1109 Fleming St, Key West, FL 33040
Property image
Property image
SOLD
MAR 26, 2026

1109 Fleming St
Key West, FL 33040

Historic Seaport
  • 6 Beds
  • 6.5 Baths
  • 3,443 sqft

$5,745,000

Last Sold: Mar 26, 2026
3% below list $5.89M
$1,669/sqft
Est. Refi. Payment $32,840/mo*
Refinance Your Home

$5,745,000

Last Sold: Mar 26, 2026
3% below list $5.89M
$1,669/sqft
Est. Refi. Payment $32,840/mo*
Refinance Your Home
6 Beds
6.5 Baths
3,443 sqft

Local Information

  • Map ViewExplore the area around 1109 Fleming St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

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.
1109 Fleming St, Key West, FL 33040 is a 6 bedroom, 7 bathroom, 3,443 sqft single-family home in Historic Seaport, built in 1925. It last sold for $5,745,000 on Mar 26, 2026 (3% below the $5,895,000 asking price). It is currently off market. The Trulia Estimate is $5,771,700, with a rent estimate of $7,325/month.

Home Highlights

Parking
2 Parking Spaces
Outdoor
Porch, Pool
View
No Info
HOA
None
Price/Sqft
$1,669/sqft
Listed
180+ days ago

Home Details for 1109 Fleming St

Interior Features

Interior Details
Wet Bar
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3443 Square Feet
Appliances & Utilities
Utilities: FKAA, Cable ConnectedAppliances: Washer, Stainless Steel Appliance(s), Wine Cooler, Ice Machine, Gas Appliances, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Coffee Station, Tankless Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Propane,Propane StoveHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Propane
Windows, Doors, Floors & Walls
Window: Drapes/Blinds Incl, Window Treatments, Impact Rstnce WindowDoor: Impact Rstnce DoorsFlooring: Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Tile, Wood
Security
Security: Smoke Detector(s), Fire Sprinkler System, Electric Gate

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/BalconyFencing: Fenced, PrivacyOther Structures: Guest House, Detached Guest QtrsExterior: Water Display, Sprinkler System, Outdoor Shower, Lighting, Rain GuttersHas a Private PoolSprinkler System
Parking & Garage
No CarportNo GarageNo Attached GarageNo Open ParkingParking Spaces: 2Parking: Off Street
Pool
Pool: Heated, In Ground, Concrete, Salt WaterPool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Property Information

Year Built
Year Built: 1925
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Eyebrow
Building
Construction Materials: Frame, Hardi Board Siding
Property Information
Parcel Number: 00005020000000

Price & Status

Price
List Price: $5,895,000Price Per Sqft: $1,669/sqft

Active Status

MLS Status: Closed

Location

Direction & Address
City: Key WestCommunity: Old Town - Unrecord (1.0)

HOA

HOA Fee Includes: NoneAssociation for this Listing: Key West AssociationNo HOA

Lot Information

Lot Area: 8712 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 617783Water View: None
Last check for updates: about 23 hours ago
Listed by Brenda J Donnelly, (305) 304-1116
Brenda Donnelly Real Estate LLC
Bought with: Paige Bethel, (305) 395-0550, Island Home Realty Inc.
Originating MLS: Key West Association
Source: FLKMLS, MLS#617783

Price History for 1109 Fleming St

DatePriceEventSource
03/26/2026$5,745,000Sold
FLKMLS #617783
02/04/2026$5,895,000PendingFLKMLS #617783
12/21/2025$5,895,000Listed For SaleKey West AOR #617783
08/10/2025$6,300,000ListingRemovedFLKMLS #614974
05/10/2025$6,300,000Listed For SaleFLKMLS #614974
05/06/2025$6,300,000ListingRemovedFLKMLS #613179
04/10/2025$6,300,000PriceChange
Key West AOR #613179
03/11/2025$6,400,000PriceChange
FLKMLS #613179
01/17/2025$6,700,000Listed For SaleKey West AOR #613179
05/01/2024ListingRemovedKey West AOR #608018
01/03/2024$6,950,000Listed For SaleFLKMLS #608018
05/24/2023ListingRemovedFLKMLS #604307
02/23/2023$7,500,000Listed For SaleKey West AOR #604307
06/07/2022ListingRemovedKey West AOR #599989
03/06/2022$7,699,000Listed For SaleKey West AOR #599989
05/27/2021ListingRemovedFLKMLS #594313
01/24/2021$7,500,000Listed For SaleFLKMLS #594313
12/19/2014$1,300,600Sold
FLKMLS #120484
03/27/2000$500,000Sold
N/A

Market trends in Key West

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.2M
$61.67KMoM
Sale-to-List Price
94.9%
0.4%MoM
Price per sq ft
$940
$14MoM
Available listings
304
28MoM
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Property Tax and Assessment

Year2025
Tax$30,859
Assessment$4,187,478
Home facts updated by county records

Comparable Sales for 1109 Fleming St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1006 & 1008 Fleming St, Key West, FL
0.10
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
1014 Southard St, Key West, FL
0.15
Single-Family Home
$4,700,000
04/30/26
4
3.5
3,026
525 Simonton St, Key West, FL
0.45
Single-Family Home
$6,500,000
06/17/26
11
11
3,034
810 Eisenhower Dr, Key West, FL
0.44
Single-Family Home
$4,000,000
08/20/25
4
4
2,177
1020 Southard St, Key West, FL
0.14
Single-Family Home
$3,350,000
12/03/25
3
3.5
2,438
1022 Packer St, Key West, FL
0.51
Single-Family Home
$3,422,500
03/12/26
5
5.5
3,006
407-415 Olivia St, Key West, FL
0.70
Single-Family Home
$3,500,000
08/08/25
6
5
3,171
400 Aronovitz Ln, Key West, FL
0.65
Single-Family Home
$3,300,000
05/21/26
5
6
3,667

Nearby homes

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Assigned Schools

These are the assigned schools for 1109 Fleming St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Historic Seaport
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Historic Seaport

At least 38 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 90 % Say people would walk alone at night

  • 88 % Say it's walkable to restaurants

  • 84 % Say it's walkable to grocery stores

  • 83 % Say there are sidewalks

  • 79 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 59 % Say there are community events

  • 57 % Say it's quiet

  • 43 % Say parking is easy

  • 42 % Say neighbors are friendly

  • 35 % Say kids play outside

  • 30 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Mari.lindsley
    "I've lived here for 2 years and enjoy the walkability to local theatres and restaurants. There's a strong homeless contingency that detracts from the seaport. But you can't blame them for wanting to be in paradise."
    11
    Flag
  • Tom
    "There are many festivals and events that include the Key West Historic Harbor. Venues include Schooner Wharf, Waterfront Brewery, The Marker, etc.."
    2
    Flag
  • Bwruble
    "Tourist don’t clean up after their dogs, but locals do. This is a wonderful neighborhood. Gecko lane is especially beautiful and very private. "
    1
    Flag
  • Ctmortman
    "Perfect place for dogs. There are several dog pearls on the island and some restaurants are pet friendly. I own a dog watching business on Marco Island...a service much needed there"
    2
    Flag
  • Sue S.
    "We vacationed here for the month of February 2014. We did not rent a car but had bikes for a week. We are walkers and walked an average of 1-2 miles for dinner and many miles during the day touring, hiking, etc. This area is accessible to most anything."
    1
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 1109 Fleming St

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Off Market Homes Near 1109 Fleming St

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MLS Internet Data Exchange (IDX) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.