806 Truman Avenue, Key West, FL 33040

New Listing

$5,365,000

Welcome to Casa Victoria at 806 Truman Avenue, featuring classic Key West architecture, decorative wraparound porches, tropical landscaping, and a charming white picket fence.

A tropical courtyard retreat featuring a private swimming pool, lush landscaping, and a charming pool house overlooking the inviting poolside setting.

A welcoming entry foyer showcases rich wood-paneled walls, beautiful wood floors, an elegant chandelier, and a traditional staircase.

Another view of the inviting foyer highlights the home's original-style architectural details, natural light, and distinctive wood finishes.

French doors connect the foyer to the dining room, creating an inviting transition between the home's living spaces.

The dining room features wood floors, plantation shutters, tropical-inspired furnishings, and a statement light fixture, perfect for entertaining.

A second dining room perspective highlights the French doors, built-in display shelving, and abundant natural light.

The dining room opens toward the living area, offering a comfortable layout for everyday living and gatherings with family and friends.

The comfortable living room features wood floors, high ceilings, generous windows, and tropical-inspired furnishings that convey with the sale.

A charming sitting area with architectural archways, colorful accents, and wood floors provides additional space to relax and unwind.

Cozy breakfast nook with cheerful green walls, wood flooring, plantation shutters, and colorful tropical furnishings that convey with the sale.

Another view of the breakfast nook highlights its convenient location beside the kitchen, distinctive wood accent wall, and natural light.

The kitchen features white cabinetry, dark countertops, stainless steel appliances, a mosaic tile backsplash, and a distinctive arched window.

A second kitchen view showcases the stainless steel appliance package, generous cabinetry, wood floors, and French doors connecting to the breakfast nook.

Spacious covered patio featuring a dining table, ceiling fans, and convenient access to the kitchen and interior living spaces.

Conveniently located just off the breakfast nook, this main-level half bathroom provides easy access for guests while complementing the home's inviting living and dining spaces.

Conveniently located just off the dining room, this main-level full bathroom provides easy access for residents and guests while complementing the home's thoughtfully designed living and entertaining spaces.

The upstairs landing opens to a comfortable sitting area with wood floors, classic stair railings, and access to the upper-level porch.

Inviting upstairs sitting area with beautiful wood floors, comfortable seating, decorative lighting, and large windows overlooking tropical greenery.

Spacious second-floor primary suite featuring a king bed, beautiful wood floors, a flat-screen TV, an en-suite bathroom with a shower, and direct access to the front balcony.

Another perspective of the second-floor king suite highlighting its inviting furnishings, natural light, and direct access to the private front balcony.

Charming front balcony directly accessible from the first primary suite, offering a relaxing outdoor setting overlooking the tropical surroundings.

Private en-suite bathroom serving the first second-floor primary suite, featuring a shower and convenient access from the king bedroom.

Beautifully appointed second-floor primary suite featuring a king bed, flat-screen TV, en-suite bathroom with a tub and shower combination, and direct access to the back deck.

Another view of the second-floor king suite showcasing its comfortable furnishings, natural light, and access to the private back deck.

Outdoor deck directly accessible from the second primary suite, offering an inviting space to relax and enjoy the tropical Key West setting.

Private en-suite bathroom serving the second primary suite, featuring a convenient tub and shower combination.

Cozy loft-style sitting area with a skylight, vaulted beadboard ceiling, wood floors, and a comfortable reading nook.

Charming third-floor bedroom featuring a queen bed, vaulted ceilings, a flat-screen TV, and access to a convenient half bathroom shared with the adjacent loft sitting area.

Inviting third-floor loft sitting area featuring vaulted beadboard ceilings, warm wood floors, comfortable seating, and a half bathroom also serving the adjacent queen bedroom.

Spacious third-floor bedroom featuring two queen beds, a flat-screen TV, an en-suite bathroom with a shower, and access to the upper-level deck.

Another perspective of the third-floor bedroom highlighting its two queen beds, distinctive sloped ceilings, and access to the upper-level outdoor deck.

Private en-suite bathroom serving the third-floor two-queen bedroom, featuring a shower and convenient access from the adjoining bedroom.

Private upper-level deck accessible from the third-floor bedroom featuring two queen beds, offering a peaceful outdoor retreat surrounded by tropical greenery.

Elevated views from the third-floor private deck showcase the home's tropical courtyard, pool, and inviting outdoor living spaces.

Another perspective from the third-floor private deck highlights the lush tropical surroundings, pool area, and beautifully designed outdoor entertaining spaces.

The pool house offers direct access to the private swimming pool and tropical courtyard, creating a seamless connection between indoor comfort and outdoor relaxation.

Another perspective of the pool house king bedroom, highlighting its comfortable furnishings, private accommodations, and convenient access to the poolside courtyard.

Inviting pool house bedroom featuring a king bed, flat-screen TV, en-suite full bathroom with a shower, and direct access to the tropical pool area.

Private full bathroom serving the pool house king bedroom, featuring a shower and providing convenient access for guests enjoying the poolside accommodations.

Beautiful tropical courtyard featuring a private swimming pool, expansive decking, covered outdoor dining area, upper-level balconies, a distinctive spiral staircase, and the charming pool house overlooking the poolside setting.

Expansive deck with covered outdoor dining, comfortable lounge seating, and ceiling fans creates an inviting setting for entertaining and enjoying the Key West lifestyle.

A relaxing spa nestled within the tropical courtyard, complemented by a distinctive spiral staircase leading to the upper-level outdoor deck.

Surrounded by mature palms and lush greenery, this inviting spa and sun deck offer a peaceful setting for relaxation and outdoor enjoyment.

Dedicated laundry area featuring stacked washer and dryer units, a utility sink, countertop workspace, and additional storage for everyday convenience.

Classic Key West charm welcomes you with a spacious covered front porch, traditional rocking chairs, decorative shutters, and tropical landscaping.

Lush tropical palms, a white picket fence, and brick walkways frame the home's distinctive Victorian-inspired architecture and inviting curb appeal.

A picturesque brick walkway winds through mature tropical landscaping, leading to the home's welcoming covered porch.

A beautifully landscaped front lawn with tropical palms and classic white picket fencing creates an inviting setting along Truman Avenue.

A commemorative plaque highlights the property's historic significance and recognition on the National Register of Historic Places.

Property Type: Residential Bedrooms: 5 Baths: 6 Square Footage: 3,223 Lot Size (sq. ft.): 5,729 Status: Active

Current Price: $5,365,000 List Date: 11/02/2026 Last Modified: 11/04/2026

Overview

Description

Experience the best of Old Town Key West at 806 Truman Avenue, a beautifully appointed transiently-licensed residence offering the rare combination of luxury island living and proven rental performance. This distinctive five-bedroom home features approximately 3,223 square feet of living space, thoughtfully designed for both private enjoyment and gracious entertaining. Tropical landscaping, covered porches, a private pool and spa, and separate guest accommodations create a relaxed resort atmosphere with the privacy and character buyers seek in a premier Key West property. Offered furnished, the residence is well suited as a primary home, second home, or high-end vacation rental. The property generated more than $400,000 in rental revenue in 2025, adding meaningful investment appeal to its lifestyle advantages. Ideally located in the heart of Old Town in the 'X' zone, 806 Truman Avenue places owners and guests close to Key West's renowned dining, galleries, entertainment, beaches, and ... (Read more)

Listing Details MLS# 621899

Location, Tax & Legal

Street #: 806
Street Name: Truman
Street Suffix: Avenue
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: X
Alternate Key #: 1030856
Parcel #: 00030090-000000
Zoning: HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Deed Restrictions: Unknown
Legal: KW TROPICAL SUB PB 1-37 LOT 2 SQR 2 TR 12
Taxes: 17519.04
Tax Year: 2025
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: No
Pool: Yes
Year Built: 1918
Lot SqFt: 5729
Lot Sqft Source: Tax Records
Acres: 0.13
Living Apx SqFt: 3223
SqFt Source: Tax Records
Total Bedrooms: 5
Full Baths: 5
Half Baths: Yes
Total Baths: 6
Rentals Allowed: With Restrictions
Min Rental Days: Yes
Control Depth: 0
Total Units: 0

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

License Info

Transient Rntl Licns: Yes

More Information

Building Style

Above Flood: Unknown
Stories: 3 Stories

Vehicle Storage

Car(s): 2
Assigned Parking: Yes
Off Street Parking: Yes

Specialty Rooms

Guest/Servant Qtrs: Legal
Laundry Room: Yes

Pool Info

Heated: Yes
In Ground: Yes
Concrete: Yes

Financial Status

Bank Owned: No
Potential Short Sale: No
Standard Sale: Yes

Remarks & Misc

Remarks – Consumer: Experience the best of Old Town Key West at 806 Truman Avenue, a beautifully appointed transiently-licensed residence offering the rare combination of luxury island living and proven rental performance. This distinctive five-bedroom home features approximately 3,223 square feet of living space, thoughtfully designed for both private enjoyment and gracious entertaining. Tropical landscaping, covered porches, a private pool and spa, and separate guest accommodations create a relaxed resort atmosphere with the privacy and character buyers seek in a premier Key West property. Offered furnished, the residence is well suited as a primary home, second home, or high-end vacation rental. The property generated more than $400,000 in rental revenue in 2025, adding meaningful investment appeal to its lifestyle advantages. Ideally located in the heart of Old Town in the 'X' zone, 806 Truman Avenue places owners and guests close to Key West's renowned dining, galleries, entertainment, beaches, and historic attractions. For the buyer seeking a refined island residence with transient-rental capability, established revenue, and exceptional Old Town appeal, 806 Truman Avenue presents a truly compelling opportunity.

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Microwave: Yes
Range: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes
Washer: Yes

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Central Air: Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Floor

Tile: Yes
Wood: Yes

Interior Features

Built-in Cabinets: Yes
Cathedral Ceilings: Yes
Dade County Pine: Yes
Granite Counter Top: Yes
Smoke Alarms: Yes
Split Bedroom: Yes
Window Treatments: Yes

Windows/Doors

Double Hung Windows: Yes
French Doors: Yes
Glass Doors: Yes
Wood Windows: Yes

Construction

Frame: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Furnished: Yes

Utilities

FKAA: Yes
Municipal Sewer: Yes

Porch/Balcony

Open Porch/Balcony: Yes
Patio: Yes

Title

Negotiable: Yes

Exterior Features

Detached Guest Qtrs: Yes
Fencing: Yes
Hot Tub: Yes
Lanai: Yes
Lighting: Yes
Rain Gutters: Yes
Sprinkler System: Yes
Storage: Yes

Pre-Wired

Cable: Yes

Roof

Metal Roof: Yes

Shutters

Panel: Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Vehicle Storage: Assigned Parking; Off Street Parking Furnished: Furnished Cooling: Ceiling Fans(s); Central Air Utilities: FKAA; Municipal Sewer Interior Features: Built-in Cabinets; Cathedral Ceilings; Dade County Pine; Granite Counter Top; Smoke Alarms; Split Bedroom; Window Treatments Pre-Wired: Cable Specialty Rooms: Laundry Room Appliances: Dishwasher; Dryer; Microwave; Range; Refrigerator; Stainless Steel Appliance(s); Washer Exterior Features: Detached Guest Qtrs; Fencing; Hot Tub; Lanai; Lighting; Rain Gutters; Sprinkler System; Storage Pool Info: In Ground; Concrete Construction: Frame Shutters: Panel Floor: Tile; Wood Roof: Metal Roof Pets: Pets Allowed Land Size: Less Than 1/4 Acre Title: Negotiable

Listing Office: Island Life Realty Experts

Last Updated: November - 04 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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