Situated directly across from the iconic Ernest Hemingway House, this exceptional family compound combines the rich history of Old Town Key West with modern luxury and island charm. From the famous six-toed cats that roam next door to the vibrant energy of Duval Street just steps away, this location is as legendary as it is convenient. Spanning two addresses at 407 and 415 Olivia Street, this versatile property is situated in the X flood zone and offers four off-street parking spaces. The main house, a meticulously renovated mid-century modern gem, welcomes you with a grand entrance foyer that flows into a spacious living, dining, and media area. Perfect for entertaining, the space features a working fireplace and a 76-inch TV. The gourmet kitchen boasts solid wood cabinetry, Bosch and Thermador appliances, an induction cooktop, column fridge/freezer, wine cooler, and an impressive 13-foot quartz waterfall island. Impact sliding doors open to a stunning saltwater pool complete with a sun ledge, slide, and waterfall. Surrounded by tropical landscaping, this backyard oasis also features an outdoor shower, fully equipped kitchen, and plenty of space for entertaining. The main house offers four bedrooms, each with generous closet space and outdoor access. The primary bedroom includes a new custom walk-in closet with solid maple built-ins. Another ensuite bedroom has been transformed into a stylish home office with a built-in Murphy bed. The two additional bedrooms share an elegant bathroom featuring a luxurious soaking tub and shower. Adjacent to the main house is a charming two bedroom, two bath Conch-style cottage that provides the perfect guest retreat or mother-in-law suite. This home features a fully equipped kitchen, Dade County pine accent walls, and a tranquil outdoor space to relax under the shade of swaying palm trees. Don't miss the chance to see this unique compound that provides the perfect blend of history, luxury, and the ultimate Key West lifestyle!!
Sold for $3,500,000 on 08/08/25
$3,500,000
407-415 Olivia St, Key West, FL 33040
6beds
3,171sqft
Single Family Residence
Built in 1964
8,276.4 Square Feet Lot
$3,500,100 Zestimate®
$1,104/sqft
$6,794 Estimated rent
What's special
Zillow last checked: 7 hours ago
Listing updated: August 09, 2025 at 01:46am
Listed by:
Brenda J Donnelly 305-304-1116,
Brenda Donnelly Real Estate LLC
Bought with:
Brenda J Donnelly, 3037635
Brenda Donnelly Real Estate LLC
Source: FLKMLS,MLS#: 612847
Originating MLS: Key West Association

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 5
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Wine Cooler, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
- Laundry: Laundry Room
Features
- Cathedral Ceiling(s), Quartz Countertops, Walk-In Closet(s), Storage, Dade County Pine, Built-in Cabinets, Entrance Foyer
- Flooring: Tile, Concrete, Other
- Doors: Impact Rstnce Doors
- Windows: Wood Frames, Impact Rstnce Window, Panel
Interior area
- Total interior livable area: 3,171 sqft
Property
Parking
- Total spaces: 4
- Parking features: Off Street
Features
- Patio & porch: Open Porch/Balcony
- Exterior features: Storage, Outdoor Shower, Outdoor Kitchen, Lighting
- Has private pool: Yes
- Pool features: Heated, In Ground, Concrete, Salt Water
- Fencing: Fenced,Privacy
- Water view: None
- Waterfront features: None, Dockage: None
Lot
- Size: 8,276 sqft
- Features: Less Than 1/4 Acre
- Residential vegetation: Fruit Tree(s)
Details
- Parcel number: 00017200000000
- Zoning: HMDR
- Zoning description: Historic Medium Density Residential
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS, Frame
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1964
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA, Cable Connected
Community & neighborhood
Location
- Region: Key West
- Subdivision: Old Town - Unrecord (1.0)
HOA & financial
HOA
- Has HOA: No
- Services included: None
Other
Other facts
- Listing terms: Cash,Conventional