Search

416 Fleming Street, Key West, FL 33040

New Listing
$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: 6/28/2026

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 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!

More Information MLS# 620434

Contract Information

Current Price: $3,500,000 Listing Date: 2026-06-27 Listing Board: Key West Association List Price: $3,500,000

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

General Property Description

Realtor.COM Type: Residential - Single Family Style: Multi-Units Waterfront: No Pool: No Year Built: 1938 Lot Size: 50 X 134 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: 1 Total Baths: 5 Floor Number: 3 Rentals Allowed: Yes Min Rental Days: 28

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Building Style

Above Flood: Yes Stories: 3 Stories

Vehicle Storage

Car(s): 4+

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: June - 28 - 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.

Contact Us

Or feel free to call anytime - (305) 699-8154

Compare listings

Compare