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.
For sale
$2,990,000
1327 Whitehead St, Key West, FL 33040
4beds
1,787sqft
Single Family Residence
Built in 2018
2,178 Square Feet Lot
$2,807,600 Zestimate®
$1,673/sqft
$138/mo HOA
What's special
Metal roofFour spacious bedroomsExpansive rooftop deckAbundance of storageExpansive master suiteThree modern bathroomsSoaring vaulted ceilings
- 84 days |
- 1,227 |
- 52 |
Zillow last checked:
Listing updated:
Listed by:
Rodney Culiver 863-398-8623,
Last Key Realty, Inc (KW),
Christopher B Santry 305-304-1933,
Last Key Realty, Inc (KW)
Source: FLKMLS,MLS#: 619459
Originating MLS: Key West Association
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Stainless Steel Appliance(s), Freezer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Features
- Doors: Impact Rstnce Doors
- Windows: Impact Rstnce Window
- Furnished: Yes
Interior area
- Total interior livable area: 1,787 sqft
Property
Parking
- Total spaces: 1
- Parking features: Assigned
Features
- Patio & porch: Roof Top Deck, Patio
- Has private pool: Yes
- Pool features: Heated, In Ground
- Has view: Yes
- View description: Ocean
- Has water view: Yes
- Water view: Ocean
- Waterfront features: None, Dockage: None
Lot
- Size: 2,178 Square Feet
- Features: Less Than 1/4 Acre
Details
- Parcel number: 00036180000500
- Zoning: HHDR
- Zoning description: Historic High Density Residential
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Hardi Board Siding
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 2018
Utilities & green energy
- Sewer: Public Sewer
- Utilities for property: Buyer to Verify
Community & HOA
Community
- Subdivision: Filer Boyle Sub (1.0)
HOA
- Has HOA: Yes
- Services included: Maintenance Grounds
- HOA fee: $138 monthly
Location
- Region: Key West
Financial & listing details
- Price per square foot: $1,673/sqft
- Tax assessed value: $2,146,363
- Annual tax amount: $18,218
- Date on market: 4/13/2026
- Listing terms: Cash,Conventional
Estimated market value
$2,807,600
$2.67M - $2.95M
$6,346/mo
Price history
| Date | Event | Price |
|---|---|---|
| 4/13/2026 | Listed for sale | $2,990,000+35.4%$1,673/sqft |
Source: | ||
| 2/7/2022 | Sold | $2,209,000+0.5%$1,236/sqft |
Source: | ||
| 1/3/2022 | Contingent | $2,199,000$1,231/sqft |
Source: | ||
| 12/20/2021 | Listed for sale | $2,199,000+2.3%$1,231/sqft |
Source: | ||
| 12/13/2021 | Listing removed | -- |
Source: | ||
| 11/19/2021 | Price change | $2,149,000-2.3%$1,203/sqft |
Source: | ||
| 11/2/2021 | Price change | $2,199,000-2.3%$1,231/sqft |
Source: | ||
| 8/17/2021 | Listed for sale | $2,250,000$1,259/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $18,218 +9.6% | $2,146,363 +7.2% |
| 2024 | $16,625 +1.5% | $2,002,041 +3% |
| 2023 | $16,374 +16.9% | $1,943,730 +22.2% |
| 2022 | $14,007 +7% | $1,590,337 +10% |
| 2021 | $13,088 +0.5% | $1,445,761 +0.2% |
| 2020 | $13,021 | $1,442,573 -2.5% |
| 2019 | $13,021 -3.3% | $1,479,404 +459.2% |
| 2018 | $13,459 | $264,577 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: Upper Duvall
Nearby schools
GreatSchools rating
- 3/10Horace O'bryant SchoolGrades: PK-8Distance: 1 mi
- 4/10Key West High SchoolGrades: 9-12Distance: 1.4 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Monroe County
- Key West
- 33040
- Upper Duvall
- 1327 Whitehead St





