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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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$5,745,000
1109 Fleming Street
Key West, FL 33040
MLS# 617783
Status: Closed
6 beds  |  7 baths  |  3443 sqft


1109 Fleming Street
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1109 Fleming Street 1109 Fleming Street 1109 Fleming Street

Property Description
Located in the heart of Old Town, this truly magical estate presents an opportunity to own a private compound of remarkable scale and architectural distinction. Set on an oversized lot with off-street parking for two, the property features two fully independent residences--each appointed with impact-rated windows and doors. Situated along iconic Millionaire's Row, the main residence is a masterfully restored historic home that pays homage to its original character while embracing today's highest standards of luxury and comfort. Offering four spacious ensuite bedrooms, the main home includes a versatile first-floor suite that can easily function as a first floor primary bedroom or den. Additional features include original Dade County pine walls, reclaimed river wood flooring, soaring ceilings, and generous windows that bathe the interiors in natural light. At the heart of the home lies a chef-caliber gourmet kitchen with custom cabinetry, Sub-Zero and Wolf appliances, sculpted marble countertops, a built-in wine cooler and dedicated coffee center. French doors open to the wraparound porches- offering an idyllic setting for morning coffee, sunset cocktails, or alfresco dining. The estate's newly constructed guest house features two additional ensuite bedrooms, dramatic vaulted ceilings, and a charming loft ideal for additional living. The fully equipped kitchen features high-end Miele appliances and striking artisan tile. Anchoring the property is an extraordinary outdoor living environment conceived by renowned landscape architect Craig Reynolds. This lush, resort-style sanctuary showcases a sparkling saline swimming pool, cascading waterfall, outdoor shower, and a discreet poolside half bath. 1109 Fleming is more than a residence--it is a landmark Old Town estate equally suited for full-time living, a refined second home, or a legacy property to be enjoyed for generations on one of Key West's most prestigious streets.

Details
Maps
Contract Information
Current Price: $5,745,000
Listing Date: 2025-12-21
Listing Board: Key West Association
Leased Price Monthly: $5,745,000
Location, Tax & Legal
Street #: 1109
Street Name: Fleming
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: 1925
Lot SqFt: 8722
Acres: 0.2
Living Apx SqFt: 3443
SqFt Source: Property Data Card
Total Bedrooms: 6
Full Baths: 6
Half Baths: 1
Total Baths: 7
Rentals Allowed: With Restrictions
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Appliances
Other: Coffee Station
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Unknown
# Stories: 2 Stories
Vehicle Storage
Car(s): 2
Pool Info
Heated: Yes
Financial Status
Standard Sale: Yes
Status Change Info
Under Contract Date: 2026-02-03
Leased Date: 2026-03-26
Leased Price Monthly: $5,745,000
Status: Closed
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Building Style: Eyebrow
Vehicle Storage: Off Street Parking
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Heating: Propane; Propane Stove
Utilities: FKAA; Municipal Sewer
Interior Features: Built-in Cabinets; Cathedral Ceilings; Dade County Pine; Drapes/Blinds Incl; Fire Sprinkler; Granite Counter Top; Pantry; Quartz Countertops; Smoke Alarms; Walk-in Closet(s); Wet Bar; Window Treatments
Pre-Wired: Cable
Specialty Rooms: Loft
Appliances: Dishwasher; Dryer; Gas Appliances; Ice Machine; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features: Detached Guest Qtrs; Fencing; Lighting; Outdoor Shower; Privacy Wall/Fence; Rain Gutters; Sprinkler System; Water Display
Accessibility Feat: None
Pool Info: In Ground; Salt Water; Concrete
Construction: Frame; Hardi Board Siding
Floor: Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Security: Electric Gate
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Title: Negotiable
GF-Interior Features: Tankless Hot Wtr Htr

Listing Office: Brenda Donnelly Real Estate LLC

Last Updated: September - 16 - 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)