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Listing Board: Florida Keys

As is Rght to Inspct: Yes

Current Price: $3,595,000

Listing Date: 2026-06-10

List Price: $3,595,000

KW Neighborhood: Old Town-N of Truman

City: KEY WEST

Off Shore Island: No

Mile Marker: 1

Marathon Neighborhood: N/A

Side: Bay/Gulf

Flood Zone: AE

Alternate Key #: 1003875

Parcel #: 00003710-000000

Zoning: HMDR - Historic Medium Density Residential

Deed Restrictions: No

Legal: KW PT LOT 3 SQR 22 H1-567 G4-418 OR931-368/69 OR957-632/33 OR986-1827/28 OR1470-280/81 OR1470-282/283 OR1947-959/60 OR22

Taxes: 9955.15

Tax Year: 2025

Pub Sewer HkUp: Yes

Street #: 710

Street Name: Caroline

Street Suffix: Street

Key/Island: Key West

State/Province: FL

Zip Code: 33040

County: Monroe

Subdivision: Old Town - Unlisted (1.0)

Area: 02 - Key West

Realtor.COM Type: Residential - Single Family

Waterfront: No

Control Depth: 0

Lot Size: X

Lot SqFt: 1849

Pool: Yes

Lot Sqft Source: Tax Records

Total Units: 0

Acres: 0.04

SqFt Source: Property Data Card

Rentals Allowed: Yes

Min Rental Days: 28

Style: Single Family

Year Built: 1928

Living Apx SqFt: 2250

Total Bedrooms: 4

Full Baths: 4

Half Baths: 1

Total Baths: 5

Remarks – Consumer: An extraordinary opportunity to own one of Key West's most coveted addresses -- iconic Caroline Street in the Historic Seaport, just steps from Duval Street. Fully renovated in 2023, this stunning residence was completely redesigned, raised to modern flood standards, and upgraded with impact-rated windows and doors, delivering a rare combination of historic charm, modern luxury, and total peace of mind. Spanning approximately 2,250 of high-ceiling square feet, the home showcases refinished heart pine throughout, coral-clad walls, Jerusalem limestone and terrazzo flooring, marble accents, and designer finishes abound. Four generously sized bedrooms each feature beautifully appointed en-suite bathrooms, plus an additional guest half bath. The oversized upstairs primary suite includes walk-in closets and a spa-caliber bath with double shower, custom artist-made cabinetry, and stunning coral accents. Two additional spacious bedrooms round out the upper level, while a second primary suite on the main floor offers ideal flexibility for owners or guests alike. The chef's kitchen is built for entertaining -- a large six-seat island anchors the space alongside a premium JennAir appliance package. The open living and dining areas flow naturally into a sitting room with daybed and collapsing rear doors that open to your private outdoor retreat: a heated and chilled plunge pool with waterfall, creating a true resort-style escape in the heart of Old Town. The investment story is equally compelling, should you choose to go that direction. The property comes with over $175,000 in already-booked upcoming rental revenue that transfers with the sale -- meaning your income starts on day one. A loyal base of repeat renters is in place and ready to continue, providing immediate cash flow and long-term earning potential with minimal ramp-up. Whether you're looking for a full-time residence, a seasonal getaway, or a high-performing income property, this home delivers on every

Mandatory Home Owners Asc: No

1st Right of Refusal: No

Association Fee $: 0

Non Trans Rntl Lic: 1

None: 1

None: 1

None: 1

Dishwasher: 1

Disposal: 1

Dryer: 1

Freezer: 1

Microwave: 1

Oven: 1

Range: 1

Refrigerator: 1

Stainless Steel Appliance(s): 1

Washer: 1

Wine Cooler: 1

Pets Allowed: 1

Ceiling Fans(s): 1

Central Air: 1

Central: 1

ENERGY STAR Qualified Equipment: 1

None: 1

No Waterview: 1

Combo: 1

Marble: 1

Terrazzo: 1

Tile: 1

Other: 1

Built-in Cabinets: 1

Dade County Pine: 1

Drapes/Blinds Incl: 1

Entrance Foyer: 1

Fire Sprinkler: 1

Quartz Countertops: 1

Smoke Alarms: 1

Split Bedroom: 1

Walk-in Closet(s): 1

Window Treatments: 1

New Construction: 1

Updated/Remodeled: 1

Loft: 1

Other: 1

Above Flood: Yes

Conch: 1

Stories: 2 Stories

Impact Rstnce Window: 1

Wood Windows: 1

Frame: 1

Less Than 1/4 Acre: 1

Furnished: 1

Cash: 1

Conventional: 1

Seller Finance Psble: 1

Cable Available: 1

FKAA: 1

Municipal Sewer: 1

Deck: 1

Open Porch/Balcony: 1

Negotiable: 1

Fencing: 1

Hot Tub: 1

Lighting: 1

Rain Gutters: 1

Sprinkler System: 1

In Ground: 1

Heated: Yes

Concrete: 1

Decked: 1

Cable: 1

Cat 5: 1

Metal Roof: 1

Standard Sale: Yes

LED Lighting: 1

Programmable Thermst: 1

Tankless Hot Wtr Htr: 1

Status: Active