216 Fleming Street, Key West, FL 33040

$1,950,000
Property Type: Residential Bedrooms: 2 Baths: 3 Square Footage: 1,312 Lot Size (sq. ft.): 1,880 Status: Contingent/Show
Current Price: $1,950,000 List Date: 9/18/2025 Last Modified: 12/01/2025

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: $1,950,000 Listing Date: 2025-09-18 List Price: $1,950,000

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

Contingent: Contingent/Show Status: Contingent/Show

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: December - 01 - 2025
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.