208 Fleming St, Key West, FL 33040
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 $5,993/mo*
Refinance Your Home

$1,070,000

Last Sold: Mar 2, 2026
11% below list $1.2M
$1,115/sqft
Est. Refi. Payment $5,993/mo*
Refinance Your Home
2 Beds
2.5 Baths
960 sqft

Homes for sale near 208 Fleming St

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Owner is a licensed real estate agent and listing agent.Truman Annex End Unit Featuring Secluded Backyard RetreatDiscover 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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from March 03, 2026

Home Highlights

Parking
No Info
Outdoor
Porch, Deck, Pool
View
No Info
HOA
$554/Monthly
Price/Sqft
$1,115/sqft
Listed
135 days ago

Home Details for 208 Fleming St

Interior Features

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: FKAA, Buyer to Verify, Cable ConnectedAppliances: Washer, Freezer, Disposal, Microwave, Refrigerator, Dishwasher, DryerDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: ElectricHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Electric
Gas & Electric
Electric: Elect Separate Meter
Windows, Doors, Floors & Walls
Window: Drapes/Blinds Incl, Sash/Screen WindowDoor: Impact Rstnce Doors, French DoorsFlooring: Tile
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: No, ParkingFloors: Tile
Security
Security: Smoke Detector(s), Electric Gate, Patrolled Area

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, DeckFencing: FencedExterior: LightingHas a Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageNo Open ParkingParking: Assigned
Pool
Pool: Heated, In GroundPool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Townhouse, Residential - Condo/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)

Community

Community Features: Pool

HOA

HOA Fee Includes: Cable TV, Other, Security, Maintenance GroundsAssociation for this Listing: Key West AssociationHas an HOAHOA Fee: $1,662/Quarterly

Lot Information

Lot Area: 1306.8 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Energy

Energy Efficiency Features: Thermostat, Lighting

Miscellaneous

Mls Number: 617827Attic: Pull Down StairsWater View: None

Additional Information

Pool
Last check for updates: about 6 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
Originating MLS: Key West Association
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
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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
0.11
Townhouse
$1,220,000
09/30/25
2
2.5
1,216

Assigned Schools

These are the assigned schools for 208 Fleming St.
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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

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 Board of Realtors.

Homes for rent near 208 Fleming St

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Off Market Homes Near 208 Fleming St

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Explore by feature

208 Fleming St, Key West, FL 33040 is a 2 bedroom, 3 bathroom, 960 sqft townhouse built in 1995. 208 Fleming St is located in Truman Annex, Key West. This property is not currently available for sale. 208 Fleming St was last sold on Mar 2, 2026 for $1,070,000 (11% lower than the asking price of $1,199,000). The current Trulia Estimate for 208 Fleming St is $1,066,700.