About 1327 Whitehead Street
Modern luxury meets historic charm at this ultimate Key West sanctuary! Experience the pinnacle of island living in this stunning multi-story home built in 2018. Situated on the largest and most private parcel within an exclusive gated community, this home offers a rare combination of space and privacy in an unbeatable location. Tucked away off Whitehead Street, you'll be just steps from the Southernmost Point, access to the beach, and Duval Street. The crown jewel of this home is the expansive rooftop deck-- offering breathtaking views of the Atlantic Ocean and Old Town, coupled with refreshing breezes all day long. Built for peace of mind, the home features termite-resistant Hardie board siding, a metal roof, and impact rated doors and windows throughout. Inside, the open-concept first floor is an entertainer's dream, anchored by a chef-inspired kitchen with a large island that flows seamlessly into the living room. The 1,787 sq ft floor plan features four spacious bedrooms and three modern bathrooms, offering plenty of space for both privacy and entertaining, in addition to an abundance of storage - a rarity in Key West. The expansive master suite is a true luxury retreat, highlighted by soaring vaulted ceilings and an oversized en-suite bathroom. The outdoor space is equally as impressive, with a saltwater pool that includes a dual-temp heater (installed in late 2022) for year-round comfort. The IPE wood pool deck offers ample room for lounging, grilling, and dining, complemented by custom landscaping. Enjoy the security and tranquility of a well-managed HOA with low fees and active management, ensuring your property value remains protected. Whether you're seeking a primary residence or a high-performing vacation rental investment, this property is being sold completely turnkey. Complete with designated off-street parking and low insurances, this home truly has it all.
Features of 1327 Whitehead Street
| MLS® # | 619459 |
|---|---|
| Price | $2,990,000 |
| Bedrooms | 4 |
| Bathrooms | 3.00 |
| Full Baths | 3 |
| Square Footage | 1,787 |
| Acres | 0.05 |
| Year Built | 2018 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 1327 Whitehead Street |
|---|---|
| Area | 01 - Key West |
| Subdivision | Filer Boyle Sub (1.0) |
| City | Key West |
| County | Monroe |
| State | FL |
| Zip Code | 33040 |
Amenities
| Utilities | Buyer to Verify |
|---|---|
| Parking Spaces | 1 |
| Parking | Assigned Parking |
| View | Ocean View |
| Is Waterfront | No |
| Waterfront | None |
| Has Pool | Yes |
| Pool | In Ground |
Interior
| Appliances | Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Freezer, Stainless Steel Appliance(s) |
|---|---|
| Cooling | Central Air, Ceiling Fans(s) |
| Fireplace | No |
| Has Basement | No |
Exterior
| Lot Description | Less Than 1/4 Acre |
|---|---|
| Windows | Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | Hardi Board Siding |
Additional Information
| Date Listed | April 13th, 2026 |
|---|---|
| Days on Market | 29 |
| Zoning | HHDR - Historic High Density Residential |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 138 |
Listing Details
| Agent | Rodney Culiver |
|---|---|
| Office | Last Key Realty, Inc (KW) |