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$3,500,000
416 Fleming Street
Key West, FL 33040
MLS# 620434
5 beds  |  5 baths  |  2575 sqft


416 Fleming Street
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416 Fleming Street 79 Paces to Duval Street 6+ Parking Spaces Additional Handicapped Parking 1,000+ SqFt of porched 4 Units Three Full Kitchens 2 Bed 2Bath with Balconies Upper Room 2/2 Iconic Expansive Sideyard & Garden Cottage Custom cabinets IMG_1653 IMG_1629 Overlooking the garden IMG_1625 IMG_1627 Stunning views IMG_1624 IMG_1623 High 12’ ceilings IMG_1619 IMG_1618 Balcony door IMG_1615 IMG_1617 Granite countertops IMG_1616 IMG_1612 IMG_1611 IMG_1610 IMG_1609 DE County Pine IMG_1605 ADA compliant ADA compliant Commercial restroom 1938 Commercial office IMG_1597 Office Store Mixed Use IMG_1587 Office or 5th Bedroom First floor Primary IMG_1583 IMG_1582 Two Primary’s with entrance ram 2/1 Vaulted ceiling Historic Architecture Great Room IMG_1567 Bike rack Room for pool/cistern 15,000 gallon dual chamber cistern IMG_1565 Bonus Space Vaulted ceiling Board Walk 4 Units Privacy Fence Garden seating Side yard 416 Fleming Street

Property 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!

Details
Maps
Contract Information
Listing Board: Key West Association
Current Price: $3,500,000
Listing Date: 2026-06-27
List Price: $3,500,000
Location, Tax & Legal
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
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
Waterfront: No
Control Depth: 0
Lot Size: 50 X 134
Lot SqFt: 6700
Pool: No
Lot Sqft Source: Tax Records
Total Units: 0
Acres: 0.15
SqFt Source: Tax Records
Rentals Allowed: Yes
Min Rental Days: 28
Floor Number: 3
Style: Multi-Units
Year Built: 1938
Living Apx SqFt: 2575
Total Bedrooms: 5
Full Baths: 4
Half Baths: 1
Total Baths: 5
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!
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
License Info
Non Trans Rntl Lic: 1
Fee Includes
Other: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
Oven: 1
Refrigerator: 1
Pets
Pets Allowed: 1
Cooling
Central Air: 1
Wall/Window Unit(s): 1
Heating
Electric: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Tile: 1
Wood: 1
Neighborhood Feature
Other Area Features: 1
Interior Features
Built-in Cabinets: 1
Cathedral Ceilings: 1
Drapes/Blinds Incl: 1
Entrance Foyer: 1
Granite Counter Top: 1
Lobby: 1
Pull Down Stairs: 1
Smoke Alarms: 1
Storage: 1
Property Condition
Updated/Remodeled: 1
Building Style
Above Flood: Yes
Stories: 3 Stories
Vehicle Storage
Car(s): 4+
Off Street Parking: 1
Construction
Frame: 1
Other: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Unfurnished: 1
Utilities
Cistern: 1
Elect Separate Meter: 1
FKAA: 1
Well: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Patio: 1
Title
Negotiable: 1
Exterior Features
Storage: 1
Roof
Metal Roof: 1
Accessibility Feat
Grab Bars: 1
Parking: 1
Wheelchair Ramp: 1
Shutters
Panel: 1
Status Change Info
Status: Active
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

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