216 Fleming St, Key West, FL 33040
SOLD
JAN 7, 2026

216 Fleming St
Key West, FL 33040

Truman Annex
  • 2 Beds
  • 2.5 Baths
  • 1,312 sqft

$1,850,000

Last Sold: Jan 7, 2026
5% below list $1.95M
$1,410/sqft
Est. Refi. Payment $10,308/mo*
Refinance Your Home

$1,850,000

Last Sold: Jan 7, 2026
5% below list $1.95M
$1,410/sqft
Est. Refi. Payment $10,308/mo*
Refinance Your Home
2 Beds
2.5 Baths
1,312 sqft

Homes for sale near 216 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

Located in the coveted gated community of Truman Annex, this impeccably styled 2-bedroom, 2.5-bath single family home blends refined coastal elegance with effortless Old Town living, just steps from Duval Street and the Truman Waterfront. A private entrance opens to a turnkey interior highlighted by Serena & Lily accents and an airy open floor plan. The chef's kitchen boasts Bosch stainless-steel appliances, an induction range, farmhouse sink, and a waterfall-edge peninsula with bar seating. Flowing seamlessly from the kitchen, the dining and living areas offer striking furnishings, a large wall-mounted TV, and ample space for entertaining. A convenient first floor powder room completes the main level. Two sets of French doors lead to a fully fenced patio designed for al-fresco dining and relaxation. There is a small front and side yard, perfect for growing flowers, herbs or whatever makes your green thumb happy. Both upstairs bedrooms feature king beds and serene finishes. The primary suite opens through French doors to a covered balcony to capture the island breeze, while the spa-style ensuite offers dual sinks, waterfall faucets, and a beautifully tiled walk-in shower. The second bedroom includes generous closet space and access to a stylish hall bath with a walk-in shower.Enjoy a private paver patio with seating and a grill, or stroll over to the heated community pool with lounge chairs, shaded tables, and restrooms. A dedicated parking space sits just steps from the front door. Only blocks from world-class dining, shopping, and entertainment. This property is offered fully furnished, holds a Truman Annex transient license, and includes future rental bookings through the end of 2025. Ideal as a full-time residence, vacation getaway, or investment property.
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 January 07, 2026

Home Highlights

Parking
1 Parking Spaces
Outdoor
Porch, Patio, Pool
View
No Info
HOA
$565/Monthly
Price/Sqft
$1,410/sqft
Listed
180+ days ago

Home Details for 216 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: 1312 Square Feet
Appliances & Utilities
Utilities: FKAA, Cable Available, Cable ConnectedAppliances: Washer, Stainless Steel Appliance(s), Microwave, Range, Refrigerator, Dishwasher, DryerDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Ceiling Fans(s)
Windows, Doors, Floors & Walls
Window: Double Hung Windows, Impact Rstnce WindowDoor: Impact Rstnce Doors, French DoorsFlooring: Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Tile, Vinyl
Security
Security: Electric Gate, Patrolled Area

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, PatioFencing: PrivacyExterior: LightingHas a Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageNo Open ParkingParking Spaces: 1Parking: Assigned
Pool
Pool: 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: Single Family Residence
Building
Construction Materials: Hardi Board Siding

Price & Status

Price
List Price: $1,950,000Price Per Sqft: $1,410/sqft

Active Status

MLS Status: Closed

Location

Direction & Address
City: Key WestCommunity: Old Town - Unrecord (1.0)

Community

Community Features: Pool

HOA

HOA Fee Includes: Maintenance Grounds, SecurityAssociation for this Listing: Key West AssociationHas an HOAHOA Fee: $1,695/Quarterly

Lot Information

Lot Area: 1742.4 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 616543Water View: None

Additional Information

Pool
Last check for updates: about 6 hours ago
Listed by Brenda J Donnelly, (305) 304-1116
Brenda Donnelly Real Estate LLC
Bought with: Tommy Mack, (305) 731-7910, Coastal Collection Real Estate Inc.
Originating MLS: Key West Association
Source: FLKMLS, MLS#616543

Price History for 216 Fleming St

DatePriceEventSource
01/07/2026$1,850,000Sold
FLKMLS #616543
01/02/2026$1,950,000PendingFLKMLS #616543
11/17/2025$1,950,000ContingentKey West AOR #616543
09/18/2025$1,950,000Listed For SaleKey West AOR #616543
08/12/2025$1,995,000ListingRemovedFLKMLS #613648
07/15/2025$1,995,000PriceChange
FLKMLS #613648
02/11/2025$2,095,000Listed For SaleFLKMLS #613648
08/26/2021$1,712,500Sold
FLKMLS #597219
08/08/2021$1,750,000ContingentFLKMLS #597219
08/06/2021$1,750,000Listed For SaleFLKMLS #597219
06/14/2019$1,115,000Sold
N/A
06/07/2019$1,199,000PendingAgent Provided
06/05/2019$1,199,000PendingToActiveAgent Provided
05/27/2019$1,199,000PendingAgent Provided
01/21/2019$1,199,000PriceChange
Agent Provided
10/17/2018$1,279,000PriceChange
Agent Provided
09/15/2018$1,339,000Listed For SaleAgent Provided
08/26/2016$1,082,500Sold
N/A
08/09/2016$1,150,000PendingToActiveAgent Provided
05/31/2016$1,150,000PendingAgent Provided
01/15/2016$1,150,000Listed For SaleAgent Provided
05/22/2014$1,049,000ListingRemovedAgent Provided
05/08/2014$1,049,000Listed For SaleAgent Provided
06/01/2013$995,000ListingRemovedAgent Provided
02/09/2013$995,000Listed For SaleAgent Provided
02/05/2004$860,000Sold
N/A
03/20/1995$300,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$17,257
Assessment$2,029,507
Home facts updated by county records

Comparable Sales for 216 Fleming St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
214 Fleming St, Key West, FL
0.01
Single-Family Home
$1,800,000
07/08/25
2
2.5
1,312
212 Fleming St, Key West, FL
0.01
Single-Family Home
$1,650,000
04/15/26
2
2.5
1,420
618 Mickens Ln, Key West, FL
0.13
Single-Family Home
$800,000
12/09/25
2
2.5
1,056
612 Mickens Ln, Key West, FL
0.12
Single-Family Home
$979,000
04/09/26
2
1.5
823
715 Chapman Ln, Key West, FL
0.21
Single-Family Home
$1,700,000
10/28/25
1
2
1,212
515 Petronia St, Key West, FL
0.31
Single-Family Home
$1,400,000
03/31/26
2
2
1,200
322 Southard St, Key West, FL
0.11
Single-Family Home
$1,695,000
04/10/26
3
3
1,553

Assigned Schools

These are the assigned schools for 216 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 216 Fleming St

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Off Market Homes Near 216 Fleming St

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Explore by feature

216 Fleming St, Key West, FL 33040 is a 2 bedroom, 3 bathroom, 1,312 sqft single-family home built in 1995. 216 Fleming St is located in Truman Annex, Key West. This property is not currently available for sale. 216 Fleming St was last sold on Jan 7, 2026 for $1,850,000 (5% lower than the asking price of $1,950,000). The current Trulia Estimate for 216 Fleming St is $1,837,800.