Monroe, FL Homes

• 

  

  

  /25

  $1,110,000 Sold Apr 28, 2025

  • 1,188 Sq Ft
  • $934/SF
  • 197 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1928

  840 Olivia St, Key West, FL 33040

  Step into this bright and airy two-story single-family move in ready home nestled in the heart of Historic Old Town Key West. Boasting 3 inviting bedrooms, 2 baths, and an open floor plan with a spacious kitchen and dining or bonus room, this residence offers the perfect blend of comfort and entertainment space. With the added convenience of off-street parking for 2 vehicles and its prime

  Dean Townsend Keller Williams Key West Compass Realty

  840 Olivia St, Key West, FL 33040
• 

  

  

  /5

  Est $2,676,215 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,812 Sq Ft

  929 United St, Key West, FL 33040

  929 United St, Key West, FL 33040
• 

  

  

  /35

  $1,195,000

  • 2 Beds
  • 1 Bath
  • 723 Sq Ft

  729 Windsor Ln, Key West, FL 33040

  Charming Historic Gem in the Heart of Old Town Key West!Welcome to 729 Windsor Lane--a rare opportunity to own a piece of Key West history nestled in one of the island's most desirable residential neighborhoods. Set on an expansive nearly 3,000 sq.ft. lot, this classic home offers a generous footprint that's almost unheard of in Old Town, along with the luxury of coveted off-street parking.Step

  Amber DeBevec LoKation Real Estate

  729 Windsor Ln, Key West, FL 33040
• 

  

  

  /68

  $8,500,000 Sold Apr 25, 2025

  • 4,008 Sq Ft
  • $2,121/SF
  • 268 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1958

  400 South St, Key West, FL 33040

  OFFERED IN A LUXURY AUCTION!Experience unparalleled luxury at 400 South Street, the true Southernmost private residence in the Continental United States. This iconic Key West estate, winter home to esteemed American artist, the late Seward Johnson and his wife, seamlessly blends timeless elegance with modern amenities. The expansive 4,008-square-foot concrete home, situated on a generous lot plus

  Ellen Gvili Ocean Sotheby's International Realty

  400 South St, Key West, FL 33040
• 

  

  /2

  Est $2,287,173 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,623 Sq Ft

  1113 Fleming St, Key West, FL 33040

  1113 Fleming St, Key West, FL 33040
• 

  

  /30

  $1,199,000

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  1025 Elgin Ln, Key West, FL 33040

  Welcome to 1025 Elgin Lane, an exquisite residence nestled in the heart of Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay

  Jimmy Lane Island Life Realty Experts

  1025 Elgin Ln, Key West, FL 33040
• 

  

  /7

  $1,500,000 Sold Apr 21, 2025

  • 2,020 Sq Ft
  • $743/SF
  • 262 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1944

  324 Truman Ave, Key West, FL 33040

  DEVELOPER ALERT !!!!!PERMIT IS READY TO BE PICKED UP**Historic Old Town Home Ready for Rehabilitation**This charming property is located in a highly desirable X flood zone and offers 5,470 sq ft of land. HARC has already approved the rehabilitation of this historic home, increasing the current square footage from 2,020 to 2,575. The finished product will include 4 bedrooms, 4.5 bathrooms, a pool,

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  324 Truman Ave, Key West, FL 33040
• 

  /2

  Est $3,338,412 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 2,456 Sq Ft

  922 Thomas St, Key West, FL 33040

  922 Thomas St, Key West, FL 33040
• 

  

  /7

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  620 White St, Key West, FL 33040

  This legal duplex offers fantastic potential with two separate units. The front unit is a 2-bedroom, 1-bath home and a rear unit is a 1-bedroom, 1-bath unit. The property features an in-ground pool and is ideally laid out for investment or owner-occupancy with rental income. While some work has been done, the entire property is in need of finishing renovations-- perfect for a buyer ready to

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  620 White St, Key West, FL 33040
• 

  

  /47

  $3,250,000 Sold Apr 18, 2025

  • 2,448 Sq Ft
  • $1,328/SF
  • 18 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1933

  621 Eaton St, Key West, FL 33040

  Presenting an exquisite, newly renovated Conch-style home--a true Key West gem that combines historic charm with contemporary luxury. This remarkable two-story residence, offering 5 bedrooms and 5.5 baths, is an idyllic retreat, featuring classic gingerbread trim, generous porches, private parking, and a pool. As you enter, you're greeted by a bright and airy living space that effortlessly

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  621 Eaton St, Key West, FL 33040
• 

  

  /4

  Est $2,581,575 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  727 Love Ln, Key West, FL 33040

  727 Love Ln, Key West, FL 33040
• 

  

  /25

  $880,000

  • 2 Beds
  • 3 Baths
  • 1,056 Sq Ft

  618 Mickens Ln, Key West, FL 33040

  Opportunity awaits in the heart of Old Town Key West! Just steps from the legendary Green Parrot and only 1.5 blocks from world-famous Duval Street, 618 Mickens Lane offers the perfect blend of location, privacy, and potential. Tucked away on a quiet, brick-paved lane, this 2-bedroom, 2.5-bath home is your chance to create a custom island retreat in one of Key West's most walkable

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  618 Mickens Ln, Key West, FL 33040
• 

  

  /37

  $2,175,000 Sold Apr 18, 2025

  • 1,058 Sq Ft
  • $2,056/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1993

  711 Ashe St, Key West, FL 33040

  Step into a hidden indoor-outdoor sanctuary with the charm of a secret garden, blending timeless Key West style with lush sophistication. This extraordinary property invites you along a tropical pathway lined with exotic palms, unveiling a classic Key West home framed by a serene water feature, a spacious covered porch, and one of the island's most captivating gardens.Inside, the home boasts

  Team Kaufelt Truman & Co. (KW)

  711 Ashe St, Key West, FL 33040
• 

  

  /24

  Est $968,230 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,048 Sq Ft

  900 White St Unit 2, Key West, FL 33040

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

  

  /32

  $995,000

  • 4 Beds
  • 3 Baths
  • 1,226 Sq Ft

  1121 Elgin Ln, Key West, FL 33040

  NEW PRICE!!! Don't miss out on this incredible opportunity to own a historic Eyebrow home in Old Town Key West, available on the market for the first time since 1999! This charming two-story residence has been lovingly occupied by its owners but would also serve as an excellent rental property, second home, or primary residence in the vibrant heart of town. The main level features a spacious

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1121 Elgin Ln, Key West, FL 33040
• 

  

  /54

  $4,500,000 Sold Apr 14, 2025

  • 3,015 Sq Ft
  • $1,493/SF
  • 292 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1938

  524 Frances St, Key West, FL 33040

  Welcome to 524 Frances Street, where sophisticated style meets Old Town charm. Rarely does an architectural gem such as this property become available for purchase. This iconic home has been completely and professionally updated, including impact windows and doors. Enter the property through a white picket fence and ascend the front porch steps with views of Frances Street. Just beyond the

  Bobby Coe RE/MAX Keys Connection (KW)

  524 Frances St, Key West, FL 33040
• 

  

  /41

  Est $954,793 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 754 Sq Ft

  616 Caroline St Unit 5, Key West, FL 33040

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

  

  /29

  $3,395,000

  • 2 Beds
  • 3 Baths
  • 1,650 Sq Ft

  806 Southard St, Key West, FL 33040

  Welcome to your private oasis in the heart of Old Town Key West, where modern luxury meets historic charm. This beautifully renovated home perfectly blends timeless island architecture with sleek, contemporary comforts, offering an unparalleled living experience just steps from the Seaport and world-renowned Duval Street. Behind its classic facade, an airy, open floor plan awaits, thoughtfully

  Richard Patten Your Keys Real Estate, LLC

  806 Southard St, Key West, FL 33040
• 

  

  /34

  $1,250,000 Sold Apr 09, 2025

  • 1,046 Sq Ft
  • $1,195/SF
  • 75 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1912

  804 Ashe St, Key West, FL 33040

  Imagine owning a home where history whispers through the walls and legendary figures once found inspiration. 804 Ashe street is a lovingly preserved Conch Cottage, located on one of the most sought-after streets in the vibrant Historic District. Built prior to 1912, this home has hosted notable literary icons like Tennessee Williams, Leonard Bernstein, Tom McGuane, and John Hersey, adding a layer

  Team Kaufelt Truman & Co. (KW)

  804 Ashe St, Key West, FL 33040
• 

  /2

  Est $877,261 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  616 Caroline St Unit 1, Key West, FL 33040

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

  

  /6

  $11,888,000

  • 3 Beds
  • 2 Baths
  • 2,071 Sq Ft

  1430 Vernon Ave Unit 1-2, Key West, FL 33040

  Fabulous Find on the Atlantic Side of Key West!Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing

  Irina Pytlik Keys Top Realty LLC

  1430 Vernon Ave Unit 1-2, Key West, FL 33040
• 

  

  /32

  $910,000 Sold Apr 08, 2025

  • 1,111 Sq Ft
  • $819/SF
  • 284 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1942

  1208 Varela St, Key West, FL 33040

  This well maintained one bedroom plus loft home is located in the popular and conveniently located Varela St. compound in Old Town. The compound consists of 6 houses which share a common pool. This home with a private entrance has cathedral ceilings in the living and dining room with French doors that exit to the fenced deck area at the rear of the property. The 20x20 second floor loft is

  Mitzi Krabill Truman & Co. (KW)

  1208 Varela St, Key West, FL 33040
• 

  

  /18

  Est $534,042 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 528 Sq Ft

  1209 William St Unit 4, Key West, FL 33040

  1209 William St Unit 4, Key West, FL 33040
• 

  

  /31

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  414 Virginia St, Key West, FL 33040

  Lovely 3 bedroom 2 bath home in the midst of Old Town just off Duval St. Central AC with nice room sizes and great lot size. Flood Zone Z500. Ready to sell As-Is. Seller motivated but firm on price.

  Bernard Isler Isler Realty & Investments LLC

  414 Virginia St, Key West, FL 33040
• 

  

  /23

  $3,700,000 Sold Apr 07, 2025

  • 2,616 Sq Ft
  • $1,414/SF
  • 0 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1938

  925 Whitehead St, Key West, FL 33040

  This grand completely renovated piece of history is situated across the street from the iconic Key West Lighthouse. This stunning 5 bedroom, 5 bath home boasts a rich and storied past, dating back to the 1800's. Lovingly restored, this large 2720 Square foot home blends classic charm with modern luxury. You'll be swept away by the grandeur of this magnificent home. With soaring ceilings,

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  925 Whitehead St, Key West, FL 33040
• 

  

  /7

  Est $453,717 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
• 

  

  /55

  $2,150,000

  • 4 Beds
  • 4 Baths
  • 1,967 Sq Ft

  708 William St, Key West, FL 33040

  Price reduced by almost $350,000 and ready for your personal touches. If you are looking for location and a historic home, this wonderful home is tucked away on one of Old Town Key West's most peaceful lanes. This charming Conch home won the distinguished Historic Florida Keys Preservation Star in 1988 and has been in the same family for over 40 years--a true testament to its warmth, character,

  Ellen Gvili Ocean Sotheby's International Realty

  708 William St, Key West, FL 33040
• 

  

  /4

  $800,000 Sold Apr 03, 2025

  • 557 Sq Ft
  • $1,436/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1933

  306 Olivia St, Key West, FL 33040

  Looking For Backup Offers!!!Welcome to your dream getaway! This enchanting conch cottage is just two blocks from Duval Street, featuring a delightful pool house that enhances its charm with a desirable off street parking space. A true Slice of Paradise featuring high ceilings with exposed beams and trapezoid transom windows create an airy, open atmosphere. Modern upgrades include a beautifully

  Bobby Coe RE/MAX Keys Connection (KW)

  306 Olivia St, Key West, FL 33040
• 

  

  /26

  Est $471,128 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
• 

  

  /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
• 

  

  /33

  $3,690,000 Sold Apr 02, 2025

  • 1,800 Sq Ft
  • $2,050/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1933

  716 Duval St, Key West, FL 33040

  This magnificent TRANSIENT rental property is located in the heart of Key West's downtown historic neighborhood on world famous Duval Street. This single family home is known as Pilar's Secret and is a strong income producing property with a luxurious pool and wonderful outdoor space with multiple dining areas, lounging and sunbathing as well as a large outdoor shower and landscape lighting.

  Jennifer Newman Truman & Co. (KW)

  716 Duval St, Key West, FL 33040
• 

  /2

  Est $941,748 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
• 

  

  /18

  $1,100,000

  • 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
• 

  

  /26

  $1,225,000 Sold Apr 01, 2025

  • 594 Sq Ft
  • $2,062/SF
  • 48 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1938

  903 Southard St, Key West, FL 33040

  Welcome to Limelight Cottage on Southard, a beautifully renovated historic Conch-style home that exudes charm and modern comfort. This inviting 2-bedroom, 1-bathroom residence sits on a desirable corner lot with a fully fenced yard for privacy. Inside, high ceilings create an open and airy feel, while the kitchen's French doors lead to a large outdoor patio, complete with a heated 12' x 15'

  Jody Clark Key West Luxury Real Estate Inc (KW)

  903 Southard St, Key West, FL 33040
• 

  

  /9

  Est $907,050 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 726 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /24

  $1,249,000

  • 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! Desired X

  Bascom Grooms Bascom Grooms Real Estate (KW)

  611 Simonton St, Key West, FL 33040
• 

  

  /42

  $2,000,000 Sold Mar 31, 2025

  • 2,412 Sq Ft
  • $829/SF
  • 60 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 1999

  1223 Margaret St, Key West, FL 33040

  Located in Old Town of Key West, this 2412 Sq Ft, 3-story single-family home offers the perfect blend of space, comfort, and island charm. The main house features 3 spacious en-suite bedrooms and 3.5 bathrooms, providing plenty of privacy for family and guests. The 2nd floor has 2 en-suite bedrooms and the 3rd floor features a spacious full-floor primary suite, complete with a sitting room that

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

  1223 Margaret St, Key West, FL 33040
• 

  

  /15

  Est $553,151 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 389 Sq Ft

  416 Petronia St Unit 2, Key West, FL 33040

  416 Petronia St Unit 2, Key West, FL 33040
• 

  

  /21

  $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
• 

  

  /25

  $739,000 Sold Mar 28, 2025

  • 754 Sq Ft
  • $980/SF
  • 42 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2003

  604 Truman Ave Unit 3, Key West, FL 33040

  Absolutely unbeatable value in Old Town Key West! This is the best-priced condo per square foot, and with $60,000 in recent price reductions, it's ready for its next owner.This spacious one-bedroom plus bonus space offers modern comfort just steps from Duval Street and within walking distance of all the best restaurants, shopping, and attractions. Fully renovated over the past two years, this

  Jimmy Lane Island Life Realty Experts

  604 Truman Ave Unit 3, Key West, FL 33040

Showing Results 161 - 200, Page 5 of 18