Galleon Square - Spaces For Lease

218 Whitehead St, Key West, FL 33040

Property Information

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

Description

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.

3 Spaces Available

218 Whitehead St 4, Key West, FL 33040

Space Type

Street Retail

Lease Rate

$5,250.00/MO

Total Space

950 SF

Divisible Space

950 - 950 SF

Available Date

Immediate

Lease Type

NNN

Renewal Option

Yes

Sublease

No

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

Divisible Space

501 - 501 SF

Available Date

Immediate

Lease Type

NNN

Renewal Option

Yes

Sublease

No

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

Divisible Space

1,407 - 1,407 SF

Available Date

Immediate

Lease Type

Full Service

Renewal Option

Yes

Sublease

No

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

Location

Located at 218 Whitehead St, Key West, FL 33040, this property is part of the Truman Annex neighborhood.

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