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


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Iconic 6 Parking Spaces 79 Paces to Duval Street 416 Fleming Street Herringbone pattern pavers Board Walk Great Room - digitally enhanced Breakfast Bar - digitally enhanced Kitchen - digitally enhanced Ensuite Bath - staged digitally 3 Units + Owners Shed Owners Shed Bonus Space Additional Handicapped Parking IMG_1629 Outdoor living Overlooking the garden Well maintained Added living Space Upper Room 2/2 Dade County Pine Historic architecture Primary Master Upper Bedrooms 2 Bed 2Bath with Balconies Expansive Sideyard & Garden Breakfast Kitchen Bar Upper Kitchen High 12’ ceilings Full Bath ADA compliant ADA compliant Commercial restroom Mixed Use Professional Office Commercial office First floor Primary 2/1 Vaulted ceiling Historic Architecture Bike rack Privacy Fence Garden seating Side yard Shed Historic

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
Current Price: $3,500,000
Listing Date: 2026-06-27
Listing Board: Key West Association
Monthly Rent: $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
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+
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: August - 30 - 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)