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

$1,095,100

Trulia Estimate
  • 2 Beds
  • 2.5 Baths
  • 960 sqft

208 Fleming St, Key West, FL 33040

Truman Annex
Est. Refi. Payment $6,646/mo*
Refinance Your Home
Currently Off Market - Sold Mar 2, 2026 for $1,070,000 (11% below list price)

Home Value

Trulia Estimate
$1.09M
Since last month
Increased$10K (+0.9%)
Since last year
Decreased$117K (-9.6%)
Since last sale
Increased$25K (+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 +29% in the last 10 years
MonthEstimated value
2026
September 2026$1.1M
August 2026$1.08M
July 2026$1.08M
June 2026$1.07M
May 2026$1.06M
April 2026$1.07M
March 2026$1.07M
February 2026$1.16M
January 2026$1.15M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
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 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
548 Porter Ln, Key West, FL 33040
0.04
$1,160,000
2
2.5
960
Recently Sold
214 Fleming St, Key West, FL 33040
0.01
$1,937,000
2
2.5
1,312
Off Market
212 Fleming St, Key West, FL 33040
0.01
$1,650,000
2
2.5
1,420
Recently Sold
216 Fleming St, Key West, FL 33040
0.01
$1,850,000
2
2.5
1,312
Recently Sold
528 Porter Ln, Key West, FL 33040
0.05
$1,245,000
2
2.5
960
Recently Sold
530 Porter Ln, Key West, FL 33040
0.05
$1,231,100
2
1.5
960
Off Market
532 Porter Ln, Key West, FL 33040
0.06
$1,075,000
2
1.5
960
Recently Sold
273 Southard St, Key West, FL 33040
0.07
$1,347,600
2
1.5
960
Off Market
564 Porter Ln, Key West, FL 33040
0.07
$1,350,000
2
2.5
960
For Sale
208 Fleming St #0, Key West, FL 33040
0.00
$830,300
2
2.5
-
Off Market
510 Porter Ln, Key West, FL 33040
0.04
$1,301,200
2
2.5
960
Off Market

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

Townhouse
Built in 1995
960 sqft
$1,115/sqft
HOA $554/mo

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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,095,100, with a rent estimate of $5,467/month.
Last check for updates: about 22 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

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

Price and Tax history

DateEventPrice
Mar 2, 2026
Source: FLKMLS #617827
Sold
$1,070,000
Jan 7, 2026
Source: Key West AOR #617827
Contingent
$1,199,000
Dec 25, 2025
Source: Key West AOR #617827
Listed For Sale
$1,199,000
Jul 1, 2025
Source: Key West AOR #612500
ListingRemoved
$1,295,000
Mar 28, 2025
Source: FLKMLS #612500
PriceChange
$1,295,000
Price decreased by 4%

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

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

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 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 $1,095,100.
  • 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 $1.14M. That is down $143K 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.

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