A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.
Single-familyProperty Type
1889Year Built
4,525 sq ftLot Size
$1,698Price/Sq.Ft.
Listed by Julie Keller• Realty ONE Group Destination
Tucked away down a quiet path off Fleming Street lies this secluded 3 bed, 2 bath cottage surrounded by lush landscape and stunning poinciana trees. From the Dade County Pine to cathedral ceilings this home exudes old Key West character and charm. A wall of French doors expands the great room to the outdoor deck and dining space with T. V. , speakers and built-in grill; a perfect spot to entertain! There are two spacious bedrooms on the first floor plus a sleeping loft on the second floor. You will find an updated bath with a shower & tub off the main living space & another bathroom with a shower off the kitchen. There is also a laundry room, several storage spaces throughout the home & a spacious side garden. Come view this idyllic home just walking distance to the Historic Seaport.
FLKMLS #588715
May 2, 2020
Listing Removed
—
Dec 16, 2019
Listed
$799,000
$256/sq ft
FLKMLS #576541
May 15, 2020
Listing Removed
—
Aug 8, 2017
Listed
$1,575,000
$505/sq ft
FLKMLS #586451
Dec 16, 2019
Listing Removed
—
Jul 12, 2019
Listed
$865,000
$277/sq ft
FLKMLS #577048
Jul 27, 2018
Sold
$1,450,000
$465/sq ft
Oct 12, 2017
Listed
$1,575,000
$505/sq ft
Public Records
Apr 3, 2018
Sold
$583,000
$187/sq ft
FLKMLS #114721
Aug 1, 2011
Listing Removed
—
Apr 29, 2011
Listed
$549,000
$176/sq ft
Public Records
Apr 3, 2008
Sold
$590,000
$189/sq ft
Public Records
Aug 7, 1996
Sold
$98,000
$31/sq ft
Public Records
Feb 1, 1972
Sold
$7,500
$2/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$9,084 (−4.6%)
$882,611 + $194,677
$1,077,288
2024
$9,522 (+10.1%)
2023
$8,648 (+60.3%)
$785,309 + $193,153
$978,462
2022
$5,395 (−2.2%)
2021
$5,518 (+2.7%)
$450,060 + $171,894
$621,954
2020
$5,373 (−5.0%)
$474,529 + $92,415
$566,944
2019
$5,653 (+9.6%)
$474,529 + $92,415
$566,944
2018
$5,159 (−1.4%)
2017
$5,230 (+18.4%)
$518,086 + $95,464
$613,550
2015
$4,418 (+4.4%)
$466,663 + $87,845
$554,508
2014
$4,233
Public record
Public record
Zoning
Permits
Beds
3
Baths
1
Stories
1
Lot width
—
Lot depth
—
Lot size
2,800 Sq. Ft.
Year renovated
2010
Finished Sq. Ft.
1,002
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,002
Year built
1928
Style
Single Family Residential
County
Monroe County
APN
0668 25 00005460000000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 9, 2026.
HMDR
Historic Medium Density Residential District
The historic medium density residential district HMDR is established to implement comprehensive plan policies for areas designated HMDR on the comprehensive plan future land use map. The HMDR district shall accommodate historic Old Town medium density residential development for permanent residents, including single-family, duplex, and multiple-family residential structures. The HMDR district shall provide a management framework for preserving the residential character and historic quality of the medium density residential areas within Old Town.; In addition, accessory uses, including approved home occupations conducted within the residential structure, and customary community facilities can be located in the HMDR designated area. This area shall not accommodate transient residential uses, including guesthomes, motels or hotels. Similarly, the area shall not accommodate commercial office, retail, or other commercial uses. Lawfully existing office or commercial uses shall be permitted to continue to exist as lawful nonconforming uses if such uses continue to comply with conditions invoked when the respective uses were approved. In the event the city owns the portion of the Truman Waterfront Parcel designated HMDR, the site will be developed for 100 percent affordable housing. If the site is privately owned, one-third of the dwelling units will be affordable.
Permitted uses
Include but are not limited to:
Housing-Group
Housing-Single unit
Housing-Multiple units
Jun 21, 2024 • Final
Renovation exterior
Remodel
Jan 10, 2022 • Final
Renovation exterior
Remodel
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Climate risks
7/10 Flood Factor
Estimated 80%+ chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
Heat Factor
We're working on getting current and accurate heat risk information for this home.
10/10 Wind Factor
99% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Key West, FL • 33040
Average low and high temperatures (°F)
73
65
76
67
79
71
81
75
86
81
88
82
89
83
90
81
87
80
85
78
80
73
77
69
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
86/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Key West. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.5 hrs
7.2 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 923 Fleming St
$5,091,816
$208K under list price of $5.30M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $2.3M to $5.7M.