascom Grooms Bascom Grooms Real Estate (KW)

  611 Simonton St, Key West, FL 33040
• 

  

  /25

  $1,015,000 Sold Mar 18, 2025

  • 1,230 Sq Ft
  • $825/SF
  • 73 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  1001 16th Terrace, Key West, FL 33040

  Look no further than this impeccably maintained single family home in the heart of New Town. You'll love how meticulously cared for it is and how the fabulous tropical living centers around a beautiful heated pool with water feature, a pool cabana featuring ceiling fans allowing for dining and lounging. The lighted tropical gardens further enhance this feeling. There's a workshop storage

  Mike Caron Keller Williams Key West Compass Realty

  1001 16th Terrace, Key West, FL 33040
• 

  

  /7

  Est $558,288 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 510 Sq Ft

  1010 Grinnell St Unit C, Key West, FL 33040

  1010 Grinnell St Unit C, Key West, FL 33040
• 

  

  /43

  $1,897,000

  • 3 Beds
  • 4 Baths
  • 1,644 Sq Ft

  1332 Duncan St, Key West, FL 33040

  This one-of-a-kind Conch house effortlessly blends island charm with modern sophistication. Featuring three spacious bedrooms and four luxurious bathrooms, the home boasts stunning wall-to-wall Dade County pine that adds character and warmth throughout. The open floor plan is ideal for both entertaining and everyday living, seamlessly connecting the living area to a chef-inspired kitchen.The

  Derek Epperly Keys Atlantic Realty

  1332 Duncan St, Key West, FL 33040
• 

  

  /18

  $460,000 Sold Mar 18, 2025

  • 522 Sq Ft
  • $881/SF
  • 112 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1991

  3930 S Roosevelt Blvd Unit S202, Key West, FL 33040

  Las Salinas Key West condo 1 bedroom 1 bath freshly renovated in 2022, with onsite security. The community amenities include a pool, fitness center, laundry, meeting room, bike room and an extra storage unit. Ideally located off South Roosevelt Boulevard this spot is prefect for walking, jogging, running, rollerblading or biking around the island, minutes from downtown, beaches and Mallory

  Letisia Powell Robert Slack LLC

  3930 S Roosevelt Blvd Unit S202, Key West, FL 33040
• 

  

  /26

  Est $469,530 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 138 Sq Ft

  1016 Howe St Unit 5, Key West, FL 33040

  1016 Howe St Unit 5, Key West, FL 33040
• 

  

  /22

  $749,000

  • 1 Bed
  • 1 Bath
  • 805 Sq Ft

  1222 Florida St, Key West, FL 33040

  Tucked away in the tranquil heart of Mid Town, this spacious one-bedroom concrete home offers both comfort and privacy. The open floor plan is filled with natural light, accentuating the warmth with brand new floors throughout. Step outside to a tropical retreat, where a serene deck area is enveloped by lush bamboo fencing, creating the perfect environment for relaxation or outdoor

  Derek Epperly Keys Atlantic Realty

  1222 Florida St, Key West, FL 33040
• 

  

  /71

  $5,700,000 Sold Mar 17, 2025

  • 3,342 Sq Ft
  • $1706/SF
  • 115 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1869

  522 Simonton St, Key West, FL 33040

  Historic Luxury Meets Modern Elegance in Old Town Key West!Step into a piece of Key West history with this remarkable home built in 1869 by Robert Watson, now completely reimagined as a luxury retreat while preserving its historic charm. Located on iconic lower Simonton Street, X Flood, this 6,608 sq ft sanctuary boasts 3,342 sq ft of living space with 5 en-suite bedrooms, including two primary

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  522 Simonton St, Key West, FL 33040
• 

  

  /7

  Est $2,799,093 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,500 Sq Ft

  109 Front St Unit 113, Key West, FL 33040

  109 Front St Unit 113, Key West, FL 33040
• 

  

  /34

  $1,949,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 332, Key West, FL 33040

  Condo living with hotel caliber amenities, this 3rd floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors/windows are designed

  Team Spottswood/Vazquez Truman & Co. (KW)

  3841 N Roosevelt Blvd Unit 332, Key West, FL 33040
• 

  

  /42

  $1,147,500 Sold Mar 14, 2025

  • 703 Sq Ft
  • $1632/SF
  • 50 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1933

  1213 Watson St, Key West, FL 33040

  Welcome to 1213 Watson St, a charming tropical retreat located in the heart of Old Town Key West! This updated and beautifully maintained cottage exudes character and tranquility, surrounded by lush greenery and vibrant foliage. The ivy-covered exterior and inviting entry create a picture-perfect escape. Inside, you'll find cozy living spaces filled with natural light, blending modern

  Jimmy Lane Island Life Realty Experts

  1213 Watson St, Key West, FL 33040
• 

  

  /26

  Est $902,434 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,099 Sq Ft

  1901 S Roosevelt Blvd Unit 203S, Key West, FL 33040

  1901 S Roosevelt Blvd Unit 203S, Key West, FL 33040
• 

  

  /32

  $1,949,000

  • 2 Beds
  • 2 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 315, Key West, FL 33040

  Condo living with hotel caliber amenities, this first floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/ gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors & windows are

  Team Spottswood/Vazquez Truman & Co. (KW)

  3841 N Roosevelt Blvd Unit 315, Key West, FL 33040
• 

  

  /39

  $505,000 Sold Mar 14, 2025

  • 750 Sq Ft
  • $673/SF
  • 146 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  1210 Bay St, Key West, FL 33040

  A new roof and new impact windows & doors make this VA & FHA eligible property with 4375 square feet of fully fenced yard worth a look. 5 minutes from the Seaport and downtown Key West this 2 bedroom single story townhome is located just across Roosevelt from Garrison Bight on a quiet street in a great central location. The amazing and incredibly large backyard is a perfect opportunity to

  Jennifer Newman Truman & Co. (KW)

  1210 Bay St, Key West, FL 33040
• 

  /2

  Est $981,803 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  313 Catherine St Unit 3, Key West, FL 33040

  313 Catherine St Unit 3, Key West, FL 33040
• 

  

  /21

  $1,900,000

  • 3 Beds
  • 4 Baths
  • 2,157 Sq Ft

  1417 Ashby St, Key West, FL 33040

  This historic property was originally a single family home and could be converted back to same. Currently configured as 3 apartments in the main building, you'll find treasured Dade County Pine and hardwood floors throughout. Hansen & Bringle cabinetry, central A/C down. Upstairs configuration is 2 studio apartments, both with outdoor space and these could be additional bedrooms with en-suite

  Suzanne Washburn Coldwell Banker Schmitt Real Estate Co. (KW)

  1417 Ashby St, Key West, FL 33040
• 

  /2

  $1,700,000 Sold Mar 14, 2025

  • 2,436 Sq Ft
  • $698/SF
  • 218 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1938

  1320 Johnson St, Key West, FL 33040

  MOTIVATED SELLER. This is not a property to be missed! Prestigious Johnson Street LEGAL TRIPLEX, just four blocks from beach and the White Street Pier. Live your best life in this wonderful neighborhood. Peaceful and quiet and only 3/4 mile to downtown Duval action. This property sits on an enormous corner double lot, walled in for privacy, it encompasses over 8600 square feet. Parking outside

  Sherri Blasingame Berkshire Hathaway HomeServices Knight & Gardner Realty

  1320 Johnson St, Key West, FL 33040
• 

  

  /22

  Est $500,675 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  3314 Northside Dr Unit 35, Key West, FL 33040

  3314 Northside Dr Unit 35, Key West, FL 33040
• 

  

  /40

  $1,490,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,276 Sq Ft

  1413 Olivia St, Key West, FL 33040

  Stunning and impeccably maintained, this 3 bed, 2 bath Conch home in the highly sought-after Meadows neighborhood seamlessly blends historic charm with modern luxury. The custom-designed kitchen is a chef's dream, featuring new quartz countertops, sleek backsplash, remodeled cabinetry, and stainless steel appliances. Rich Brazilian hardwood floors run throughout, and a powerful 17.5kW Generac

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1413 Olivia St, Key West, FL 33040
• 

  

  /17

  $557,000 Sold Mar 13, 2025

  • 370 Sq Ft
  • $1505/SF
  • 32 Days On Market

  • 1 Bath
  • Built 1938

  524 Margaret St Unit 101, Key West, FL 33040

  Beautiful studio with full kitchen.Prime location in Old Town, walkable to restaurants and shops. Steps from Bob's on Margaret, Mangia Mangia, and Date & Thyme. Condo newly furnished and now includes deeded off street parking.Building has a total of 4 condos and private backyard with a large pool. The condo and building have been well maintained.

  Joe Bracciale Select Properties of NWFL

  524 Margaret St Unit 101, Key West, FL 33040
• 

  

  /16

  Est $298,729 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft

  3312 Northside Dr Unit 310, Key West, FL 33040

  3312 Northside Dr Unit 310, Key West, FL 33040

Showing Results 481 - 520, Page 13 of 18