Old Town Homes

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  /33

  $1,650,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  530 Grinnell St, Key West, FL 33040

  Situated in the heart of the Historic Seaport area, 530 Grinnell St is a charming property that perfectly encapsulates the island's unique character and vibrant lifestyle. This beautifully maintained home features a blend of classic architecture and modern amenities, making it an ideal retreat for both residents and vacationers alike. As you enter, you're greeted by an inviting open floor

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  (305) 676-8537

  530 Grinnell St, 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
• 

  

  

  /19

  $689,000 Sold Jul 17, 2025

  • 500 Sq Ft
  • $1378/SF
  • 181 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1929

  617 Fleming St Unit 6, Key West, FL 33040

  You can't beat this location, it's superb! This delightful 1/1 condo in the coveted Campbell Courtyard has a well-documented rental history as a monthly vacation rental. Secure and private, the Campbell Courtyard is a long-established small association of only 9 units. The front porch looks out to the pool. Offered fully furnished, this is a must see!

  Tyler Caudell Key West Realty, LLC (KW)

  617 Fleming St Unit 6, Key West, FL 33040
• 

  

  

  /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
• 

  

  

  /50

  $1,550,000

  • 3 Beds
  • 1.5 Baths
  • 1,251 Sq Ft

  1215 Margaret St, Key West, FL 33040

  Enjoy the perfect Key West location - Old Town bordering the Casa Marina neighborhood - in this 3 bedroom, 2.5 bath pool home. You'll have peace of mind knowing that the home was completely renovated from the ground up in 2019 while keeping with the historic style of the home's origins - tongue in groove ceilings, wood floors, pecky Cypress wall accent - but adding modern amenities such as impact

  

  Shane Wilson

  Cypress Realty, Inc.

  (786) 882-9251

  1215 Margaret 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
• 

  

  /23

  $600,000 Sold Jul 15, 2025

  • 599 Sq Ft
  • $1002/SF
  • 191 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1933

  651 William St Unit 1, Key West, FL 33040

  Ground floor 1b/1b condo features a 599sf interior that includes a loft, which basically makes this a two bedroom unit; which basically makes this the best priced condominium in Old Town Key West. Open floor plan is bright and airy. High ceilings. Renovated kitchen. French doors open to private courtyard to enjoy the indoor-outdoor living for which Key West is known. The great room opens to

  Barbara Bowers Preferred Properties (KW)

  651 William St Unit 1, Key West, FL 33040
• 

  

  /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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  /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
• 

  

  /44

  $1,425,000 Sold Jul 10, 2025

  • 2,671 Sq Ft
  • $534/SF
  • 58 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1901

  602 Southard St, Key West, FL 33040

  TRIPLEX in Old Town Key West on large corner lot. Close to famous Duval Street. This historic Circa 1901 property offers almost 2700 sf ft of living space. Currently configured as three apartments but would make a grand conversion to a single-family home. Main floor offers two apartments, and the upper level has a spacious apartment with access to finished 3rd story attic space. Ideal

  Bascom Grooms Bascom Grooms Real Estate (KW)

  602 Southard 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
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  /28

  $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
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  /12

  $5,000 per month

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Condo for Rent

  1022 Fleming St Unit Lower, Key West, FL 33040

  Property Id: 1249660Fully Furnished, amazing 2 bedroom, 1 bathroom (upper level) newly furnished, gorgeous home in Key West on spectacular Fleming street in the old town, historic district, just a few blocks from famous Duval street. Amenities included: central air, central heat, deck, dishwasher, hardwood floors, stainless steel appliances, washer and dryer and pool. Small dog or two

  1022 Fleming St Unit Lower, Key West, FL 33040
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  /30

  $1,350,000 Sold Jul 09, 2025

  • 1,148 Sq Ft
  • $1176/SF
  • 125 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1938

  1122 Margaret St, Key West, FL 33040

  Behind the quintessential white picket fence you will find this delightful historic cottage currently set up as a duplex with off street parking and pool. Lots of opportunity with the ability to generate income and have your own slice of Paradise to enjoy, or marry the spaces and convert to a single family dream home. Each unit enjoys privacy from the other including separate outdoor living

  Wendy Zintsmaster Truman & Co. (KW)

  1122 Margaret St, 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
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  /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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  /12

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Property for Rent

  417 Southard St Unit B, Key West, FL 33040

  This 2-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 with seating,

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  417 Southard St Unit B, Key West, FL 33040
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  /24

  $1,525,000 Sold Jul 08, 2025

  • 1,860 Sq Ft
  • $820/SF
  • 42 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1979

  737 Olivia St, Key West, FL 33040

  Price Reduced, Owner's motivated! This triplex is situated in a prime area of Old Town, just three blocks away from Duval Street. It presents an attractive investment opportunity with its three separate units, offering potential for rental income, extended family stays, or versatile usage. Constructed from concrete blocks in 1979, this property's main unit is currently occupied by the owners,

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  737 Olivia 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
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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
• 

  

  /14

  $2,800 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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  /10

  $1,250,000 Sold Jul 03, 2025

  • 877 Sq Ft
  • $1425/SF
  • 118 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1933

  412 Louisa St, Key West, FL 33040

  Welcome to 412 Louisa Street, an enchanting Key West Conch Cottage nestled on a serene one-way street between Duval and Whitehead in Old Town. This charming 2-bedroom, 2-bathroom home offers a pool, parking and proximity to all that Key West has to offer. Built in 1933, the property seamlessly blends historic charm with modern comforts. As you step inside, you'll be greeted by an open-concept

  Bobby Coe RE/MAX Keys Connection (KW)

  412 Louisa St, Key West, FL 33040
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  /8

  Est $790,947 Not Listed For Sale

  • 1 Bed

  951 Caroline St Unit 1, Key West, FL 33040

  951 Caroline St Unit 1, 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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  /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
• 

  

  /30

  $860,000 Sold Jul 03, 2025

  • 936 Sq Ft
  • $919/SF
  • 206 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1948

  319 Julia St, Key West, FL 33040

  This charming Old Town property offers the perfect blend of historic character and future potential just steps from world-famous Duval Street. Rich with the classic charm of Old Key West, this property is a blank canvas waiting for your personal touch. The permitted main home features two spacious bedrooms, a bonus den that can easily function as an additional bedroom or office, a full

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  319 Julia St, Key West, FL 33040
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  /53

  Est $5,194,617 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
• 

  

  /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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  /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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  /7

  $2,400,000 Sold Jul 02, 2025

  • 1,968 Sq Ft
  • $1220/SF
  • 5 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2025

  1215 Georgia St, Key West, FL 33040

  Attention New Construction Seekers!New Construction close to completion with exceptional Quality and World Class Workmanship. Almost 2000 Air-conditioned Space on 4000 Sq Ft. Lot.Located in Excellent Old Town Corner Lot Location, one Block From White St. Gallery District, This Elevated X-Flood Zone Location will keep you high and Dry so rising waters will never be a worry.Built with Hardie Board

  Suzanne Moore Suzanne Moore Real Estate

  1215 Georgia St, Key West, FL 33040
• 

  

  /19

  Est $962,613 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

  • 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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  /14

  $3,450 per month

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft
  • Property for Rent

  623 Whitehead St, Key West, FL 33040

  Charming 1-Bedroom Home in Old Town with Bonus Loft Space! Fully renovated 1-bedroom, 1-bathroom rental home in the heart of Old Key West, featuring a bonus loft, one off-street parking space and a washer/dryer inside. Fully furnished, the property includes a cozy sitting room, a well-equipped kitchen, large bedroom, and updated bathroom with new shower. Relax on the porch, surrounded by lush

  Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty

  623 Whitehead St, Key West, FL 33040
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  /17

  $865,000 Sold Jun 26, 2025

  • 575 Sq Ft
  • $1504/SF
  • 14 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1908

  624 United St, Key West, FL 33040

  Nestled within the charming and storied streets of Key West's old town, this exquisite property presents an unparalleled opportunity to own a slice of paradise in one of the most coveted locations in the Florida Keys. Located in the heart of the historic district, mere steps away from the pristine beaches and the vibrant entertainment scene of Key West. Enjoy the convenience of living within

  Douglas Miller Amerirealty Corp (KW)

  624 United 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
• 

  

  /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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  /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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  /29

  $1,995,000 Sold Jun 24, 2025

  • 3,660 Sq Ft
  • $545/SF
  • 80 Days On Market

  • 1 Bed
  • 4 Baths
  • Built 1945

  1114 White St, Key West, FL 33040

  An exceptional investment opportunity awaits in Old Town just south of Truman in the Gallery District on White Street. This income-producing property features four newly renovated (2023) commercial spaces and a legal leasable renovated residential apartment, offering a diverse and steady revenue stream. Located in the desirable X Flood Zone, this property is built for durability featuring impact

  Kate Green Old Town Realty

  1114 White 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

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