1327 Whitehead St
Key West, FL 33040
Upper Duvall
4 Beds
3 Baths
1,787 sqft
4 Beds
3 Baths
1,787 sqft
We estimate this home will sell faster than 84% nearby.
Local Information
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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 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.
We estimate this home will sell faster than 84% nearby.
Home Highlights
Parking
1 Parking Spaces
Outdoor
Patio, Deck, Pool
View
Ocean
HOA
$138/Monthly
Price/Sqft
$1,673
Listed
25 days ago
Home Details for 1327 Whitehead St
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Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 1787 Square Feet |
Appliances & Utilities Utilities: Buyer to VerifyAppliances: Washer, Stainless Steel Appliance(s), Freezer, Microwave, Oven, Range, Refrigerator, Dishwasher, DryerDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Has CoolingAir Conditioning: Central Air,Ceiling Fans(s) |
Windows, Doors, Floors & Walls Window: Impact Rstnce WindowDoor: Impact Rstnce Doors |
View Has a ViewView: Ocean |
Room & Shared Space Shared space is furnished |
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Exterior Home Features Roof: MetalPatio / Porch: Roof Top Deck, PatioHas a Private Pool |
Parking & Garage No CarportNo GarageNo Attached GarageNo Open ParkingParking Spaces: 1Parking: Assigned |
Pool Pool: Heated, In GroundPool |
Frontage Waterfront: None, Dockage: NoneNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
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Days on Market: 25 |
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Year Built Year Built: 2018 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Building Construction Materials: Hardi Board SidingNot a New Construction |
Property Information Condition: Updated/RemodeledParcel Number: 00036180000500 |
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Price List Price: $2,990,000Price Per Sqft: $1,673 |
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MLS Status: Active |
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Direction & Address City: Key WestCommunity: Filer Boyle Sub (1.0) |
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Listing Agent Listing ID: 619459 |
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HOA Fee Includes: Maintenance GroundsAssociation for this Listing: Key West AssociationHas an HOAHOA Fee: $138/Monthly |
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Lot Area: 2178 sqft |
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Listing Terms: Cash, Conventional |
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Furnished |
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Mls Number: 619459Water ViewWater View: Ocean |
Last check for updates: about 10 hours ago
Listing courtesy of Rodney Culiver, (863) 398-8623
Last Key Realty, Inc (KW)
Christopher B Santry, (305) 304-1933
Last Key Realty, Inc (KW)
Originating MLS: Key West Association
Source: FLKMLS, MLS#619459
Price History for 1327 Whitehead St
| Date | Price | Event | Source |
|---|---|---|---|
| 04/13/2026 | $2,990,000 | Listed For Sale | FLKMLS #619459 |
| 02/07/2022 | $2,209,000 | Sold | FLKMLS #598887 |
| 01/03/2022 | $2,199,000 | Contingent | FLKMLS #598887 |
| 12/20/2021 | $2,199,000 | Listed For Sale | FLKMLS #598887 |
| 12/13/2021 | ListingRemoved | Key West AOR #597343 | |
| 11/19/2021 | $2,149,000 | PriceChange | FLKMLS #597343 |
| 11/02/2021 | $2,199,000 | PriceChange | FLKMLS #597343 |
| 08/17/2021 | $2,250,000 | Listed For Sale | FLKMLS #597343 |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $18,218 |
| Assessment | $2,146,363 |
Home facts updated by county records
Comparable Sales for 1327 Whitehead St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.16 | Single-Family Home | $1,725,000 | 04/22/26 | 3 | 3 | 1,750 | |
0.23 | Single-Family Home | $3,050,000 | 04/07/26 | 4 | 2.5 | 1,440 | |
0.13 | Single-Family Home | $2,200,000 | 10/15/25 | 3 | 3 | 1,391 | |
0.24 | Single-Family Home | $1,330,000 | 08/13/25 | 3 | 3.5 | 1,324 | |
0.24 | Single-Family Home | $2,180,000 | 03/24/26 | 3 | 3.5 | 1,820 | |
0.17 | Single-Family Home | $1,400,000 | 05/29/25 | 3 | 2 | 1,100 | |
0.30 | Single-Family Home | $1,685,000 | 11/25/25 | 3 | 2.5 | 1,440 | |
0.42 | Single-Family Home | $2,170,000 | 03/31/26 | 3 | 3 | 1,662 | |
0.30 | Single-Family Home | $1,750,000 | 02/26/26 | 3 | 2 | 1,036 | |
0.19 | Single-Family Home | $1,950,000 | 05/15/25 | 3 | 2 | 1,128 |
Assigned Schools
These are the assigned schools for 1327 Whitehead St.
- Key West High School
- 9-12
- Public
- 1288 Students
3/10GreatSchools RatingParent Rating AverageSmall town, small mentality, the teachers are amazing but the overall quality is poor. Lots of bullying and old bubba mentality of your not from key West, you'll never truly fit inParent Review5mo ago - Horace O'bryant School
- PK-8
- Public
- 884 Students
3/10GreatSchools RatingParent Rating AverageI used to go to this school and my experience was not as bad as my little brother. I was bullied by the other students sometimes when the teachers SHOULD have saw it and was often confused by the messy learning system. However for my little brother not only has he been bullied by students but by a teacher as well A GROWN ADULT would mock him and yell at him for every little thing he has done despite him being a child and the worst part is when he'd try to talk to the office people they would NEVER listen to his side of the story even the one person I had a good terms with when I used to go there would tell him to shut up every time he'd try to talk to him who would then send him home causing his grades to drop. I sense discrimination but it could be them just being lazy at their job regardless of if they can't even LISTEN to a child when they try to speak for themselves, they should not have this job in the first place.Other Review2y ago 
Check out schools near 1327 Whitehead St.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Upper Duvall
At least 25 Trulia users voted on each feature.
90 % Say it's walkable to restaurants
87 % Say it's dog friendly
77 % Say there are sidewalks
74 % Say it's walkable to grocery stores
74 % Say people would walk alone at night
72 % Say streets are well-lit
60 % Say there's holiday spirit
59 % Say yards are well-kept
58 % Say it's quiet
52 % Say there's wildlife
44 % Say they plan to stay for at least 5 years
43 % Say there are community events
41 % Say kids play outside
38 % Say neighbors are friendly
22 % Say parking is easy
10 % Say car is needed
Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Rodney Culiver, Last Key Realty, Inc (KW)
Agent Phone: (863) 398-8623
MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.
1327 Whitehead St, Key West, FL 33040 is a 4 bedroom, 3 bathroom, 1,787 sqft single-family home built in 2018. 1327 Whitehead St is located in Upper Duvall, Key West. This property is currently available for sale and was listed by FLKMLS on Apr 13, 2026. The MLS # for this home is MLS# 619459.