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Property Description

Exceptional Old Town compound with pool, gardens, and two 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 and gate, the estate includes a grand main residence and two fully equipped guest houses, offering 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 and dining areas, vaulted ceilings, a unique bath with outdoor shower, and a private porch overlooking the pool and 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. Two off-street parking spaces on Fleming Street complete this remarkable Old Town retreat.

Overview

Property Status
For Sale
Lot Size
9,180 Sq.Ft.
MLS ID
617020
Property Type
Residential
Year Built
1938

Features & Amenities

Total Area
3,336 Sq.Ft.
Neighborhood
Old Town
Water Frontage
None
View Description
No Waterview
Stories
1
Utilites
FKAA, Whole House Generatr, Buyer to Verify, Municipal Sewer
Pool
In Ground, Concrete, Salt Water
Roof
Metal Roof
Parking
Off Street Parking
Heat Type
Central
Air Conditioning
Central Air, Ceiling Fans(s)
Other Interior Features
Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Whirlpool Bath Tub, Entrance Foyer, Cathedral Ceilings, Wet Bar, Surround Sound, Bahama, Glass Doors, Impact Rstnce Doors, Other Windows/Doors
HOA Amenities
None
Other Exterior Features
Fencing, Water Display, Outdoor Shower, Lanai, Lighting, Detached Guest Qtrs
Sales Price
$5,595,000
Real Estate Tax
$24,447/yr
Zoning
HMDR - Historic Medium Density Residential

Downloads

1008 Fleming Street

Schedule a Tour

We would love to help you see this beautiful home! As a full-service brokerage, we can help you tour. Please submit an offer, and answer questions about the buying process.

Enter a valid email

Thank you

for your interest in 1008 Fleming Street, Key West, FL 33040

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Property Description

Exceptional Old Town compound with pool, gardens, and two 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 and gate, the estate includes a grand main residence and two fully equipped guest houses, offering 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 and dining areas, vaulted ceilings, a unique bath with outdoor shower, and a private porch overlooking the pool and 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. Two off-street parking spaces on Fleming Street complete this remarkable Old Town retreat.

Overview

Property Status
For Sale
Lot Size
9,180 Sq.Ft.
MLS ID
617020
Property Type
Residential
Year Built
1938

Features & Amenities

Total Area
3,336 Sq.Ft.
Neighborhood
Old Town
Water Frontage
None
View Description
No Waterview
Stories
1
Utilites
FKAA, Whole House Generatr, Buyer to Verify, Municipal Sewer
Pool
In Ground, Concrete, Salt Water
Roof
Metal Roof
Parking
Off Street Parking
Heat Type
Central
Air Conditioning
Central Air, Ceiling Fans(s)
Other Interior Features
Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Whirlpool Bath Tub, Entrance Foyer, Cathedral Ceilings, Wet Bar, Surround Sound, Bahama, Glass Doors, Impact Rstnce Doors, Other Windows/Doors
HOA Amenities
None
Other Exterior Features
Fencing, Water Display, Outdoor Shower, Lanai, Lighting, Detached Guest Qtrs
Sales Price
$5,595,000
Real Estate Tax
$24,447/yr
Zoning
HMDR - Historic Medium Density Residential

Downloads

1008 Fleming Street

Schedule a Tour

We would love to help you see this beautiful home! As a full-service brokerage, we can help you tour. Please submit an offer, and answer questions about the buying process.

Enter a valid email

Thank you

for your interest in 1008 Fleming Street, Key West, FL 33040

back to page
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