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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$2,980,000
1019 Whitehead Street
Key West, FL 33040
MLS# 620747
3 beds  |  3 baths  |  1373 sqft


Whitehead Street View
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Whitehead Street View Entry In Parking Whitehead Front View Whitehead Front View Private Parking & Gate Whitehead Entry View Entry Front Setting Room Entry Front Setting Room 2 Dining Area Dining View 2 Front Setting View 3 Setting and Dining Area Half Bath Lower Level Kitchen View 1 Kitchen View 2 Kitchen View 3 Kitchen View 4 Kitchen into Family Back Family Room Second Setting/Family Second Setting/Family 2 Master Bedroom 1 Master Bedroom 2 Master Bath Ensuite Master Bath Ensuite 2 Master Ensuite 3 Second Level Bedroom 1 Second Level Bedroom View 2 Second Level Bath 2 Second Level Bath 2 View 2 Washer/Dryer Second Level Second Level Bedroom 3 Second Level Bedroom 3 View 2 Pool and Deck Area Pool and Deck Area 2 Pool and Deck 3 Pool and Deck 4 1019 Whitehead Wade Meyer Large--21

Property Description
PRICE IMPROVEMENT- 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. This home is carefree, furnished, and turnkey-bring your personal bag and you are home immediately. 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.

Details
Maps
Contract Information
Current Price: $2,980,000
Listing Date: 2026-07-25
Listing Board: Key West Association
Monthly Rent: $2,980,000
As is Rght to Inspct: Yes
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
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: No
Pool: Yes
Year Built: 1928
Lot Size: 40 X 65
Lot SqFt: 2430
Acres: 0.05
Living Apx SqFt: 1373
SqFt Source: Property Data Card
Total Bedrooms: 3
Full Baths: 2
Half Baths: 1
Total Baths: 3
Rentals Allowed: With Restrictions
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Building Style
Above Flood: Yes
# Stories: 2 Stories
Vehicle Storage
Car(s): 1
Pool Info
Heated: Yes
Dimensions: 7 x 15
Pre-Wired
Other: Zoned and Extenders
Status Change Info
Status: Active
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: Furnished
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: September - 25 - 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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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)