Old Town 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
• 

  

  

  /10

  Est $1,487,515 Not Listed For Sale

  Unlisted Address

  Unlisted Address
• 

  

  

  /47

  $3,999,000

  • 7 Beds
  • 7 Baths
  • 3,015 Sq Ft

  919 Thomas St Unit A,1-3, Key West, FL 33040

  This is the entire four-unit Lighthouse View Condominium Association. It is currently four lucrative long-term rentals. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence is secluded in the rear with its own private heated pool, hot tub and expansive garden with brick terrace. A free-standing two

  Mabry Binnicker Preferred Properties (KW)

  919 Thomas St Unit A,1-3, Key West, FL 33040
• 

  

  

  /68

  $8,500,000 Sold Apr 25, 2025

  • 4,008 Sq Ft
  • $2121/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
• 

  

  

  /27

  Est $1,564,769 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,243 Sq Ft

  1105 Petronia St, Key West, FL 33040

  1105 Petronia St, Key West, FL 33040
• 

  

  /37

  $1,550,000

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  830 Fleming St, Key West, FL 33040

  NEW LISTING!!! First time on the market since the mid 70s! Prime Old Town Location mixed-use property. Endless possibilities with this corner location in the heart of the historic district and just two blocks from the Seaport. Commercial space with full bath and occupied by successful gallery tenant. Three Residential apartments with 1BED/1BATH each. Corner of Fleming and Margaret St near

  Bascom Grooms Bascom Grooms Real Estate (KW)

  830 Fleming St, 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 $1,860,396 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,588 Sq Ft

  700 Elizabeth St, Key West, FL 33040

  700 Elizabeth St, Key West, FL 33040
• 

  

  /37

  $3,750,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 6 Baths
  • 3,666 Sq Ft

  400 Aronovitz Ln, Key West, FL 33040

  Zen Villa represents a rare opportunity in the heart of Old Town, Key West, comprised of three homes on a spacious 5,891 SF lot. The main residence at 400 Aronovitz Lane is a luxurious 3-bedroom, 4-bathroom contemporary island estate and an active vacation rental, while 621 and 623 Whitehead Street offer two charming 1-bedroom, 1-bathroom cottages, currently rented long-term.The main home

  Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty

  400 Aronovitz Ln, Key West, FL 33040
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  /47

  $3,250,000 Sold Apr 18, 2025

  • 2,448 Sq Ft
  • $1328/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
• 

  

  /5

  Est $4,353,738 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,441 Sq Ft

  720 Simonton St, Key West, FL 33040

  720 Simonton St, Key West, FL 33040
• 

  

  /37

  $1,299,000

  • 2 Beds
  • 1 Bath
  • 749 Sq Ft

  1116 Eaton St, Key West, FL 33040

  Charming Key West Cottage with Pool, Rooftop Deck & Prime Old Town Location.Discover the ultimate island lifestyle in this lovely Key West cottage located in the vibrant heart of Old Town. Perfectly sized for effortless living, this beautifully maintained home offers all the charm, comfort, and convenience you could dream of--without the hassle of high-maintenance upkeep.From the moment you

  Margarita Villoch Island Group Realty (KW)

  1116 Eaton St, Key West, FL 33040
• 

  

  /37

  $2,175,000 Sold Apr 18, 2025

  • 1,058 Sq Ft
  • $2056/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
• 

  

  /62

  Est $2,419,585 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,897 Sq Ft

  822 Thomas St, Key West, FL 33040

  822 Thomas St, Key West, FL 33040
• 

  

  /60

  $7,995,000

  • 11 Beds
  • 11 Baths
  • 3,034 Sq Ft

  525 Simonton St, Key West, FL 33040

  A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom

  Paige Bethel Island Home Realty Inc.

  525 Simonton St, Key West, FL 33040
• 

  

  /54

  $4,500,000 Sold Apr 14, 2025

  • 3,015 Sq Ft
  • $1493/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
• 

  /2

  Est $9,114,920 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 10,822 Sq Ft

  620 Southard St, Key West, FL 33040

  620 Southard St, Key West, FL 33040
• 

  

  /48

  $1,750,000

  • 3 Beds
  • 5 Baths
  • 1,442 Sq Ft

  1001 United St Unit B, Key West, FL 33040

  Enjoy your tropical retreat in the heart of Old Town Key West with this stunning, fully remodeled, three-story corner lot island oasis. The first floor of this expansive attached home welcomes you with soaring vaulted ceilings, an open floor plan drenched in natural light, and seamless indoor-outdoor living. Throw open the French doors and lounge on your poolside veranda, or take a dip in the

  Michael Sorah Truman & Co. (KW)

  1001 United St Unit B, Key West, FL 33040
• 

  

  /30

  $1,150,000 Sold Apr 10, 2025

  • 1,462 Sq Ft
  • $787/SF
  • 147 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1948

  1029 United St, Key West, FL 33040

  This light-filled and airy home is priced at appraisal price, and is being offered furnished, excluding some artwork and personal items. With 2 bedrooms and 2 baths, 1,242 sq ft of indoor living space (per appraisal), it boasts a vaulted ceiling in the living and kitchen area, the kitchen as the heart of the home. With a view of the pool from the kitchen, entertain your family and friends in a

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1029 United St, Key West, FL 33040
• 

  

  /67

  Est $2,849,216 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,752 Sq Ft

  630 Elizabeth St, Key West, FL 33040

  630 Elizabeth St, Key West, FL 33040
• 

  

  /10

  $1,699,000

  • 8 Beds
  • 10 Baths
  • 2,432 Sq Ft

  720 Emma St, Key West, FL 33040

  Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops

  Wendy Zintsmaster Truman & Co. (KW)

  720 Emma St, Key West, FL 33040
• 

  

  /34

  $1,250,000 Sold Apr 09, 2025

  • 1,046 Sq Ft
  • $1195/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 $4,715,680 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 2,993 Sq Ft

  613 Margaret St, Key West, FL 33040

  613 Margaret St, Key West, FL 33040
• 

  

  /62

  $3,000,000

  • 3 Beds
  • 3 Baths
  • 1,514 Sq Ft

  215 Whitehead St, Key West, FL 33040

  Welcome to 215 Whitehead Street, a captivating Mediterranean Revival home that artfully blends historic charm with sophisticated updates in one of Old Town Key West's most iconic locations. Once the beloved residence of Burt and Hazel Burnett, the property carries a rich legacy. Burt Burnett, a renowned artist, actor, and passionate supporter of the local theatre scene, infused the home with a

  Tommy Mack Coastal Collection Real Estate Inc.

  215 Whitehead St, 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 $2,223,559 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 2,280 Sq Ft

  622 Grinnell St, Key West, FL 33040

  622 Grinnell St, Key West, FL 33040
• 

  

  /21

  $2,450,000

  • 6 Beds
  • 5 Baths
  • 2,587 Sq Ft

  1122 Simonton St, Key West, FL 33040

  Excellent income producing rental property and/or employee housing with multiple units. All apartments are currently rented at below market rents. With its downtown location, low flood risk, and turn-key income, this property is perfectly positioned for savvy investors. Three 1bed 1bath units, One 2 bed 1 bath separate cottage. One studio. Please note that advanced notice is required to arrange

  Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  1122 Simonton St, Key West, FL 33040
• 

  

  /23

  $3,700,000 Sold Apr 07, 2025

  • 2,616 Sq Ft
  • $1414/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
• 

  /2

  Est $1,794,172 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,030 Sq Ft

  1021 Angela St, Key West, FL 33040

  1021 Angela St, Key West, FL 33040
• 

  

  /16

  $499,000

  • Land

  906 Williams Alley, Key West, FL 33040

  NEW PRICE!!! Rare opportunity to obtain a vacant lot in Old Town. Prime location near the new Amphitheater, Community Center, fantastic dining and close to Duval Street. Located on a cul-de-sac Alley in the heart of Historic Old Town Key West, this vacant lot offers potential for development and owning your custom dream house in paradise. Lot is 41.25 x 89. Zoning is HMDR

  Bascom Grooms Bascom Grooms Real Estate (KW)

  906 Williams Alley, Key West, FL 33040
• 

  

  /4

  $800,000 Sold Apr 03, 2025

  • 557 Sq Ft
  • $1436/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
• 

  

  /31

  Est $2,593,627 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  613 Ashe St, Key West, FL 33040

  613 Ashe St, Key West, FL 33040
• 

  

  /31

  $895,000

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

  1428 Virginia St, Key West, FL 33040

  Old Town 'Diamond in the Rough' across from Bay View Park. City of Key West recognizes this property as a duplex with two ROGO's. Two story main house along with detached cottage. County Property appraiser says main house is 1900+sq ft, with cottage of 300+ sq ft. Does have off-street parking and possibly room for a pool. Lots of potential. Major renovation project. Foundation issues, evidence of

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  1428 Virginia St, Key West, FL 33040
• 

  

  /33

  $3,690,000 Sold Apr 02, 2025

  • 1,800 Sq Ft
  • $2050/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
• 

  

  /40

  Est $1,435,778 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,512 Sq Ft

  401 Margaret St, Key West, FL 33040

  401 Margaret St, Key West, FL 33040
• 

  

  /21

  $489,000

  • 1 Bed
  • 1 Bath
  • 454 Sq Ft

  1124 Catherine St Unit 201, Key West, FL 33040

  Charming 1-bedroom, 1-bathroom condo offering 454 square feet of living space. The condo boasts an open floor plan with hurricanes rated windows, one assigned parking spot and also located in the X Flood Zone. The property is just few a few blocks from vibrant Duval Street, known for entertainment and dining options and additionally, it's within walking distance to the dog park, beaches, wildlife

  Team Spottswood/Vazquez Truman & Co. (KW)

  1124 Catherine St Unit 201, Key West, FL 33040
• 

  

  /26

  $1,225,000 Sold Apr 01, 2025

  • 594 Sq Ft
  • $2062/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
• 

  

  /14

  Est $1,543,958 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,628 Sq Ft

  1122 Eaton St, Key West, FL 33040

  1122 Eaton St, Key West, FL 33040
• 

  

  /56

  $3,800,000

  • 3 Beds
  • 4 Baths
  • 2,532 Sq Ft

  316 Southard St, Key West, FL 33040

  Located in the heart of Old Town Key West, 316 Southard Street is a meticulously renovated single-family home that pairs modern comfort with classic Conch-style architecture. Originally built in 1938, the home has undergone a comprehensive renovation, blending timeless character with thoughtful, high-quality upgrades. Offering over 2,500 square feet of finished living space on a 6,165-square-foot

  Team Spottswood/Vazquez Truman & Co. (KW)

  316 Southard 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

Showing Results 121 - 160, Page 4 of 18