1327 Whitehead St

Key West, FL 33040

$2,990,000
Price
4
Beds
1,787 Sq. Ft.
$1,673 / Sq. Ft.
1,787
Sq. Ft.
$1,673
per Sq. Ft.
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a couple of cars parked in front of a house
a view of a backyard with a patio
a living room with furniture and a large window
a view of a entryway door front of house
a view of outdoor space yard and patio
a view of outdoor space yard and patio
a view of a backyard with swimming pool
a view of swimming pool with seating area and garden
a balcony with furniture and a potted plant
a outdoor living space with furniture and a potted plant
a view of deck with patio
a front view of a house with yard and outdoor seating
a view of a dining room with furniture window and outside view
a living room with couch and a potted plant
a view of a dining room with furniture window and outside view
a sink with a window
a view of a livingroom with furniture and a flat screen tv
a kitchen with a stove a sink and a white cabinets
a kitchen with stainless steel appliances a table and a chair
a view of entryway with a window and chandelier
a bedroom with windows and cabinet
a bedroom with a bed and a window
a bedroom with a bed and a painting on the wall
a bathroom with a sink and a mirror
a bathroom with a shower
a bedroom with a bed and a window
a bedroom with a bed and a window
a bedroom with a bed and a lamp on dresser
a bathroom with a shower
a en suite bathroom with a granite countertop sink a mirror and shower
a bedroom with a bed and a television
a bedroom with a large bed and a tv
a living room with window and a flat screen tv
a bedroom with a large bed and windows
a room with painting on the wall and a dresser
a bathroom with a granite countertop sink and a mirror
a bathroom with a sink and a mirror

Description

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...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.
  1. Listed by Rodney Culiver • Last Key Realty, Inc (KW)
  2. Listed by Christopher B Santry • Last Key Realty, Inc (KW)

Property Details for 1327 Whitehead Street

Waterfront
None
Waterfront
No
Zoning
HHDR - Historic High Density Residential
Subdivision
Filer Boyle Sub (1.0)
Vehicle Storage
Assigned Parking
LISTING UPDATED: 05/12/2026 12:25 AM

Property Details for 1327 Whitehead Street

StatusActive
MLS #619459
Days on Market30
Taxes$18,218 / year
HOA Fees$138
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built2018
Lot Size0.06 AC / 2,443 SF
CountyMonroe County
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Location

Listing Courtesy of Last Key Realty, Inc (KW)
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Building Information for 1327 Whitehead Street

Stories-Year Built2018Building Size-Lot Size0.06 AC / 2,443 SF

Payment Calculator

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$16,712 per month

30 year fixed, 6.46% Interest

Principal and Interest

$15,056

Property Taxes

$1,518

HOA Dues

$138

The Payment Calculator is for illustrative purposes only.

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Property Information for 1327 Whitehead Street

Summary
Location and General Information
  • Waterview: Ocean View
  • Area: 01 - Key West
  • Absolute Longitude: 81.797269
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Ocean
  • KW Neighborhood: Old Town-S of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: 1st Right of Refusal: No
  • License Info: # of City License: 1
  • Fee Includes: Common Area Mnt
  • Furnished: Furnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.05
  • Parcel #: 00036180000500
  • Land Size: Less Than 1/4 Acre
  • License Info: Non Trans Rntl Lic
Property and Assessments
  • Legal: Residential Unit 5 Of Whkw (A/K/A Pt Lt 6 Sqr 3 Tr 16 Kw Filer Boyle Sub N-476) Or2758-1625 Or2795-1649 Or2895-1734 Or31
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 37
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Property Condition: Updated/Remodeled
  • Title: Negotiable
Utilities
  • Utilities: Buyer to Verify
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground
  • Porch/Balcony: Roof Top Deck, Patio
Interior and Exterior Features
Interior Features
  • Appliances: Washer, Stainless Steel Appliance(s), Freezer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Hardi Board Siding
  • Dockage: None
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors

Property History for 1327 Whitehead Street

DateEvent & SourcePriceAppreciation
Apr 13, 2026

Listed (Active)

FKMLS #619459

$2,990,000—
Feb 7, 2022

Sold (Public Record)

Public Record #1483627075

$2,209,000—
Feb 7, 2022

Sold

FKMLS #598887

$2,209,000—
DateEvent & SourcePrice
04/13/2026

Listed (Active)

FKMLS #619459

$2,990,000
02/07/2022

Sold (Public Record)

Public Record #1483627075

$2,209,000
02/07/2022

Sold

FKMLS #598887

$2,209,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1327 Whitehead Street

Taxable ValueLand$1,046,581Additions$1,099,782Total$2,146,363
Tax Record2024$16,625 ($1,385 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt1,787 SqFtAbove Grade Finished SqFt1,787 SqFtStories2Lot Size2,443 SqFtStyleSingle Family ResidenceYear Built2018CountyMONROEAPN00036180-000500

Schools near 1327 Whitehead Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Horace O'bryant School
Public - PK to 8
Key West High School
Public - 9 to 12
May Sands Montessori School
Charter - PK to 8
Keys Center
Public - 8 to 12
Rating
School
Distance
Horace O'bryant School
PublicPK to 8

Key West High School
Public9 to 12

May Sands Montessori School
CharterPK to 8

Keys Center
Public8 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1327 Whitehead Street, Key West, FL 33040

1327 Whitehead Street is a single family home for sale in Key West, FL 33040. This property was listed for sale on April 13, 2026 by Last Key Realty, Inc (KW), it's currently listed at $2,990,000. It has been on the market for a total of 30 days and was last sold on February 7, 2022. This listing's school district is Monroe. Nearby schools include Horace O'bryant School, Key West High School and May Sands Montessori School. 1327 Whitehead Street is a 4-bed, 3-bath, 1,787 sqft single family home built in 2018.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Last Key Realty, Inc (KW)

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.