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  4. Key West

Galleon Square - Spaces For Lease

For Lease 2,858 SF

218 Whitehead St, Key West, FL 33040

Located at the highly visible corner of Whitehead Street and Front Street, this premier Old Town Key West property offers one of the most desirable commercial locations on the island. Situated just steps from Duval Street, Mallory Square, the Historic Seaport, and the Cruise Ship District, the property benefits from exceptional year-round pedestrian traffic generated by tourists, locals, and cruise ship visitors. Neighboring renowned attractions such as the Mel Fisher Maritime Museum and the Audubon House, this location provides outstanding visibility and exposure for retail, gallery, restaurant, office, or specialty businesses. Few commercial locations in Key West offer this combination of prestige, accessibility, and consistent foot traffic.Now leasing commercial and residential spaces at one of Old Town Key West's most iconic mixed-use properties. Located at the prominent corner of Whitehead Street and Front Street, the property offers a variety of spaces suitable for retail, office, gallery, restaurant, and residential uses. Tenants benefit from exceptional visibility, steady year-round pedestrian traffic, and a prime location just steps from Duval Street, the Historic Seaport, Mallory Square, and Key West's most popular attractions. Rare leasing opportunities in this premier location provide the perfect setting for businesses and residents looking to be in the heart of Old Town Key West.

Rental Details

  • Number of spaces 3
  • Total square feet available 2,858 SF
  • For Lease $2,750.00 - $5,500.00/MO
  • Space Type Street Retail, Creative Office, Other
  • Lease Type NNN, Full Service
  • Latest Update Jul 22, 2026
Want more info on this listing?

Reach out to the broker for more info on lease terms and amenities

True

3 Spaces Available

Space Name Space Type Lease Rate Total Space Floor Lease Type Expand
218 Whitehead St 4, Key West, FL 33040 Street Retail $5,250.00/MO 950 SF - NNN

218 Whitehead St 4, Key West, FL 33040

Space Type

Street Retail

Lease Rate

$5,250.00/MO

Additional Rent

Price on request

Total Space Available

950 SF

Divisible Space

950 - 950 SF

Available Date

Immediate

Lease Type

NNN

Renewal Option

Yes

Sublease

No

Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease

Prime Old Town Key West Retail/Office Opportunity - Galleon Square Position your business in one of Key West's most sought-after commercial locations. This 950 square foot space at Galleon Square offers exceptional visibility and steady pedestrian traffic in the heart of Old Town. Surrounded by some of the island's most recognizable attractions, the property is located next door to the Mel Fisher Maritime Museum, directly across from the Custom House Museum and Mallory Square, and just steps from the historic waterfront, Duval Street, cruise ship visitors, and countless restaurants and boutiques. NNN charges are in addition to the quoted base rent.

218 Whitehead St 7, Key West, FL 33040 Creative Office $2,750.00/MO 501 SF - NNN

218 Whitehead St 7, Key West, FL 33040

Space Type

Creative Office

Lease Rate

$2,750.00/MO

Additional Rent

Price on request

Total Space Available

501 SF

Divisible Space

501 - 501 SF

Available Date

Immediate

Lease Type

NNN

Renewal Option

Yes

Sublease

No

Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease

Open commercial space available for lease in the heart of Old Town, ideally located at the corner of Greene and Whitehead Streets. Situated on the second floor, this suite features an open floor plan that is ideal for office or professional use. The space offers excellent natural light from two south-facing windows, a quiet professional setting, and shared access to common restrooms. An excellent opportunity for businesses seeking a centrally located office space in one of Key West's most desirable locations.

218 Whitehead St Apartment, Key West, FL 33040 Other $5,500.00/MO 1,407 SF - Full Service

218 Whitehead St Apartment, Key West, FL 33040

Space Type

Other

Lease Rate

$5,500.00/MO

Additional Rent

Price on request

Total Space Available

1,407 SF

Divisible Space

1,407 - 1,407 SF

Available Date

Immediate

Lease Type

Full Service

Renewal Option

Yes

Sublease

No

Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease

Rare opportunity to lease a spacious 1,407-square-foot second-floor apartment in the heart of Old Town Key West. This 3-bedroom, 2-bath residence features an expansive open-concept floor plan, generous living and dining areas, and two private balconies overlooking one of the city's most iconic intersections. Filled with natural light and offering ample space for comfortable living, the apartment is ideally suited for employee housing or a long-term residence. Located at the corner of Whitehead Street and Front Street, tenants will enjoy immediate access to the Historic Seaport, Duval Street, world-class dining, shopping, and Key West's most popular attractions. A unique opportunity to lease a residence in one of the island's most desirable and walkable locations.

218 Whitehead St 4, Key West, FL 33040

Space Type
Street Retail
Lease Rate
$5,250.00/MO
Total Space
950 SF
Lease Type
NNN
Space Type

Street Retail

Lease Rate

$5,250.00/MO

Additional Rent

Price on request

Total Space Available

950 SF

Divisible Space

950 - 950 SF

Available Date

Immediate

Lease Type

NNN

Renewal Option

Yes

Sublease

No

Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease

Prime Old Town Key West Retail/Office Opportunity - Galleon Square Position your business in one of Key West's most sought-after commercial locations. This 950 square foot space at Galleon Square offers exceptional visibility and steady pedestrian traffic in the heart of Old Town. Surrounded by some of the island's most recognizable attractions, the property is located next door to the Mel Fisher Maritime Museum, directly across from the Custom House Museum and Mallory Square, and just steps from the historic waterfront, Duval Street, cruise ship visitors, and countless restaurants and boutiques. NNN charges are in addition to the quoted base rent.

218 Whitehead St 7, Key West, FL 33040

Space Type
Creative Office
Lease Rate
$2,750.00/MO
Total Space
501 SF
Lease Type
NNN
Space Type

Creative Office

Lease Rate

$2,750.00/MO

Additional Rent

Price on request

Total Space Available

501 SF

Divisible Space

501 - 501 SF

Available Date

Immediate

Lease Type

NNN

Renewal Option

Yes

Sublease

No

Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease

Open commercial space available for lease in the heart of Old Town, ideally located at the corner of Greene and Whitehead Streets. Situated on the second floor, this suite features an open floor plan that is ideal for office or professional use. The space offers excellent natural light from two south-facing windows, a quiet professional setting, and shared access to common restrooms. An excellent opportunity for businesses seeking a centrally located office space in one of Key West's most desirable locations.

218 Whitehead St Apartment, Key West, FL 33040

Space Type
Other
Lease Rate
$5,500.00/MO
Total Space
1,407 SF
Lease Type
Full Service
Space Type

Other

Lease Rate

$5,500.00/MO

Additional Rent

Price on request

Total Space Available

1,407 SF

Divisible Space

1,407 - 1,407 SF

Available Date

Immediate

Lease Type

Full Service

Renewal Option

Yes

Sublease

No

Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease
Galleon Square - Spaces For Lease

Rare opportunity to lease a spacious 1,407-square-foot second-floor apartment in the heart of Old Town Key West. This 3-bedroom, 2-bath residence features an expansive open-concept floor plan, generous living and dining areas, and two private balconies overlooking one of the city's most iconic intersections. Filled with natural light and offering ample space for comfortable living, the apartment is ideally suited for employee housing or a long-term residence. Located at the corner of Whitehead Street and Front Street, tenants will enjoy immediate access to the Historic Seaport, Duval Street, world-class dining, shopping, and Key West's most popular attractions. A unique opportunity to lease a residence in one of the island's most desirable and walkable locations.

Contacts

broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

Building Details

  • For Lease $2,750.00 - $5,500.00/MO
  • Property Type Other
  • Property Size 7,755 SF
  • Units 8
  • Lot Size 0.16 Acre
  • Additional Rent Price on request
  • Building Class C
  • Year Built 1942
  • Date Updated Jul 22, 2026

Location

  • City Key West, FL
  • Neighborhood Truman Annex
  • Zip Code 33040
  • Map
  • Street
  • Walk score 85/100 Very Walkable
  • Transit score 28/100 Some Transit
  • Bike score 81/100 Very Bikeable
Powered by Walk Score ®

Points of Interest

Chevron

0.93 miles

Citgo

0.95 miles

Circle K

1.41 miles

Shell

1.45 miles

Owen's Oco-Pep

1.60 miles

Electrify America

2.68 miles

Mobil

2.74 miles

201 Front Street Garage

0.06 miles

Old Town Garage

0.51 miles

Key West Tropical Forest & Botanical Garden

3.76 miles

Oceans Edge Resort & Marina Parking

4.95 miles

Hydro Thunder

0.19 miles

Tropical Rent-A-Car

0.90 miles

Enterprise

2.01 miles

Key West Jeep Adventures

2.97 miles

Uppy's Clean Machine

3.22 miles

Avis

3.33 miles

Dollar Rent-A-Car

3.34 miles

Garbo's Grill

0.05 miles

Turquoise Restaurant

0.06 miles

Smokin' Tuna Saloon

0.07 miles

Capt Tony's Saloon

0.08 miles

Roof Top Cafe

0.09 miles

Amigo's Tortilla Bar

0.09 miles

Lucy’s Retired Surfer Bar and Restaurant

0.11 miles

Flying Monkeys

0.11 miles

The Lazy Gecko

0.11 miles

Señor Frog's

0.11 miles

Faustos

0.30 miles

Olivia Street Grocery

0.69 miles

Fausto's Food Palace

1.04 miles

Bealls Outlet

1.96 miles

Gordon Food Service

1.98 miles

Ross

2.19 miles

Winn-Dixie

2.25 miles

Publix

2.33 miles

Atlantic Grocery

2.60 miles

TJ Maxx

2.72 miles

Sunset Key Fire Station

0.54 miles

Key West Police Department

1.20 miles

Key West Central Fire Station

1.22 miles

Walgreens

2.18 miles

dePoo Medical Building

2.48 miles

Key West Fire Station 3

2.57 miles

Key West Police Substation

3.01 miles

Monroe County Sheriff's Office Aviation Division

3.68 miles

Monroe County Sheriff's Office Headquarters

3.73 miles

Lower Keys Medical Center

4.31 miles

Listing Summary

  • What is the asking price at Galleon Square - Spaces For Lease?

    The asking price for spaces at Galleon Square - Spaces For Lease rests at $4,500.00/MO.

  • How many office spaces for rent are listed at Galleon Square - Spaces For Lease?

    1 office space is listed at Galleon Square - Spaces For Lease.

  • What is the total size of Galleon Square - Spaces For Lease?

    Galleon Square - Spaces For Lease has a total of 7,755 square feet.

  • What is the year built for Galleon Square - Spaces For Lease?

    The year built for Galleon Square - Spaces For Lease is 1942.

Contact Team Gardner-Langley
broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

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