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

$5,878,500

Trulia Estimate
  • 6 Beds
  • 6.5 Baths
  • 3,443 sqft

1109 Fleming St, Key West, FL 33040

Historic Seaport
Est. Refi. Payment $35,065/mo*
Refinance Your Home
Currently Off Market - Sold Mar 26, 2026 for $5,745,000 (3% below list price)

Home Value

Trulia Estimate
$5.88M
Since last month
Increased$61K (+1%)
Since last year
Increased$280K (+5%)
Since last sale
Increased$134K (+2.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +98% in the last 10 years
MonthEstimated value
2026
September 2026$5.88M
August 2026$5.82M
July 2026$5.79M
June 2026$5.76M
May 2026$5.71M
April 2026$5.73M
March 2026$5.74M
February 2026$5.3M
January 2026$5.27M
2025
2024
2023
2022
2021
2020

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1006 & 1008 Fleming St, Key West, FL
0.21
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
616 Eaton St, Key West, FL
0.42
Single-Family Home
$7,250,000
08/13/26
5
6
4,000
525 Simonton St, Key West, FL
0.45
Single-Family Home
$6,500,000
06/17/26
11
11
3,034
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
400 Aronovitz Ln, Key West, FL
0.65
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
326 Caroline St, Key West, FL
0.72
Single-Family Home
$6,350,000
01/15/26
5
5.5
4,279

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1110 Elgin Ln, Key West, FL 33040
0.02
$1,850,000
3
3
1,256
Recently Sold
1112 Elgin Ln, Key West, FL 33040
0.03
$1,476,500
2
2
1,260
Off Market
413 Frances St, Key West, FL 33040
0.03
$2,134,300
3
3
1,536
Off Market
1116 Elgin Ln, Key West, FL 33040
0.03
$2,200,000
3
2
1,516
Recently Sold
1115 Fleming St, Key West, FL 33040
0.01
$1,875,000
4
2
1,760
For Sale
1120 Elgin Ln #A, Key West, FL 33040
0.04
$1,556,200
4
2.5
1,150
Off Market
1121 Elgin Ln, Key West, FL 33040
0.05
$974,300
4
3
1,226
Off Market
1118 Eaton St, Key West, FL 33040
0.05
$1,105,000
2
2.5
1,277
Recently Sold
1123 Elgin Ln #3, Key West, FL 33040
0.05
$2,787,800
5
3
-
Off Market
1113 Curry Ln #2, Key West, FL 33040
0.04
$1,341,000
4
3
1,528
Off Market
1025 Elgin Ln, Key West, FL 33040
0.07
$1,150,000
2
2
885
For Sale

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

Home Highlights

Single-Family Home
Built in 1925
3,443 sqft
$1,669/sqft

About this House

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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,878,500.
Last check for updates: about 12 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.
Source: FLKMLS, MLS#617783

Home Details for 1109 Fleming St

Interior Features

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
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Gas Appliances, Ice Maker, Wine Cooler, Stainless Steel Appliance(s)DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile, Wood
Levels, Entrance, & Accessibility
Accessibility: NoneFloors: Tile, Wood
View
No View
Security
Security: Security Gate, Fire Sprinkler System

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/BalconyFencing: Fenced, PrivacyOther Structures: Guest HouseExterior: Rain Gutters, Lighting, Outdoor Shower, Water DisplayHas a Private Pool
Parking & Garage
No Attached Garage
Pool
Pool: In Ground, Salt Water, ConcretePool
Frontage
Not on Waterfront

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)

Building

Building Area
Building Area: 3443 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 8712 sqft

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 617783

Price and Tax history

DateEventPrice
Mar 26, 2026
Source: FLKMLS #617783
Sold
$5,745,000
Feb 4, 2026
Source: FLKMLS #617783
Pending
$5,895,000
Dec 21, 2025
Source: Key West AOR #617783
Listed For Sale
$5,895,000
Aug 10, 2025
Source: FLKMLS #614974
ListingRemoved
$6,300,000
May 10, 2025
Source: FLKMLS #614974
Listed For Sale
$6,300,000

Market trends in Key West

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.14M
$143KMoM
Sale-to-List Price
—
Price per sq ft
$865
$67MoM
Available listings
255
17MoM

Around this home

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

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 MLS.

Frequently asked questions about 1109 Fleming St

  • What is 1109 Fleming St estimated to be worth?
    Trulia's estimated value for 1109 Fleming St in Key West, FL is $5,878,500.
  • What is the price history for 1109 Fleming St?
    1109 Fleming St in Key West, FL last sold for $5,745,000 in March 2026.
  • Is Key West a buyer's or seller's market?
    Key West is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Key West?
    The median sale price in Key West is $1.14M. That is down $143K from the prior month.
  • Does 1109 Fleming St have air conditioning?
    Yes, 1109 Fleming St in Key West, FL has air conditioning.
  • Does 1109 Fleming St have a pool?
    Yes, 1109 Fleming St in Key West, FL has a pool.

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