208 Fleming St, Key West, FL 33040
Property image
Property image
SOLD
MAR 2, 2026

208 Fleming St
Key West, FL 33040

Truman Annex
  • 2 Beds
  • 2.5 Baths
  • 960 sqft

$1,070,000

Last Sold: Mar 2, 2026
11% below list $1.2M
$1,115/sqft
Est. Refi. Payment $6,217/mo*
Refinance Your Home

$1,070,000

Last Sold: Mar 2, 2026
11% below list $1.2M
$1,115/sqft
Est. Refi. Payment $6,217/mo*
Refinance Your Home
2 Beds
2.5 Baths
960 sqft

Local Information

  • Map ViewExplore the area around 208 Fleming St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
1995
Living Area
960 sqft
Price/Sqft
$1,115/sqft
HOA
$554/Monthly

About this House

Owner is a licensed real estate agent and listing agent.

Truman Annex End Unit Featuring Secluded Backyard Retreat

Discover island living at its finest in this exceptional end unit townhome, perfectly situated in the prestigious Truman Annex community. Offering an ideal blend of privacy, comfort, and upscale coastal charm, this residence places you just moments from the vibrant energy of Old Town Key West and the natural beauty of Fort Zachary Taylor State Park.

Step inside to an inviting open floor plan filled with natural light pouring through large windows. The thoughtfully designed kitchen and dining areas provide generous space for everyday living or hosting friends, while the airy living room flows effortlessly to your own private backyard tropical oasis. Surrounded by lush landscaping and swaying palms, this secluded outdoor retreat is perfect for morning coffee, alfresco dining, or unwinding with an evening cocktail in true Key West style.

Upstairs, two spacious bedrooms each feature ample closet space and en-suite bathrooms. Both bedrooms open to private balconies overlooking vibrant tropical foliage, creating peaceful hideaways ideal for relaxation.

This well-maintained home includes a designated parking space, access to a sparkling community pool, and the security of a gated neighborhood—one of the most desirable in all of Key West.

Whether you're seeking a full‑time residence or the ideal seasonal retreat for snowbird living, this townhome offers an unparalleled opportunity to own a piece of paradise.

Owner has $43,000+ in monthly bookings for 2026. Repeat Guests would like to continue if future owner will allow.


Please provide 24-48 hour notice for showings as the home is currently an active rental.
208 Fleming St, Key West, FL 33040 is a 2 bedroom, 3 bathroom, 960 sqft townhouse in Truman Annex, built in 1995. It last sold for $1,070,000 on Mar 2, 2026 (11% below the $1,199,000 asking price). It is currently off market. The Trulia Estimate is $1,083,000, with a rent estimate of $4,835/month.

Home Details for 208 Fleming St

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Bedroom 1, Bedroom 2, Half Bathroom, Full Bathroom, Kitchen, Living Room, Other Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 960 Square Feet
Appliances & Utilities
Utilities: Water Separate Meter, Elect Separate MeterAppliances: Washer, Dryer, Dishwasher, Refrigerator, Microwave, Disposal, FreezerDishwasherDisposalDryerMicrowaveRefrigeratorWasher
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
Levels, Entrance, & Accessibility
Accessibility: ParkingFloors: Tile
View
No View
Security
Security: Security Gate, Security Guard

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, DeckFencing: FencedExterior: LightingHas a Private Pool
Parking & Garage
No Attached Garage
Pool
Pool: In GroundPool
Frontage
Not on Waterfront

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: TownhouseArchitecture: Townhouse
Building
Construction Materials: Frame, Hardi Board SidingNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00010120000711

Price & Status

Price
List Price: $1,199,000Price Per Sqft: $1,115/sqft

Active Status

MLS Status: Closed

Location

Direction & Address
City: Key WestCommunity: Presidents Lane (1.0)

Building

Building Area
Building Area: 960 Square Feet

HOA

HOA Fee Includes: Cable TV, Common Area Mnt, Security, OtherHas an HOAHOA Fee: $1,662/Quarterly

Lot Information

Lot Area: 1306.8 sqft

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 617827Attic: Pull Down Stairs
Last check for updates: about 15 hours ago
Listed by Tracy L M Dubensky, (717) 327-9801
Real Estate Management of Key West, LLC
Wade J Meyer, (305) 432-6373
Real Estate Management of Key West, LLC
Bought with: Tracy L M Dubensky, (717) 327-9801, Real Estate Management of Key West, LLC
Co-Buyer's Agent: Wade J Meyer, (305) 432-6373, Real Estate Management of Key West, LLC
Source: FLKMLS, MLS#617827

Price History for 208 Fleming St

DatePriceEventSource
03/02/2026$1,070,000Sold
FLKMLS #617827
01/07/2026$1,199,000ContingentKey West AOR #617827
12/25/2025$1,199,000Listed For SaleKey West AOR #617827
07/01/2025$1,295,000ListingRemovedKey West AOR #612500
03/28/2025$1,295,000PriceChange
FLKMLS #612500
12/03/2024$1,350,000Listed For SaleKey West AOR #612500
11/02/2023ListingRemovedFLKMLS #606159
07/31/2023$1,450,000Listed For SaleKey West AOR #606159
04/30/2019$900,000Sold
FLKMLS #580414
04/25/2019$949,000PendingToActiveAgent Provided
02/28/2019$949,000PendingAgent Provided
02/28/2019$949,000Listed For SaleAgent Provided
01/14/2019$949,000ListingRemovedAgent Provided
05/31/2018$949,000Listed For SaleAgent Provided
08/29/2000$322,500Sold
N/A
03/31/1999$295,000Sold
N/A
07/13/1995$212,300Sold
N/A

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
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Property Tax and Assessment

Year2025
Tax$10,127
Assessment$1,217,226
Home facts updated by county records

Comparable Sales for 208 Fleming St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
201-2 Southard St, Key West, FL
0.10
Townhouse
$1,000,000
02/02/26
2
1.5
960
548 Porter Ln, Key West, FL
0.04
Townhouse
$1,160,000
01/16/26
2
2.5
960
532 Porter Ln, Key West, FL
0.06
Townhouse
$1,075,000
01/21/26
2
1.5
960
237 Southard St, Key West, FL
0.08
Townhouse
$1,075,000
10/17/25
2
1.5
960
528 Porter Ln, Key West, FL
0.05
Townhouse
$1,245,000
04/01/26
2
2.5
960
212 Southard St, Key West, FL
0.11
Townhouse
$1,050,000
05/01/26
2
2.5
960
101 Front St #15, Key West, FL
0.13
Townhouse
$1,220,000
09/30/25
2
2.5
1,216
101 Front St #8, Key West, FL
0.13
Townhouse
$1,345,000
05/20/26
2
2.5
1,216

Nearby homes

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Assigned Schools

These are the assigned schools for 208 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

Truman Annex
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Truman Annex

At least 1 Trulia users voted on each feature.

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's quiet

  • 100 % Say there's wildlife

  • 100 % Say neighbors are friendly

  • 100 % Say it's walkable to restaurants

  • 100 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "It’s a great neighborhood, we absolutely love having the opportunity to be able to live here!! We don’t have young kids so can’t really express things that are impt for them to know!!"
    1
    Flag
  • Langanlady
    "I have a 2 minute commute to the county courthouse. I could walk or bike but I am lazy and drive a car. "
    0
    Flag
  • Maya T.
    "This is the heart of historic Old Town Key West!"
    1
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 208 Fleming St

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Off Market Homes Near 208 Fleming St

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Frequently asked questions about 208 Fleming St

  • What is 208 Fleming St estimated to be worth?
    Trulia's estimated value for 208 Fleming St in Key West, FL is $1,083,000.
  • What is the price history for 208 Fleming St?
    208 Fleming St in Key West, FL last sold for $1,070,000 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 $1.23M. That is up $20.83K from the prior month.
  • Does 208 Fleming St have air conditioning?
    Yes, 208 Fleming St in Key West, FL has air conditioning.
  • Does 208 Fleming St have a pool?
    Yes, 208 Fleming St in Key West, FL has a pool.
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.