Old Town Homes

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  /29

  $775,000

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

  1115 Varela St, Key West, FL 33040

  **Investor Alert, reduced $180,000 from the original listed price. ** Nestled on a charming street in the heart of Old Town Key West, 1115 Varela Street is the renovation project that you have been waiting for. This historic treasure would be a perfect project for an investor, developer or anyone looking to restore a historic Key West gem. Currently configured as a 3BD/2BA with a large outside

  

  Terry Garcia

  Keller Williams Key West Compass Realty

  (786) 244-8439

  1115 Varela St, Key West, FL 33040
• Explore Old Town

• 

  

  

  /25

  $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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  /33

  $3,690,000 Sold Apr 02, 2025

  716 Duval St, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1933

  Last Sold Summary

  • 14% Below List Price
  • $2,050/SF
  • 14 Days On Market

  Current Estimated Value $3,618,077

  Last Listing Agent Jennifer Newman Truman & Co. (KW)

  716 Duval St, Key West, FL 33040
• 

  

  

  /17

  Est $489,582 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 412 Sq Ft

  416 Petronia St Unit 4, Key West, FL 33040

  416 Petronia St Unit 4, Key West, FL 33040
• 

  

  

  /22

  $789,000

  • 2 Beds
  • 1 Bath
  • 1,057 Sq Ft

  1102 Whitehead St, Key West, FL 33040

  Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden

  

  Margarita Villoch

  Island Group Realty (KW)

  (786) 949-2683

  1102 Whitehead St, Key West, FL 33040
• 

  

  /8

  $5,000 per month

  • 3 Beds
  • 1 Bath
  • 800 Sq Ft
  • Property for Rent

  927 Catherine St, Key West, FL 33040

  Furnished 2-bedroom plus loft area with one-bath Conch house in the heart of Old Town Key West. Classic island charm with a functional floor plan and bright living spaces. All utilities and internet included for easy, turnkey living. Prime location close to dining, shopping, and entertainment. Available March 1st.

  Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

  927 Catherine St, Key West, FL 33040
• 

  

  /45

  $2,900,000 Sold Jan 09, 2026

  1224 Florida St, Key West, FL 33040

  • 5 Beds
  • 6 Baths
  • 2,760 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $1,051/SF
  • 56 Days On Market

  Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

  1224 Florida St, Key West, FL 33040
• 

  

  /49

  Est $1,208,068 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,625 Sq Ft

  1012 Whitehead St, Key West, FL 33040

  1012 Whitehead St, Key West, FL 33040
• 

  

  /44

  $1,199,000

  • 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
• 

  

  /20

  $17,240 per month

  • 2 Beds
  • 2 Baths
  • 2,023 Sq Ft
  • Condo for Rent

  536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040

  Experience the allure of this luxurious 2,000+ square foot penthouse, The Maloney, which occupies the entire second story of a historic red brick building at the corner of Fleming and Simonton. Originally constructed in 1908 as Key West's first pharmacy, this building now features two penthouse units and a first-floor boutique. The Maloney is available exclusively for monthly rentals, requiring a

  536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040
• 

  

  /4

  $1,200,000 Sold Nov 20, 2025

  1108 Whitehead St, Key West, FL 33040

  • Land

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Terri Spottswood Truman & Co. (KW)

  1108 Whitehead St, Key West, FL 33040
• 

  

  /24

  Est $1,942,396 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,286 Sq Ft

  1100 Williams Ln, Key West, FL 33040

  1100 Williams Ln, Key West, FL 33040
• 

  

  /53

  $2,899,000

  • 3 Beds
  • 4 Baths
  • 2,286 Sq Ft

  814 Ashe St, Key West, FL 33040

  Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 981-0872

  814 Ashe St, Key West, FL 33040
• 

  

  /8

  $6,500 per month

  • 4 Beds
  • 2 Baths
  • Property for Rent

  417 Southard St Unit A, Key West, FL 33040

  Long term or short 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

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  417 Southard St Unit A, Key West, FL 33040
• 

  

  /36

  $835,000 Sold Feb 10, 2025

  809 Southard St, Key West, FL 33040

  • 3 Beds
  • 1.5 Baths
  • 953 Sq Ft
  • Built 1915

  Last Sold Summary

  • 27% Below List Price
  • $876/SF
  • 44 Days On Market

  Current Estimated Value $928,986

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  809 Southard St, Key West, FL 33040
• 

  

  /27

  Est $1,556,057 Not Listed For Sale

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

  207 Virginia St, Key West, FL 33040

  207 Virginia St, 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

  (786) 981-9652

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

  

  /20

  $9,000 per month

  • 2 Beds
  • 3 Baths
  • 1,345 Sq Ft
  • Condo for Rent

  629 Elizabeth St Unit ID1297833P, Key West, FL 33040

  Casa Azul is a luxurious modern cottage featuring an open-concept living area that is bathed in natural sunlight. Enjoy a dip in the heated saltwater plunge pool with a waterfall feature and night lighting. Located in Old Town Key West, just two blocks from Duval Street, this pet-friendly home offers private parking and is perfect for your next extended stay.Casa Azul perfectly blends comfort

  629 Elizabeth St Unit ID1297833P, Key West, FL 33040
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  /34

  $1,550,000 Sold Jun 02, 2025

  1400 Virginia St, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Built 1923

  Last Sold Summary

  • 3% Below List Price
  • $1,160/SF
  • 124 Days On Market

  Current Estimated Value $1,607,291

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  1400 Virginia St, Key West, FL 33040
• 

  

  /29

  Est $1,427,002 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
• 

  

  /69

  $3,168,000

  • 3 Beds
  • 3 Baths
  • 2,262 Sq Ft

  524 Southard St, Key West, FL 33040

  Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated & Green-certified mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character.

  

  Tommy Mack

  Coastal Collection Real Estate Inc.

  (786) 396-7585

  524 Southard St, Key West, FL 33040
• 

  

  /18

  $4,000 per month

  • 2 Beds
  • 1 Bath
  • 775 Sq Ft
  • Property for Rent

  1116 Truman Ave Unit 1, Key West, FL 33040

  Beautifully renovated Old Town second floor condo, furnished. High ceilings, freshly painted, and a wonderful front porch to relax on. Walk or Bike to everything Old Town, local restaurants, steps to Sandy's Cafe for your morning cuban coffee, Walk on White event, food store, and more! This unit has a beautiful kitchen with a dish washer, an in unit washer and dryer, and access to a shared pool.

  Elaine Coyle Keller Williams Key West Compass Realty

  1116 Truman Ave Unit 1, Key West, FL 33040
• 

  

  /30

  $930,000 Sold Aug 01, 2025

  608 Roberts Ln, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1933

  Last Sold Summary

  • 41% Below List Price
  • $547/SF
  • 189 Days On Market

  Current Estimated Value $1,276,271

  Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

  608 Roberts Ln, Key West, FL 33040
• 

  

  /45

  Est $2,011,485 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
• 

  

  /32

  $3,699,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,663 Sq Ft

  805 Shavers Ln, Key West, FL 33040

  Income producing 300k+/yr - Tucked behind a classic white picket fence in the heart of Old Town Key West just steps from Duval St, 805 Shavers Lane is a completely restored historic 3 Bedroom 3 Bath residence that seamlessly blends timeless island architecture with refined modern luxury. From arrival, the cheerful island exterior, standing-seam metal roof and Bahama shutters set the tone for

  

  Tommy Mack

  Coastal Collection Real Estate Inc.

  (305) 930-7583

  805 Shavers Ln, Key West, FL 33040
• 

  

  /21

  $5,178 per month

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft
  • Condo for Rent

  120 Angela St Unit ID1384034P, Key West, FL 33040

  Feel at home in this bright, modern 2-bedroom, 2-bath second-floor condo, ideal for comfortable long-term stays in Key West.Fully renovated in Summer 2024, the condo features an open-concept living area and a modern kitchen with new countertops, stainless steel appliances, and all home cooking essentials. Outside, relax by the shared heated pool or unwind in the grill and lounge area

  120 Angela St Unit ID1384034P, Key West, FL 33040
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  /53

  $3,500,000 Sold Aug 08, 2025

  407-415 Olivia St, Key West, FL 33040

  • 6 Beds
  • 5 Baths
  • 3,171 Sq Ft
  • Built 1964

  Last Sold Summary

  • 18% Below List Price
  • $1,104/SF
  • 134 Days On Market

  Current Estimated Value $3,599,975

  Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

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

  

  /31

  Est $1,634,677 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
• 

  

  /37

  $3,600,000

  • 5 Beds
  • 6 Baths
  • 3,667 Sq Ft

  400 Aronovitz Ln, Key West, FL 33040

  Discover a rare investment and lifestyle opportunity at 'Zen Villa,' a prestigious compound anchored in the coveted X-Flood Zone of Old Town, Key West. Spanning a spacious 5,891 SF lot, this unique offering encompasses three distinct residences: the luxurious main estate at 400 Aronovitz Lane and two charming, income-generating cottages at 621 and 623 Whitehead Street.The main residence is a

  

  Damian Vantriglia

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  (786) 699-6375

  400 Aronovitz Ln, Key West, FL 33040
• 

  

  /20

  $5,082 per month

  • 1 Bed
  • 1 Bath
  • 419 Sq Ft
  • Condo for Rent

  817 Terry Ln Unit ID1297837P, Key West, FL 33040

  "Lil Bit" is a rare find in the historic Bahama Village neighborhood. This classic "conch" home is modern and renovated to have an elevated feel but retains the charm and character of old Key West. Perfect for a couple or visitors looking for a monthly stay, this home is equipped with everything you need. While it is a "Lil Bit," the space feels large, open, and fresh, and is a short walk to Fort

  817 Terry Ln Unit ID1297837P, Key West, FL 33040
• 

  

  /31

  $750,000 Sold Oct 03, 2025

  1428 Virginia St, Key West, FL 33040

  • 4 Beds
  • 2 Baths
  • 2,236 Sq Ft
  • Built 1933

  Last Sold Summary

  • 16% Below List Price
  • $335/SF
  • 111 Days On Market

  Current Estimated Value $857,369

  Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  1428 Virginia St, Key West, FL 33040
• 

  

  /22

  Est $1,408,238 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  800 Fleming St Unit C1, Key West, FL 33040

  800 Fleming St Unit C1, Key West, FL 33040
• 

  

  /37

  $1,699,000

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  621 Elizabeth St, Key West, FL 33040

  This gorgeous two-cottage property is located at the top of Solares Hill in the heart of Old Town Key West and offers exceptional flexibility along with strong rental and income potential. The lovely main house sits at the front of the property and features a main-floor primary bedroom and bath, an open living and dining area with vaulted ceilings, and central air. Stairs lead to a second bedroom

  

  Jennifer Newman

  Truman & Co. (KW)

  (786) 980-9176

  621 Elizabeth St, Key West, FL 33040
• 

  

  /20

  $13,514 per month

  • 4 Beds
  • 3.5 Baths
  • 1,797 Sq Ft
  • Condo for Rent

  1315 Whitehead St Unit ID1297834P, Key West, FL 33040

  Southernmost View is a modern and luxurious waterfront home located in a private seven-home gated community, just steps from the beach and the Southernmost Point of the continental USA. Enjoy turquoise blue waters from the rooftop sundeck, perfect for tanning, reading, and sipping your morning coffee. Relax under the southernmost stars or watch the sunset over the horizon.This upscale beach

  1315 Whitehead St Unit ID1297834P, Key West, FL 33040
• 

  

  /35

  $1,675,000 Sold Jun 02, 2025

  1075 Duval St Unit 1, Key West, FL 33040

  • 2 Beds
  • 2.5 Baths
  • 1,225 Sq Ft
  • Built 1987

  Last Sold Summary

  • $1,367/SF
  • 4 Days On Market

  Current Estimated Value $1,676,540

  Last Listing Agent Richard Haskins Buy The Keys

  1075 Duval St Unit 1, Key West, FL 33040
• 

  /2

  Est $789,320 Not Listed For Sale

  • 1 Bed

  951 Caroline St Unit 5, Key West, FL 33040

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

  

  /36

  $1,149,000

  • 4 Beds
  • 1 Bath
  • 1,343 Sq Ft

  206 Truman Ave, Key West, FL 33040

  Step into timeless Key West charm at 206 Truman Avenue, a classic Conch cottage rooted in Key West's Bahama Village neighborhood soaked in tradition and nestled in the heart of Old Town. This historic residence effortlessly blends character and comfort, offering original architectural details, Dade County pine, and breezy porches that whisper stories of the island's rich past.Situated on a

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (645) 218-2934

  206 Truman Ave, Key West, FL 33040
• 

  

  /12

  $2,950 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  1209 Pearl St Unit upstairs, Key West, FL 33040

  Lovely upstairs loft style apartment available now.Located in upper old town Key West, near Bayview Park. Apartment is completely furnished, private full size W/D, gas range, large tiled shower, and covered deck for tropical outside living! All utilities and internet are included in rent! First and last mo rent required to move in. Property is very well maintained, and suitable for a clean,

  1209 Pearl St Unit upstairs, Key West, FL 33040
• 

  

  /23

  $600,000 Sold Jul 15, 2025

  651 William St Unit 1, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 599 Sq Ft
  • Built 1933

  Last Sold Summary

  • 28% Below List Price
  • $1,002/SF
  • 191 Days On Market

  Current Estimated Value $706,926

  Last Listing Agent Barbara Bowers Preferred Properties (KW)

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

  

  /8

  Est $778,453 Not Listed For Sale

  • 1 Bed

  951 Caroline St Unit 1, Key West, FL 33040

  951 Caroline St Unit 1, Key West, FL 33040

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