Seller's Agent in 2026
Terri Spottswood
Truman & Co. (KW)
(305) 587-3407
89 in this area
224 Total Sales
1006 Fleming St Key West, FL 33040
Old Town Neighborhood
4
Beds
5
Baths
3,336
Sq Ft
9,148
Sq Ft Lot Lot
About This Home
As of May 2026MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and four-and-a-half baths. The main house welcomes you with an open floor plan, soaring ceilings, and a light-filled living and dining area. A dramatic wall of glass featuring new 40-foot impact-rated Nana doors and skylights opens to reveal lush tropical gardens and a resurfaced PebbleTec pool with a cascading waterfall. The heated, chilled, and saltwater-converted pool includes new tiled coping and a remote-controlled waterproof outdoor TV for movies or game nights under the stars. The gourmet kitchen features top-of-the-line appliances, Italian cabinetry, Silestone countertops, and a new espresso bar with wine cooler and beverage center. Real stone and hardwood floors run throughout, including two spacious bedrooms, each with an en-suite bath. The primary suite offers French doors and a spa-like bathroom with premium fixtures. The front guest house provides flexible living space currently a den or ''man cave'' with a bedroom, pantry kitchen, and a stunning bath clad in rare iridescent Czechoslovakian green glass from the 1950s. The rear guest cottage, tucked at the back of the property, includes its own sitting & dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower & a private porch overlooking the pool & garden. Additional upgrades include a whole-house generator, new exterior lighting and irrigation by Blue Island, a state-of-the-art sound system, hurricane and plantation shutters, fresh exterior paint, and lush landscaping. 2 off-street parking spaces complete this remarkable Old Town retreat.
Last Agent to Sell the Property
Truman & Co. (KW) Brokerage Phone: 305-587-3407 License #161619 Listed on: 10/24/2025
Co-Listed By
The Spottswood Team
Truman & Co. (KW) Brokerage Phone: 305-587-3407
Home Details
Home Type
- Single Family
Year Built
- 1938
Interior Spaces
- Vaulted Ceiling
- Plantation Shutters
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Home Values in the Area
Average Home Value in this Area
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 05/26/2026 05/26/26 | Sold | $4,425,000 | -7.7% | $1,326 / Sq Ft | |
| 03/30/2026 03/30/26 | Price Changed | $4,795,000 | -2.1% | $1,437 / Sq Ft | |
| 03/17/2026 03/17/26 | Price Changed | $4,898,000 | -2.0% | $1,468 / Sq Ft | |
| 01/30/2026 01/30/26 | Price Changed | $4,998,000 | -6.5% | $1,498 / Sq Ft | |
| 01/28/2026 01/28/26 | Price Changed | $5,345,000 | -0.9% | $1,602 / Sq Ft | |
| 12/30/2025 12/30/25 | Price Changed | $5,395,000 | -1.8% | $1,617 / Sq Ft | |
| 12/01/2025 12/01/25 | Price Changed | $5,495,000 | -1.8% | $1,647 / Sq Ft | |
| 10/24/2025 10/24/25 | For Sale | $5,595,000 | +11.9% | $1,677 / Sq Ft | |
| 02/23/2024 02/23/24 | Sold | $5,000,000 | -13.8% | $1,513 / Sq Ft | View Prior Sale |
| 02/15/2024 02/15/24 | Pending | -- | -- | -- | |
| 12/27/2023 12/27/23 | For Sale | $5,800,000 | +87.1% | $1,755 / Sq Ft | |
| 02/28/2018 02/28/18 | Sold | $3,100,000 | -13.8% | $911 / Sq Ft | View Prior Sale |
| 01/17/2018 01/17/18 | Pending | -- | -- | -- | |
| 10/19/2017 10/19/17 | For Sale | $3,595,000 | +30.7% | $1,056 / Sq Ft | |
| 02/13/2015 02/13/15 | Sold | $2,750,000 | -7.6% | $808 / Sq Ft | View Prior Sale |
| 01/05/2015 01/05/15 | Pending | -- | -- | -- | |
| 01/06/2014 01/06/14 | For Sale | $2,975,000 | -- | $874 / Sq Ft |
Source: Key West Association of REALTORS®
Agents Affiliated with this Home
-
Terri Spottswood
-
T
Seller Co-Listing Agent in 2026
The Spottswood Team
Truman & Co. (KW)
-
Suzanne Moore
Buyer's Agent in 2026
Suzanne Moore
Suzanne Moore Real Estate
(305) 797-0699
41 in this area
119 Total Sales
-
C
Seller's Agent in 2024
Chris Remmert
Century 21 Executive Team
-
J
Buyer's Agent in 2024
Jessica Prescott
Century 21 Schwartz Realty (KW)
-
Debora Bent
D
Buyer Co-Listing Agent in 2024
Debora Bent
Coastal Collection Real Estate
(305) 393-3872
2 in this area
5 Total Sales
Map
Source: Key West Association of REALTORS®
MLS Number: 617020
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