208 Fleming St

$1,199,000
Price
2
Beds
960 Sq. Ft.
$1,249 / Sq. Ft.
960
Sq. Ft.
$1,249
per Sq. Ft.

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...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.
  1. Listed by Tracy L M Dubensky • Real Estate Management of Key West, LLC
  2. Listed by Wade J Meyer • Real Estate Management of Key West, LLC

Property Details for 208 Fleming Street

Waterfront
None
Waterfront
No
Zoning
HPRD - Hist Planned Redevelopment & Dev Dist
Subdivision
Presidents Lane (1.0)
Building Style
Townhouse
Vehicle Storage
Assigned Parking
Pets
Other See Remarks
LISTING UPDATED: 12/28/2025 01:42 PM

Property Details for 208 Fleming Street

StatusActive
MLS #617827
Days on Market4
Taxes$10,127 / year
HOA Fees$1,662 / quarter
Condo/Co-op Fees-
Compass TypeTownhouse
MLS TypeResidential / Townhouse
Year Built1995
Lot Size0.03 AC / 1,479 SF
CountyMonroe County

Location

Listing Courtesy of Real Estate Management of Key West, LLC
Add your commute

Building Information for 208 Fleming Street

Stories2Residences-Year Built1995Lot Size0.03 AC / 1,479 SF

Payment Calculator

$7,323 per month

30 year fixed, 6.28% Interest

Principal and Interest

$5,925

Property Taxes

$844

HOA Dues

$554

The Payment Calculator is for illustrative purposes only.

Property Information for 208 Fleming Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 01 - Key West
  • Absolute Longitude: 81.805291
  • Control Depth: 0
  • Off Shore Island: No
  • Listing Board: Key West Association
  • Side: Ocean
  • KW Neighborhood: Truman Annex
  • Mile Marker: 0.0
  • Marathon Neighborhood: N/A
  • Accessibility Feat: Parking
  • 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: # of City License: 1
  • License Info: # of County License: 1
  • Fee Includes: Cable, Other, Security, Common Area Mnt
  • Furnished: Negotiable
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.03
  • SqFt Remarks: 2 Story
  • Parcel #: 00010120-000711
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 2 SQR 52 (A/K/A UNIT 1 FLEMING COURT) OR1361-1554/57 OR1568-721/722 OR1650-1725/27 OR2961-2288
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Property Data Card
  • Flood Zone: 0.2 PCT ANNUAL CHANC
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 33
  • Document Count: 0
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
  • Security: Electric Gate, Patrolled Area
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Water Separate Meter, Elect Separate Meter, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Handicap Access: No
  • Pool Info: Heated: Yes
  • Pool Info: In Ground
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile
  • GF-Interior Features: Programmable Thermst, LED Lighting, Low Flow Toilets
  • Interior Features: Drapes/Blinds Incl, Bar, Pull Down Stairs, Built-in Cabinets, Smoke Alarms
  • Pre-Wired: Cable
  • Appliances: Washer, Freezer, Disposal, Microwave, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: Frame, Hardi Board Siding
  • Dockage: None
  • Exterior Features: Fencing, Lighting
  • Windows/Doors: Sash/Screen Window, Impact Rstnce Doors, French Doors
Room Information
Room 1 Information
  • Room Type: Living Room
  • Level: M
  • Remarks: First Floor
Room 2 Information
  • Room Type: Kitchen
  • Level: M
  • Remarks: First Floor
Room 3 Information
  • Room Type: Half Bathroom
  • Level: M
  • Remarks: First Floor
Room 4 Information
  • Room Type: Bedroom 1
  • Level: 2
  • Remarks: Second Floor
Room 5 Information
  • Room Type: Full Bathroom
  • Level: 2
  • Remarks: Second Floor
Room 6 Information
  • Room Type: Bedroom 2
  • Level: 2
  • Remarks: Second Floor
Room 7 Information
  • Room Type: Full Bathroom
  • Level: 2
  • Remarks: Second Floor
Room 8 Information
  • Room Type: Other Room
  • Level: 2
  • Remarks: Laundry on Second Floor

Property History for 208 Fleming Street

DateEvent & SourcePriceAppreciation
Dec 25, 2025

Listed (Active)

FKMLS #617827

$1,199,000
Jun 30, 2025

Expired

FKMLS #612500

Dec 3, 2024

Price Change

FKMLS #612500

$1,350,000
Dec 3, 2024

Listed (Active)

FKMLS #612500

$1,295,000
Nov 1, 2023

Expired

FKMLS #606159

Jul 31, 2023

Listed (Active)

FKMLS #606159

$1,450,000
Apr 30, 2019

Sold

FKMLS #580414

$900,000
Apr 29, 2019

Sold (Public Record)

Public Record #645135439

$900,000
Feb 28, 2019

Pending

FKMLS #580414

Jun 1, 2018

Listed (Active)

FKMLS #580414

$949,000
Aug 24, 2000

Sold

FKMLS #90327

$322,500
Jun 20, 2000

Pending

FKMLS #90327

May 18, 2000

Listed (Active)

FKMLS #90327

$329,000
DateEvent & SourcePrice
12/25/2025

Listed (Active)

FKMLS #617827

$1,199,000
06/30/2025

Expired

FKMLS #612500

12/03/2024

Price Change

FKMLS #612500

$1,350,000
12/03/2024

Listed (Active)

FKMLS #612500

$1,295,000
11/01/2023

Expired

FKMLS #606159

07/31/2023

Listed (Active)

FKMLS #606159

$1,450,000
04/30/2019

Sold

FKMLS #580414

$900,000
04/29/2019

Sold (Public Record)

Public Record #645135439

$900,000
02/28/2019

Pending

FKMLS #580414

06/01/2018

Listed (Active)

FKMLS #580414

$949,000
08/24/2000

Sold

FKMLS #90327

$322,500
06/20/2000

Pending

FKMLS #90327

05/18/2000

Listed (Active)

FKMLS #90327

$329,000

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

Public Records for 208 Fleming Street

Taxable ValueLand$905,148Additions$312,078Total$1,217,226
Tax Record2024$9,404 ($784 / month)
Home Facts
Beds2Baths1.5Total Finished SqFt960 SqFtAbove Grade Finished SqFt960 SqFtStories2Lot Size1,479 SqFtStyleSingle Family ResidenceYear Built1995Year Renovated2015CountyMONROEAPN00010120-000711

Schools near 208 Fleming Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 2 to 12
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Franchise
Public2 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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208 Fleming Street is a townhouse for sale in Key West, FL 33040. This property was listed for sale on December 25, 2025 by Real Estate Management of Key West, LLC, it's currently listed at $1,199,000. It has been on the market for a total of 4 days and was last sold on April 30, 2019. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Franchise and Key West High School. 208 Fleming Street is a 2-bed, 3-bath, 960 sqft townhouse built in 1995.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Real Estate Management of Key West, 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.