1019 Whitehead Street, Key West, FL 33040

New Listing

$3,180,000

Whitehead Front View Private Parking & Gate

Property Type: Residential Bedrooms: 3 Baths: 3 Square Footage: 1,373 Lot Size (sq. ft.): 2,430 Status: Active

Current Price: $3,180,000 List Date: 7/26/2026 Last Modified: 7/26/2026

Overview

Description

Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from th ... (Read more)

Listing Details MLS# 620747

Location, Tax & Legal

Street #: 1019
Street Name: Whitehead
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West
KW Neighborhood: Old Town-S of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: X Flood Zone
Alternate Key #: 1028169
Parcel #: 00027390000000
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: No
Legal: Kw Pt Subs 3 And 4 Pt Lt 4 Sqr 3 Tr 11 Or67-439/40 Or647-10 Or1183-2183/84 Or1199-594/95 Or1735-1231/33 Or1872-25/26 Or2
Taxes: 12231.1
Tax Year: 2025
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association
As is Rght to Inspct: Yes

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: No
Pool: Yes
Year Built: 1928
Lot SqFt: 2430
Acres: 0.05
Living Apx SqFt: 1373
SqFt Source: Property Data Card
Total Bedrooms: 3
Full Baths: 2
Half Baths: Yes
Total Baths: 3
Rentals Allowed: With Restrictions
Control Depth: 0

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Building Style

Above Flood: Yes
Stories: 2 Stories
Conch: Yes

More Information

Vehicle Storage

Car(s): Yes
Off Street Parking: Yes

Pre-Wired

Other: Zoned and Extenders
Cable: Yes

Pool Info

Heated: Yes
Dimensions: 7 x 15
In Ground: Yes
Concrete: Yes
Decked: Yes

Remarks & Misc

Remarks – Consumer: Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from this front door, your front door. Your new home. And by new, that's what we mean-this home was carefully and completely renovated in the last couple years, essentially creating a classic Key West house, with all the comfort and benefits of a new home. A completely custom Bosch appliance filled kitchen, with virtually every modern convenience a new home would hold. Modern upscale interior, zoned central A/C system with whole-house ventilating dehumidifier, advanced internet modem and router system, maintenance free composite decking, complete security and camera system, are just a few of the extra steps the owners took when creating a time-honored but luxurious, self contained and above the norm renovation of this truly one of a kind Key West home. Lets set up your private showing today.

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dishwasher: Yes
Disposal: Yes
Dryer: Yes
Microwave: Yes
Oven: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes
Washer: Yes

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Central Air: Yes

Heating

Central: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Floor

Tile: Yes

Interior Features

Cathedral Ceilings: Yes
Drapes/Blinds Incl: Yes
Quartz Countertops: Yes
Security System: Yes
Smoke Alarms: Yes
Walk-in Closet(s): Yes
Window Treatments: Yes

Property Condition

Updated/Remodeled: Yes

Windows/Doors

Double Hung Windows: Yes
French Doors: Yes
Glass Doors: Yes
Impact Rstnce Doors: Yes
Impact Rstnce Window: Yes

Security

On Premises System: Yes

Construction

Frame: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Negotiable: Yes

Terms

Cash: Yes
Conventional: Yes
FHA: Yes
VA: Yes

Utilities

Buyer to Verify: Yes
Cable Available: Yes
FKAA: Yes

Porch/Balcony

Deck: Yes
Patio: Yes

Title

Negotiable: Yes

Exterior Features

Fencing: Yes
Privacy Wall/Fence: Yes
Rain Gutters: Yes
Storage: Yes

Roof

Metal Roof: Yes

Shutters

Panel: Yes

GF-Interior Features

LED Lighting: Yes
Programmable Thermst: Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Updated/Remodeled Building Style: Conch Vehicle Storage: Off Street Parking Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air Heating: Central Utilities: Buyer to Verify; Cable Available; FKAA Interior Features: Cathedral Ceilings; Drapes/Blinds Incl; Quartz Countertops; Security System; Smoke Alarms; Walk-in Closet(s); Window Treatments Pre-Wired: Cable Appliances: Dishwasher; Disposal; Dryer; Microwave; Oven; Refrigerator; Stainless Steel Appliance(s); Washer Exterior Features: Fencing; Privacy Wall/Fence; Rain Gutters; Storage Pool Info: In Ground; Concrete; Decked Construction: Frame Shutters: Panel Floor: Tile Roof: Metal Roof Pets: Pets Allowed Security: On Premises System Land Size: Less Than 1/4 Acre Terms: Cash; Conventional; FHA; VA Title: Negotiable GF-Interior Features: LED Lighting; Programmable Thermst

Listing Office: Real Estate Management of Key West, LLC

Last Updated: July - 26 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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