1223 Flagler Avenue, Key West, FL 33040

$1,550,000
Property Type: Residential Bedrooms: 4 Baths: 3 Square Footage: 2,260 Lot Size (sq. ft.): 4,563 Status: Closed
Current Price: $1,550,000 List Date: 9/10/2025 Last Modified: 11/04/2025

Description

Discover your own private oasis in the heart of Key West! This spacious 4BR/3BA two-story home offers over 2,200 sq ft of living space designed for both relaxation and entertaining. Located in desirable Midtown, just minutes from the Casa Marina, Higgs Beach, and White Street Pier, you'll enjoy the perfect balance of island living and everyday convenience. Step inside to find an open floor plan with multiple living and dining areas, a modern kitchen with stainless steel appliances and wine cooler, and flexible spaces ideal for guests or family. The home's layout includes two bedrooms on each level, providing privacy and options for hosting or working from home. Outside, the resort-style backyard is the true highlight: a heated pool with expansive deck, surrounded by lush tropical landscaping and tall privacy fencing. Enjoy the covered lanai for dining al fresco, rinse off in the outdoor shower after a day at the beach, or simply unwind in the shade of palm trees. This fully fenced property is perfect for both peaceful relaxation and lively gatherings. Additional features include off-street parking for 2-3 vehicles, central air, laundry room, ceiling fans, and negotiable furnishings. With a 30-day minimum rental allowance, this property also offers excellent potential as a vacation rental or investment. Whether you're seeking a year-round residence, second home, or income-producing property, 1223 Flagler Avenue delivers the best of Key West living with comfort, charm, and convenience.

More Information MLS# 616436

Contract Information

Listing Board: Key West Association Potential Short Sale: No Bank Owned: No Current Price: $1,550,000 Listing Date: 2025-09-10 Sold Price: $1,550,000

Location, Tax & Legal

KW Neighborhood: Midtown West City: KEY WEST Mile Marker: 2 Marathon Neighborhood: N/A Side: Ocean Flood Zone: AE Alternate Key #: 1041203 Parcel #: 00040490-000000 Zoning: SF - Single Family Deed Restrictions: Unknown Legal: BK 1 LT 6 TRACT 19 KW TROPICAL BLDG AND INVESTMENT CO SUB PB1-34 OR129-344/46 OR544-191 OR792-1156 OR914-1841 OR1411-17 Taxes: 10607.8 Tax Year: 2024 Pub Sewer HkUp: Yes Street #: 1223 Street Name: Flagler Street Suffix: Avenue Key/Island: Key West State/Province: FL Zip Code: 33040 County: Monroe Subdivision: Tropical Bldt & Investment Co Sub (2.0) Area: 03 - Key West

General Property Description

Realtor.COM Type: Residential - Single Family Waterfront: No Control Depth: 0 Lot SqFt: 4563 Pool: Yes Total Units: 0 Acres: 0.1 SqFt Source: Tax Records Rentals Allowed: With Restrictions Min Rental Days: 30 Style: Single Family Year Built: 1958 Living Apx SqFt: 2260 Total Bedrooms: 4 Full Baths: 3 Total Baths: 3

Remarks & Misc

Remarks – Consumer: Discover your own private oasis in the heart of Key West! This spacious 4BR/3BA two-story home offers over 2,200 sq ft of living space designed for both relaxation and entertaining. Located in desirable Midtown, just minutes from the Casa Marina, Higgs Beach, and White Street Pier, you'll enjoy the perfect balance of island living and everyday convenience. Step inside to find an open floor plan with multiple living and dining areas, a modern kitchen with stainless steel appliances and wine cooler, and flexible spaces ideal for guests or family. The home's layout includes two bedrooms on each level, providing privacy and options for hosting or working from home. Outside, the resort-style backyard is the true highlight: a heated pool with expansive deck, surrounded by lush tropical landscaping and tall privacy fencing. Enjoy the covered lanai for dining al fresco, rinse off in the outdoor shower after a day at the beach, or simply unwind in the shade of palm trees. This fully fenced property is perfect for both peaceful relaxation and lively gatherings. Additional features include off-street parking for 2-3 vehicles, central air, laundry room, ceiling fans, and negotiable furnishings. With a 30-day minimum rental allowance, this property also offers excellent potential as a vacation rental or investment. Whether you're seeking a year-round residence, second home, or income-producing property, 1223 Flagler Avenue delivers the best of Key West living with comfort, charm, and convenience. Directions: Off White Street and Flagler Avenue.

Status Change Info

Sold Comments: Thanks to all involved Sold Date: 2025-11-04 Sold Price: $1,550,000 Status: Closed

Association Info

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

License Info

# of City License: 1 # of County License: 1 Non Trans Rntl Lic: 1

Fee Includes

None: 1

Dockage

None: 1

Tax Exemptions

None: 1

Appliances

Dishwasher: 1 Dryer: 1 Microwave: 1 Oven: 1 Refrigerator: 1 Stainless Steel Appliance(s): 1 Washer: 1 Wine Cooler: 1

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1

Waterfront

None: 1

Waterview

No Waterview: 1

Floor

Carpet: 1 Tile: 1 Wood: 1

Interior Features

Bar: 1 Drapes/Blinds Incl: 1 Smoke Alarms: 1 Split Bedroom: 1 Window Treatments: 1

Building Style

Above Flood: Yes Stories: 2 Stories

Windows/Doors

Jalousie Windows: 1

Vehicle Storage

Car(s): 2 Covered Parking: 1 Off Street Parking: 1

Security

No Security: 1

Construction

CBS: 1

Land Size

Less Than 1/4 Acre: 1

Furnished

Furnished: 1 Negotiable: 1

Terms

Cash: 1 Conventional: 1 FHA: 1 No Seller Finance: 1

Utilities

FKAA: 1 Municipal Sewer: 1

Porch/Balcony

Deck: 1 Open Porch/Balcony: 1

Exterior Features

Outdoor Shower: 1 Privacy Wall/Fence: 1

Pool Info

In Ground: 1 Decked: 1

Pre-Wired

Cable: 1

Roof

Metal Roof: 1

Financial Status

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

Property Features

Fee Includes: None Tax Exemptions: None License Info: Non Trans Rntl Lic Waterfront: None Waterview: No Waterview Dockage: None Vehicle Storage: Covered Parking; Off Street Parking Furnished: Furnished; Negotiable Cooling: Ceiling Fans(s); Central Air Utilities: FKAA; Municipal Sewer Interior Features: Bar; Drapes/Blinds Incl; Smoke Alarms; Split Bedroom; Window Treatments Pre-Wired: Cable Appliances: Dishwasher; Dryer; Microwave; Oven; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler Exterior Features: Outdoor Shower; Privacy Wall/Fence Pool Info: In Ground; Decked Construction: CBS Floor: Carpet; Tile; Wood Roof: Metal Roof Pets: Pets Allowed Security: No Security Land Size: Less Than 1/4 Acre Terms: Cash; Conventional; FHA; No Seller Finance
Listing Office: Preferred Properties (KW)
Last Updated: November - 04 - 2025
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