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

$1,900,000

Trulia Estimate
  • 2 Beds
  • 2.5 Baths
  • 1,312 sqft

216 Fleming St, Key West, FL 33040

Truman Annex
Est. Refi. Payment $11,475/mo*
Refinance Your Home
Currently Off Market - Sold Jan 7, 2026 for $1,850,000 (5% below list price)

Home Value

Trulia Estimate
$1.9M
Since last month
Increased$21K (+1.1%)
Since last year
Increased$29K (+1.5%)
Since last sale
Increased$50K (+2.7%)
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 +74% in the last 10 years
MonthEstimated value
2026
September 2026$1.9M
August 2026$1.88M
July 2026$1.87M
June 2026$1.85M
May 2026$1.83M
April 2026$1.84M
March 2026$1.84M
February 2026$1.84M
January 2026$1.85M
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
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
4 Aronovitz Ln, Key West, FL
0.18
Single-Family Home
$1,275,000
07/24/26
3
3
1,748
515 Petronia St, Key West, FL
0.34
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
306 Truman Ave, Key West, FL
0.41
Single-Family Home
$1,750,000
02/26/26
3
2
1,036
312 William St, Key West, FL
0.46
Single-Family Home
$1,650,000
10/30/25
3
2
1,376

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
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
0.05
$1,075,000
2
1.5
960
Recently Sold
273 Southard St, Key West, FL 33040
0.06
$1,347,600
2
1.5
960
Off Market
564 Porter Ln, Key West, FL 33040
0.06
$1,350,000
2
2.5
960
For Sale
208 Fleming St, Key West, FL 33040
0.01
$1,070,000
2
2.5
960
Recently Sold
208 Fleming St #0, Key West, FL 33040
0.01
$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 216 Fleming St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1995
1,312 sqft
$1,410/sqft
HOA $565/mo

About this House

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.
216 Fleming St, Key West, FL 33040 is a 2 bedroom, 3 bathroom, 1,312 sqft single-family home in Truman Annex, built in 1995. It last sold for $1,850,000 on Jan 7, 2026 (5% below the $1,950,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,900,000, with a rent estimate of $5,738/month.
Last check for updates: about 11 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.
Source: FLKMLS, MLS#616543

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: Cable AvailableAppliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Microwave, Stainless Steel Appliance(s)DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Ceiling Fans(s)
Windows, Doors, Floors & Walls
Flooring: Tile, Vinyl
Levels, Entrance, & Accessibility
Floors: Tile, Vinyl
View
No View
Security
Security: Security Gate, Security Guard

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, PatioFencing: PrivacyExterior: 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: 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)

Building

Building Area
Building Area: 1312 Square Feet

HOA

HOA Fee Includes: Common Area Mnt, SecurityHas an HOAHOA Fee: $1,695/Quarterly

Lot Information

Lot Area: 1742.4 sqft

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 616543

Price and Tax history

DateEventPrice
Jan 7, 2026
Source: FLKMLS #616543
Sold
$1,850,000
Jan 2, 2026
Source: FLKMLS #616543
Pending
$1,950,000
Nov 17, 2025
Source: Key West AOR #616543
Contingent
$1,950,000
Sep 18, 2025
Source: Key West AOR #616543
Listed For Sale
$1,950,000
Aug 12, 2025
Source: FLKMLS #613648
ListingRemoved
$1,995,000

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 216 Fleming St

  • What is 216 Fleming St estimated to be worth?
    Trulia's estimated value for 216 Fleming St in Key West, FL is $1,900,000.
  • What is the price history for 216 Fleming St?
    216 Fleming St in Key West, FL last sold for $1,850,000 in January 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 216 Fleming St have air conditioning?
    Yes, 216 Fleming St in Key West, FL has air conditioning.
  • Does 216 Fleming St have a pool?
    Yes, 216 Fleming St in Key West, FL has a pool.

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