416 Fleming Street, Key West, FL 33040

$3,500,000

Property Type: Residential Bedrooms: 5 Baths: 5 Square Footage: 2,575 Lot Size (sq. ft.): 6,700 Status: Active

Current Price: $3,500,000 List Date: 6/28/2026 Last Modified: 7/13/2026

Overview

Description

First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property i ... (Read more)

Listing Details MLS# 620434

Location, Tax & Legal

Street #: 416
Street Name: Fleming
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unlisted (1.0)
Area: 02 - Key West
KW Neighborhood: Old Town-S of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: X
Alternate Key #: 1010171
Parcel #: 00009900-000000
Zoning: HRO - Historic Residential/Office
Deed Restrictions: Unknown
Legal: KW PT LOT 3 SQR 51 OR298-36/37 OR321-306/08 OR398-938/39 OR972-2202/03 OR1078-824 OR1093-2402 OR1078-824 OR1093-2402 OR1
Taxes: 19952.19
Tax Year: 2025
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Multi-Units
Waterfront: No
Pool: No
Year Built: 1938
Lot SqFt: 6700
Lot Sqft Source: Tax Records
Acres: 0.15
Living Apx SqFt: 2575
SqFt Source: Tax Records
Total Bedrooms: 5
Full Baths: 4
Half Baths: Yes
Total Baths: 5
Floor Number: 3
Rentals Allowed: Yes
Min Rental Days: 28
Control Depth: 0
Total Units: 0

Association Info

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

Building Style

Above Flood: Yes
Stories: 3 Stories

More Information

Vehicle Storage

Car(s): 4+
Off Street Parking: Yes

Remarks & Misc

Remarks – Consumer: First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

License Info

Non Trans Rntl Lic: Yes

Fee Includes

Other: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Microwave: Yes
Oven: Yes
Refrigerator: Yes

Pets

Pets Allowed: Yes

Cooling

Central Air: Yes
Wall/Window Unit(s): Yes

Heating

Electric: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Floor

Tile: Yes
Wood: Yes

Neighborhood Feature

Other Area Features: Yes

Interior Features

Built-in Cabinets: Yes
Cathedral Ceilings: Yes
Drapes/Blinds Incl: Yes
Entrance Foyer: Yes
Granite Counter Top: Yes
Lobby: Yes
Pull Down Stairs: Yes
Smoke Alarms: Yes
Storage: Yes

Property Condition

Updated/Remodeled: Yes

Construction

Frame: Yes
Other: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Unfurnished: Yes

Utilities

Cistern: Yes
Elect Separate Meter: Yes
FKAA: Yes
Well: Yes

Porch/Balcony

Deck: Yes
Open Porch/Balcony: Yes
Patio: Yes

Title

Negotiable: Yes

Exterior Features

Storage: Yes

Roof

Metal Roof: Yes

Accessibility Feat

Grab Bars: Yes
Parking: Yes
Wheelchair Ramp: Yes

Shutters

Panel: Yes

Property Features

Fee Includes: Other Tax Exemptions: None License Info: Non Trans Rntl Lic Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Updated/Remodeled Vehicle Storage: Off Street Parking Furnished: Unfurnished Cooling: Central Air; Wall/Window Unit(s) Heating: Electric Utilities: Cistern; Elect Separate Meter; FKAA; Well Interior Features: Built-in Cabinets; Cathedral Ceilings; Drapes/Blinds Incl; Entrance Foyer; Granite Counter Top; Lobby; Pull Down Stairs; Smoke Alarms; Storage Appliances: Dishwasher; Dryer; Microwave; Oven; Refrigerator Exterior Features: Storage Accessibility Feat: Grab Bars; Parking; Wheelchair Ramp Construction: Frame; Other Shutters: Panel Floor: Tile; Wood Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Other Area Features Land Size: Less Than 1/4 Acre Title: Negotiable

Listing Office: Keller Williams Key West Compass Realty

Last Updated: July - 13 - 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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