Old Town Homes

• 

  

  

  /19

  Est $2,644,367 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  526 Rose Ln, Key West, FL 33040

  526 Rose Ln, Key West, FL 33040
• 

  

  

  /23

  $1,275,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  606 Truman Ave Unit 1, Key West, FL 33040

  A rare blend of charm, privacy, and prime location--this Old Town stunner is just steps from Duval but feels worlds away.Just two blocks from Duval Street, this updated 2-bedroom, 2-bath home in the gated Windward Park community offers the ideal balance of island ease and elevated design--all in a quiet, tucked-away setting within Key West's coveted X Flood Zone, the highest and safest elevation

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  606 Truman Ave Unit 1, 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
• 

  

  

  /25

  Est $1,890,346 Not Listed For Sale

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

  315 William St, Key West, FL 33040

  315 William St, Key West, FL 33040
• 

  

  

  /35

  $1,395,000

  • 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
• 

  

  /24

  $1,462,000 Sold Mar 26, 2025

  • 1,260 Sq Ft
  • $1160/SF
  • 50 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1930

  1112 Elgin Ln, Key West, FL 33040

  Step back in time with this enchanting Key West cottage, built in 1899 and lovingly preserved through the years. This 2-bedroom, 2-bathroom home offers the perfect blend of historic charm and modern comfort. Both bedrooms are en-suite, with one conveniently located on the main level and the master suite spanning the entire second floor.The home's rich history is evident in the abundance of Dade

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  1112 Elgin Ln, Key West, FL 33040
• 

  

  /5

  Est $2,682,106 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
• 

  

  /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
• 

  

  /58

  $5,800,000 Sold Mar 26, 2025

  • 3,209 Sq Ft
  • $1807/SF
  • 170 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 1924

  522 Elizabeth St, Key West, FL 33040

  Introducing 522 Elizabeth Street, a fully reimagined Key West masterpiece offering 6 bedrooms, 6.5 bathrooms, and over 3,000 sq ft of luxurious living space. Just 2 blocks from vibrant Duval Street, this rare gem combines historic charm with modern sophistication. The home has been meticulously rebuilt with all-new concrete footings, structural lumber, impact windows, copper gutters, a brand-new

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  522 Elizabeth St, Key West, FL 33040
• 

  /2

  Est $2,286,970 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
• 

  

  /48

  $1,495,000 Open Sun 12PM - 3PM

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  820 Carsten Ln, Key West, FL 33040

  A true Old Town treasure tucked away in one of the most coveted corners of Key West's Historic District, this charming 2-bedroom, 2-bath cottage offers everything on your wishlist: a prime location, timeless character, a private heated pool surrounded by lush tropical landscaping, gated off-street parking, and rare dual access from both Carsten Lane and Carey Lane for ultimate convenience and

  Dina Schoneck Berkshire Hathaway HomeServices Knight & Gardner Realty

  820 Carsten Ln, Key West, FL 33040
• 

  

  /15

  $1,100,000 Sold Mar 25, 2025

  • 636 Sq Ft
  • $1730/SF
  • 1 Day On Market

  • 1 Bed
  • 1 Bath
  • Built 1983

  611 Southard St Unit 3, Key West, FL 33040

  New Listing. Key West Transient Licensed Condo in Old Town. Great location near Duval, Street dining, shopping and more. Second floor unit with balcony overlooking Southard St. Offered turnkey and totally furnished. Spacious bedroom with king size bed. Gated grounds with POOL (heated) and bricked courtyard. Parking available, unassigned spaces for complex.

  Bascom Grooms Bascom Grooms Real Estate (KW)

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

  /2

  Est $3,550,468 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
• 

  

  /53

  $1,399,900

  • 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

  1118 Eaton St, 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
• 

  

  /4

  Est $2,624,523 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
• 

  

  /7

  $1,125,000

  • 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
• 

  

  /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
• 

  

  /18

  Est $1,257,879 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 945 Sq Ft

  1401 Simonton St Unit 6, Key West, FL 33040

  1401 Simonton St Unit 6, Key West, FL 33040
• 

  

  /54

  $6,300,000

  • 6 Beds
  • 7 Baths
  • 3,443 Sq Ft

  1109 Fleming St, Key West, FL 33040

  Located on iconic Millionaire's Row in the heart of Old Town Key West, this extraordinary estate offers a rare combination of timeless charm, modern luxury, and unmatched privacy. With two stunning homes both with impact rated windows and doors on one oversized lot, this tropical compound is an exceptional opportunity to own one of the most unique properties in Key West.The main residence, a

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1109 Fleming St, 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
• 

  

  /24

  Est $956,691 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
• 

  

  /39

  $1,599,000

  • 2 Beds
  • 3 Baths
  • 1,360 Sq Ft

  1209 Grinnell St Unit G, Key West, FL 33040

  Discover a rare opportunity to own a refined retreat in the heart of Old Town Key West. Tucked away in the exclusive, gated Grinnell Gardens enclave, this beautifully updated end-unit townhouse offers the perfect blend of island serenity and sophisticated living.This 2-bedroom, 2.5-bath home is one of just seven residences in a private community prized for its tranquil ambiance, X-Flood Zone

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1209 Grinnell St Unit G, 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
• 

  

  /41

  Est $1,004,882 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
• 

  

  /25

  $947,500

  • 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
• 

  

  /3

  $1,000,000 Sold Mar 10, 2025

  • 1,216 Sq Ft
  • $822/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1923

  3 Fletcher Ln, Key West, FL 33040

  This charming 2-bedroom, 2-bathroom home is nestled on a quiet lane in Key West, offering the perfect blend of privacy and convenience. Just minutes from the island's top attractions, this home is ideal for both relaxation and entertainment. The first floor was expanded to add a guest bedroom, while the second floor features a large primary suite with a private rear deck that overlooks the

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

  3 Fletcher Ln, Key West, FL 33040
• 

  /2

  Est $878,918 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
• 

  

  /29

  $1,225,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  1127 Packer St, Key West, FL 33040

  At the quiet, palm-lined intersection of Packer and Catherine Streets, you'll find this picture-perfect 1928 cottage that truly captures the essence of classic Key West living. Lovingly maintained and effortlessly stylish, 1127 Packer Street blends island charm with relaxed coastal elegance, making it an ideal retreat in one of Key West's most desirable neighborhoods.The colorful and bright

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1127 Packer St, Key West, FL 33040
• 

  

  /21

  $2,115,000 Sold Mar 07, 2025

  • 1,747 Sq Ft
  • $1211/SF
  • 119 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2024

  1324 Duncan St, Key West, FL 33040

  POSSIBLE OWNER FINANCING FOR QUALIFIED BUYER:Exquisite newly built residence showcasing world class architecture and luxury in one of Key West's more idyllic Old Town neighborhoods.Located just a leisurely stroll from the iconic White St. Gallery District, where one can indulge in a local cuban coffee, dine in a Mediterranean restaurant or browse through the wide selection of art galleries and

  Suzanne Moore Suzanne Moore Real Estate

  1324 Duncan St, Key West, FL 33040
• 

  

  /18

  Est $564,202 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
• 

  

  /32

  $1,075,000

  • 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
• 

  

  /66

  $1,275,000 Sold Mar 05, 2025

  • 974 Sq Ft
  • $1309/SF
  • 15 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1943

  812 Carsten Ln, Key West, FL 33040

  A Timeless Sanctuary in the Heart of Key WestDiscover a private oasis where historic charm meets modern luxury. Nestled on high ground at 812 Carsten Lane, this elegant six-room residence with space for a third bedroom and second bath is a masterpiece of thoughtful design. Bathed in natural light and surrounded by lush tropical gardens, every inch of this home invites you to savor the

  Scott Forman Royal Palms Realty (KW)

  812 Carsten Ln, 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
• 

  

  /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
• 

  

  /29

  $3,675,000 Sold Mar 03, 2025

  • 1,870 Sq Ft
  • $1965/SF
  • 387 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1923

  533 Petronia St, Key West, FL 33040

  Located in the Heart of Old Town, this Rare Home has It all. 3 Bedrooms with 3.5 Baths in the Main House plus a Guest Cottage with Bedroom & Bath and Outdoor Shower. Completed in 2021 to the Highest Standards with Design by Matthew Stratton Architecture, Landscape and Pool Design by Craig Reynolds Landscape Architecture, and Custom Cabinetry by Hansen and Bringle. No Expense was Spared. All

  Ralph Sanchez Century 21 All Keys Inc (KW)

  533 Petronia St, 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
• 

  

  /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
• 

  

  /26

  $620,000 Sold Feb 28, 2025

  • 486 Sq Ft
  • $1276/SF
  • 9 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1928

  1209 William St Unit 7, Key West, FL 33040

  Unique stand alone cottage in a 7 unit condo community in Old Town Key West! Provides the privacy of a single family home with the shared maintenance of a condominium. Charming unit, fantastic walkable Old Town location, a private backyard outdoor space and sizable storage loft give this condo multiple reasons to consider this as your Key West home. One bedroom plus bonus second room ideal for

  Gwendolyn Esbensen Berkshire Hathaway HomeServices Knight & Gardner Realty

  1209 William St Unit 7, 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

Showing Results 161 - 200, Page 5 of 18