216 Fleming Street, Key West, FL 33040
$1,850,000
Property Type:
Residential
Bedrooms:
2
Baths:
3
Square Footage:
1,312
Lot Size (sq. ft.):
1,880
Status:
Closed
Current Price:
$1,850,000
List Date:
9/18/2025
Last Modified:
1/07/2026
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.
More Information MLS# 616543
Contract Information
Listing Board: Key West Association
As is Rght to Inspct: Yes
Current Price: $1,850,000
Listing Date: 2025-09-18
Sold Price: $1,850,000
Location, Tax & Legal
KW Neighborhood: Truman Annex
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: 0.2 PCT ANNUAL CHANC
Alternate Key #: 8862415
Zoning: HPRD - Hist Planned Redevelopment & Dev Dist
Deed Restrictions: Unknown
Taxes: 15531
Tax Year: 2024
Pub Sewer HkUp: Yes
Street #: 216
Street Name: Fleming
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: No
Control Depth: 0
Lot SqFt: 1880
Pool: Yes
Lot Sqft Source: Property Data Card
Total Units: 0
Acres: 0.04
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Style: Single Family
Year Built: 1995
Living Apx SqFt: 1312
Total Bedrooms: 2
Full Baths: 2
Half Baths: 1
Total Baths: 3
Remarks & Misc
Remarks – Consumer: 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.
Association Info
Mandatory Home Owners Asc: Yes
1st Right of Refusal: Yes
Condo Doc's: Yes
Association Fee $: 1695
Assoc/Mnt Fee Per: Quarterly
License Info
Transient Rntl Licns: Yes
Fee Includes
Common Area Mnt: 1
Security: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Tile: 1
Vinyl: 1
Neighborhood Feature
Community Pool: 1
Interior Features
Built-in Cabinets: 1
Granite Counter Top: 1
Quartz Countertops: 1
Walk-in Closet(s): 1
Building Style
Above Flood: Unknown
Stories: 2 Stories
Windows/Doors
Double Hung Windows: 1
French Doors: 1
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Car(s): 1
Assigned Parking: 1
Security
Electric Gate: 1
Patrolled Area: 1
Construction
Hardi Board Siding: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Negotiable: 1
Terms
Cash: 1
Conventional: 1
Utilities
Cable Available: 1
FKAA: 1
Municipal Sewer: 1
Porch/Balcony
Open Porch/Balcony: 1
Patio: 1
Title
Negotiable: 1
Exterior Features
Lighting: 1
Privacy Wall/Fence: 1
Pool Info
In Ground: 1
Pre-Wired
Cable: 1
Roof
Metal Roof: 1
Financial Status
Standard Sale: Yes
Status Change Info
Sold Date: 2026-01-07
Sold Price: $1,850,000
Status: Closed
Property Features
Fee Includes: Common Area Mnt; Security
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Vehicle Storage: Assigned Parking
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Utilities: Cable Available; FKAA; Municipal Sewer
Interior Features: Built-in Cabinets; Granite Counter Top; Quartz Countertops; Walk-in Closet(s)
Pre-Wired: Cable
Appliances: Dishwasher; Dryer; Microwave; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Lighting; Privacy Wall/Fence
Pool Info: In Ground
Construction: Hardi Board Siding
Floor: Tile; Vinyl
Roof: Metal Roof
Neighborhood Feature: Community Pool
Security: Electric Gate; Patrolled Area
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Title: Negotiable
Listing Office:
Brenda Donnelly Real Estate LLC
Last Updated: January - 07 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
