1109 Fleming St

$5,895,000
Price
3,443 Sq. Ft.
$1,712 / Sq. Ft.
3,443
Sq. Ft.
$1,712
per Sq. Ft.

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...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.
  1. Listed by Brenda J Donnelly • Brenda Donnelly Real Estate LLC

Property Details for 1109 Fleming Street

Waterfront
None
Waterfront
No
Zoning
HMDR - Historic Medium Density Residential
Subdivision
Old Town - Unrecord (1.0)
Building Style
Eyebrow
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 01/05/2026 03:10 PM

Property Details for 1109 Fleming Street

StatusActive
MLS #617783
Days on Market16
Taxes$30,859 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1925
Lot Size0.20 AC / 8,722 SF
CountyMonroe County

Location

Listing Courtesy of Brenda Donnelly Real Estate LLC
Add your commute

Building Information for 1109 Fleming Street

Stories2Year Built1925Building Size-Lot Size0.20 AC / 8,722 SF

Payment Calculator

$31,303 per month

30 year fixed, 6.15% Interest

Principal and Interest

$28,731

Property Taxes

$2,572

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 1109 Fleming Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.795803
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Accessibility Feat: None
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Negotiable
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.2
  • Parcel #: 00005020-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 4 SQR 31 V-191 CO JUDGES DOCKET 79-113 AND 79-114 AND 79-115 OR788-1216 OR788-1241 OR791-1432 OR815-1846 OR115
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE,AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 44
  • Document Count: 2
  • Building Style: Above Flood: Unknown
  • Security: Electric Gate
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Concrete, Salt Water
  • Porch/Balcony: Open Porch/Balcony
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • GF-Interior Features: Tankless Hot Wtr Htr
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Quartz Countertops, Walk-in Closet(s), Smoke Alarms, Fire Sprinkler, Dade County Pine, Granite Counter Top, Built-in Cabinets, Pantry, Cathedral Ceilings, Wet Bar
  • Pre-Wired: Cable
  • Appliances: Other: Coffee Station
  • Appliances: Washer, Stainless Steel Appliance(s), Wine Cooler, Ice Machine, Gas Appliances, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Frame, Hardi Board Siding
  • Dockage: None
  • Exterior Features: Fencing, Water Display, Sprinkler System, Privacy Wall/Fence, Outdoor Shower, Lighting, Rain Gutters, Detached Guest Qtrs
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
Room Information
  • Specialty Rooms: Loft
  • Specialty Rooms: Guest/Servant Qtrs: Legal

Property History for 1109 Fleming Street

DateEvent & SourcePriceAppreciation
Dec 21, 2025

Listed (Active)

FKMLS #617783

$5,895,000
Aug 9, 2025

Expired

FKMLS #614974

May 9, 2025

Listed (Active)

FKMLS #614974

$6,300,000
May 1, 2025

Expired

FKMLS #613179

Jan 15, 2025

Price Change

FKMLS #613179

$6,700,000
Jan 15, 2025

Price Change

FKMLS #613179

$6,400,000
Jan 15, 2025

Listed (Active)

FKMLS #613179

$6,300,000
Apr 30, 2024

Expired

FKMLS #608018

Jan 3, 2024

Listed (Active)

FKMLS #608018

$6,950,000
May 23, 2023

Expired

FKMLS #604307

Feb 23, 2023

Listed (Active)

FKMLS #604307

$7,500,000
Jun 6, 2022

Expired

FKMLS #599989

Mar 6, 2022

Listed (Active)

FKMLS #599989

$7,699,000
May 26, 2021

Expired

FKMLS #594313

Jan 24, 2021

Listed (Active)

FKMLS #594313

$7,500,000
Jul 1, 2016

Expired

FKMLS #122911

Mar 10, 2016

Expired

FKMLS #121272

Feb 21, 2016

Listed (Active)

FKMLS #122911

$1,795,000
Oct 1, 2015

Expired

FKMLS #121290

Mar 11, 2015

Listed (Active)

FKMLS #121290

$1,450,000
Mar 11, 2015

Listed (Active)

FKMLS #121272

$1,450,000
Dec 19, 2014

Sold

FKMLS #120484

$1,300,600
Dec 18, 2014

Pending

FKMLS #120484

Dec 16, 2014

Sold (Public Record)

Public Record #486638715

$1,300,700
Oct 13, 2014

Listed (Active)

FKMLS #120484

$995,500
DateEvent & SourcePrice
12/21/2025

Listed (Active)

FKMLS #617783

$5,895,000
08/09/2025

Expired

FKMLS #614974

05/09/2025

Listed (Active)

FKMLS #614974

$6,300,000
05/01/2025

Expired

FKMLS #613179

01/15/2025

Price Change

FKMLS #613179

$6,700,000
01/15/2025

Price Change

FKMLS #613179

$6,400,000
01/15/2025

Listed (Active)

FKMLS #613179

$6,300,000
04/30/2024

Expired

FKMLS #608018

01/03/2024

Listed (Active)

FKMLS #608018

$6,950,000
05/23/2023

Expired

FKMLS #604307

02/23/2023

Listed (Active)

FKMLS #604307

$7,500,000
06/06/2022

Expired

FKMLS #599989

03/06/2022

Listed (Active)

FKMLS #599989

$7,699,000
05/26/2021

Expired

FKMLS #594313

01/24/2021

Listed (Active)

FKMLS #594313

$7,500,000
07/01/2016

Expired

FKMLS #122911

03/10/2016

Expired

FKMLS #121272

02/21/2016

Listed (Active)

FKMLS #122911

$1,795,000
10/01/2015

Expired

FKMLS #121290

03/11/2015

Listed (Active)

FKMLS #121290

$1,450,000
03/11/2015

Listed (Active)

FKMLS #121272

$1,450,000
12/19/2014

Sold

FKMLS #120484

$1,300,600
12/18/2014

Pending

FKMLS #120484

12/16/2014

Sold (Public Record)

Public Record #486638715

$1,300,700
10/13/2014

Listed (Active)

FKMLS #120484

$995,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1109 Fleming Street

Taxable ValueLand$2,099,560Additions$2,087,918Total$4,187,478
Tax Record2024$29,019 ($2,418 / month)
Home Facts
Beds6Baths6.5Total Finished SqFt3,443 SqFtAbove Grade Finished SqFt3,443 SqFtStories2Lot Size8,722 SqFtStyleSingle Family ResidenceYear Built1925Year Renovated2020CountyMONROEAPN00005020-000000

Schools near 1109 Fleming Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 2 to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Franchise
Public2 to 12

Key West High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

1109 Fleming Street is a single family home for sale in Key West, FL 33040. This property was listed for sale on December 21, 2025 by Brenda Donnelly Real Estate LLC, it's currently listed at $5,895,000. It has been on the market for a total of 16 days and was last sold on December 19, 2014. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Franchise and Key West High School. 1109 Fleming Street is a 6-bed, 7-bath, 3,443 sqft single family home built in 1925.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Brenda Donnelly Real Estate LLC

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.