216 Fleming St

1,312 Sq. Ft.
$1,410 / Sq. Ft.
1,312
Sq. Ft.
$1,410
per Sq. Ft.

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...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.
  1. Listed by Brenda J Donnelly • Brenda Donnelly Real Estate LLC

Property Details for 216 Fleming Street

Waterfront
None
Waterfront
No
Zoning
HPRD - Hist Planned Redevelopment & Dev Dist
Subdivision
Old Town - Unrecord (1.0)
Vehicle Storage
Assigned Parking
LISTING UPDATED: 01/07/2026 03:37 PM

Property Details for 216 Fleming Street

StatusClosed
MLS #616543
Days on Market58
Taxes$15,531 / year
HOA Fees$1,695 / quarter
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1995
Lot Size0.04 AC / 1,880 SF
CountyMonroe County

Location

Listing Courtesy of Brenda Donnelly Real Estate LLC

Sold By Coastal Collection Real Estate Inc.

Add your commute

Building Information for 216 Fleming Street

Stories2Year Built1995Building Size-Lot Size0.04 AC / 1,880 SF

Payment Calculator

$10,876 per month

30 year fixed, 6.15% Interest

Principal and Interest

$9,017

Property Taxes

$1,294

HOA Dues

$565

The Payment Calculator is for illustrative purposes only.

Property Information for 216 Fleming Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.805112
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Truman Annex
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Neighborhood Feature: Community Pool
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: Condo Doc's: Yes
  • Association Info: 1st Right of Refusal: Yes
  • License Info: Transient Rntl Licns: Yes
  • Fee Includes: Common Area Mnt, Security
  • Furnished: Negotiable
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.04
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: 0.2 PCT ANNUAL CHANC
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 33
  • Document Count: 2
  • Building Style: Above Flood: Unknown
  • Security: Electric Gate, Patrolled Area
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Cable Available, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: In Ground
  • Porch/Balcony: Open Porch/Balcony, Patio
Interior and Exterior Features
Interior Features
  • Floor: Tile, Vinyl
  • Interior Features: Built-in Cabinets, Quartz Countertops, Walk-in Closet(s), Granite Counter Top
  • Pre-Wired: Cable
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Hardi Board Siding
  • Dockage: None
  • Exterior Features: Lighting, Privacy Wall/Fence
  • Windows/Doors: Double Hung Windows, Impact Rstnce Window, Impact Rstnce Doors, French Doors

Property History for 216 Fleming Street

DateEvent & SourcePriceAppreciation
Jan 7, 2026

Sold

FKMLS #616543

$1,850,000
Jan 2, 2026

Sold (Public Record)

Public Record #1927152240

$1,850,000

+1.8% / yr

Jan 2, 2026

Pending

FKMLS #616543

Nov 17, 2025

Backup Contract

FKMLS #616543

Nov 15, 2025

Pending

FKMLS #616543

Sep 18, 2025

Listed (Active)

FKMLS #616543

$1,950,000
Aug 11, 2025

Expired

FKMLS #613648

Feb 11, 2025

Price Change

FKMLS #613648

$2,095,000
Feb 11, 2025

Listed (Active)

FKMLS #613648

$1,995,000
Aug 26, 2021

Sold (Public Record)

Public Record #1471409475

$1,712,500

+21.3% / yr

Aug 26, 2021

Sold

FKMLS #597219

$1,712,500
Aug 14, 2021

Pending

FKMLS #597219

Aug 8, 2021

Backup Contract

FKMLS #597219

Aug 6, 2021

Listed (Active)

FKMLS #597219

$1,750,000
Jun 14, 2019

Sold

FKMLS #584539

$1,115,000
Jun 10, 2019

Pending

FKMLS #584539

Jun 5, 2019

Sold (Public Record)

Public Record #647274434

$1,115,000

+1.0% / yr

Mar 2, 2019

Listed (Active)

FKMLS #584539

$1,199,000
Feb 28, 2019

Expired

FKMLS #581911

Sep 14, 2018

Listed (Active)

FKMLS #581911

$1,199,000
Aug 26, 2016

Sold

FKMLS #122698

$1,082,500
Jul 6, 2016

Sold (Public Record)

Public Record #579496003

$1,082,500

+1.9% / yr

May 27, 2016

Pending

FKMLS #122698

Jan 15, 2016

Listed (Active)

FKMLS #122698

$1,150,000
May 22, 2014

Temp Off Market

FKMLS #119777

May 7, 2014

Listed (Active)

FKMLS #119777

$1,049,000
May 31, 2013

Expired

FKMLS #117679

Feb 8, 2013

Listed (Active)

FKMLS #117679

$995,000
Jun 1, 2009

Expired

FKMLS #109511

Oct 23, 2008

Listed (Active)

FKMLS #109511

$999,000
Jun 26, 2008

Expired

FKMLS #107691

Jan 28, 2008

Listed (Active)

FKMLS #107691

$1,095,000
Feb 5, 2004

Sold (Public Record)

Public Record #130514039

$860,000
Jan 30, 2004

Sold

FKMLS #92843

$860,000
Dec 9, 2003

Pending

FKMLS #92843

Nov 26, 2003

Listed (Active)

FKMLS #92843

$895,000
DateEvent & SourcePrice
01/07/2026

Sold

FKMLS #616543

$1,850,000
01/02/2026

Sold (Public Record)

Public Record #1927152240

$1,850,000

+1.8% / yr

01/02/2026

Pending

FKMLS #616543

11/17/2025

Backup Contract

FKMLS #616543

11/15/2025

Pending

FKMLS #616543

09/18/2025

Listed (Active)

FKMLS #616543

$1,950,000
08/11/2025

Expired

FKMLS #613648

02/11/2025

Price Change

FKMLS #613648

$2,095,000
02/11/2025

Listed (Active)

FKMLS #613648

$1,995,000
08/26/2021

Sold (Public Record)

Public Record #1471409475

$1,712,500

+21.3% / yr

08/26/2021

Sold

FKMLS #597219

$1,712,500
08/14/2021

Pending

FKMLS #597219

08/08/2021

Backup Contract

FKMLS #597219

08/06/2021

Listed (Active)

FKMLS #597219

$1,750,000
06/14/2019

Sold

FKMLS #584539

$1,115,000
06/10/2019

Pending

FKMLS #584539

06/05/2019

Sold (Public Record)

Public Record #647274434

$1,115,000

+1.0% / yr

03/02/2019

Listed (Active)

FKMLS #584539

$1,199,000
02/28/2019

Expired

FKMLS #581911

09/14/2018

Listed (Active)

FKMLS #581911

$1,199,000
08/26/2016

Sold

FKMLS #122698

$1,082,500
07/06/2016

Sold (Public Record)

Public Record #579496003

$1,082,500

+1.9% / yr

05/27/2016

Pending

FKMLS #122698

01/15/2016

Listed (Active)

FKMLS #122698

$1,150,000
05/22/2014

Temp Off Market

FKMLS #119777

05/07/2014

Listed (Active)

FKMLS #119777

$1,049,000
05/31/2013

Expired

FKMLS #117679

02/08/2013

Listed (Active)

FKMLS #117679

$995,000
06/01/2009

Expired

FKMLS #109511

10/23/2008

Listed (Active)

FKMLS #109511

$999,000
06/26/2008

Expired

FKMLS #107691

01/28/2008

Listed (Active)

FKMLS #107691

$1,095,000
02/05/2004

Sold (Public Record)

Public Record #130514039

$860,000
01/30/2004

Sold

FKMLS #92843

$860,000
12/09/2003

Pending

FKMLS #92843

11/26/2003

Listed (Active)

FKMLS #92843

$895,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 216 Fleming Street

Taxable ValueLand$1,293,440Additions$736,067Total$2,029,507
Tax Record2024$16,178 ($1,348 / month)
Home Facts
Beds2Baths2.5Total Finished SqFt1,312 SqFtAbove Grade Finished SqFt1,312 SqFtStories2Lot Size1,880 SqFtStyleSingle Family ResidenceYear Built1995Year Renovated2017CountyMONROEAPN00010120-000715

Schools near 216 Fleming Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - K to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Instruction Program
PublicK to 12

Key West High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of Brenda Donnelly Real Estate LLC

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.