About 208 Fleming Street
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.
Features of 208 Fleming Street
| MLS® # | 617827 |
|---|---|
| Price | $1,199,000 |
| Bedrooms | 2 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 960 |
| Acres | 0.03 |
| Year Built | 1995 |
| Type | Residential |
| Sub-Type | Townhouse |
| Style | Townhouse |
| Status | Contingent |
Community Information
| Address | 208 Fleming Street |
|---|---|
| Area | 01 - Key West |
| Subdivision | Presidents Lane (1.0) |
| City | KEY WEST |
| County | Monroe |
| State | FL |
| Zip Code | 33040 |
Amenities
| Amenities | Community Pool |
|---|---|
| Utilities | FKAA, Water Separate Meter, Elect Separate Meter, Buyer to Verify, Municipal Sewer |
| Parking | Assigned Parking |
| View | No Waterview |
| Is Waterfront | No |
| Waterfront | None |
| Has Pool | Yes |
| Pool | In Ground |
Interior
| Interior Features | Drapes/Blinds Incl, Bar, Pull Down Stairs, Built-in Cabinets, Smoke Alarms |
|---|---|
| Appliances | Washer, Freezer, Disposal, Microwave, Refrigerator, Dishwasher, Dryer |
| Heating | Electric |
| Cooling | Central Air, Ceiling Fans(s) |
| Fireplace | No |
| Stories | 2 Stories |
Exterior
| Exterior Features | Fencing, Lighting |
|---|---|
| Lot Description | Less Than 1/4 Acre |
| Windows | Sash/Screen Window, Impact Rstnce Doors, French Doors |
| Roof | Metal Roof |
| Construction | Frame, Hardi Board Siding |
Additional Information
| Date Listed | December 25th, 2025 |
|---|---|
| Days on Market | 24 |
| Zoning | HPRD - Hist Planned Redevelopment & Dev Dist |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 1662.00 |
| HOA Fees Freq. | Quarterly |
Listing Details
| Agent | Tracy L M Dubensky |
|---|---|
| Office | Real Estate Management of Key West, LLC |