1006-1008 Fleming St

3,336 Sq. Ft.
$1,437 / Sq. Ft.
3,336
Sq. Ft.
$1,437
per Sq. Ft.

Description

Motivated 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...Motivated 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.
  1. Listed by Terri Spottswood • Truman & Co. (KW) • 305-587-3407
  2. Listed by The Spottswood Team • Truman & Co. (KW)

Property Details for 1006-1008 Fleming Street

Waterfront
None
Waterfront
No
Zoning
HMDR - Historic Medium Density Residential
Subdivision
Old Town - Unlisted (1.0)
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 04/26/2026 02:35 PM

Property Details for 1006-1008 Fleming Street

StatusPending
MLS #617020
Days on Market184
Taxes$24,447 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1938
Lot Size0.21 AC / 9,180 SF
CountyMonroe County

Location

Listing Courtesy of Truman & Co. (KW)
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Building Information for 1006-1008 Fleming Street

Stories1Year Built1938Building Size-Lot Size0.21 AC / 9,180 SF

Payment Calculator

$25,931 per month

30 year fixed, 6.36% Interest

Principal and Interest

$23,894

Property Taxes

$2,037

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 1006-1008 Fleming Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.796591
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.21
  • SqFt Remarks: Buyer to verify square footage
  • Parcel #: 00007460-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 3 SQR 45 G36-487 OR80-390 OR459-595 OR1479-1601 OR1740-1862 OR2406-1715 OR2547-1508 OR2692-262 OR2724-2495 OR
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 48
  • Document Count: 2
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
Utilities
  • Utilities: FKAA, Whole House Generatr, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Other: Chilled
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Concrete, Salt Water
  • Porch/Balcony: Deck, Patio
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Whirlpool Bath Tub, Entrance Foyer, Cathedral Ceilings, Wet Bar
  • Pre-Wired: Surround Sound
  • Appliances: Washer, Wine Cooler, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Shutters: Bahama
  • Construction: Frame
  • Dockage: None
  • Exterior Features: Fencing, Water Display, Outdoor Shower, Lanai, Lighting, Detached Guest Qtrs
  • Windows/Doors: Glass Doors, Impact Rstnce Doors, Other Windows/Doors
Room Information
  • Specialty Rooms: Guest/Servant Qtrs: Legal

Property History for 1006-1008 Fleming Street

DateEvent & SourcePriceAppreciation
Apr 26, 2026

Pending

FKMLS #617020

Apr 11, 2026

Backup Contract

FKMLS #617020

Oct 24, 2025

Price Change

FKMLS #617020

$5,595,000
DateEvent & SourcePrice
04/26/2026

Pending

FKMLS #617020

04/11/2026

Backup Contract

FKMLS #617020

10/24/2025

Price Change

FKMLS #617020

$5,595,000

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

Schools near 1006-1008 Fleming Street

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

Monroe Virtual Instruction Program
PublicK 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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Listing Courtesy of Truman & Co. (KW)

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.